I’ve been percolating on a series of Italy itinerary posts for awhile. After all, we’ve spent several weeks in Italy every single year since 2015 (minus 2020). Most of our trips are longer than a week, but I recognize that the United States offers the shortest vacation times in the modern world. For a lot of people, taking more than a week off at a time is incredibly challenging, if not impossible. Thus, I thought the best place to start these itinerary posts are at one week. Obviously you could combine some of these if you are able to plan a longer trip, but on the longer itinerary posts, I’ll give you more ideas that might not be on the one week Italy itinerary plans simply because of how challenging it can be to get to some places. This is particularly true in parts of Northern Italy, as well as Southern Italy
For all intents and purposes, this post is going to cover 7 day itineraries for Italy. If you can leave on a Thursday evening and return the following Sunday (or Monday if it’s a holiday week!), you can fully utilize both weekends and get a little extra time without having to take a lot of extra vacation time. When I worked in consulting, this is how I would maximizing my 7 (yes, 7 per year) days of vacation – by creating long weekends over holiday weekends when we already had Mondays off.
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Making the Most of One Week in Italy
Italy in 7 Days
A week in Italy is doable but you can’t do Italy in a week, so let’s kick of these Italy itineraries. If you’re someone who is going to have to leave on a Friday (or a Saturday) and come back the following Sunday, these one week Italy itinerary ideas are for you. You’re going to have to figure out what is most important to you (architecture, art, history, food?) and choose a single city as your starting point.
For each of these itinerary ideas, I will share some of my favorite things to do in each destination. Hopefully this can help you figure out what you want to explore – and get a better idea of what is important to a place! That said, travel is personal, so use my suggestions as a jumping off point – not a point-by-point map or checklist.
Open Jaw Ticketing
If you want to cover a lot of ground, the best tip I can give you to make the most of your one week Italy itinerary is to utilize open jaw flights. What does this mean? It means that you will fly into one city and out of another city. Often times, if you plan in advance, this does not result in a more expensive airline ticket. It will save you money on having to backtrack to get back to your original point of departure though. I use ITA Matrix to search for open jaw itineraries and use Book with Matrix to actually book the itinerary.
I always book with the airline directly. It makes things so much easier when flights change. Our Thanksgiving 2021 itinerary had multiple cancellations due to British Airways schedule changes. We changed our airport of departure 3-4 times. In every case, because I booked with American Airlines directly, I could search their availability, call in with what worked best for me, and they would rebook us.
Go Beyond the “Big Three” Italian Cities
There are a lot of tour companies that will sell you an Italy itinerary that visits Rome, Florence, and Venice (and likely includes a drive-by of Tuscany, lol). All of these cities are amazing and they should be visited, but it’s not necessary to do all of them on a single one week Italy itinerary! In fact, I would argue that the best way to see Italy for the first time is to see both sides of it – see one of the “big” cities and see small town Italy. Not only will this give you a more authentic look at the country as a whole, but it will also help you figure out what you enjoy.
If you’re traveling to check off as many big sites on your Italy bucket list as you can, this might be the itinerary for you… but if you’re traveling to experience La Dolce Vita, slow down and see the smaller cities as well.
Skip the Day Trip
Recently, one of the Italians I follow posted a link to the proliferation of Florence day trips and asked how people felt about it. I’ve already railed against the Cinque Terre day trip on this blog; I can’t imagine spending one day in Florence. The truth is, no matter where you go, if you spend one day in a destination, you’ll spend most of your time getting there. You’ll likely arrive at the most crowded time of the day and you’ll leave before magic hours – the time when a place slows down, the skies go from blue hour to inky blue, and only the locals are left.
No matter how popular a place is as a day trip, I can promise you that if you slow down and spend or night or two, you’ll unlock some of the magic that is absolutely missed on day trips. There is magic to be found everywhere. I promise.
Transportation within Italy Matters
How you plan to get around will influence your itinerary for Italy. If you absolutely do not want to drive in Italy, you’ll want to visit places that are well-connected by train or bus. The train in Italy is a lovely way to travel, and they have certainly improved since I first studied abroad here.
We also really enjoy driving in Italy because we can get to places that are not easily reachable by train or bus. It also gives us the flexibility to have dinner at agriturismos outside of town, visit wineries, and have a few experiences that would be more difficult without a car. And, since I’m being totally honest here, I can only travel by train if we don’t drive. I get very carsick on buses. When we drive, I have a bit more control over the elements that affect my carsickness. (This is true in the US, as well. It’s not just an Italy thing.)
Rome Itinerary Ideas
American Airlines offers a direct flight from DFW-FCO (Rome), so a lot of our Italian itineraries start by flying into Rome. Rome can be difficult as a first destination in Italy, but it’s also popular for a reason. There is truly something for everyone in Rome. Food, history, culture, religion – whatever your reason for visiting Rome is, you’ll find it there.
