“Whenever he is discouraged, I tell him that if I can survive on three continents, then there is no obstacle he cannot conquer. While the astronauts, heroes forever, spent more hours on the moon, I have remained in this new world for nearly thirty years. I know that my achievement is quite ordinary. I am not the only man to seek his fortune far from home, and certainly I am not the first. Still, there are times when I am bewildered by each mile I have traveled, each meal I have eaten, each person I have known, each room in which I have slept. As ordinary as it all appears, there are times when it is beyond my imagination.”

- Interpreter of the Maladies, Jhumpa Lahiri

Best of Tuscany – Tips for a Perfect Trip

I think it’s ambitious to say that a single post can give you every single best of Tuscany.  In fact, I don’t think there’s one single blog post on anything (particularly a travel destination) that can fully inform you of everything you need to know.  I’m realistic about that fact.  If you’re anything like me, you draw inspiration from multiple sources, books, blogs, videos, and photos.    (Just check out these pre-trip posts about my Tuscany and Cinque Terre trip planning!) That’s what I aim to do with this little space of mine – share information about what I enjoy and focus on the (mostly) positive.

I’m choosing to focus this post on the smaller towns of Tuscany.  As I was choosing photos for this post, I realized that I may need to do some additional posts on different parts of Tuscany because I have a lot to share!  If there’s something you want to hear more about, drop a note in the comments.

Also, I plan to do a couple more Florence posts later, but you can check out some of my previous posts if you’re planning a trip to Florence.

Disclosure:  This post contains affiliate links for tours or products I love.  You can read my full disclosure policy here.

journey of doing - Best of Tuscany; where to stay in Tuscany, what to do in Tuscany, where to eat in Tuscany, and tips to plan the best trip to Tuscany

Best of Tuscany – Where to Stay

First things first, there’s Tuscany and there’s Florence.  Yes, you can day trip to all the lovely Tuscan towns from Florence, but the experience isn’t the same.  I recommend finding a home base and exploring the region with a car.  (Did you read my guest post on planning your first trip to Italy?  My favorite thing to do is to pair a city with a smaller town.)  My two favorite home bases (so far!) are Montepulciano and Siena (in that order) and you can’t go wrong with either.  They seem more “real” to me.  (Pienza and San Gimignano seem too postcard perfect (but lovely nonetheless).  Arezzo feels too big.  All are worth visiting though.)

Best of Tuscany – Palazzo Carletti

Given my appreciation for exploring cities at night, I knew I wanted to stay in Montepulciano.  Palazzo Carletti offers the perfect location.  It’s a short walk from the main square and a short walk from the best restaurant ever.  The beautiful room and fancy bathroom are merely bonuses, given the rustic location.  When you add in the free parking and breakfast, it’s a steal.  Martine is the most wonderful hostess; she provided everything we needed before arrival and sought to make every detail of our stay perfect.  (She even seemed concerned that we were skipping breakfast and wanted to know if she could make us something – anything – specific.  Nope, we’re just weirdos who skip breakfast.)

journey of doing - Best of Tuscany; where to stay in Tuscany, what to do in Tuscany, where to eat in Tuscany, and tips to plan the best trip to Tuscany

journey of doing - Best of Tuscany; where to stay in Tuscany, what to do in Tuscany, where to eat in Tuscany, and tips to plan the best trip to Tuscany

Best of Tuscany – La Terrazza sul Campo

This was our second year staying at La Terrazzo sul Campo.  You cannot and will not beat the view or the location.  If you booked it for those reasons alone, I wouldn’t fault you.  But the best part of this property (aside from its beautiful rooms and the view) is Viola and her brother.  (Viola even remembered us from our stay last year!)  They go above and beyond to make your stay comfortable.  Breakfast is custom, made-to-order, and even when we forgot to turn in our order the night before, they were happy to accommodate us.  The parking garage is about a 10-minute walk from the hotel and we didn’t have any trouble bringing our luggage up.  (To be honest, it was WAY easier than Montepulciano, lol.)

journey of doing - Best of Tuscany; where to stay in Tuscany, what to do in Tuscany, where to eat in Tuscany, and tips to plan the best trip to Tuscany

journey of doing - Best of Tuscany; where to stay in Tuscany, what to do in Tuscany, where to eat in Tuscany, and tips to plan the best trip to Tuscany journey of doing - Best of Tuscany; where to stay in Tuscany, what to do in Tuscany, where to eat in Tuscany, and tips to plan the best trip to Tuscanyjourney of doing - Best of Tuscany; where to stay in Tuscany, what to do in Tuscany, where to eat in Tuscany, and tips to plan the best trip to Tuscany

