cruises on the road in tuscany

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Exploring Tuscany by car opens up a world of unparalleled beauty and timeless charm. Imagine winding roads bordered by cypress trees, leading to vineyard-clad hills and medieval towns perched on hilltops.

Each turn offers a breathtaking panorama, from the sun-kissed valleys of Chianti to the wild beaches of the Maremma and the mystical towers of San Gimignano.

Along the way, you’ll discover hidden gems such as tranquil olive groves, ancient monasteries, and thermal baths nestled in the heart of nature.

Tuscany calls to those who seek beauty in every journey, to travelers who find joy in the open road. This is where you feel most alive, amidst landscapes that whisper tales of centuries past and vistas that capture the heart.

Go where you feel most alive.

the most popular car cruises

Let the roads of Tuscany guide you through vineyards, historic towns, and serene countryside, each mile bringing you closer to the soul of Italy. Here, every path promises discovery, and every sunset brings a sense of belonging.

Secrets of Chianti Classico: A Wine Lover’s Retreat

Uncover the secrets of the Chianti Classico region with exclusive tastings and visits to the top wineries, nestled in scenic landscapes.

Chianti Classics: A Wine Connoisseur’s Tour

Delve into the heart of the Chianti wine region with a tour dedicated to tasting renowned varietals and exploring historic estates.

Lucca’s Vintages & Ramparts: A Cultural Sip & Stroll

Combine the joys of wine tasting with a historic exploration of Lucca’s ancient defense systems on this unique cultural tour.

Etruscan Wonders: A Timeless Journey

Step back in time on a captivating tour exploring the rich Etruscan history and archaeological marvels dotted throughout the region.

Tuscan Wine Odyssey: Exclusive DOCG Tour

Savor the finest DOCG wines of Tuscany on a guided journey through legendary vineyards and charming ancient wineries.

Tailored Tuscan Treasures

Experience Tuscany your way. Our personalized tours invite you to tailor your journey through the vineyards, historic towns, and enchanting landscapes, ensuring your Tuscan adventure is as unique as you are.

Beyond Tuscany: Iconic Italian Journeys

Venture beyond the Tuscan borders with Cruises on the Road in Tuscany as your guide, exploring Italy’s celebrated landscapes and vibrant cities. Each journey unfolds Italy’s rich tapestry, from the dramatic coastlines of Cinque Terre to the historic splendors of Rome and the untouched charm of Southern villages. With us, every road leads to an unforgettable adventure, and each destination deepens your connection with Italy’s enduring allure.

Splendors of Northern Italy: A Comprehensive Journey

Explore the heart of Northern Italy with an all-inclusive tour, from the bustling cities to serene lakes and historic landmarks.

Southern Italy Unveiled: Grandeur & Tradition

Discover the rich heritage and stunning landscapes of Southern Italy, featuring exclusive insights into local customs and hidden gems.

Cinque Terre's Hidden Pearl: Coastal Splendor

Experience the enchanting beauty of Cinque Terre with a tour of its picturesque villages, stunning coastlines, and vibrant local life.

Port of Call Adventures: Tailored Shore Excursions

Maximize your cruise with tailor-made shore excursions at each port of call, offering a perfect blend of culture, history, and leisure.

Ultimate Italian Escape: Grand Tour Experience

Immerse yourself in the ultimate Italian adventure, encompassing iconic sites, culinary delights, and cultural treasures across the country.

Custom Italian Escapes

Discover Italy on your terms. From the rolling hills of Tuscany to the bustling streets of Rome, we offer customizable tours that cater to your interests and pace, crafting a uniquely personal Italian experience.

Live life with no excuses, travel with no regret

Discover Tuscany Through the Eyes of Our Travelers

Here, we share their genuine experiences and reviews, highlighting the memorable journeys across Tuscany’s stunning landscapes and historic cities. Let their stories guide your next adventure in the heart of Italy.