Why do I say Rome is difficult? One, it is a big city and isn’t necessarily well-connected by public transportation. You’ll need to be comfortable exploring Rome on your own two feet. Two, there are a lot of tourist traps for restaurants. I think most of the worst meals I’ve had in Italy were in Rome. (Don’t worry – I have tips for you to avoid this.) Three, there’s no way to see it all. You have to make concessions. You can see the Colosseum and the Trevi Fountain, but they’re on the other side of the river from the Vatican Museums. The most delicious restaurant areas are a pretty good walk (or metro ride) away from the sites of ancient Rome. It doesn’t mean you shouldn’t visit them, but it is really important to do your research ahead of time and decide what is most important to your group.
Religious Rome & Assisi
(This itinerary does not require a car. You can do it by train.)
Day One in Rome
- Morning: Arrive in Rome and check-in to your hotel. Get out, walk around, and start beating the jet lag. If you must take a nap, don’t sleep for more than 20 minutes. Walk into every church you find. You never know what is beyond the facade.
- Evening: Book a Rome food tour for dinner on your first night in Rome. This will save you a lot of bad meals. Our family favorite was the Trastevere food tour, but the Testaccio food tour gives you a great look at local life in Rome, too.
Day Two in Rome
- Morning: Book an early access tour of the Vatican Museums. This will allow you to see the Sistine Chapel in almost private conditions. If you’re traveling with a bigger group, we booked a private tour with Deborah from LivTours. (I loved our experience so much that I’m going to share my discount code with you – save 10% by using DEBORAH10.) (Read more of my tips for visiting the Vatican City.) After visiting the museums, head over to St. Peter’s and take a DIY tour using Rick Steves’ Audio Guide for St. Peter’s Basilica.
- Evening: Take a sunset walking tour of Rome and see the monuments at their best. Make sure that you have a late dinner reservation ready to go!
Day Three in Rome
- Morning: Head to the Pantheon before the line gets too long. You can purchase an audioguide or use Rick Steves Audio Guide to the Pantheon. (Tom loves doing these.)
Day Four in Rome / Assisi
- Afternoon: Assisi is only 2-2.5 hours away from Rome by train (or car). I recommend traveling after you check out from your hotel. This will allow you to miss the most crowded parts of the day and minimize having to store your luggage. By the time you get settled into Assisi, you’ll have the place all to yourself. (Check out some of my Assisi recommendations!)
Day Five in Assisi
- Morning: Take this Assisi walking tour. Seriously. It shouldn’t be missed. You’ll visit a lot of the churches in Assisi, including the famous Basilica of St. Francis. I learned so much on this tour, and all of the churches are worth visiting. You’ll have the afternoon to go back and visit the ones that intrigued you for longer. (Please don’t forget to respect the Basilica’s wishes and don’t take pictures of the inside of the church. It’s really disruptive to everyone else when they have to yell at you.)
Day Six in Assisi and Rome
- Late Morning: Before heading back to Rome, don’t miss this wine tasting in Assisi. If you aren’t a wine drinker, they also offer olive oil tastings. (You can book a private transfer to their vineyard.) This family provides the most delicious and entertaining experience in Assisi. We visited in June 2021, and I would go back in a heartbeat. They fed us a delicious meal using fresh ingredients, allowed us to try their olive oils and wines (and taught us the difference in quality), and provided so many laughs along the way. This is a wonderful way to end your time in Assisi and enjoy some incredible views, too.
Day Seven in Rome
- If you have time, do anything that you missed out on or wanted to experience again. (I keep an on-going list of my favorite tours in Rome that is updated every time I find a new one to love!)
Historical Rome & Pompeii
(This itinerary does not require a car. You can do it by train.)
Day One in Rome
- Morning: Arrive in Rome and check-in to your hotel. Get out, walk around, and start beating the jet lag. If you must take a nap, don’t sleep for more than 20 minutes.
- Evening: Book a Rome food tour for dinner on your first night in Rome. This will save you a lot of bad meals. Our family favorite was the Trastevere food tour, but the Testaccio food tour gives you a great look at local life in Rome, too.
Day Two in Rome
- Morning: Skip the line at the Colosseum and visit the Roman Forum with a guide. Honestly, this was probably the most interesting tour we’ve done in Rome and I’m not nearly as obsessed with the Romans as my husband is. If you don’t use a guide, you’re just looking at ruins. This tour made everything come alive for me.
- Evening: Take a night walking tour of Rome and see everything from the Piazza Popolo to the Campo dei Fiori and everything in between. As of late 2021, the Roman Forum is not illuminated in the evening again, so while you might want to take a night tour of the Colosseum, you won’t be able to see much else.
Day Three in Rome
- Rome is your oyster! Visit the Pantheon, take a tour of the Capitoline museum (Tom loved this), take the train out to Ostia Antica, or visit Hadrian’s Villa and Villa d’Este.
