Top Tuscany Private Sightseeing Tours

Florence makes an ideal base from which to explore the beautiful region of Tuscany—but organizing travel and tickets individually is time-consuming. On this private tour, zip around the Tuscan countryside by private vehicle with your guide. Visit top attractions including UNESCO–listed Pisa and medieval Siena, and gaze out over vineyards and olive orchards in Chianti.

Discover the delights of Tuscany on a private day trip from Florence. With a knowledgeable private driver, travel through the renowned Chianti wine region to visit the towns of Siena and San Gimignano. See famous landmarks like Siena’s Piazza del Campo, home to the annual Palio horserace, and the medieval hilltop towers of San Gimignano.

Seeing the sights of Florence can involve a lot of walking. Cover the ground, including hidden lanes that traditional cars can’t enter, without wearing out your shoe leather on this private tour. Open sides offer wraparound views of the city’s UNESCO World Heritage–listed historic center. Upgrade to the panoramic tour to include a stop at a romantic fountain and Piazzale Michelangelo for sweeping rooftop vistas.

Discover Cortona, the town made famous by the novel Under the Tuscan Sun, during a prvate walking tour. With a local guide, you’ll hear fun facts about the book and the film as you stroll through the Roman square of Piazza della Repubblica and see landmarks such as Teatro Signorelli and the Palazzo Comunale. Choose between a morning or afternoon tour when you book.

Discover Pisa and its picturesque environs by bike during this private self-guided cycling tour. Follow an easy-to-use, GPS-based smartphone app as you ride on bike lanes from the city out to the Tyrrhenean sea. Explore the area at your own pace, stopping wherever and whenever you want, with bicycle rentals included.

Commence your journey at the iconic Piazza del Campo, immersing yourself in the vibrant atmosphere of Siena's renowned square. Delve into the city's history at Palazzo Pubblico, an architectural marvel serving as the seat of governance. Meander through historic streets, passing Palazzo Tolomei and Palazzo Salimbeni, both UNESCO-listed treasures. Continue to the Basilica of San Domenico, housing the relics of Saint Catherine, before a visit to the Sanctuary of St. Catherine of Siena. Admire the Baptistery and opt for a guided tour of the awe-inspiring Siena Cathedral, adorned with masterpieces of Italian artistry.

The Cinque Terre and Pisa are two popular excursions from Florence, but visiting both in one day by public transportation is a challenge. Save time and skip the stress of the train with this day trip that includes hassle-free hotel pickup in Florence. Relax and enjoy the views along the drive, then explore the Cinque Terre villages and Leaning Tower of Pisa at your own pace before returning to Florence.

Florence's finest views of the Duomo and terracotta rooftops come from the hills surrounding the city, and this private golf cart tour takes in the best of them. Roll up to Piazzale Michelangelo and San Miniato al Monte, with photo stops along the way, then settle in for a picnic in the Arcetri hills, one of the quieter corners above the city.

Siena is one of Tuscany's most fascinating hill towns, but most visitors check off a handful of famous sights and move on. Get a more in-depth, personalized introduction to this medieval city on this private walking tour, fully customized to your pace and interests. Focus on the historic architecture, traditional Palio festival, or local food scene, or combine culture and cuisine to create a unique itinerary. Choose an express tour of just a few hours or a full-day deep dive that takes you to little-known gems most tourists miss.

Discover the best of Florence's city center, without the hassle of planning, on this private tour by golf cart. Explore the city without long walks or crowded buses, and breeze between historic neighborhoods, hidden corners, and stunning viewpoints, including Piazzale Michelangelo. Enjoy open-air views, capture plenty of photos, and hear about the city’s history and culture from your guide.

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.

Get the most out of your visit to Florence's Accademia Gallery—and ensure your sightseeing logistics are totally hassle-free—on this private guided tour that also includes skip-the-line admission tickets. This must-visit museum can be crowded or sold-out during the high season, but booking a private tour means guaranteed entry and quick access. Once inside, listen to in-depth commentary and get up close and personal to Michelangelo's David, plus other Renaissance masterpieces.

