Top Tuscany Private Sightseeing Tours - page 5

Private Sightseeing Tours

1,000+ results

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4.9

(17)

Exclusive Uffizi Gallery Private Visit

3 hoursFree Cancellation

from

$303

$318

Price varies by group size

Likely to Sell Out

Tuscany's Val d'Orcia is famous for its postcard-perfect scenery and hill towns, but getting around by public transportation can be frustrating. With this private tour, enjoy hassle-free pickup in Florence and soak in the views while your professional driver takes on the tricky country roads. Spend time exploring the villages of Montalcino, Pienza, and Montepulciano plus stop to snap photos of the Madonna di Vitaleta Chapel.

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4.9

(34)

Val d'Orcia private tour: Montalcino, Pienza and Montepulciano

10 hoursFree Cancellation

from $655

Price varies by group size

Likely to Sell Out

the view from the high piazzale michelangelo

4.5

(69)

Florence by golf Cart Piazzale Michelangelo

1 hour 30 minutesFree Cancellation

from $106

Experience the cultural and culinary treasures of Tuscany on a private full-day shore excursion from the port of Livorno. Journey inland to the historic city of Pisa to see the iconic Leaning Tower and other architectural marvels of Piazza dei Miracoli. Continue on to beautiful Florence, the birthplace of the Renaissance, where time seems to have frozen in the 15th century. Finish the day with a visit to a local winery for a tasting of renowned Tuscan varietals. Enjoy a customizable schedule and the personalized attention of a private guide.

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5.0

(21)

Livorno Shore Excursion: Pisa, Florence and Chianti Wine Private Day Trip

9 hoursFree Cancellation

from $485

Price varies by group size

The Leaning Tower of Pisa is one of Italy’s most iconic landmarks. With millions of annual visitors, you probably spend more time waiting outside than exploring inside. This private tour offers skip-the-line access to the famous Leaning Tower and the gorgeous Cathedral, combined with a walking tour of highlights such as Piazza dei Miracoli, Piazza dei Cavalieri, and Piazza Arcivescovado as well as an optional lunch at a traditional trattoria.

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4.7

(29)

Private Pisa Discovery Walking Tour with Leaning Tower Access

1 hour 30 minutesFree Cancellation

from $169

Price varies by group size

Treat your senses to a memorable day in the world-famous Chianti wine region on this private tour from Florence. Travel in a luxury minivan through a landscape of historic vineyards, rolling hills and medieval villages, with a private driver at your disposal throughout the day. Taste renowned Chianti wines and authentic Tuscan cuisine at estates of your choosing, or let your local driver make suggestions for the best places to wine, dine and explore.

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4.9

(20)

Chianti Vineyards Tours in Private Luxury Van from Florence

8 hoursFree Cancellation

from $830

Per group

Immerse yourself in the beauty of Cinque Terre on this full-day, private shore excursion. Don’t worry about organizing logistics: your driver will pick you up directly from the Livorno port, and you’ll travel in the comfort of an air-conditioned minivan. Visit three Cinque Terre villages based on weather conditions and ferry and train schedules, and take advantage of a flexible itinerary with time for shopping and lunch (own expense).

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5.0

(77)

Cinque Terre Private Tour from Livorno

9 hoursFree Cancellation

from $1,322

Per group

5.0

(31)

Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence

8 hoursFree Cancellation

from $661

Price varies by group size

5.0

(8)

Cortona private walking Tour

2 hours 30 minutesFree Cancellation

from $178

Price varies by group size

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.

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5.0

(18)

Private Off Road Wine Tour in Chianti from Florence

7 hoursFree Cancellation

from $489

Price varies by group size

Savor the sights and tastes of Tuscany on this private wine-tasting tour of the famed Chianti region. From Florence, journey across the Chianti hills, covered with vineyards and olive groves, toward Greve where you will make a first stop before heading for a respected Chianti winery to visit the cellars and learn about the production methods of the Chianti Classico. After a Tuscan-style lunch paired with wine, you'll head towards a second Chianti winery for another wine tasting.