Day Four in Rome / Amalfi Coast
- Morning: Head south by train! The most cost effective way to enjoy Pompeii with time constraints (and enjoy Amalfi) is to make Sorrento your home base. Sorrento is about 2.5 hours from Rome by train and 30 minutes from Pompeii. You could venture further south to the more popular Positano, but you’re going to pay much higher prices and it will be more difficult to get around.
- Afternoon: Take some time to relax, recharge, and enjoy the view. You can take a hydrofoil to some of the more glitzy towns of Amalfi if you’re feeling ambitious. Just make sure to plan how you’re going to get back to your home base. Driving in Amalfi isn’t for the faint of heart!
Day Five in Pompeii and Herculaneum
- Book a guide and board the Scavi train to Pompeii. I recommend getting out early before it gets too hot and too crowded. If you can’t make the morning work, go in the late afternoon before the site closes. You’ll have less crowds to contend with than if you go in the middle of the day. Whatever you do, skip a midday arrival if you can!
Day Six in Sorrento and Rome
- Give yourself a leisurely morning to relax and enjoy the coastal views before heading back to Rome. The train is only 2.5 hours, so there’s no reason to be in a hurry. If you can store your luggage at your hotel, maybe it’s worth taking a day trip over to Capri and heading back to Rome in the evening. Either way, make it an easy travel day so you’re ready to wrap up your time in Rome tomorrow.
Day Seven in Rome
- If you’re not leaving today, make sure to do anything that you missed out on or wanted to experience again. (I keep an on-going list of my favorite tours in Rome that is updated every time I find a new one to love!)
Rome & Umbria
If you are flying into Rome but were hoping to visit Tuscany for wine and food, may I suggest Umbria instead? Umbria is a more rustic Tuscany with beautiful hill towns, amazing resorts, and extremely tasty food… and it’s largely ignored by guidebooks and tourists! While it’s no secret that I love a beautiful Tuscan hill town, I also really love Umbria. I recommend doing three nights in Rome and two or three nights in Umbria.
If you’re really ambitious, you can do what we do and drive from Umbria to the Rome airport on the morning of your flight. We’ve done that multiple times to extend our time in the Italian countryside.
For Food & Wine, Visit Montefalco
Montefalco was our first foray into Umbria during winter 2018. We drove over for dinner and were completely flummoxed by the fact that it wasn’t in our guidebooks. It’s a very well-preserved walled city that is underrated and under appreciated. It’s about 2 hours northeast of Rome.
If you love food and wine, I highly recommend adding Montefalco to your Italy itinerary. Montefalco is a quiet town with a beautiful town square, amazing restaurants, and delicious wines. You can book a wine tasting of Sagrantino, Montefalco Rosso, Passito, and even Trebbiano white wines. (We’ve purchased two dozen bottles of Bocale wines in less than a year.) Truffles are very popular here, so if you’ve been wanting to experience truffles, Montefalco is a great place to go.
In addition to food and wine, Montefalco has some incredible frescos and old churches to see. On our last trip to Montefalco, we walked all the small streets beyond the town center and stumbled upon numerous very old churches that had remnants of beautiful art. Again, you won’t read about these things in the guidebooks. You just have to explore.
STAY: Palazzo Bontadosi
For Meat and Mountains, Visit Norcia
Norcia is one of the new places we discovered on our trip in summer 2021. 2.5 hours northeast of Rome, you’ll wind through some mountains and valleys and stumble upon a small town that need you to visit. In the past, Norcia was famous for its butchers, which means it is famous for its sausages and salumi. Norcia has some truly amazing sausage pasta dishes. (One of our waiters in Cortona recommended Norcia to us for the food. He definitely wasn’t wrong in his recommendations!) While we couldn’t bring home sausages, we did bring home truffle cheese from Norcia. It did not disappoint.
If you look up Norcia online, you’ll probably find that it was severely damaged by an earthquake in 2016 and 2017, which significantly damaged a lot of the town. The cathedral is closed and covered in scaffolding and you can hear work being done non-stop during the day. While there isn’t a lot to see in town, they need you to visit. Tourism has largely disappeared because of the damage. In the summer (May – July), the mountains and fields are in bloom with the Castelluccio di Norcia, so bring your hiking gear but stay in town to support the local economy that needs you.
STAY: Palazzo Seneca (We booked through Tablet Plus so we could take advantage of a room upgrade, a hotel credit, a welcome amenity, and a late checkout. It is a Relais & Chateaux property, so these benefits may also be available through your favorite travel agent.)
For Relaxation Away from Rome
If all the hustle of Rome has you overwhelmed and in need of a break, head to my favorite spa resort two hours north of Rome. Borgo dei Conti is the perfect place to unplug from Rome, enjoy nature, and indulge in wellness. We stayed at Borgo dei Conti after Christmas in 2018, for easter in 2019, and in summer 2021.
