Top Tuscany Day Trips - page 10

(18)

from $354

Experience the hidden beauty of Tuscany like never before—aboard a Land Rover Defender, journey through the region’s legendary "strade bianche" (white roads), the secret gravel paths winding through vineyards, olive groves, and deep forests. Your journey includes three winery visits, each offering a unique perspective on Chianti Classico and its appellations. The experience culminates in a traditional Tuscan lunch, where authentic flavors meet world-class wines, creating a true taste of Tuscany.

Private Off Road Wine Tour in Chianti from Florence

(18)

from $480

Florence walking guided tour with Uffizi & Accademia

4.6

(17)

from $804

SUPER LUXURY MERCEDES VAN. What can you expect for Pisa & Florence?: Private Shore Excursion, full day tour which takes about 8 hrs, our driver will come pick you up from the Livorno dock in a private air conditioned sedan or Mercedes Limo minivan to see Pisa’s Miracle Square, experience Pisa’s Leaning Tower and explore the charming city of Florence. PIsa: Square of Miracles, formally known as Piazza del Duomo (Pisa Cathedral, Duomo and Leaning Tower) one hour. Florence: where you'll spent the most time, Piazzale Michelangelo, Chiesa Santa Croce, Duomo, Ponte Vecchio. Drop off (pick up in the afternoon) in Repubblic Square where you will have your free time cross the city walking, among art, shops and many shops to eat delicacies of Tuscan food. Will be a Fun Tour with experienced, professional, warm and friendly driver! Return to the ship on time 100% GUARANTEED. DON'T CATCH THE SHUTTLE BUS (LIVORNO DOCKS).

Private Shore Excursion Livorno Port "Discovery Pisa & Florence"

Private Shore Excursion Livorno Port "Discovery Pisa & Florence"

(17)

from $1,039

Discover two of Italy’s most iconic destinations in one day from Florence to the breathtaking Cinque Terre and the historic Pisa. Travel by air-conditioned coach with a tour leader who shares insights throughout the journey. Visit Manarola and Monterosso al Mare, enjoying free time to explore colorful streets, relax on the beach, or swim in the clear Ligurian Sea. Move between villages and continue to Pisa by train, taking in spectacular coastal views. In Pisa, discover Piazza dei Miracoli and admire the world-famous Leaning Tower of Pisa. Return to Florence after a day of stunning scenery and cultural highlights.

Small Group Best of Cinque Terre and Pisa from Florence

Small Group Best of Cinque Terre and Pisa from Florence

12 hours 30 minutesFree Cancellation

4.6

(17)

from $89

During the tour, there'll be lots of time to relax and to enjoy the good company while cycling in the famous Eroica Gravel roads of the Chianti.

Embark on an adventure that will take you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and contemplative way, an area rich in food and wine traditions, cradle of the famous Chianti Classico wine (tasting included) and proud of its tradition and culture linked to the long rivalry between Siena and Florence. In addition, the experience includes a guided tour of one of Chianti's most characteristic castles, the castle of Brolio, from which you can take in magnificent panoramic views to the vineyards and the city of Siena. To experience the most out of the territory, we'll book lunch at a local family owned restaurant where you, in addition to enjoying its tranquility and warm welcome, can savour the dishes of the Tuscan tradition. The way back is mainly descending and the guide will stop in magnificent sightseeing spots before getting back to the starting point.

E-Bike Tour: Explore the Chianti, its Enogastronomy and Castles

7 hours 15 minutesFree Cancellation

4.7

from $295

Avoid the stress of coordinating transport and trying to fit two iconic cities into a short stop on your own with a guided day trip from Livorno. This experience connects the Renaissance art and historic streets of Florence with the architectural landmarks of Pisa, letting you move smoothly between both without planning headaches. Spend your time exploring, tasting local specialties, and seeing the highlights without worrying about logistics.

