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):
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.
Tuscany Trip Planning – Researching the Hill Towns
- Escaping the Crowds in Montepulciano
- 3 Hill Towns Worth Seeing
- Must See Towns in Tuscany
- Discover Tuscany – the Tower Town
- The Best of Cortona
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.
Tuscany Trip Planning – The Food (and Wine)
- Discovering Culinary Tuscany
- Visiting a Vineyard in Tuscany
- 10 Best Restaurants in Montepulciano
- 10 Best Restaurants in Tuscany
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.
Tuscany Trip Planning – Other Things to Do
- Scenic Drives in Tuscany
- Planning a Road Trip through Tuscany and Umbria
- Must See Towns and Things to Do in Tuscany
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.
Tuscany Trip Planning – Offline Resources
- 25 Great Drives in Italy
- 25 Great Drives in Tuscany and Umbria
- Back Roads Italy
- Back Roads in Northern and Central Italy
- 10 Best – Florence and Tuscany
- Florence and Tuscany – Day by Day
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!
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.