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.
The Epic Weekend Escape in Tuscany
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.
Tours of Chianti and Florence
Top-Rated Experience
Florence Day Trip to Tuscany: Siena, San Gimignano & Winery Lunch
Planning a day in Tuscany’s countryside can be tricky, with winding roads, remote villages, and countless wineries to choose from. With a 3-course lunch and 5 wine tastings, allow us to take the guesswork out of your Tuscan experience. Start in Florence, drive through Siena’s rolling hills, walk the medieval streets of San Gimignano, and tour a family-run Chianti winery. Along the way, learn the stories behind Chianti’s renowned wines and soak in the charm of Tuscany’s most stunning landscapes.
Planning to hit all of Florence’s highlights in one day can be a lot to manage. We’ll take care of every detail so all you have to do is enjoy the experience. With skip-the-line access, insider stories, and a charismatic guide who knows the city inside and out, you’ll see everything from Michelangelo’s David and the Florence Duomo to Ponte Vecchio and masterpieces by Caravaggio and Botticelli at the Uffizi Gallery. Experience Florence with all the must-sees, and none of the stress.
Not ready to book a tour? Check out our Tuscany guide for more info.
Step 3: Rent a Car
As a rule of thumb, the most beautiful and well-preserved areas are the least connected by train or highways. For me, I would not travel to Tuscany without renting a car. Does that make you nervous?
You can rent a car from any online agency and they’re pretty much all the same. I wouldn’t stress much about being charged extra for scratches you aren’t at fault for. I’ve rented dozens of cars in Italy and have never been charged extra due to a false accusation.
In general, a small cross-over SEO is a good option for two people. If you are driving with kids, look at the larger SUVs or a station wagon. A station wagon may not sound sexy but they are pretty popular in Europe and easy to drive.
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 Stay in Tuscany
Again, if you can’t make time to stay in the countryside, our Chianti day trip visits Tuscany for a full day and includes lunch in the vineyard. Here’s a quick guide on where to stay in Tuscany based on the number of nights you have.
Two to three nights
If you’re going to spend two to three nights in Tuscany, you’ll want to pick one destination and spend your time there. We have a great article on the best vineyards to stay at in Tuscany. If you’re renting a car, think about staying at Fonte de’ Medici or near Montalcino. Medici Villa is a great option if you’re not renting a car.
Four nights or more
If you’re going to spend more than four nights or possibly a week, you should move around a bit. With some money set aside to buy wine, possibly €50 to €150 per day, you could explore some really cool areas and have a great experience. Here are the areas I would dive into:
Montalcino and Val d’Orcia
Chianti Classico (specifically near Tignanello)
Bolgheri (where Sassicaia is made)
Step 7: Don’t Ask “How Much For a Tasting”
I will rarely walk in and ask, “how much does a tasting cost?” On your trip to Tuscany, be prepared to buy wine. If you have a great budget, ship some home.
If not, plan to buy a few bottles per person at each vineyard and they’ll normally waive any tasting fees. When staying in Tuscany, you may well be consuming a bottle of wine per day minimum, so it’s better to stock up!
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!
Tours of Chianti and Florence
Top-Rated Experience
Florence Day Trip to Tuscany: Siena, San Gimignano & Winery Lunch
Planning a day in Tuscany’s countryside can be tricky, with winding roads, remote villages, and countless wineries to choose from. With a 3-course lunch and 5 wine tastings, allow us to take the guesswork out of your Tuscan experience. Start in Florence, drive through Siena’s rolling hills, walk the medieval streets of San Gimignano, and tour a family-run Chianti winery. Along the way, learn the stories behind Chianti’s renowned wines and soak in the charm of Tuscany’s most stunning landscapes.
Planning to hit all of Florence’s highlights in one day can be a lot to manage. We’ll take care of every detail so all you have to do is enjoy the experience. With skip-the-line access, insider stories, and a charismatic guide who knows the city inside and out, you’ll see everything from Michelangelo’s David and the Florence Duomo to Ponte Vecchio and masterpieces by Caravaggio and Botticelli at the Uffizi Gallery. Experience Florence with all the must-sees, and none of the stress.
Sean is a co-founder and owner of The Tour Guy and its subsidiary The Roman Guy. He studied finance and statistics, but that is his "Dr. Jekyll" side! His "Mr. Hyde" is in love with travel, art, history, and culture. Sean has read libraries of historical text and believes that all internet content should come from books. A practice he follows!
Reader Interactions
Comments (2)
sue schiwetz
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
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.
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.