From Livorno: Florence & Pisa Tour with Local Food Tasting

From Livorno: Florence & Pisa Tour with Local Food Tasting

Half-day Chianti Classico Wine tour from Florence - Small Group

3.8

(13)

from $70

5 hoursFree Cancellation

Taste your way through Tuscan wine country on a private, full-day tour from Florence. Travel through the scenic Orcia Valley and visit the birthplaces of several prized Italian wines. Explore the medieval villages, tour historic wine cellars and vineyards, or savor a farm-fresh lunch (own expense): your private driver and guide customizes the itinerary for you. Price is per group, based on a maximum of 7 passengers per vehicle.

from $177

Private Tour: Orcia Valley to Montalcino and Montepulciano with Brunello Wine Tasting

from $1,165

Explore three different sides of Tuscany in a single day on this private tour from Florence—no need to plan a route or itinerary yourself. Explore Siena's medieval streets and cathedral with a guide, then settle in at a Chianti estate for a farmhouse lunch and wine tasting. Wander San Gimignano at your own pace before ending in Pisa with time to see the Leaning Tower, the Baptistery, and the Cathedral.

Private Tuscany Tour in One Day to Pisa, Siena and San Gimignano with Winery Lunch from Florence

Private Tuscany Tour: Siena, San Gimignano and Pisa from Florence

11 hoursFree Cancellation

Getting around Tuscany by public transport can be daunting. Skip the hassle of coordinating train and bus schedules and cover two top Tuscan towns in a single day with this San Gimignano and Siena tour. Explore the medieval old town of San Gimignano and enjoy a wine tasting before continuing on to Siena. Skip the line to enter the magnificent cathedral and explore the sights, shops, and eateries at your own pace.

from $685

Florence: San Gimignano & Siena Tasting Experience

Florence: San Gimignano & Siena Tasting Experience

4.4

From Florence:Tuscany Tuk Tuk with Lunch, Wine & San Gimignano

from $118

Bike along the rolling hills of Tuscany’s Chianti region as you follow a GPS route and go at your own pace from Florence without getting lost. An e-bike will help with the steeper hills and the map will guide you to beautiful sights, including Machiavelli’s home, a monastery, and beautiful olive oil farms and vineyards. You can stop at one for lunch (not included), or be flexible and explore more.

from $235

Special Offer

Enjoy lunch at a farm or anywhere you prefer along the route!

E-bike Tuscany and Chianti Self-Guided Tour with Vineyard Visit

6 to 7 hoursFree Cancellation

The mountainous Tuscan region of Chianti is home to vineyards and wineries that produce some of Italy’s most popular vintages, but they can be difficult to reach without a car. On this full-day private tour, your driver transports you to several dispersed towns and villages in the region, all with a unique attachment to winemaking. Opt to join wine tastings (own expense) and explore each location on short walks.

Private Chianti Wine Tour

(15)

from $708

Complete your Livorno cruise with this smart travel package that includes the hop-on hop-off service in Livorno and the transfer service in Pisa; visit one of the most iconic Italian art sites in the world, the Leaning Tower of Pisa! Depart for Pisa to visit the wonderful Piazza dei Miracoli with its iconic Leaning Tower; take the time for your free visit to the art area and then we will take you back to your ship right on time. Explore the most interesting points of Livorno, a port city in Tuscany rich in ancient and modern history. Be captivated by the beautiful Mascagni Terrace and the historic indoor central market.

Special Offer

Day Tour in Livorno and Pisa Shore Excursion from Livorno

Day Tour in Livorno and Pisa Shore Excursion from Livorno

5 hoursFree Cancellation

With spotty public transportation and winding rural roads, the Brunello di Montalcino wine country can be tricky to explore on your own. Discover the history and flavor of one of Italy’s premier wines with ease on this full-day tour from Florence. Travel through the Tuscan countryside to the Brunello hills and the village of Montalcino. Visit a small, family-run winery to learn about traditional production methods and taste renowned varietals like Brunello DOCG and Rosso di Montalcino DOC. Savor a farm-fresh lunch of Tuscan specialties at the estate, and finish the day with more tastings at another local winery.

