“Tuscany is the poetry of the earth”
Explore dreamy Tuscany and the captivating Cinque Terre area of Italy with Tripmasters’ unique Chauffeured Collection Series packages. Our package includes private car service between your destinations, with stops at charming towns, local attractions, UNESCO World Heritage Sites, and more! Let us help transform your journey into an unforgettable experience as our friendly local drivers share their insights and offer tips on what to do at your destinations. With our door-to-door service, you can sit back and enjoy the ride!
Florence & Siena: You will enjoy your first nights in Tuscan staples. Florence is the capital of Tuscany and the cradle of the Renaissance. This incredible history is palpable everywhere you look; the city itself is an open-air museum. It’s home to masterpieces like Michelangelo’s David at the Accademia, Botticelli’s Birth of Venus and Primavera at the Uffizi Gallery, and Brunelleschi’s magnificent Duomo. Beyond the art, landmarks like the Ponte Vecchio (Old Bridge), Palazzo Pitti, and the Boboli Gardens are instantly recognizable and offer stunning beauty. Florence also boasts incredible Tuscan cuisine, from hearty bistecca alla fiorentina to delicious gelato, and is a significant hub for high-quality leather goods and fashion. Siena offers a remarkably well-preserved medieval cityscape. Its historic center is a UNESCO World Heritage site. Siena’s Duomo (Cathedral) is a breathtaking example of Italian Gothic architecture, with intricate facades, stunning interiors, and a rich history. Compared to Florence, Siena often feels a bit more intimate, offering a charming and authentic Tuscan experience. Both cities offer a deep dive into Italy’s artistic, historical, and culinary heritage, making them essential stops for travelers to Tuscany.
However, we don’t want you to experience just these “essential” Tuscan cities. We want to help you form a deeper connection by visiting cities that many people often overlook. You don’t need to stay the night; with our signature door-to-door transfers, you can stop for a brief visit, wander and explore, grab a snack (the crema Santa Fina at Gelateria Dondoli in San Gimignano is a personal favorite!), shop, and meet locals! During your private transfer between Florence and Siena, you will visit Monteriggioni and San Gimignano, two captivating Tuscan hill towns that offer distinct yet equally enchanting experiences. Monteriggioni is famous for its almost perfectly preserved circular wall, punctuated by 14 towers, as mentioned by Dante Alighieri in his Inferno; the UNESCO-listed San Gimignano is instantly recognizable by its impressive medieval towers, which were symbols of wealth and power for the noble families, creating a unique and dramatic skyline.
Cinque Terre: After spending time in charming Tuscany, you’ll enjoy a few days in the Cinque Terre area. Cinque Terre is truly special and “epic” for several compelling reasons, making it a unique and unforgettable destination: Its most iconic feature is the collection of five ancient, colorful fishing villages (Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore) precariously perched on rugged cliffs overlooking the sparkling Ligurian Sea. This dramatic, almost gravity-defying, setting is breathtakingly picturesque. Despite its popularity, Cinque Terre retains a strong sense of its roots as a fishing village and Ligurian culture. Due to regulations prohibiting cars in some of the villages, not all are accessible directly via private transfer. We strongly recommend staying in La Spezia, where you can easily take the train to the five magnificent villages that comprise the UNESCO-preserved cultural landscape.
We suggest not trying to see all five towns in one day (which is why we have arranged several days’ stay in the area), while it IS possible, it is exhausting – trust us, we’ve done it! We also recommend making dinner reservations in advance at one of the cities. You’ll find charming local restaurants serving fresh seafood, traditional pesto, and local wines from the terraced vineyards, but they are small and fill up quickly!
Along the way, we have arranged visits to Lucca and Colle Val d’Elsa. Lucca is renowned for its well-preserved Renaissance walls, medieval towers, and impressive churches, while Colle Val d’Elsa is one of the leading centers for crystal glass production in Italy. It’s also well-known for its medieval history and architecture. The upper town, Colle Alta, is a gem of medieval architecture. You’ll find ancient walls, towers, and historic palaces.
Finally, after staying in Cinque Terre, you’ll return to Florence for your flight home, but we aren’t quite done showing you the best of Tuscany yet! Tripmasters has a few surprises up our sleeves for you. You’ve undoubtedly heard of the famous Leaning Tower of Pisa, and we’ll make sure you visit Pisa to see it up close for yourself. However, during your visit, be sure to enjoy the other architectural marvels in Piazza dei Miracoli, including the majestic Cathedral and the intricate Baptistery. Lastly, you’ll visit Montecatini Alto, a historic medieval hilltop village where you can explore the ruins of its ancient fortress or wander Piazza Giusti, the heart of the village – a picturesque square lined with quaint restaurants, cafes, and artisan shops.
Tripmasters’ Chauffeured Collection Series Tuscany & Cinque Terre vacation package offers you the opportunity to see and do more without requiring additional overnight stays. You don’t always need to stay in a city to experience and enjoy it – ultimately, our packages save you time and money while allowing you to have a more engaging and authentic getaway!
Additional Chauffeured Collection Italy Vacation Packages
What is a Tripmasters Chauffeured Collection Transfer?
Tripmasters’ Chauffeured Collection Transfers are private, door-to-door transfers between cities. This service replaces commonly used alternative methods, such as trains, buses, or rental cars. It also gives you the opportunity to explore sights and attractions along the way. We drive, you discover.
Who are the drivers? Do they speak English?
The drivers are locals who are familiar with the cities you are visiting, as well as any stops included. While they are not guides, they are more than happy to discuss their personal knowledge and make recommendations. Our partner drivers speak English in addition to their native language, so if you’re looking to practice your Italian, go ahead!
Additionally, all drivers must submit their traffic records. All cars must be less than ten years old, in excellent operating condition, and insured as required by local law. Drivers must provide the registration, insurance, and technical inspection record. And because the drivers are locals, they’re familiar with the rules and customs of the road. This provides a safer, more relaxing experience for you.
Will the driver provide a child car seat?
Everywhere except the USA, drivers will supply appropriate child seats (just let us know during booking). In the USA, certain states require you to supply your own child seats.
What if I need more time at one of the stops on the day?
We understand that sometimes it’s hard to tear yourself away from your sightseeing stop. If you find you’d like extra time, please make arrangements directly with your driver. There will be an hourly fee based on the country in which you are traveling. While they’ll do their best to accommodate, sometimes their schedule won’t allow for them to stay longer.
What type of vehicle will I get?
You will receive the vehicle that best suits the number of travelers in your group, ranging from sedans to vans for groups of up to six. Depending on where you travel, you may end up with anything from a sedan comparable to a Toyota Corolla to a Mercedes V-Class. While the exact model may vary, we always ensure that the vehicle provided meets your needs in terms of safety, reliability, and comfort. You may be upgraded to a larger vehicle class free of charge depending on availability. Since the largest vehicle seats six, for groups larger than six, a combination of vehicles will be used. We will send you the exact vehicle details a few days before your trip.
Where will my driver pick me up?
Your driver can pick you up at your hotel, apartment, or any other pick-up point accessible by car. This also applies to your drop-off location. No need to worry about buses, cabs, or other connections – we provide door-to-door service! If you happen to be in a pedestrian-only area, your driver will meet you at a designated pick-up location.
Will my driver call me to confirm pick-up?
Your driver will meet you at the agreed time and place and won’t be contacting you before, unless necessary. You’ll receive a reminder with your driver’s name and mobile number a few days before departure in case you need to contact them.
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