Pubblicato su Tripadvisor
Beth S profile picture
Beth S
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Wonderful Italian anniversary trip! Rick and Asia helped us plan a phenomenal 10 year anniversary trip. We were able to see an incredible amount of sights and cities in our 8 day trip. Our trip included visiting Venice, Florence, Rome, Chianti region, Parma, and Lucca. Our trip was enhanced by wonderful tour guides including Francesca in Rome where we got to see the Vatican and colosseum in a personalized way. We sent home wine from our wine tasting at Le Palaie with the owner, Andre, in Greve Chianti region. We savor every sip as we reminisce on our beautiful trip. In summary- we highly recommend Rick and his team to plan your trip!
Pubblicato su Tripadvisor
Kyle Y profile picture
Kyle Y
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Wonderful Experience. Highly Recommend! From the moment we reached out to Riccardo and his team, we felt comfortable and prepared for our family trip to Italy. He and Asia helped us craft an itinerary and iterate on that itinerary both prior and during our visit to make it incredibly memorable, overall! From airport transfers, to train recommendations, to tour guides (Valentina was great in Rome at Colosseum + Vatican, and the golf cart ride is a must way to see the sights), everything was well organized and thorough. A huge highlight of Florence and Tuscany was the day spent with Riccardo, himself, and meeting his son Lorenzo (our driver) as well. We were picked up in Florence and visited Lucca for lunch and a walking tour, on our way to Forte dei Marni and Club Pennone Beach Club -- which was a last minute add because of the heat and desire to cool off in the sea! On our way back, we saw Pisa at Sunset and got all the photos needed. This day was one that will live in our minds forever! We'll stay in touch with Rick and plan to recommend the company to any friends and family looking to match our wonderful experience!
Pubblicato su Tripadvisor
amanda b profile picture
amanda b
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Amazing and seamless experience Riccardo and Asia did an AMAZING job planning and coordinating a rather complicated and very last minute trip for my family. With less than 2 week’s notice (I do not recommend), they arranged transportation and tours as my party of 6 adults and a 6month old baby made our way through Italy. From Rome to Tuscany, Tuscany to Florence and Florence to Venice we were transported in comfort and safety (they even provided a car seat) and had some truly memorable tours along the way. Rather than just driving from one destination to the next, we made use of our time on the road and got to see smaller towns and really explore the less known attractive Italy has to offer. Riccardo is incredibly knowledgeable and his enthusiasm for Italy’s history and culture makes the experience truly worthwhile. We toured Luca and Pisa in one day and got a unique perspective of each ( definitely different than the experiences we heard about from friends who stopped with a cruise ship). We also toured amazing locally owned farms, wineries, and truly felt immersed in the culture which varied as we made our way through the country. Riccardo became part of our family and even held my baby so we could all finish lunch. I cannot recommend this company enough!
Pubblicato su Tripadvisor
Steven R profile picture
Steven R
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Family Italy trip Ricardo was very knowledgeable and kind. He made our trip 10x better then we anticipated and I can’t recommend him enough
Pubblicato su Tripadvisor
CanadianAtLarge1000 profile picture
CanadianAtLarge1000
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Wonderful experiences with the Cruises on the Road team We cannot say enough good things about our experiences with Riccardo and his team - Asia, Lorenzo, Alex, and Enzo. Thank you, all! We were a group of four friends, without a car, and Riccardo and his drivers led us on some wonderful adventures while we were in Tuscany, ending with a fun-filled ride to Venice, via a tour around Bologna. The tour to San Gimignano and Siena was excellent as was a day spent in and around Greve in Chianti. Ask Riccardo to take you to La Palaie winery - fabulous wine and wonderful hospitality. Everything was expertly and perfectly planned. Riccardo is the consummate professional. Along with being highly knowledgeable and accommodating, he is lots of fun. We recommend, without hesitation, Cruises on the Road as your Tuscan touring partner!
Pubblicato su Tripadvisor
philip l profile picture
philip l
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Outstanding Tour of Lucca area with Riccardo & team We were a group of seven travelers who had an outstanding experience touring Lucca and the surrounding area with Riccardo and his team. Every step along the way was thoughtfully planned and delivered with big passion for the region. Riccardo led us on a fantastic guided trip to Cinque Terre. His deep knowledge of the area, easygoing personality, and ability to move through the villages without ever making us feel rushed made the day one of the true highlights of our stay. The experience ended with an unforgettable dining stop—authentic, local, and genuinely unique, the kind of place only a real insider would know to share. Lorenzo’s tour of the Carrara marble quarries was equally impressive—informative, engaging, and providing the local color we could not have experienced on our own. A special mention goes to Bruno, our driver, who was professional, friendly, and very skilled on the winding local roads. And behind the scenes, Asia kept everything running smoothly with quick, responsive support. Overall, this team delivers the perfect blend of expertise, hospitality, and local authenticity. If you’re visiting Lucca or the surrounding region, you won’t find a better group to explore with. Highly recommended.
Pubblicato su Tripadvisor
Tina Y profile picture
Tina Y
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Riccardo is the best!!!! We had the pleasure of spending 3 days in Tuscany with Riccardo as our tour guide. It was an amazing experience and we truly appreciated the care and recommendations you gave us. We loved the sandwiches in Lucca, the delicious seafood in Cinqe Terra, the lemon farm, Sienna and San Gimignano. We didn't want to leave. Having a private tour made our experience extra special to go at our own pace.
Pubblicato su Tripadvisor
Ashley G profile picture
Ashley G
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Tuscan adventure Rick planned the most amazing Tuscany tour to help us celebrate our 25th wedding anniversary. We learned how Parmigiano Reggiano is made, saw the mountains where marble is quarried, and experienced the walled city of Lucca. We wish we could have stayed longer, learned more about the region, and experienced more of Rick's stories!
Pubblicato su Tripadvisor
Chad D profile picture
Chad D
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Tuscany get away Riccardo and Lorenzo, father and son team did a wonderful job showing us the countryside in Tuscany. They are very knowledgeable of the history and know where to find the hidden gems that we otherwise would have missed entirely. We visited the Greve in Chianti at Montefioralle, a nearby Italian meat shop and a private engagement at the beautiful Le Palaie Winery! I highly recommend both of these authentic Italians.
Pubblicato su Tripadvisor
Bruce S profile picture
Bruce S
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Amazing month in Tuscany As a seasoned traveler, I am extremely particular about who I trust to assist with designing and coordinating my travel experiences. Riccardo is, without question, one of the finest travel professionals I have encountered in all of my years of travel. From the very beginning, he was pleasant, knowledgeable, responsive, and genuinely committed to making our Tuscany experience exceptional. Together with his assistant, Asia, they carefully listened to everything we hoped for and ensured that every detail of our trip was thoughtfully arranged and flawlessly executed. What truly set Riccardo apart was his personal attention and dedication. Not only was he always available to help, but he even took the time to meet us personally in Lucca for a wonderful dinner, which added such a warm and memorable touch to our experience. I would strongly recommend Riccardo and Cruises in Tuscany to anyone considering travel throughout Tuscany. If you are looking for a tour operator and guide who combines professionalism, local expertise, responsiveness, and genuine hospitality, you will be in excellent hands with Riccardo and his team.