Brunello di Montalcino Wine Tour with 2 Wineries & Lunch at Farm

Discover the authentic flavors of Tuscany on our Family-Friendly Tuscany Tour — a perfect mix of food, wine, and fun for all ages! Travel through the scenic Chianti countryside and visit a local farm overlooking San Gimignano, where you’ll taste local honey, cheeses, and fresh bruschetta with seasonal ingredients. Continue to a traditional winery for a light lunch with balsamic and olive oil tastings. Adults can enjoy a tasting of three Tuscan wines, while younger guests and non-drinkers are treated to grape juice or refreshing soft drinks. Finish the day with free time to explore the medieval streets of San Gimignano before returning to Florence. A delicious and family-friendly Tuscan experience that everyone will love!

(15)

from $306

Family-Friendly Tuscany Day Tour for Wine Lovers and Non-Drinkers

Family-Friendly Tuscany Day Tour for Wine Lovers and Non-Drinkers

(15)

from $179

Experience the highlights of southern Tuscany on a full-day tour from Siena through the rolling landscapes of the Val d’Orcia. Travel in comfort and enjoy a perfect blend of food, wine, history, and scenery. Your first stop is Montepulciano, where you’ll enjoy an authentic Tuscan lunch featuring local cured meats and cheeses, followed by handmade Pici pasta with ragù, or tomato sauce for vegetarian guests. During lunch, take part in a guided tasting of Rosso di Montepulciano and the renowned Nobile di Montepulciano, perfectly paired with the regional cuisine. Continue to Pienza, the “ideal Renaissance city,” and enjoy free time to stroll its picturesque streets, admire panoramic countryside views, and browse artisan food shops. In the afternoon, reach Montalcino, home of the prestigious Brunello di Montalcino. Visit a local winery for a guided tasting and learn about the traditions and aging process behind one of Italy’s most celebrated wines.

From Siena Best of Tuscany Wines and Lunch in Montepulciano

From Siena Best of Tuscany Wines and Lunch in Montepulciano

4.0

Siena - San Gimignano Private Tour

from $116

from $649

Tuscany Wine Tastings with Panoramic View - Florence to Chianti

5 hoursFree Cancellation

4.7

Diving into the past has never been easier. From the majesty of the medieval Piazza dei Miracoli in Pisa where a tower stands crooked as if by magic to the Renaissance city where a cathedral stands out with the dome of an architectural genius. We are talking about the fifth and second most visited cities in Italy, both UNESCO heritage sites. And on the journey between these two cities the Tuscan countryside. Our drivers can enter in sites where other can't. They will always be available if you want to stop for a break or extend the duration of the tour or customize the itinerary (within certain km). The highlights are the same for everyone in cities like these but we always know the best route with the right compromise between landscape and speed. Our drivers are all Tuscan and therefore will be able to give you genuine information and advice to improve the quality of the tour. The Tuscan way of life is "slow but enjoying every single moment". What are you waiting for?

from $83

The Art of Surprising You: Pisa/Florence Luxury Limo Private Tour

8 to 9 hoursFree Cancellation

4.8

from $1,121

Once on the bus it will be time to leave for the first stop of this tour, Pisa! Along the way to this iconic city you will be provided with useful information to make you fully enjoy your experience in Pisa in total freedom! By choosing the option with the entrance ticket to the Leaning Tower you will be able to climb to the top of the famous Tower of Pisa and enter withpriority access inside the spectacular Cathedral. After discovering the beauties of Pisa you will get back on the bus and you will arrive in Manarola, the smallest and most characteristic village of the Cinque Terre. We will arrive at the parking lot of the village, where the bus will be waiting for you on your return. During your visit to the beautiful and colorful village you can relax by bathing in the crystal clear water of the Mediterranean Sea. After taking lots of photos of your unique experience you will return to the bus and together we will leave to return to the port on time for your departure