From the moment you check in, you’re encouraged to relax. Seriously. They sent us to the bar to enjoy a glass of wine while they prepared our room. The chateaux rooms are beautifully decorated but maintain the charm of the original architecture with exposed beams and period art throughout the hotel. There is a beautiful library where you can curl up with a book (or peruse their collection). The spa has a jacuzzi and a small pool, as well as a steam room and sauna, and you can book treatments as well. There are multiple restaurants on property, so you really don’t have to leave… though I do love the pizza restaurant (Valpino) that is a short walk or drive from the hotel!
There are multiple pools, tennis courts, and other opportunities for wellness, but what I loved most in summer 2021 were the guided mediation walks throughout the park around the property. You’ll feel miles away from Rome and the only noise you’ll hear are the birds. It’s truly lovely.
My favorite memory is buying a bottle of wine from the bar and watching the sunset over the lake from one of the many terraces at the hotel.
STAY: Borgo dei Conti Resort
Venice Itinerary Ideas
The second easiest place in Italy for us to visit from the US is Venice. American Airlines offers a direct flight from PHL-VCE (Philadelphia to Venice), and we used this flight for anniversary trips in September. Tom loves Venice. It’s his favorite place to visit in Italy. I like Venice because it’s beautiful and unique. Given it’s location, my recommendation for spending a week in Venice is to do a few days in one sestiere (district) and move to a second sestiere or one of the Venice islands for a few days for a different experience.
One of my favorite sesitere to stay in is Dorsoduro. This area has a lot of quieter canals and art galleries that I love to visit. I’ve also stayed in San Marco and Guidecca, as well as the island of Murano and the Isola della Rose. I loved staying in Murano. After walking around Castello, I think it would be a neat and very local place to stay (as local as Venice can be these days).
I think it’s really important to understand how the over-saturation of tourism and daytrippers from cruise ships has contributed to a Venice that is not sustainable for locals to live there. For that reason, I think it’s important to stay in Venice and slow down, as well as contribute to the economy. Susana has a great 3-day sustainable Venice itinerary if you don’t want to spend a week in Venice.
Making the Most of Your Venice Trip
Here are just a few Venice travel tips to make your trip more enjoyable.
- Find a hotel in Venice and stay in Venice. Not in Mestre. Not a train ride away. In Venice. We really love Palazzo Veneziano in Dorsoduro. The Hotel Danieli is perfect for a romantic trip to Venice. The Hilton is perfectly fine, especially with a vaporetto pass.
- Buy a vaporetto pass for the duration of your stay. It is far more cost effective than individual rides and it will save your feet. (There are a lot of stairs in Venice.)
- Give yourself plenty of time to get places, particularly if you have a reservation to honor. Because of the tight roads, sometimes internet doesn’t work perfectly. (And, really, put the phone away. The beauty is in the walk.)
- Practice sustainable tourism. If you want Venice to be there when you go back, patronize local businesses. This means buying locally made glass and masks, instead of things manufactured and mass produced elsewhere. It includes not contributing to the affordable housing problem by encouraging the proliferation of AirBnB. And, book local guides and tours, rather than just looking for the perfect instagram background. We’ve been to Venice twice post-COVID, and in a lot of ways, it is so much nicer to visit now because it doesn’t feel overrun with mass tourism. Let’s do our part to help continue to grow Venice back to a place where locals can and want to live and tourists can enjoyably visit!
Suggested One Week Itinerary for Venice
Day One in Venice
- Morning: Book a walking tour of Venice with a to get your bearings. I love Lu with Secret Venice Tour or these free Venice walking tours. By doing this early, you can get local recommendations and avoid the tourist traps, of which there are many.
- Evening: Give your feet a break, board the #1 Vaporetto before sunset, and grab an outdoor seat in the front. Cruise down the Grand Canal with this DIY audio tour.
Day Two in Venice
- Morning: Head to St. Mark’s Square before the daytrippers arrive and enjoy the quiet beauty of Europe’s oldest and most beautiful living room. Visit the Basilica of San Marco, take the stairs to the rooftop, and enjoy a bird’s eye view of the square as it starts to fill up. If you need a coffee (or gelato) break, we love the iconic (and expensive) Caffe Florian.
- Afternoon: Visit the Frari Church, one of Venice’s famous churches that is far from where the tourists usually wander. (Another under appreciated church nearby is the Chiesa di San Pantalon.)
- Evening: Prepare for apertivo and learn more about the Venetian tradition of cicchetti with a wine tasting at Venice bar off a small canal. While Venice doesn’t create its own wine, the Veneto does and this is a great place to try it without leaving the islands! The owner provided us with an entire rainbow of wines to try!
Day Three in Venice
- Morning: Take a guided tour of the Doges Palace. Yes, you can visit on your own, but unless you know a lot about Venetian history, you won’t really know what you’re seeing. You’ll even be able to cross the Bridge of Sighs from the inside.