frequently asked questions

Bespoke Day Trips: Enjoy private or semi-private excursions across Italy in luxury vehicles, complete with English-speaking driver-guides and door-to-door service.

Custom Grand Tours: Tailor your dream Italian journey, from Florence to the Amalfi Coast, with personalized itineraries crafted to your preferences, including all transport and accommodation.

Efficient Planning: Our expert planning optimizes your time, crafting perfect routes to enhance your vacation experience.

Expertly Trained Guides: Benefit from our academy-trained driver-guides, offering in-depth insights and stories.

Unique Experiences:

Venture off the beaten path.

Savor exclusive wine and culinary experiences at small, organic family-run locales.

Enjoy scenic transfer tours, integrating sightseeing en route.

Celebrate special moments with unique experiences like balloon rides or gondola excursions.

Seamless connections to major transport hubs, skip-the-line access, and guided tours.

Embark on a journey where every detail is tailored to your discovery and delight. We're not just your guide; we're your gateway to unforgettable Italian adventures.

The English-speaking Driverguide can help you travelling all around the country, thanks to his knowledge of the territory and his cultural and historical background.

He can also help you understand the country lifestyle, provide assistance, tips and suggestions. He drives you by car, in order to make better use of time.

According to the Italian Law, the driver cannot leave his car unattended, but thanks to special permits, he is able to move quickly inside the city and reach every destination.

Your tour might be accompanied by a trainee, since Cruises on the Road in Tuscany always trains new Driverguides.

The local tourist guide has the task to walk you and to show and give you all the historical explanations, the information required about all monuments, museums and sites of the area or town for which he is licensed.

We cruise you… by car!!!

WE PROUDLY ACCEPT PAYMENTS VIA CREDIT/DEBIT CARD AND VIA PAYPAL.

For the confirmed services, we require a deposit equal to 40% of the total amount and the balance 30 days before your arrival date.

While the payment of meals, wine/oil tastings, entrance tickets for monuments, museums, churches or any other attraction, transport tickets and other services are to be paid directly to the service supplier.

30 days prior to your scheduled service/departure, no cancellation fee applies, with the exception of museum, event tickets and bank transfers will not be refunded.

Any cancellation within 30 days of your scheduled service/departure and before the 10th day of your scheduled service, a 50% cancellation fee will apply.

Any cancellation within 10 days of your scheduled service/departure a 100% cancellation fee will apply.

Cancellation fees for the extra services are applied according to the cancellation policy of the services supplier.
Booking fees , museum entrances and bank transactions are never refundable .

Cancellation fees for hotel rooms, train tickets and balloon service are applied according to the cancellation policy of the service supplier.

To book our services, you can contact us by e-mail or make your request through our booking forms. Click here

Entrance fees to the historical sites are not included in our fees, except where specifically mentioned in the description of the tour.

Only in some cases, in order to skip the long lines at the ticketing office, is necessary to book the entrance tickets ahead of time. To ensure the success of the trip and follow the schedule of the day, we prefer to arrange this for you. Thanks to our experience, your trip will go smooth and you will spend a day in full comfort and relax.

Please note, that we do not apply any agency fee on the entrance tickets.

Usually it is possible to join a tour sharing the van with other few persons (maximum 8), in order to optimize costs and meet new people.

At least for the next few months and until the easing of the emergency due to the COVID-19 pandemic, we will not carry out any kind of shared excursions or transfers. We will only deal with small private groups considered as families, using vehicles up to 8 passengers not to the maximum of their capacity.

Tuscany’s landscape is a canvas painted with the hues of history, culture, and natural beauty, making every road trip an unforgettable journey through the essence of Italy.