Planning a trip to Tuscany? Lucky you! It’s one of the most scenic and peaceful places most of us mortals will ever visit. Tuscany is an incredible destination that absorbs your anxiety and turns it into vino! But, where do you start? Here are eight steps to planning your ideal Tuscany trip.
Step-by-Step Tips For Planning Your Trip To Tuscany
Planning a trip can be daunting. Not to worry—we’ve got you covered. This article is composed of two parts. The first will cover some basic facts about Tuscany and the second offers some actionable tips on how to plan including where to stay, what vineyards to visit, and how to get around. Enjoy!
Step 1: How Long To Go For
There are three options for visiting Tuscany, really. You can do a day trip, spend a few days there (four days of your 10-day Italy trip, for example), or spend your entire trip in Tuscany. Don’t worry, I will make deciding easy. Ask yourself these questions to narrow it down.
Have you ever been to Italy?
If you’ve been to Italy’s main cities already, you should gravitate towards the option of a few days in Tuscany or your entire trip there. If this is your first visit to Italy, then choose a day trip or spend a maximum of a few days of your trip there.
Are you willing to rent a car and drive in Tuscany?
If you’re willing to rent a car in Tuscany and have visited the main cities of Italy on a past trip, I recommend doing a week in Tuscany, which could be your entire trip. There are such a variety of towns to visit and plenty to keep you occupied.
Take a day trip if you don’t like the idea of renting a car. Our Chianti Wine Day Trip from Florence is a top-rated option. If you have decided on a day trip, the good news is that your journey ends here and the planning is over!
If you don’t want to rent a vehicle but want to spend a few nights in Tuscany, maybe two or three, there are some great accommodations right outside Florence. We share some great vineyards with hotels and accommodation in this article.
Step 2: Start in Florence
Florence is a great starting point. You’ll probably arrive in Italy via Rome, but I don’t recommend driving in Rome if you’ve not been before. You can take a train to Florence in less than two hours and navigate easily from there.
Florence is an amazing city that is always worth another visit. It’s full of wonders like the Uffizi Gallery, which I visit every time I’m in Florence if only to see the Birth of Venus.
There is an international airport in Florence and, as mentioned, many fast trains arrive in the city from Rome, Naples, Venice, Bologna, Milan, and Torino. It is the perfect jump-off point for a visit to Tuscany, especially Chianti, which is very close. If you’re willing to rent a car you can pick it up at the Santa Maria Novella station and easily get out of the city using your phone’s GPS.
You’ll have to decide if you want to spend the night in Florence or not. If you don’t, schedule to pick up your rental car early. Ask if you can leave it in the garage for the rest of the day and leave your bags inside the car while you sightsee.
Travel Hack: If you can find wi-fi, you can use your phone even on airplane mode. Pull up your map and search for directions. Hit “go” when you’re ready, then keep your phone on airplane mode and leave wi-fi. Your GPS will still work, and you shouldn’t be eating away at your roaming data. Be sure to turn that off in your settings. You won’t be able to search for a new destination when you leave wi-fi, but your GPS pin will work all the same.
Top Tours That Making Planning Easy
Not ready to book a tour? Check out our Tuscany guide for more info.
Step 3: Getting To & Around Tuscany
- By Train: You can take a train to Florence, Siena, or other major towns, but to truly explore, you’ll need a car.
- By Plane: Fly into Rome for international flights, then take a train to Florence or Siena. Florence’s airport is nice, but domestic only.
- By Car: Ideal way to get around Tuscany. Rent a car in Florence or Siena to avoid Rome’s chaotic traffic.
- Driving Tips: Roads are scenic and mostly quiet. Use a GPS, and don’t count on reliable cell service in the hills.
Step 4: Decide on Mobile Roaming Data
Traveling abroad with mobile usage turned on used to be the key to bankruptcy, but today it’s actually affordable. AT&T charges $10/day and some carriers charge nothing.
With AT&T, the only one I am familiar with, you just have to tell them you are traveling and they will only charge you if you go off airplane mode. If I’m in a city with wi-fi, I keep airplane mode on. If I’m renting a car and using my phone to navigate, I turn data on.
Step 5: Get Advice
We want to be your end-all source for advice on traveling to Tuscany and we make it as free as we possibly can. All our tours are designed to make your trips memorable and stress-free, so you can enjoy being in Tuscany without worrying about any details. Check out our Florence and Tuscany tours.