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4.9

(20)

Chianti Wine Tour - Private Wine experience in Tuscany Countryside

8 hoursFree Cancellation

from $758

Price varies by group size

Likely to Sell Out

5.0

(251)

PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence

8 to 9 hoursFree Cancellation

from $397

Price varies by group size

4.9

(32)

Cinque Terre Private Tour by Minivan and Ferry-Boat Shore excursion from Livorno

9 hoursFree Cancellation

from $479

Price varies by group size

Likely to Sell Out

Visit the Italian cities of Pisa and Lucca on this private tour from Florence. Visit the Leaning Tower of Pisa, part of the World Heritage–listed Piazza dei Miracoli, the Cathedral, Baptistery, and the Monumental Graveyard in Pisa. Then head to Lucca to see Guinigi Tower, an example of Romanesque-Gothic architecture for more insight into Tuscan culture and history. Go beyond the guidebooks with insider knowledge from your guide.

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4.6

(20)

Full-Day Private Pisa and Lucca Tour with optional Leaning Tower

8 hoursFree Cancellation

from $475

Price varies by group size

Take in the highlights of Italy’s Renaissance capital without getting footsore with this tuk-tuk tour of Florence. Hop aboard this and zip through the city center to admire iconic sights like Ponte Vecchio, the Duomo, and Piazza della Signoria. Learn about the history and culture of the city with commentary from the driver and stop to snap photos and savor the views. Upgrade for a slightly longer tour that also rides up to Piazzale Michelangelo, a square with panoramic views of Florence

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4.1

(258)

Terrazze di Firenze tour Panorami golfcart minimo 2 persone

1 hour 10 minutes

from $50

Likely to Sell Out

Discover the best that Florence has to offer on a full-day private walking tour through the Renaissance city. Visit the city’s historic landmarks like the Duomo, Giotto’s bell tower, Ponte Vecchio, the Baptistry and more as you listen to informative commentary from your guide about the history of Florence. Then visit the world-renowned Uffizi and Accademia galleries to see works from Michelangelo, Botticelli, Caravaggio, Raphael, and more.

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4.9

(30)

Private Full Day Walking Tour of Florence Highlights with Uffizi and Accademia

6 hours

from $713

Price varies by group size

Florence’s cathedral is the city’s crown jewel and most iconic monument, but its sprawling size and long lines can be discouraging. Skip the lines and enjoy an in-depth look at this vast complex on this private tour. Visit the Duomo from its soaring dome to its ancient crypt (depending on availability, see itinerary below), admire the view from Giotto’s bell tower, marvel at the richly decorated baptistery, and tour the renovated museum.

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4.7

(21)

VIP Private Tour of the Opera Duomo Complex

3 hours

from $297

Price varies by group size

Step into Florence's rich history with a private tour of Palazzo Vecchio and Palazzo Pitti, once home to the powerful Medici family. Discover the secrets of this influential dynasty as you explore their palaces and the stunning Boboli Gardens. Enjoy a personalized experience with a professional guide, starting with a hotel pickup from central Florence. Uncover the fascinating stories behind Renaissance Florence on this unforgettable 4-hour journey.

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5.0

(19)

Palazzo Vecchio, Palazzo Pitti and Boboli gardens private tour

4 hoursFree Cancellation

from $234

Price varies by group size

4.8

(10)

The Best Of Classic Florence - Private Tour

2 hoursFree Cancellation

from $114

Price varies by group size

Likely to Sell Out

Steep in Florence's art history on this expert guided Accademia Gallery tour—the perfect way to experience one of the city's cultural treasures. Skip the lines and admire masterpieces like Michelangelo's David and Giambologna's Rape of the Sabines in an intimate setting. Your knowledgeable guide will bring the 15th and 16th-century Mannerist art to life, and you can even upgrade to include an optional walking tour of Florence.

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5.0

(7)

The Accademia Gallery in Florence with your private guide

2 hoursFree Cancellation

from $162

Price varies by group size

Discover the charm of San Gimignano on this private culinary experience. Guided by a family member who shares stories and insights into their sustainable craft, you'll taste and learn about this special region. Then, savor a private tasting featuring organic wines, premium extra virgin olive oils, and a freshly prepared farm-to-table meal. It's the perfect way to immerse yourself in the flavors and traditions of Tuscany.