- Evening: If it is in your budget, take a gondola ride in Venice. (I have a few suggestions for ways to make it work in that post!) I think sunset and blue hour is the most magical hour for gondola rides in Venice. Night gondola rides are extremely romantic though.
Day Four in Venice
- Depending on whether or not you decide to stay in Venice or move to one of the islands, today should be a day for exploring the islands. We’ve stayed at the Hyatt Centric Murano in December 2021 and loved the experience. We saw parts of Murano that tourists don’t usually see and some of the more beautiful glass shops are deep in Murano.
- If you decide not to change hotels and what an introduction of the most popular Venetian islands, take this day trip to Murano, Burano and Torcello.
- If you are feeling adventurous and want to DIY this tour so you won’t feel rushed, I love Torcello. The ancient church is incredible.
- If you’re looking for souvenirs, head to Murano for glass or Burano for lace.
- If you’re looking for the colorful Venetian buildings, they are on Burano.
Days Five through Seven in Venice
- Your goal for the rest of the trip should be to experience the “real” Venice away from all the touristy sites. I strongly recommend taking another walking tour of Venice to see a different area that you’ve visited before. However, you could take a traditional Venetian Carnival mask-making workshop or try your hand at Venetian glass-making, as well.
- Don’t underestimate the beauty of exploring Venice at night. First of all, it’s very safe. Second of all, it’s incredibly captivating to have the canals to yourself. I also love this night walking tour of Venice, which can provide you a lot more insight into Venetian history and help the city feel even more magical and mysterious.
- Don’t be afraid to get lost. Put the phone away. Look up. Go wherever intrigues you. (I love the left, right, or straight game.) One, Venice isn’t *that* big. Two, you’re never far from a vaporetto stop if you get tired. Three, you are on islands and can’t get off (unless you walk back across the causeway). The beauty of Venice is found in smaller canals and campos, far away from the Rialto Bridge and St. Mark’s Square, though you can’t miss those either.
Florence and Tuscany Itinerary Ideas
I could dedicate an entire post for one week Italy itinerary ideas for Florence and Tuscany. Arguable one of our favorite regions of Italy and where we return to because there is just so much to explore, it is hard to know where to begin. You could put together a Tuscany road trip, bypassing Florence completely, or you could put together an entire 7-day itinerary for Florence, and in either case, you would only scratch the surface of either place.
If Tuscany’s small towns don’t appeal to you, but you’re still looking for good food, you can board a train and be in Bologna in 35 minutes. Bologna is delicious and a short train ride away from Parma and Modena, which offer more delicious delights. Visiting Emilia-Romagna (twice) is one of our highlights from our 2021 travels, and it can easily be coupled with Florence.
Similar to the Rome itinerary ideas I shared above, I’m going to give you a day-by-day look at what I think you should consider doing in Florence. From there, I’ll give you a little bit of information of places in Tuscany that you could add on to your itinerary with options for travel by train or by car.
For what its worth, there are multiple airports to start (and end) your Florence trip. While Florence (FLR) does have its own airport, Bologna (BLQ) and Pisa (PSA) are very popular airports to fly into to visit Tuscany and Florence. We generally fly British Airways into Bologna or Pisa from LHR.
Suggested One Week Itinerary for Florence
Day One in Florence:
- Take a free walking tour of Florence. If you are extra ambitious, take both the morning and the afternoon tours. It’s the best introduction to the city, the Renaissance and its history. We have taken both of these tours multiple times and always learn something new.
- Evening: Head to the Piazzale Michelangelo for sunset and the best view of Florence. (You can also climb a little bit further up to San Miniato and avoid some of the crowds.)
Day Two in Florence:
- Morning: Book a guided tour of the Accademia or the Uffizi Museum (but not both in one day) to learn more about the evolution of the Renaissance artists. If guided tours aren’t your thing, make a museum reservation for an early timeslot to avoid the crowds Grab lunch at one of Florence’s famous panini places. I recommend ‘Ino near the Uffizi and Sandwichic near the Accademia.
- Afternoon: If you aren’t museumed out, I recommend switching gears and learning more about the scientific discoveries of the Renaissance. I love the small DaVinci Museum and the Galileo Museum. Choose one and create your own adventure!
Day Three in Florence:
- Morning: Visit Santa Croce or the Duomo when it first opens to avoid the lines. I prefer Santa Croce because the interior is just stunning, but you can’t come to Florence and not appreciate the Duomo. If you want to marvel at Brunelleschi Dome, book a ticket to climb the dome OR the bell tower. Climbing the dome will let you go in between the two-dome system. Climbing the bell tower will give you a view of the dome.
- For lunch you could head to the Mercato Centrale (near the Duomo) or the Sant’Ambrogio market (near Santa Croce).