Best of Tuscany – All about Food

We all know I love my bistecca.  It might have been what I was most looking forward to when I started planning a trip to Tuscany.  I scoured restaurant reviews, photos, books, and blogs to find where to eat in Tuscany.  All roads led to Montepulciano.  All roads led to Osteria Acquacheta.  When we arrived in Montepulciano and found that it would be closed the entire time we were there, I was disappointed.  After we had relocated to Siena, my husband convinced me that we should drive over to Montepulciano and check it out for lunch.  I was dubious.  Could it really be that good?  Could a steak be so good that it was worth driving in the rain for over an hour?  (Perhaps the rain is what convinced me – after all – what would we do instead?)

Yes.  Yes, it could.

I recommend absolutely anything on the menu, but do not miss the bistecca and the pici pasta with fried garlic and chilies.  We told the waiter to “cook it the way Italians like it.”  He chuckled and brought us the most delicious steak.  We ordered the toasted bread with olive oil, the cured meats, the bistecca, the pasta, water, and wine… and it cost less than 75 euro.  Is it a splurge meal?  Yes.  Is it worth every penny?  Yes.  If you eat one meal in Tuscany, let this be it.  (We tried other places.  This one stands out on its own.)  When we return to Tuscany, I fully intend to take a cooking class and learn to make pici pasta.

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Best of Tuscany – Best Light Meal

La Proscuitteria is a place we discovered last year and it’s delicious.  The wine is cheap, you have to grab a seat as soon as you can find it, and they don’t serve you, so don’t expect a restaurant meal.  (It’s also part of a chain, but don’t think of it like a U.S. chain – the food is all fresh!)  We dined on the most delicious open-faced sandwiches with fresh bread, olive oil, proscuitto and poppy seeds!  If you’re looking for a snack to hold you over, this place is fantastic.  (We also enjoy the Florence location.)

Best of Tuscany – Best Cafe with a View

I could have also titled this best cafe to escape the rain.  We did not have the best weather when we were in Montepulciano.  In fact, it might have rained EVERY single time we were in the city.  Fortunately, it wasn’t non-stop torrential rain, but it did make for cooler, damp days.  Cafe Poliziano provides a great place to warm up and enjoy a coffee or a pastry.  If the weather is nice, there’s also a balcony with a view.  (Even the view with the fog was lovely though.)  It reminds me of some of my favorite cafes in Vienna – dark, elegant decor, delicious pastries, and fancy coffee drinks.

journey of doing - Best of Tuscany; where to stay in Tuscany, what to do in Tuscany, where to eat in Tuscany, and tips to plan the best trip to Tuscany

Best of Tuscany – When You’re Tired of Italian Food

After being burned by a terrible bistecca in Siena, my husband started researching more bistecca and he convinced me that we should try Hamburgeria al Buongusto.  I was resistant.  I did not come to Italy for this.  It happens to be one of the only places open late though, which is how we found ourselves standing in line at a sandwich counter in Italy.  No one spoke any English and the man behind my husband told him which bread to choose.  We walked down to a piazza where we could sit down and I sunk my teeth into the most delicious burger I’ve ever had outside the United States.  (Definitely better than most burgers in the U.S. as well…)  Everything was fresh and made to order.  And – like most good food in Italy – it was cheap.  I’ll be back to try the bistecca.)

Best of Tuscany – Gelato

I don’t know who goes to Italy and doesn’t get serious about gelato.  (I wrote a whole post dedicated to my hunt for the best gelato in Cinque Terre for goodness’ sakes!)  Gelato is a mainstay for me.  I’ll happily skip a meal for gelato.  (By the end of this trip, I think I was doing that.  I think I had gelato three (maybe four) times on our last night in Rome.)

A short drive from Montepulciano is the tiny town of Pienza.  Now, Pienza is lovely.  It looks like something out of a Disney movie.  It’s almost too perfect, if you know what I mean.  But, there’s one reason to go back to Pienza again and again, and it’s BuonGusto.  This man makes good gelato.  Again, I was dubious.  It seemed fancy… and by that I mean he had fancy flavors.  I didn’t trust fancy gelato.  The first time I went, he didn’t have anything “normal,” but he recommended the saffron.  Fortunately, I had just experienced a palate-changing moment with saffron in San Gimignano, so I was up for the adventure.

