8 Steps For Planning an Epic Trip to Tuscany

Trying to plan a trip to Tuscany? Good for you! It is one of the most scenic and peaceful places most of us mortals will ever visit. An incredible destination that absorbs your anxiety and turns it into vino! But, where do you start?

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Step by Step Tips For Planning Your Trip to Tuscany

Not to worry. I have 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 Can You Go For?

There are really 3 options for visiting Tuscany.

1. A day trip
2. A few days (i.e. 4 days of your 10 day Italy trip)
3. Entire trip in Tuscany

Don’t worry, I will make deciding easy. Ask yourself these questions too narrow it down.

Question 1:

Have you ever been to Italy?

If you have 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 a day trip to max a few days of your trip.

Question 2:

Are you willing to rent a car and drive in Tuscany?

If you are willing to rent a car in Tuscany and drive 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 tons of diverse towns to visit and plenty to keep you occupied.

If you are not willing to rent a car, you should either take a day trip, which can be done with us via our Chianti Wine Day Trip from Florence which 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!

Tuscany Day Trip Teaser Video

Tuscany Wine Tour from Florence with Farm to Table Lunch

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 accomodations right outside Florence. We have some great vineyards with hotels and accommodation on-site in this article.

Step 2:

Start in Florence

Florence is a great starting point. You probably will arrive to Italy via Rome but I don’t recommend driving in Rome if you have not 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 will visit each and every time am in Florence if only to see the Birth of Venus.

There is an international airport in Florence and as mentioned many fast trains arriving 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 are willing to rent a car you can pick it up at Santa Maria Novella station and easily get out of the city using your phone GPS.

You have to decide if you should 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 the rest of the day and leave your bags inside the car while you sightsee!

Travel Hack:

If you can find wifi 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 wifi. Your GPS will still work and you shouldn’t be eating away at your data roaming. Be sure to turn that off in your settings. You won’t be able to search for a new destination when you leave wifi, but your GPS pin will work all the same.

Tours of Chianti & Florence

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 it is pretty much all the same. I wouldn’t stress much about being charged extra for scratches you are not at fault for. I have rented dozens of cars in Italy and 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 is 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 am in a city with wifi access, I keep airplane mode on. If I am 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. Hopefully, you buy a tour or ten from us, and karma is restored. Our Tuscany page has tons of free advice. If you are ok paying for advice and a helping hand, 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 including lunch on the vineyard.

2 to 3 Nights

If you are going to spend two to three nights in Tuscany, you’ll want to pick one destination and spend your time there. Again, we have a great article on the best vineyards to stay at in Tuscany. If you are renting a car, think about staying at Fonte de’ Medici or near Montalcino. If you are not renting a car, Medici Villa is a great option.

4 Nights +

If you are going to spend more than four nights or possibly a week you should move around a bit. If you have 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?” If you are going to Tuscany be prepared to buy wine. If you have a great budget, ship some home. If you don’t, plan to buy a few bottles per person at each vineyard and they normally wave any tasting fees.

If you are staying in Tuscany, you should at least be consuming a bottle of wine per day minimum so it is better to stock up!

Step 8:

Be Spontaneous

It almost always pays to plan ahead but you can leave yourself 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.

If you have a certain vineyard you “have” to see, it is better to call the day before 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 & Florence