There is also a wealth of free information on our online Tuscany guide to help you plan. If you’re looking for a more customized experience, we offer trip planning services through Finelli & Shaw.
Step 6: Book Your Accommodation in Tuscany
Below are our favorite places to stay in Tuscany. For more, check out our Where to Stay in Tuscany guide.
Siena: A bit bigger, with train access and great restaurants. Walkable, medieval, and perfect if you don’t want to drive every day.
Agriturismo: The real Tuscan experience. These farm stays legally must produce agricultural goods. Expect vineyards, views, and homemade meals.
San Gimignano Area: Good for everyone. Central, scenic, and full of charm.
Val d’Orcia (Montalcino, Pienza): For wine lovers and romantics. Cypress-lined roads, endless vineyards, and unforgettable views.
Chianti Region: Forested hills, iconic wineries, and villages like Greve and Radda. Great for day trips.
Looking for an all-inclusive stay? Check out these options!
Step 7: Pick Out Places to Eat and Vineyards to Visit
Here’s our Tuscany travel tips for where to eat:
- At your agriturismo: Homemade meals, no menu needed.
- Certaldo Alto: A quiet hilltop town with excellent local cuisine.
- Montalcino & Pienza: Top-tier wine and food pairing options.
- San Gimignano: Great lunch spots and streets made for strolling.
Favorite Vineyards:
Call or book ahead to ensure the winery is open for tastings.
- Tignanello: Super Tuscan legend, popular for a reason.
- Tenuta Casanova: Upscale yet rustic, homemade pasta, and wines not sold anywhere else.
- Poggio di Sotto: Modern, gorgeous views, and well worth scheduling in a long afternoon for.
- Fattoria dei Barbi, Casanova di Neri, Banfi: All worth a stop in Brunello country.
👉 Learn to make Tuscan classics yourself during a Florence cooking class.
Step 8: Be Spontaneous
It almost always pays to plan ahead, but you can leave yourself some wiggle room to be spontaneous. You can stop by most vineyards unannounced in the summer to have a tasting.
If you have a phone plan working in Italy, you can call ahead by 20 or 30 minutes to see if you can stop by, but I have also popped in unannounced. That said, vineyards prefer a little notice.
It’s better to call the day before if there’s a vineyard you really want to visit, but you can fill in the blanks around that stop. That said, when you see a beautiful road that you simply must drive down or a vineyard calling your name, then you should change your plans and follow your dreams!
Bonus Step: Copy This 72-Hour Tuscany Itinerary
Day 1: Hit the Highlights in Florence
- Arrive and see the Accademia, Uffizi, and the Duomo on a guided tour.
- Grab an iconic affogato (gelato and espresso) at Vivoli il Gelato.
- Evening spritz at Volume Bar in Piazza Santo Spirito.
Day 2: Into the Countryside
- Pick up your rental car and head to wine country.
- Visit Tenuta Casanova for wine and lunch.
- Stop in San Gimignano to wander medieval streets.
- Drive into Val d’Orcia and stay in Montalcino or Pienza.
Day 3: The Grand Finale
- Morning: Head to Siena to see the striped Duomo and grab coffee near Piazza del Campo.
- Afternoon: Explore Montepulciano’s underground wine cellars.
- Optional detour to Pisa for the Leaning Tower photo-op.
- Last dinner at a countryside agriturismo, paired with a bottle of wine or two.
Not ready to book a tour? Check out our article on the best Florence tours to take and why.
Where To Stay in Florence
Florence has a small historical center packed with iconic landmarks to explore. Plan where to stay in the best neighborhoods in this beautiful city.
Do you have any ideas of a location to stay in Tuscany and be able to stay in one place but take day trips? If so I would appreciate your suggestions. Will be in Tuscany at last 5 days
Thanks
I prefer the area surrounding Siena. I just wrote this article on places to stay near Siena. The countryside there, especially near Montalcino, is so beautiful.
Montalcino is more remote, but if you are ok with 2 hour drives it’s perfect. You’re near Siena, Florence, Orvieto, and a ton of other cities. To answer your question, I would stay near Siena if you want a great balance between beauty and proximity and near Montalcino if you want to be in the most beautiful place in the world.