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4.9

(19)

Private Wine & Evo Oil Tasting with Tuscan Meal

1 hour 30 minutesFree Cancellation

from $82

Private Chianti Wine Tasting from Florence, Half Day Experience

Experience Tuscany’s iconic Chianti wine country without the hassle of navigating the country roads on your own with this private tour from Florence. Head directly to a historic winery in the Chianti hills for a visit and tasting, then continue on to a boutique winery overlooking San Gimignano. Stop for a tasty lunch overlooking the medieval hill town featuring classic Tuscan specialties.

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5.0

(11)

Private Chianti Wine Tasting from Florence, Half Day Experience

6 hoursFree Cancellation

from $679

Price varies by group size

Likely to Sell Out

Spend a day in Tuscany, visiting the cities of Siena, Pisa, and the medieval town of San Gimignano, without worry about getting lost among a large group. With a private driver, benefit from a more flexible itinerary with plenty of free time to explore at your own pace. Enjoy a stroll through Siena’s history-rich Old Town, then admire views over the Tuscan countryside from San Gimignano. Finish with a visit to Pisa’s Piazza dei Miracoli, and snap a photo in front of the Leaning Tower of Pisa.

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4.8

(146)

Premium Private Tour to Siena, Pisa, San Gimignano and Tuscany

10 hoursFree Cancellation

from $697

Price varies by group size

Visit the historic town of San Gimignano and discover a hidden gem— local wineries where the views are almost as good as the wine. Enjoy wandering through two wineries, take in views of the vineyards and the surrounding rolling countryside, and learn about how wine is made. Then taste some of the local wine with your hosts, and visit the cellars where wine is kept in wooden barrels to age.

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5.0

(13)

Bella Toscana - San Gimignano plus 2 Chianti Wineries and lunch

8 hoursFree Cancellation

from $449

Price varies by group size

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Top Attractions in Tuscany

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Attractions

What are people saying about Tuscany

Private Tour of Uffizi and Accademia Gallery with David

Leslie_M, May 2026

A must do in Florence!

Renata was a wonderful guide- so very knowledgeable about art history. I felt like I could ask her anything related to the Uffizi Museum/Gallery or the Accedemia and she would know the answer. The private tour with skip the line entrance was 1000% worth it. This is a MUST do when traveling to Florence.

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The Best of Tuscany: Private Full Day Tour From Florence

Arianna_C, May 2026

Alex the great!!!

Alex was phenomenal! He picked us up and took us to 3 medieval towns and 2 wineries. His knowledge of the area was quite extensive! He was really kind, patient and had the best recommendations both along our route and in Florence. We sincerely enjoyed our day with him and would book with him again if we had more time! Thank you to the coordinator Max for all of the communication leading up to our day. 10000/10! Highly recommended!

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Lucca Bikes and Bites with food tastings for Small Groups or Private

Lillian_A, Apr 2026

Biking around Lucca

We had a wonderful time biking around Lucca. Claudia was a wonderful, friendly, and informative guide. She offered a great perspective of the history of Lucca as well as offering suggestions for further sight seeing in the area. It was a nice way to spend the day. The two stops for refreshments were amazing. We completely enjoyed the experience.

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Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region

Chris_P, Apr 2026

We were on a 2-1/2 week...

We were on a 2-1/2 week vacation and this was by far one of the best experiences we had. The countrysides are beautiful and mostly breathtaking. Our drive (Valetine) was awesome - friendly, knowledgeable and informative. The cities we visited (Siena and San Gimignano), as well as the ChiantiWinery were all fantastic! I would definitely recommend this tour!

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Golf Cart Tour of Florence Michelangelo & Panoramic Hills

MiaGentry, Apr 2026

Olga Is amazing. She has...

Olga Is amazing. She has such a big, friendly personality. feels like I’m leaving behind someone I’ve known for years. The views, the laughter and experience, was unforgettable. I don’t know what I was expecting you but I was not expecting this. This exceeded anything that I could’ve imagined for a golf cart to work. This is a must do experience.

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DAVID and Accademia Gallery Private Tour in Florence

Daphne_M, Apr 2026

Early private tour is worth every dime!

We were able to be some of the very first people to enter in the early morning tour with our private guide, Irina. We were able to walk right up to David, take unobstructed photos, and see every detail Irina explained right up close. (Just 20 minutes later the room was packed with visitors and getting close would have been impossible!) She was incredibly knowledgeable and truly brought the history and process to life. She’s an amazing guide and I will be pointing my friends who travel to Florence straight to her. Don’t hesitate to book this one!