Oh my stars, it was good.  So good in fact that we drove back to Pienza on the way to Assisi (i.e. completely out of the way) so I could have it again.  EXCEPT there was no saffron!  (He told me if I came back the next day, he would have saffron for me.)  BuonGusto makes his flavors fresh every day, and he recommended that I try his strawberry and his orange-lemon.

And that, my friends, is why I refused to eat gelato that wasn’t sorbetto for the rest of the trip.  (I still dream of his flavors.)

journey of doing - Best of Tuscany; where to stay in Tuscany, what to do in Tuscany, where to eat in Tuscany, and tips to plan the best trip to Tuscany

Best of Tuscany – Second Best Gelato

When we were in Siena last year, I walked across the city in search of the best gelato only to be let down.  Multiple times.  (Some places close early during the “off season,” and some aren’t open at all.)  This year, I was determined to find good gelato.  I knew it had to exist.  There had to be one place that was good (even if it wasn’t as good as BuonGusto).  Enter Kopakabana.  Did you laugh at that?  I did.  This gelato is no laughing matter though.  It’s rich, creamy, and cheap.  Get the nocciola (hazelnut).  If you’ve already been to BuonGusto, try any of the sorbetto.  Why can’t we make ice cream like this in the states?!      

journey of doing - Best of Tuscany; where to stay in Tuscany, what to do in Tuscany, where to eat in Tuscany, and tips to plan the best trip to Tuscany

Best of Tuscany – What to Do

In addition to scenery, Tuscany is known for its delicious products: wine, olive oil, meats, and cheeses.  Those are all things my husband I both love.  I knew food tours would be in our future.

San Gimignano Olive Oil, Balsamic, and Wine Tour – Best of Tuscany

When I found a tour that included wine, olive oil and balsamic vinegar, I booked it immediately!  I scheduled it when were driving form Cinque Terre to Montepulciano.  My thinking was that it could break up the day.  I wasn’t wrong.

The vineyard overlooks San Gimignano, and it was incredibly easy to find.  (They provide detailed instructions when booking.)  If you decide to stay there, it would be an easy walk to the vineyard.  The hospitality is incredible.  Illaria provided us a tour of the vineyard and showed us the correct way to taste wine.  (We learned so much in a short time!)  We started with white wine (named after one of the winery dogs!).  The first course included a few different bruschetta, including tomato, olive oil and salt, pate, and purple cabbage.  Once we finished that, Ilaria brought out a fresh bowtie pasta with classic tomato sauce.  It was  absolutely delicious, and the red wine complemented it perfectly.

Following that, we tried olive oils and balsamic vinegars (saffron and truffle were my favs!) and a selection of salami and pecorino cheeses.  This included another red wine.  Once we finished those savory treats, Illaria had another surprise – traditional almond cookies and sweet wine!

Given my appreciation for oil and vinegar, I purchased several bottles (which I shipped home).  That being said, we didn’t feel rushed or pressured to buy anything. The goods arrived in the U.S. shortly after we did, and when DHL delivered a broken bottle, the shipping company replaced it immediately.  I highly recommend this tour if you enjoy oil, vinegar, and wine.  We definitely did not need another meal after our tour.  We ended up picking up a few light things from the grocery store and having a picnic in our room that night.

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Arezzo Wine Tour – Best of Tuscany

Real talk: This wine tour taught us that we underestimated the difference between driving distance and time.  Arezzo is only 32 miles from Montepulciano, but it took us over an hour to get to the winery.  Once we got to Arezzo, we thought we would be at the winery within 10 minutes and called to let them know.  Thirty minutes later, we rolled up.  Yikes.  They had already started the tour of the vineyard, but we were able to catch up to them and they didn’t mind getting us up to speed.  Our tour was during golden hour, and the views of the countryside are unparalleled.  The most amazing thing about this winery is how self-contained and eco-friendly it is.  It’s the most environmentally-conscious business I’ve ever visited.  Every part of the process is remarkably thoughtout for sustainability.

