Top Tuscany Day Trips

There are tons of great Tuscany day trips from Florence. Based on ratings and reviews from previous customers, these are the best tours available right now:

• Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery
• Pisa, Siena, San Gimignano with Lunch & Wine Tasting at a Winery
• SMALL-GROUP Wine Safaris: Tuscany Wine Tasting Tour from Florence
• San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch
• Florence Vespa Tour: Tuscan Hills, Food and Chianti Wine

Yes, Tuscany day trips are well worth it. While you’re welcome to explore on your own, booking a guided excursion is a great way to maximize your travel time and budget. These tours include transportation and activities, along with the insider services of a guide, whose local insights on history, culture, and food will enrich your experience in Tuscany.

Day trips can cost as little as US$40 for bus excursions or upwards of US$1,500 for private tours with your own guide, so you can find an experience for every budget. Generally, the most popular Tuscany day trips, from wine tasting to Vespa riding, fall in the US$100–US$200 range.

Some of the most popular towns to visit on a Tuscany day trip, ideally from Florence, are Pisa, Siena, and Lucca, and San Gimignano. Wine tasting is also a top day trip activity—choose from tons of vineyards in Chianti or near Montalcino, Montepulciano, and Pienza. If you’re up for a longer travel day, you can also visit the seaside towns of Cinque Terre from Tuscany.

Generally, round-trip transportation and the services of a tour guide are covered by your day trip, though inclusions vary among different excursions. Some tours also include admission to ticketed attractions, lunch, and wine tasting, while others offer you the option to explore the destination on your own or upgrade to enjoy additional experiences.

You’ll need at least three days to explore Tuscany’s cities, villages, and vineyards, though closer to a week is ideal. Dedicate a full day or more to the capital city of Florence, and plan day trips to small medieval towns such as Siena, San Gimignano, and Lucca. End your trip by wine tasting in the scenic rolling hills around Chianti, Montalcino, or Montepulciano.

There are tons of fun tours and excursions in Tuscany aside from day trips. According to previous travelers, these are the best activities to book for your next trip:

• Wine Tasting
• Cooking Classes
• Private Drivers
• Horseback Riding
• Vespa Rentals

Tuscany day trip prices vary depending on duration and inclusions. If you’re looking for high-quality experiences on the lower end of the price range, these are the best tours to book now:

• Self-Guided Bike Tour from Lucca to Pisa
• Livorno Shore Excursion to Lucca & Pisa optional Leaning Tower Ticket
• Pisa to Lucca Self-Guided Bike Tour Along the Puccini Trail
• Full-Day Shore Excursion to Florence from Livorno with Tasting

Tuscany day trips allow you to choose from a variety of destinations and activities, from exploring the vineyards of Chianti by Vespa to admiring the exquisite architecture of Pisa and Siena. Figure out which cities and itineraries appeal to you most, then find a day trip that suits your taste and budget. Private tours are generally more expensive, while plenty of group tours cost less than US$100.

Comfortable walking shoes are a must for any Tuscan day trip, whether you’re climbing up bell towers in San Gimignano or hiking from one coastal town to the next in Cinque Terre. If you’ll have free time for lunch or to explore your destination on your own, remember that your guide is also a great source of information about things to see, do, and eat.

Most Tuscany day trips involve a fair amount of time outdoors, so it’s best to book your experience when the weather is most pleasant from April–May or September–October. Tuscany gets fewer visitors in these months than in summer, allowing you to experience its picturesque cities and countryside with minimal crowds.

Yes, it’s very easy to take day trips in Tuscany without renting a car. Cities such as Pisa, Siena, and Lucca are reachable by train, though other destinations—such as the hill town of San Gimignano and the vineyards of Chianti and the Val d’Orcia—aren’t as easily accessible via public transportation. For the most convenient experience, book a guided day trip with included transfers from Florence or another base.

That depends on your interests and budget. Shared tours are more affordable, though they require you to stick to a tight schedule. While private tours are pricier, they can be personalized for your group, whether you want to book a later start time, spend an extra hour at lunch, or reserve a walking tour or museum visit in your destination.

Yes, guided day trips make it easy to visit all three towns without having to drive, park, or navigate bus schedules on your own. For example, this top-rated Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery, which starts at US$110 per person and runs about 12 hours, stops in three of the best places to visit in Tuscany, plus a Chianti vineyard for lunch and wine tasting. While your visits to each town will be brief, you’ll have enough time to see the grand Siena Cathedral and Piazza del Campo, medieval architecture of San Gimignano, and Leaning Tower of Pisa.

Tuscany is a world-famous wine region, so there are hundreds of tours that let you taste local wines and explore picturesque vineyards. This Small Group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner day trip is one of the top-rated wine tours in Tuscany, starting at US$175 per person and running about eight hours. The tour takes you to three different wineries for cellar tours and tastings, and it also includes a multi-course Tuscan meal, round-trip transportation from Florence, and a visit to the scenic town of Greve in the rolling hills of Chianti.

It depends on your energy level. A half-day wine tour from Florence, for example, lets you visit two Chianti vineyards over about five hours, freeing up the rest of the day to relax or sightsee in Florence. Full-day tours fit in more destinations and activities over 10 or more hours, often combining wine tasting in Chianti with visits to Siena, San Gimignano, and other towns.