Special Offer

Full Day Pisa and Jewel of the Cinque Terre Tour From Livorno

Full Day Pisa and Jewel of the Cinque Terre Tour From Livorno

Pisa, Florence and Uffizi Museum or Accademia Private Shore Excursion from Livorno

Likely to Sell Out

4.6

from $430

Experience the allure of Tuscany without the hassle of tricky logistics with this all-inclusive day trip from Rome. Save time with a high-speed train to Florence, where you’ll hop on a minibus with your tour leader and small group to visit Monteriggioni, Siena, and San Gimignano. End your Tuscan adventure with a wine and olive oil tasting in Chianti before heading back to Florence for the return train to Rome.

From Rome: Day Trip to Tuscany & Siena with lunch & Wine Tasting

14 hoursFree Cancellation

4.7

Florence Vintage Fiat 500 Tour: Tuscan Hills, Food & Chianti Wine

from $279

...

9 10 11

...

Top Attractions in Tuscany

1 / 2

Attractions

What are people saying about Tuscany

Vincent_s, Aug 2026

A dream come true

Antonio & Elena, Our bus driver, the shop mechanic, what a team! I am a car guy who has classic cars back home, my wife loved the image of Tuscany, the kids love the car & food so this package was an easy decision for everyone. Driving a classic Fiat through the hills of Tuscany, it doesn’t get any better. Cars were well maintained, They had newer electric ones if you wanted a more relaxing drive. Family of 4 with 2 young children and they fit in the back just like my ‘67 beetle back home. Gorgeous views, fantastic food & wine with a stop at a 1,000 year old church, burial of Carlo Lorenzini, the author of Pinocchio. The children and I paid our respects and thanked him for the stories while we make our own. So thank you to the entire team that put together such a wonderful memory for our family.

Full day shore excursion to Florence and Pisa from Livorno with tasting

Jemmy_L, Aug 2026

Florence and Pisa in a Day!

For our shore excursion I never thought we could actually visit Pisa and Florence within a day but our Guides Paula and Arianna made it possible. The tour was smooth sailing from the moment we gathered at the meeting point. Arianna had a lovely sense of humour and was very informative as we travelled towards Florence, where we had around 2.5hrs to explore on our own. We then hopped over to Pisa and quickly posed against the leaning tower during the hour we had there. The Guides also kindly organised a hop-on trolley (for a small fee) to take us quickly to Miracle Square. The coach back directly to the port / to the ship was also greatly appreciated after a long day. Highly recommended to get an insight into beautiful Tuscany.

From Florence: Cinque Terre & Pisa Day Trip

Pooja_G, Aug 2026

Memorable and organized tour!

Five stars for Nathan! He made our tour of Cinque Terre and Pisa completely smooth and stress-free. Managing the logistics between multiple coastal towns and a bustling landmark like Pisa can easily feel overwhelming, but Nathan kept everything running seamlessly with his fantastic organization. He’s endearingly funny (if you like Dad jokes ;)), refreshingly forthright, and full of great local tips. We could not have asked for a better guide to navigate these iconic spots!

Florence Day Trip to Siena & San Gimignano with Scenic Views

Colleen_B, Aug 2026

Amazing trip with Fred and Chiro

I had an amazing day, lead by Fred. Chiro was our driver. The trip was very well organized and punctual. Fred provided excellent commentary during the beautiful drive. The towns were lovely and his recommendations for things to see and places to eat were great. Thanks for a wonderful day!

Half-Day Excursion to Pisa and the Leaning Tower from Florence

Whitney_S, Jul 2026

Fun time in Pisa

The tour went just as described in the booking details. We left Florence in a comfortable motor coach on time and arrived in Pisa with plenty of time to explore. I appreciated the guided tour and being able skip the line to climb the tower. This saved a lot of time. After climbing the tower, we had time to explore the area and buy a few souvenirs. Overall, the excursion was a great experience and I would recommend it to anyone wanting to see Pisa.