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Private day trip to Siena, San Gimignano, Chianti and Pisa, from Florence

Kirsten_L, Mar 2026

Amazing experience and...

Amazing experience and well worth the price for our family of 6. Multigenerational. Ages 19-79. Our driver Alessio gave great recommendations and shared links with directions on what to visit in each stop. When driving he shared history and local information. He dropped us off very close to the city center in each town so that we didn’t have too much walking in. What a great day!

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Florence Exclusive PRIVATE Food Tour with 6 or 10 Tastings

megan_b, Feb 2026

Worth it

I highly recommend doing a small group or private when it’s a food tour and to do it on the first day. Our guide, Gabriel was great, has been living in Florence for 15 years and knew the smaller, quality, less touristy places to go. Besides the food, our guide gave us a nice highlight of the sites to see and advice to avoid some lines and crowds.

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Private Golf Cart Tour of Florence Michelangelo & Panoramic Hills

MIMI_L, Feb 2026

Alex, the golf cart guide experience him in person.

The communication was a bit poor initially and I had to reach out many times get any answer. I never did get any communication back when I reached out to them about a meeting point. But finally, Alex came to the rescue and gave us the best tour ever. He was so knowledgeable Alex. The guide was wonderful.

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Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence

Susan_S, Nov 2025

Great private tour!

The tour with Samuele was wonderful and he is so knowledgeable about the Florence and Tuscany areas. He gave us a lot of information and facts about the areas we did not know about. It was a fantastic end to a long trip to Greece and other parts of Italy and it was nice to have the private tour with him in a very comfortable van.. He is a great driver too!

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Florence Private Tour with a Local - Highlights & Hidden Gems

Kay_T, Sep 2025

A one-of-a-kind day in Florence

Martina emailed me ahead of time and we planned how to spend the six hour private tour. I think that was the key to the success of the day. We visited her side of Florence, enjoyed the outdoor markets, gardens and specialty stores for art. We went to an amazing place for lunch and later, stopped a wine bar. All this afforded Martina time to share her city with me. I felt like I was not a tourist but visiting with a friend. I have been to Florence before and done all the major sites. This was a unique day that I will never forget.

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Self-guided Bike Tour from Lucca to Pisa

Laura_H, Sep 2025

A great way to get to...

A great way to get to Pisa avoiding the traffic you get to ride the tracks by the river and aqueduct. We used the bikes to see more of Pisa than just the area near the Tower which was very busy. The return route was mainly on minor roads in total it took us 3:30 for the return route. The bikes were comfortable and still had 50% battery when we finished so don’t worry about using turbo if you need it. Overall an enjoyable da

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Not seeing something you are looking for?

When you’ve got limited time and lots to see, booking your own tour guide is the perfect way to maximize your vacation. Such is the appeal of private sightseeing tours in Tuscany, which can take you to any regional highlights you fancy. Have a local expert show you around Florence’s famed Renaissance art galleries and historic street food spots, or be whisked away to countryside wineries and cobblestoned villages via a luxury transfer. Private tours offer activities for every traveler, from food and wine lovers to architecture aficionados and avid cyclists.

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Top Tuscany Private Sightseeing Tours - page 5

1,000+ results

Top Attractions in Tuscany

Florence Duomo (Cattedrale di Santa Maria del Fiore)

Uffizi Galleries (Gallerie degli Uffizi)

Siena Cathedral (Duomo)

Brunelleschi’s Dome (Cupola di Brunelleschi)

Leaning Tower of Pisa

Accademia Gallery (Galleria dell'Accademia)

Florence Duomo (Cattedrale di Santa Maria del Fiore)

Uffizi Galleries (Gallerie degli Uffizi)

Siena Cathedral (Duomo)

Brunelleschi’s Dome (Cupola di Brunelleschi)

Leaning Tower of Pisa

Accademia Gallery (Galleria dell'Accademia)

Florence Duomo (Cattedrale di Santa Maria del Fiore)

Uffizi Galleries (Gallerie degli Uffizi)

Siena Cathedral (Duomo)

Brunelleschi’s Dome (Cupola di Brunelleschi)

What are people saying about Tuscany