Make the most of your time on this private full-day tour from Florence. Travel along the Chianti road to Siena to see the town’s famous Piazza del Campo and Gothic cathedral. Then, head to San Gimignano with time for sightseeing and shopping. The tour finishes in Pisa, where you’ll have the chance to visit the Leaning Tower of Pisa. Enjoy flexible scheduling and hotel pickup included.

Avoid the hassle of navigating Lucca’s historic center on foot or missing hidden local spots on your own with a relaxed bike tour through Lucca. Cycle along the city’s ancient walls and quiet streets while a guide brings local history and food culture to life. Pause to enjoy regional wine, brunch, snacks, and Tuscan specialties without needing to plan stops or reservations.

See the top sights in Siena without the hassle of a guidebook or map with this small-group walking tour through the medieval old town. Join your local guide for a stroll along picturesque historic lanes to take in landmarks like the Piazza del Campo, Basilica of San Domenico, and Sanctuary of St. Catherine of Siena. Opt to add on a visit to the city’s magnificent Cathedral, rich in artworks by Renaissance masters.

Visit the Tuscan cities of Pisa and Lucca on this private day trip from Florence for groups of up to eight people. See iconic landmarks such as the Leaning Tower of Pisa (entrance fee extra), one of Pisa’s many historical structures, and take a relaxing walk through Lucca’s picturesque streets. This day trip is a great way to see more of Tuscany with comfortable transportation and hotel pickup from Florence if you’re short on time during your stay in Italy.

The best way to see the Tuscan countryside is by car, but renting a vehicle means you have to keep your eyes on the road, instead of on the area’s bucolic beauty. Leave the driving to someone else when you head out on a private excursion to Siena and San Gimignano. Going with a guide also means you learn more about the area than you would on your own.

When your cruise ship docks in Livorno, don't waste time waiting for buses or waiting in line for attractions. Instead, maximize your time on a full-day private shore excursion to the Cinque Terre and Pisa. Your tour leader takes you to three Cinque Terre villages on the Mediterranean coast, leaving time to explore, swim, and have lunch. Afterward, stop to see the Leaning Tower of Pisa, a top attraction in Italy. This private tour ensures you'll receive undivided attention, too.

Cover a lot of ground in a short amount of time when you book this private tour of Florence's historic sights via golf cart. While a guide shares an insider's perspective on the culture and history of the birthplace of the Renaissance, you sit back and relax in the roomy electric cart. Meet the tour at a central point in the city; choose from morning or afternoon tour departures.

Take the guesswork out of reaching the UNESCO-listed fishing villages of the Cinque Terre on this private shore excursion that includes round-trip transfers from the Livorno cruise port. Visit the coastline independently by train or ferry (own expense) or upgrade for a full-day guide to help you navigate the local public transportation between the villages stress-free.

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.

I'm Simone Vergamini, "Best Sommelier of Tuscany 2023", 3rd place at the Best Sommelier of Italy 2018, 2021, 2022, and it will be a pleasure to accompany you to discover the best wineries. During the journeys I will tell you the history of the area and its traditions, the vines and the peculiarities of the area. It will be a pleasure to answer your questions and I will put all my knowledge at your service so that you return home enriched. We will visit 2 wineries representative of the denominations of the province of Lucca and, after touching the vineyards and visiting the cellars, we will taste the wines produced and local delights! I love my job and constantly travel to discover small wineries "Light lunch" option includes lunch + 5/8 wines depending on cellar For pick-ups in places more than 15 km from the center of Lucca will be calculated a surcharge that I will inform you in advance, to be paid by credit card at the end of the tour

Explore one of Florence’s top museums without wasting time in line, all thanks to this private Accademia Gallery tour that also includes fast-track admission. Meet your guide and zip past the crowds to dedicate more time to admiring Michelangelo’s “David” and other masterpieces inside the galleries. As you go, learn insider stories about the lives and works of famed Renaissance artists that you wouldn't encounter if visiting alone.

The Uffizi Gallery is known for its magnificent collection of Italian Renaissance art, but it can be overwhelming to visit on your own. This private, art historian-led tour takes you straight to the highlights of the celebrated gallery. Make the most of your visit by learning more about famous works by Giotto, Botticelli, Michelangelo, Titian, and other masters, as well as lesser-known pieces.