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch

Chris_B, Jul 2026

Fun time across Tuscany

This was a great experience if you like great views from medieval like towns. We had a great time exploring these small towns and enjoyed the lunch and wine we were served. If you’re looking for a trip around Tuscany and don’t want to drive around yourself, this is a great option! Our tour guide Aaron was funny and well informed and our bus driver Elis provided a great ride!

San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

Sarah_G, Jul 2026

Wonderful day trip, lunch and wine tasting

The tour was wonderful, we loved San Gimignano with its amazing towers. We had our own free time to explore all the stops. Our guide Ricardo was excellent. He gave us lots of interesting information on the places we were visiting and made sure we all knew the time and place we were meeting. He guided us through Sienna. The wine tasting was fabulous, we tasted 4 glasses of wine , 2 Spumante. The food was great. This is an 11 hour trip but it was only a little walking. We loved it. Christina helped Ricardo with the tour. It was really good value for money and I highly recommended doing it. Bellissimo!

Florence Day Trip: Pisa, San Gimignano and Siena with Lunch

Tracey_L, Jul 2026

Amazing Day In Tuscany with a Superb Crew

We had a fantastic time on this bus tour through Tuscany! Our guide, Emma, was incredibly knowledgeable and impressively shared detailed information in three different languages so everyone on board felt included. The bus driver did a phenomenal job; he navigated the roads with total ease, making our family feel completely safe. The itinerary was excellent, featuring stops in Siena, San Gimignano, and Pisa with a lunch stop at a winery. At each stop, times to return to the bus were communicated perfectly, giving us the freedom to explore on our own. Highly recommend!

Cinque Terre Experience From Florence

Bradford_A, Jul 2026

Cinque Terre in a Day!

I can’t think of how you could possibly put together a more complete Cinque Terre experience in one day. We went to four of the five villages, travelled by bus, train, and boat, and still were able to spend some time swimming or exploring in a couple of the villages. Cicily was a great tour guide! Thank you for the experience!

From Florence: Tuscany Wine Country Day Trip with Vineyard Lunch

Heather_A, Jul 2026

A nice day trip, good option if you’re short on time and want to squeeze in a few things.

Our guide Shirin was wonderful, the smaller group tour made for an enjoyable day. The vineyard meal was okay but we had lots of samplings of olive oils, balsamic vinegars and wines (sparkling white, 5 reds, rosé and a dessert wine). The vineyard was a beautiful setting and we sat in smaller tables. The staff were friendly hosts, but very pushy to buy items and it felt like a sales pitch. We would have enjoyed more time in Siena and San Gimignano, but it was a comfortable ride with a lovely tour guide and a nice taste of the Tuscan countryside outside of Florence. Next time I’d book more time in each town and do a vineyard experience on a seperate day. It’s a good option if you’re short on time and want to squeeze in a few things.

Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch

Lisa_D, Jun 2026

Fun outing from Florence

Excellent tour of Siena by Catherine and free time in San Gimiagno with a fun wine tasting and lunch. We were a small group which made it more enjoyable. Alessio was a fantastic driver and guide providing great information as we drove from place to place. The van was very comfortable and water was provided which came in handy on a hot day. I would definitely recommend this tour and Alessio as your guide!

Full Day Tour to Val d'Orcia and Gladiator's Fields with Wines

MICHELLE_T, May 2026

Exceptional Experience

Excellent tour! Exceeded our expectations!!! Cecilia was a wonderful guide, provided lots of background information and did it in three languages!!! The scenery is amazing and the villages are each unique. Our lunch took too long in Pienza, so I’d say go with something simple so that you don’t spend all of your time eating (but the food was delicioso!!!). There’s quite a bit of walking and the last tour has a steep climb up from the parking area to the village square and then down many steps to the winery (but it’s very cool!). The Tuscan countryside doesn’t disappoint although it’s hard to do it justice with a phone camera. Tour is great value for the money! So very happy we did it!!!