- Evening: Whether you are planning to head to Tuscany or not, I would book a food tour of Florence, a Tuscan wine tasting (at different price points!), or walking tour of Florence at sunset!
Days Four through Seven in Florence:
- Whether you choose to spend the rest of your vacation in Florence or head off to Tuscany, there are no shortage of things to do. Here are a few more suggestions for your Florence itinerary:
- Take a cooking class in Florence (one of my favorite activities)!
- Visit the Duomo Museum to see the original art that was in the Duomo.
- Tour the Bargello Museum to see more Renaissance sculpture.
- Visit the Florence Synagogue to learn more about the history of this beautiful building and the Jewish people in Florence and Italy (Make sure to get the audioguide)
- Visit the Medici Chapel and Museum
- Take a guided tour of the Palazzo Vecchio
- Ride the bus to Fiesole to see the Roman ruins and for some incredible views of Florence
- Visit the Boboli Gardens and/or the Pitti Palace.
- Head to the less popular but very beautiful Bardini Gardens.
- Hopefully this will be open to more than tour groups again soon, but you can see a grain market that was converted to a church – Orsanmichele has an alterpiece that was designed “in situ” (in and for the place it was designed) and it’s absolutely gorgeous. You can also visit the small museum upstairs, if it’s open.
- Take a vintage Fiat 500 driving tour of the Tuscan hills at sunset. You need to be able to drive a manual transmission for this. The views are incredible, but it can be stressful. Everyone needs to take their patience for this (speaking from experience, lol).
- Have more food and wine tours in Florence to learn more about local cuisine.
Tuscany Side Trips from Florence (by train)
If you want to experience Tuscany but don’t want to rent a car in Italy, there are several great Tuscan hill towns that you can reach by train or bus. I recommend spending at least two nights in the smaller Tuscan towns. Two nights gives you the opportunity to enjoy a few restaurants, experience the town in both the morning and the evening, and see a little bit more of a town. If you only spend one night, you’ll check into your room around 3, have the evening to explore, and often have to check out of your hotel by 11:00 the next morning. That’s an intense schedule.
If you just visit these towns as a day trip from Florence, you’ll miss the magic that happens before and after the tourists leave. Some of my favorite memories in Siena are sitting on the Campo in the evening, having dinner at an agriturismo outside of Pienza on a rainy evening, and watching the sunset over Montepulciano with a glass of wine. Those aren’t experiences that are easy as a daytripper. Plus, Florence hotels are expensive (comparatively). If you are going to spend the money to be in Florence, be in Florence. Tuscany hotels are less expensive, so you can splurge for train tickets (or rental cars), meals, and other adventures.
While I’ve only listed a few towns here, it’s because these are the ones where I can personally recommend where to stay and things to do based on personal experience. Other hill towns I’ve visited and that are high on my list are Volterra, Pienza, Pisa, and Lucca. My unpublished Tuscany restaurant and hotel list currently has 94 entries on it, so I’ll be adding to this post for awhile.
Siena is 1-1.5 hours from Florence by bus or train.
Siena is one of the best preserved medieval cities in Tuscany. The entirety of historical center of Siena is a UNESCO World Heritage site. I love the architecture, the views from the city walls, and I especially love watching the passeggiata around the Campo in evenings.
I loved this walking tour of Siena because we were able to learn more about the different Contrada in Siena, and the Palio. We even got to see some of the tapestries in a neighborhood museum.
Make sure you visit the Siena Duomo, and specifically don’t miss visiting the Piccolomini Library. (I overlooked it on three trips to Siena.) It’s one of my favorite things because it’s so breathtaking. It’s even more beautiful after you’ve visited the Uffizi and you have better understanding of why it’s so impressive. Truly, I’ve never seen frescos like this.
Another thing I recommend is to take a food tour in Siena. You’ll have the opportunity to taste some of the flavors of Tuscany without even leaving the city. We have ended up with so many souvenirs from taking food tours!
STAY: La Terraza Sul Campo
Cortona is 1.5 hours from Florence by train
Cortona is absolutely beautiful. It’s the subject of Under the Tuscan Sun, but don’t let its fame deter you. (I did for several years. Learn from my mistake.)
I would hardly consider Cortona off the beaten track, but it certainly felt that way when we were there in June and October 2021. We were surrounded by Italian speakers in restaurants and on the main square. This hill town feels alive and “lived in,” in a way that some more popular hill towns seem to be lacking.
We start each day with a walk through town, including an intense climb to visit the churches in the northern parts of town. Don’t miss the Basilica of Santa Margherita. It is the most beautiful church I’ve seen in Tuscany. After a mid-day nap and spa treatment at our hotel, we would start our evenings with a passeggiata, pause for an apertivo, and wrap up with dinner and gelato.
Cortona is a wonderful place to eat, drink, and walk around. Ask waiters to make recommendations for you. You’ll never go wrong. I promise.