After a tour of the vineyard and the facilities, we were escorted into a beautiful dining room overlooking the vineyard for tasting.  Similar to the San Gimignano tour, we were provided with instruction on how to hold our wine glasses to prevent temperature transfer and how to appropriately taste wine.  They served fresh bread, olive oil, cold cuts, and cheese with the wines.  My only regret is that the rose was not ready for tasting – a college student on our tour who was studying abroad in the area said it was absolutely delicious.  I would have liked to try it!  Next time…!  I purchased a bottle for later (while others on our tour sent CASES home) before we left.  The price was incredibly reasonable.  Oh Italy…. where wine is cheaper than anything else.

journey of doing - Best of Tuscany; where to stay in Tuscany, what to do in Tuscany, where to eat in Tuscany, and tips to plan the best trip to Tuscany

Siena Walking Tour – Best of Tuscany

To truly appreciate Siena, you need to do a walking tour.  This is a great introduction to the medieval city!  After learning more about the campo and its role in the Palio, we headed out to learn more about the contrade in Siena. We even lucked out and were able to see an exhibit on historical Palio costumes, flags, and tapestries depicting the win of a particular contrade.  This tour provides an incredible look into the history of Siena and its “neighborhood” pride!

She showed us some beautiful views of the Tuscan countryside before following the winding narrow streets around to the Siena Duomo.  In retrospect, I wish we had included the Duomo tour, but we have used the audioguide in the past, and we knew that guides were not allowed in the Piccolomini Library, so we opted out.  I would add that option next time.  Other tours I would add?  This Siena Food Tour.  I tried and tried and couldn’t make it work with our schedule.)

journey of doing - Best of Tuscany; where to stay in Tuscany, what to do in Tuscany, where to eat in Tuscany, and tips to plan the best trip to Tuscanyjourney of doing - Best of Tuscany; where to stay in Tuscany, what to do in Tuscany, where to eat in Tuscany, and tips to plan the best trip to Tuscanyjourney of doing - Best of Tuscany; where to stay in Tuscany, what to do in Tuscany, where to eat in Tuscany, and tips to plan the best trip to Tuscany

Best of Tuscany – DIY Walking / Driving Tours

We use the Rick Steves Hill Towns book religiously in places where there aren’t a lot of tour option in the off-season.  I think you get more out of a local guide, but this book gives you perspective on what you are seeing.  We particularly enjoy the self-guided tour of the Siena Duomo, the walking tour of Montepulciano, and the scenic driving tours of the area.  If you’re going to Florence, you can get his Florence and Tuscany book.  (They have A LOT of overlap; you don’t need both.)  The best advice I can give you as you roam around Tuscany is to pop into every church.  Venture down small alleyways.  Explore.  Get lost.  You never know what you’ll find.  One of my favorite churches is in Montepulciano and none of the big three guidebooks we use mentioned going into it.

Last year, we used trains to navigate around Tuscany, and it was fine.  Having a car gave us so much more flexibility, and it was really nice to be able to stop whenever we wanted to explore, take photos, get more Buongusto, gelato, etc.  The buses are more convenient than the trains, but a car gives you the most (and best) flexibility in Tuscany.  We had no problems with it. (We had a Fiat 500 for the first part of our trip and a Jeep SUV for the second.  I prefer the Fiat but the Jeep has more power for hills.)

If you plan on doing your own driving tour, the easiest thing to do is download Google maps and rent a mobile hotspot.  Ours offers unlimited wifi (way cheaper than a data plan!) and we’ve yet to find a place it doesn’t work.  Google maps did a great job of directing us, even on the small roads.  I know you can download google maps offline, but the wireless capability is good for navigating traffic and making sure that you aren’t taking up all the memory on your phone!

journey of doing - Best of Tuscany; where to stay in Tuscany, what to do in Tuscany, where to eat in Tuscany, and tips to plan the best trip to Tuscany

For more of the Best of Tuscany Inspiration

(and tips & tricks):

Tuscany Trip Planning, Best of Tuscany – Tips for a Perfect Trip,

Where to Stay in Tuscany: Our Favorite Hotels

Side Trip to Pisa, One Night in Siena,

Siena Postcard Photos, Pienza Postcard Photos

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  • Bri @ My Life As...Give me all the food! It looks so pretty. And that bed? That bed looks so comfy!ReplyCancel

  • MandyNext time you go to Italy, take me? I so want to do the balsamic vinegar and olive oil tasting! Wine tasting would be good too. And I want to eat all of the gelato and pasta and stay at the gorgeous hotels you stayed at … and on and on and on… Can’t wait to see more pictures from your trip to Italy. I really need to go back!!ReplyCancel

