“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

Tuscany Trip Planning – Plan Your Trip!

Tuscany trip planning is going on in earnest over here, and it has been happening for a year.  After spending one night in Siena last year, we fell in love with the region.  I started researching the area in earnest, and I realized that we needed to rent a car.  My husband went back and forth on it (after all, neither of us has forgotten our last Italian driving adventure…), but I finally convinced him that it is the right thing to do.  We picked up an International Driving Permit at our local AAA office for less than $30.

For updates from our Trip:

(and more Tuscany Trip Planning tips & tricks):

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

Side Trip to Pisa, One Night in Siena,

Siena Postcard Photos, Pienza Postcard Photos

A collection of links, ideas, and resources to begin your own Tuscany trip planning. Post will be updated with reviews on tours, towns, and tips on how to make the most of your own trip to the Tuscan countryside upon our return!

Let’s just start with the post that convinced me that we needed to start the Tuscany trip planning STAT:  Top 10 Things to Do in Tuscany.  I’ll summarize it for you.

Relax // Wine // Cooking Classes // Food

Doesn’t all that sound lovely?  It does to me.  I fully intend to recap our trip, but I want to share the resources that I am using to plan our trip (similar to what I did before our first trip to Cinque Terre) so that you can plan your own Tuscan adventure.

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

A collection of links, ideas, and resources to begin your own Tuscany trip planning. Post will be updated with reviews on tours, towns, and tips on how to make the most of your own trip to the Tuscan countryside upon our return!

Tuscany Trip Planning – Researching the Hill Towns

While I really wanted to stay at La Bandita (found via instagram), the more I read about Montepulciano, the more it appealed to me.  (I think I stumbled upon some blue hour pictures of the countryside and it was over.)  One of the books I purchased had a couple walking tours of the town that intrigued me.

A collection of links, ideas, and resources to begin your own Tuscany trip planning. Post will be updated with reviews on tours, towns, and tips on how to make the most of your own trip to the Tuscan countryside upon our return!

Tuscany Trip Planning – The Food (and Wine)

We are currently booked for olive oil tastings, balsamic vinegar tastings, multiple wine tastings, and you can bet that we will be booking a table at Acquacheta as soon as we arrive.  (We are taking cooking classes in Florence and Rome.)  I will certainly share more information on the tours and visits that we enjoy the most when we return.

A collection of links, ideas, and resources to begin your own Tuscany trip planning. Post will be updated with reviews on tours, towns, and tips on how to make the most of your own trip to the Tuscan countryside upon our return!

Tuscany Trip Planning – Other Things to Do

Truthfully, a lot of our time will be spent enjoying the views.  When we spent part of our honeymoon in Ireland, my husband mapped out routes that included seeing the sites and enjoying the countryside.  I expect that you will see us slow down and enjoy a slow pace. I am looking forward to sitting in piazzas (with wine), taking my own evening passigiata, and capturing the beautiful Tuscan skies.

A collection of links, ideas, and resources to begin your own Tuscany trip planning. Post will be updated with reviews on tours, towns, and tips on how to make the most of your own trip to the Tuscan countryside upon our return!

Tuscany Trip Planning – Offline Resources

I really like these books because they break down different regions into manageable drives and include information on where to stay, restaurants to try, and what to see in the area.  The back roads books include a lot of information and are really well made.  I purchased them a few years ago and I’m excited to explore the recommended drives!

The 10 Best and Day by Day books are perfect for sticking in your pocket or your purse.  Day by Day includes local transportation maps and 10 Best gives you more context on historical sites.

We travel with TEP and an arm-full of books everywhere we go – because you never know how reliable the internet will be.  Better safe than sorry!

If you have suggestions or experiences to share, leave them below!!  I’m always excited to hear more ideas!

Curious about how all this will go?  Follow along on instagram.

A collection of links, ideas, and resources to begin your own Tuscany trip planning. Post will be updated with reviews on tours, towns, and tips on how to make the most of your own trip to the Tuscan countryside upon our return!

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  • MandyI’ve always wanted to go to Tuscany. I can’t wait to hear how your trip goes! The pictures you shard in this post are so pretty and have me ready to return to Italy.