San Gimignano – The Towers of Tuscany
San Gimignano is 2 hours from Florence by bus or train.
San Gimignano is one of the most pleasant surprises of our hill town adventures. I thought it would be overrun by tourists, but it does have a lot to offer. It is a relatively flat hill town, which makes it a very walkable city. It’s not as flat as Pienza, but it is way less steep than Cortona, Montalcino, and Montepulciano. Even though it doesn’t have the height of the other towns, it also offers incredible views of green vineyards and rolling hills, as well as the olive groves of Tuscany. Beyond that, there seem to be a lot of art galleries scattered through town, which I loved.
Another thing that makes San Gimignano great for the traveller without a car is that they have a great winery within walking distance of the old town. You can do a wine, olive oil and balsamic vinegar tasting near San Gimignano. I love booking a tasting that includes lunch because you can enjoy a seasonal Tuscan meal, in addition to your tasting. The family that runs the winery is so hospitable, and their products are wonderful. They also ship to the US! (We’ve order a lot of wine and olive oil from them, especially during the pandemic in support of Italy in 2020.
Tuscany Side Trips by Car
If you’re not afraid of driving in Italy, you will certainly be rewarded with some incredible hill town experiences. There are some really lovely towns that are best reached by car. If you are planning to travel by car, I strongly recommend renting from a multi-national car company. I’ve had the best experiences with Sixt and Hertz. Similar to my recommendation to book open jaw airline tickets, I highly recommend one-way car rentals if it makes sense for your itinerary. As you can tell, I’m not a fan of backtracking!
When driving in Italy, make sure to reach out to your hotel for any information on directions and parking. First, some hotels have ZTL zone where only residents and cars with permits can drive. It doesn’t mean that you can’t drive there, but they will need to register your license plate so you don’t get fined. Second, sometimes parking has to be arranged in advance. This isn’t the US where valet parking is unlimited. You’ll want to reserve your spot or get details on where the best public parking is close to your hotel. Third, your hotel can give you the best instructions for getting there. Google maps doesn’t always know that you can’t drive through the city center. The point-by-point instructions that I’ve received from hotels are always – well – on point.
Montepulciano – The Classic Italian Hill Town
Montepulciano is 1.5 hours from Florence by car. (It’s 3-3.5 hours by train or bus.)
We’ve made at least overnight 4 trips to Montepulciano, not counting a few side trips to the Christmas market or for lunch on our way to another destination. The hills are steep, but you are rewarded with sweeping views of the countryside (book my favorite suite at Palazzo Carletti), a beautiful town center and fortress, and one of the best bistecca fiorentinas in Tuscany. It feels like a classic Italian hill town, and like Cortona, it feels “lived in.” You see locals going about their daily business.
From mid-November until early January, there is a fabulous Christmas market in Montepulciano that runs throughout the town. This market feels very local with a lot of typical Tuscan meats and cheeses on offer, as well as gifts that range from ceramics to wooden decor.
Montepulciano is also famous for its wines, though they are not as famous as the Brunello di Montalcino, they are very good. We really enjoy heading up to Enoilteca, a wine bar at the very top of town, that offers beautiful views of the Tuscan sunset, as well as an extensive wine-by-the-glass system so you can try numerous Tuscan wines. There are also a couple of wineries in the center of town that will let you tour their wine cellars that are actually built into the hillside.
With a car, you will have the flexibility to visit some of the wineries outside of town (or even head to Montalcino), but you will need to make an appointment in advance. Your hotel will be able to help you with this. You are also only a short drive from Pienza, home of the famous pecorino di Pienza cheese (and my favorite gelateria, Buon Gusto). There are numerous shops and farms where you can stop for tastings between Montepulciano and Pienza.
STAY: Palazzo Carletti
Staying in the Tuscan Countryside
Il Borro is about 30 minutes from Arezzo and 1 hour from Florence by car.
If you’re looking for a place where you can enjoy the Tuscan countryside, focus on wellness, and also enjoy really great food, I love Il Borro. This is truly a place to disconnect from everything, enjoy nature, and maybe – just maybe, venture into one of the nearby villages for dinner if you don’t want to stay at the resort the entire time. It’s the perfect place to slow down; I booked it in the middle of a three-week trip through Italy. It fell between Cortona and Florence on our itinerary. We spent our time going between our suite, the spa, and the pools. It was glorious.
The thing that makes Il Borro unique that it is actually a village-turned-resort by the Ferragamo family. The suites are cottages spread throughout a traditional Italian village. The rooms all have beautiful views of the mountains with a comfortable seclusion… with all the amenities of a luxury 5-star hotel at your fingertips.
Il Borro offers an on-site winery, two pools, two restaurants, and multiple craftsmen and artisan shops where you can see how products are made. As it relates to wellness, Il Borro offers hiking trails, a lovely spa, and a gym. (I had a wonderful massage in the spa. It was incredibly relaxing.) As far as activities go, Il Borro offers everything from horseback riding to cooking classes to truffle hunting.