    • sara.e.miller@gmail.comThe best part about all these hotels is that they were completely reasonable! The one in Siena is like $120/night… and I’m OBSESSED WITH THE VIEW! The cozy one in Montepulciano was only a little bit more. (The ceilings were out of this world amazing!!) The food was SO good. Nothing here compares… and ugh. I still miss the gelato! lolReplyCancel

  • SarahJust adore the photos (and FOOD) in this post and it is bringing me back to my visit last October!! The bistecca looks amazing. I really need to get on it and write some blog posts about that trip haha!ReplyCancel

  • caraI’m literally swooning over everything in this post! I hope to visit one day soon! 🙂ReplyCancel

  • RachelThat sorbetto looks absolutely incredible! What inventive flavours. I may have camped there for the rest of my trip, no exaggeration. The places you stayed look so lovely, and those winery tours look great. I would have enjoyed those a lot!ReplyCancel

  • Jessi (Two Feet, One World)This is SUCH a great guide – thank you! I visited the area, but many years ago now, so this has definitely made me want to return. I remember the beautiful streets of San Gimignano and Montepulciano, but now I have so much more to see! #WanderfulWednesdayReplyCancel

  • LydiaYour post has whetted my appetite and I would love to explore Tuscany as soon as possible, Sara. This place seems so mesmerising. Plus, that gelato seems mouth-watering. Which flavour is the best?ReplyCancel

  • Emily @ Martinis & BikinisWOW! What a gorgeous place to explore. The scenery and food options just look amazing! Emily @ Martinis & BikinisReplyCancel

  • Sharon OdegaardThe food! And I’m not a foodie! Your photos make it all look so deliciuos, especially the gelato. And your hotel is beautiful, with those amazing ceilings. I hope to make it to Tuscany some day!ReplyCancel

  • VanessaSo many gorgeous places and good food! I love combining visiting cities and the countryside as well and it really seems like Tuscany has plenty of both!ReplyCancel

  • Tanja/The Red Phone Box travelsyour post is making me hungry:) great overview. I’ve explored Tuscany too quite a lot, it’s the little towns that I prefer #theweeklypostcardReplyCancel

  • DorothyThis is a great post. You covered it all with your suggestions on where to stay, what to eat, and things to do in Tuscany. #TheWeeklyPostcardReplyCancel

  • AnisaIt’s such a beautiful area, I just loved Florence. I would love to visit more of the smaller towns in Tuscany. I think it would be fun to do a roadtrip just in that area. Thanks for sharing on #TheWeeklyPostcard.ReplyCancel

  • MichelleA surprising number of friends and colleagues have visited Tuscany in the last 2 months or so, so I’m starting to get a better idea of just how popular Tuscany is. Can totally see the appeal though, from your gorgeous photos. Would definitely love to visit one day, though for environmental reasons I try not to rent a car these days if it’s just two of us. If we were to travel via bus/train would there be any completely inaccessible areas you’d otherwise recommend?ReplyCancel

  • California GlobetrotterCan always count on you to give us thorough info on visiting Italy! Love how you even included wine tours and balsamic tours! Thanks for linking up with #TheWeeklyPostcard!ReplyCancel

  • Elizabeth (Wander Mum)All the food you ate looks mouthwatering. The Italians do cooking so well and you certainly did your research- and it paid off. Love the places you stayed too. I have fond memories of Montepulciano- would love to go back – and try that restaurant. Love Tuscany! Thanks for linking #citytrippingReplyCancel

  • EmeseWhat a great post, Sara! Love your photos, and the tour. But my favorite part is your attitude “Venture down small alleyways. Explore. Get lost.”. This is my motto when traveling to new places, no matter where I am. You feel like a true explorer when you do that, and you find something unexpected.
    Thanks for sharing on #TheWeeklyPostcard.ReplyCancel

  • CynthiaClearly you had just an incredible trip — beautiful accommodations and ate what looks like the most delicious food 🙂 Pinning for the next time I’m in the region… it’s been ten years since the last time I was in Italy!ReplyCancel

  • scots2travelWhat a thorough round up. So hard to sum up this region in so much detail. Great recommendations. Will save this for next time I visit.
    #citytrippingReplyCancel

Meet Sara

Loves adventures.

Prefers dresses to pants.

Appears to always be on vacation but really just has too many photos to share.

based in

dallas, texas.

constantly dreaming of italy

(and other beautiful places.)

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