    I appreciate you sharing all of your sources in this post. I agree with you that I love the Day-By-Day and Top Ten books. Their small size makes them easy to carry around during travels.

    I can’t say I envy the actual driving in Italy you and your husband are about to do, though. I think that was the worst part of our road trip around Europe in 2014. Then again, I’d totally do it again, so it must not have been that bad. 😉

    Hope you have fun!ReplyCancel

  • beatravellingI’ve never had a longing for Tuscany, but your photos look good! #wanderfulwednesdayReplyCancel

  • RachelTruly and seriously, is there anything better than an evening passeggiata? Just the thought makes me feel very happy and serene! I know we’ve spoken about this before but I can’t recommend Assisi highly enough. It’s a magical place.ReplyCancel

  • Emily @ Martinis & BikinisThat car is too cute and perfect to adventure through Tuscany! Wow so many beautiful sights and scenes. I can’t wait to visit Italy one day! Emily @ Martinis & BikinisReplyCancel

  • SetarraSuch a great breakdown for planning a trip to Tuscany! Also, I didn’t realize it was so easy to get an International Driving Permit – good to know!ReplyCancel

  • California GlobetrotterI TOTALLY want to rent that little car too!! I think it would be fun, but I’d definitely need to plan to have only a carry on haha Although my husband would only be able to drive it as I can’t drive a stick! #WanderfulWednedsdayReplyCancel

  • SandraWe spent one month in Italy two years ago and driving through Tuscany was one of our favorites.
    #CityTrippingReplyCancel

  • CynthiaI loved reading this not only for the Tuscany aspect (swoon), but because I am currently planning what seems like a very similar trip for this summer in Provence! Renting a car, wine tasting, the countryside… etc… planning is pretty much the best, isn’t it? It definitely gets me through the long winter months. When are you headed there?ReplyCancel

  • CynthiaForgot to mention that I LOVE that little Fiat! I was hoping we would be able to rent a car like that in France but ermmm… we have to have automatic transmission. (sighhhhhh)ReplyCancel

  • Christine KeaneI can’t stop laughing at that Fiat! I’ve seen golf carts bigger! lol

    This is a great guide! I wish we had more time last year to venture around Tuscany. A reason to go back!ReplyCancel

  • Marcella ~ WhatAWonderfulWorldI’ve always heard such great things about Tuscany! And this really does seem like a great itinerary 🙂 How exciting!!ReplyCancel

  • SharonThat tiny car — ha ha! I dream of visiting Tuscany. Fun post!ReplyCancel

  • Elizabeth (Wander Mum)Funnily enough, I was supposed to be in Tuscany this weekend. I had to cancel because of husband’s illness. I’m sure I’ll get to go when he’s better. It’s such a beautiful region and the food is incredible! Thanks for linking #citytrippingReplyCancel

  • BetsyI love that you’re like taste all the things!! I’d love to do an olive oil tasting that would be my choice for sure.ReplyCancel

  • KateOk now I have some serious wanderlust for sure! Can you pack me in your suitcase for your next trip pretty please <3
    Green FashionistaReplyCancel

  • Caity PfohlDefinitely bookmarking this for later! A Tuscan road trip sounds like a dream. Hope you have an amazing time – just found you on Instagram to follow along from afar! 🙂ReplyCancel

  • BianaThat first photo of you guys is just perfect!! I think driving around tuscany would just be the most fun thing ever!! I know for sure this is on our list of places to visit! xo, Biana –BlovedBostonReplyCancel

  • KasieOh my gosh, Tuscany! I am absolutely dying to visit and, you’re absolutely right, a car is the only way to see it! (As I start furiously planning how to convince my husband to take a roadtrip through Tuscany…)ReplyCancel

  • LaurenLove this! Thanks so much for putting it together!

    xx
    Lauren Elizabeth
    Petite in Pearls ReplyCancel

  • SarahOhhh you are making me reminisce of my trip to Tuscany with my parents in October!! You certainly have a thing for Italy and I think you’ll love staying in Montepulciano. We stayed in Siena (the second time I stayed there, and loved it!) but we went to Montepulciano on a day trip. I wish we could’ve spent longer there so I guess I’ll have to live vicariously through you!ReplyCancel

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.)

Destinations

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