While it may seem sort of like Disneyland (I wasn’t at all sure when I booked it), the resort offers a very authentic Tuscan experience (without the hill town). It is also a member of the Relais & Chateaux hotel collection, so the experiences are designed with both authenticity and quality in mind.
I booked through Tablet Hotels as a Plus member. Plus members receive a space-available upgrade (we were upgraded to an incredible junior suite), a 90 euro spa credit, daily breakfast, and a free wine tasting. These perks proved to be a great way to experience a lot of what the resort had to offer in a short time.
Rosewood Castiglion del Bosco is about 20 minutes from Montalcino and 1.5 hours from Florence by car.
We decided to spend a few days in Tuscany and Umbria at the start of the new year before flying out of Rome. I wanted to find a hotel similar to Il Borro, and the Rosewood Castiglion del Bosco fit the bill for the time of year when we were visiting.
Prior to our arrival, I was able to set up a wine tasting (because when near Montalcino), as well as a fresh pasta cooking class. One of the things that I loved about the Rosewood is that they had an extensive brochure that detailed all of the activities you could participate in – from sports (golf and tennis), to food and wine experiences, to hiking and wellness, to guided excursions throughout the area, to children’s activities. It was very detailed and caters to both couples and families.
The rooms are extremely luxurious with small touches like weighted blankets that make them especially cozy and romantic. (If I could bring the entire bed, including the bedding home, that would be amazing.) There were candles in the room and all the lights were on dimmer switches. Our bathroom had a separate extra long tub and shower – long leisurely bubble baths were my favorite and bath salts were included! We also had a private patio with lounge chairs overlooking the countryside. Turndown service included a bottle of rosso di Montalcino wine. This is the perfect hotel for a honeymoon in Tuscany.
My only regret? Neither Tom nor I were feeling at our best, so we didn’t make the most of this incredible resort.
I booked the Rosewood through a travel agent. Our stay included a room upgrade, free breakfast, a $100 hotel credit, a welcome amenity, and extended check-in/out times. The Rosewood is a splurge and a half, but if you’re looking to make one – this one to make.
Additional One Week Italy Itinerary Ideas
Bologna and Emilia Romagna
In 2021, we made two trips to Bologna and the Emilia Romagna region. With Bologna only being 35 minutes away from Florence by high speed train, it’s a wonderful side trip from Florence, but you could easily spend a week in this region, especially if you’re really into food. I loved Bologna and Parma both because they felt SO alive, especially in the evenings. We didn’t have a single bad meal while we were there.
I feel like I’m just starting to peel back the layers on this region, so I can’t give a definitive guide to how to spend your time here, however I do have a few recommendations on my mini guide and where to stay below. I highly, highly, highly recommend taking a cooking class and/or food tour. (Convincing you to do both is the dream!)
STAY: Palazzo Gozzi in Parma
STAY: 051 Suites in Bologna
Milan, Torino, and Lake Como
I find it easiest and most authentic to write about the things I know well. All of the places I’ve mentioned here are places where we have spent a lot of time over numerous visits over the years. You might notice that Milan and Lake Como are missing. While we have flown into and out of Milan a few times, we haven’t spent much time there yet.
One of our 2021 trips that didn’t happen was going to be the Piedmonte region. I’ve been inspired by Stacie Flinner’s instagram stories and visits to Torino, Lake Como, and the parts of northern Italy that we haven’t visited yet. I’m hoping that we can make that happen in 2022.
Puglia and Southern Italy
In winter 2019, we spent a little bit of time exploring the Puglia region. It was absolutely lovely. (It’s also very affordable.) This is on the Adriatic coast of Italy and is most known for the trulli houses in Alberobello and the white stone towns that line the sea front. While I loved our stay at La Sommita Relais in Ostuni, there is a Four Seasons Puglia that is supposed to be opening. It will be a beachfront property and I’m excited to see what it looks like. I’d like to head further south and check out Lecce and Matera.
If you could find a good flight into Bari or Brindisi, it would be a lovely off-the-beaten path destination for 7 days in Italy. It’s definitely more affordable than some of the other coastal regions on the opposite coast of Italy. You will definitely need to rent a car in Puglia though.
Another Italian destination that we are really interested in adding is Sicily. My sister spends quite a bit of time there, and she’s definitely sold me on it. Without a direct flight, it seems like an ambitious trip to make on a 1 week in Italy itinerary. We usually try to limit our connections to one for a 1 week Italy itinerary. Sometimes I will stretch to two stops if the flights line up really well, but I have an easier time with jetlag if we can arrive in the morning versus in the late afternoon or evening.
I think you need at least a week to explore Sicily, if not two weeks, so I would save it for another longer trip.