Tuscany Road Trip Through Vineyards & Rolling Hills

Italy Route Planning & Car Rental

Tell us your dream trip

We design your custom itinerary

You travel seamlessly

Rolling Hills, Vineyards & Timeless Villages

Tuscany is a landscape of sun-kissed hills, cypress-lined roads, and charming medieval villages. Explore vineyards producing world-class wines, wander through historic towns like Siena and San Gimignano, and savor cuisine that celebrates local flavors. Driving here is an immersive experience, with each turn unveiling postcard-perfect landscapes of olive groves and rustic farmhouses.

At Kensington, we take care of your car rentals, accommodations, restaurant reservations, and thoughtfully planned routes. Tuscany embodies timeless Italian elegance, where rolling hills, historic towns, and a rich cultural heritage create an unforgettable setting. A luxury self-drive tour invites you to explore at your own pace, with a premium vehicle reserved in your name and ready upon arrival at your hotel or the airport.

Seamless Planning

Your route, vehicle, accommodations, and logistics are all pre-planned and managed exactly the way you want.

Vehicle Arrangements

Experience the journey in comfort and style with your arranged vehicle of choice.

24/7 Support

Travel with the confidence that we’re always available with 24/7 support, should you ever need it.

Private Guided Tours

Discover the very best of each destination with an expert private local guide ready when you arrive.

Kensington Tours: Personalized and Expertly Guided

The Italian Lakes by Car: Milan, Como and Maggiore

Drive Milan to the Italian Lakes at your own pace, from Como's villa shores to a three Michelin-starred table

8 DAYS FROM$15,229per person

The Italian Lakes by Car: Milan, Como and Maggiore

Wind from Milan through Lake Como's elegant shores to the mountains of Lake Maggiore.
Set sail on a private Lake Como regatta, taking in villa-lined shores and mountain views.
Dine at Villa Crespi, one of Italy's only three Michelin-starred restaurants, on Lake Orta.

8 DAYS FROM$15,229per person

The Italian Lakes by Car: Milan, Como and Maggiore

Wind from Milan through Lake Como's elegant shores to the mountains of Lake Maggiore.
Set sail on a private Lake Como regatta, taking in villa-lined shores and mountain views.
Dine at Villa Crespi, one of Italy's only three Michelin-starred restaurants, on Lake Orta.

8-Day Tuscany Road Trip Through Italy's Val d'Orcia

Drive Tuscany's bucket list scenic routes, from Chianti vineyards to medieval hilltop towns

8 DAYS FROM$8,660per person

8-Day Tuscany Road Trip Through Italy's Val d'Orcia

Take the wheel through Tuscany's vine-covered hills and cypress-lined roads at your own pace.
Walk Siena and Florence with your private guide, from Gothic duomos to Uffizi masterpieces.
Climb San Gimignano's medieval towers and explore its UNESCO-listed streets at leisure.

8 DAYS FROM$8,660per person

8-Day Tuscany Road Trip Through Italy's Val d'Orcia

Take the wheel through Tuscany's vine-covered hills and cypress-lined roads at your own pace.
Walk Siena and Florence with your private guide, from Gothic duomos to Uffizi masterpieces.
Climb San Gimignano's medieval towers and explore its UNESCO-listed streets at leisure.

9-Day Dolomites Road Trip: Venice to Verona

Private gondolas, alpine cooking, and the Dolomites' most scenic drives, fully arranged

9 DAYS FROM$10,250per person

9-Day Dolomites Road Trip: Venice to Verona

Drive the Dolomites at your own pace, through jagged peaks, alpine lakes, and high passes.
Discover Venice and Verona with private guides, from Grand Canal palaces to Juliet's balcony.
Pause at turquoise Lago di Braies, then learn to make Knödel in a South Tyrolean farmhouse.

9 DAYS FROM$10,250per person

9-Day Dolomites Road Trip: Venice to Verona

Drive the Dolomites at your own pace, through jagged peaks, alpine lakes, and high passes.
Discover Venice and Verona with private guides, from Grand Canal palaces to Juliet's balcony.
Pause at turquoise Lago di Braies, then learn to make Knödel in a South Tyrolean farmhouse.

Amalfi Coast by Car: A Campania Road Trip

From Pompeii to Positano, the Amalfi Coast by car, fully curated and privately arranged

8 DAYS FROM$17,184per person

Amalfi Coast by Car: A Campania Road Trip

Drive the Amalfi Coast road at your own pace, from Pompeii's ruins to clifftop Positano.
Explore Capri's waters and sea caves by private boat, with time to go ashore at leisure.
Stay at the legendary Le Sirenuse in Positano and the Anantara Convento di Amalfi.

8 DAYS FROM$17,184per person

Amalfi Coast by Car: A Campania Road Trip

Drive the Amalfi Coast road at your own pace, from Pompeii's ruins to clifftop Positano.
Explore Capri's waters and sea caves by private boat, with time to go ashore at leisure.
Stay at the legendary Le Sirenuse in Positano and the Anantara Convento di Amalfi.

Sicily by Car: Ancient Temples to Mount Etna

Sicily's most extraordinary stops, privately guided, fully arranged, and driven at your pace

8 DAYS FROM$13,610per person

Sicily by Car: Ancient Temples to Mount Etna

Drive Sicily's clifftop roads, baroque hill towns, and ancient landscapes at your own pace.
Walk the Valley of the Temples at golden hour with a private archaeologist guide.
Ride Etna's lava fields by e-bike, then taste wines shaped by the volcano's fertile terrain.

8 DAYS FROM$13,610per person

Sicily by Car: Ancient Temples to Mount Etna

Drive Sicily's clifftop roads, baroque hill towns, and ancient landscapes at your own pace.
Walk the Valley of the Temples at golden hour with a private archaeologist guide.
Ride Etna's lava fields by e-bike, then taste wines shaped by the volcano's fertile terrain.

7-Day Private Puglia Road Trip

From Alberobello's trulli to clifftop Polignano, drive Puglia at your own pace with curated routes

7 DAYS FROM$7,620per person

7-Day Private Puglia Road Trip

Wind through Puglia's trulli-dotted valleys and whitewashed hill towns at your own pace.
Taste ancient olive oil at a family estate, then explore the White City of Ostuni at leisure.
Walk baroque Lecce with a local expert, where every golden facade tells a different story.

7 DAYS FROM$7,620per person

7-Day Private Puglia Road Trip

Wind through Puglia's trulli-dotted valleys and whitewashed hill towns at your own pace.
Taste ancient olive oil at a family estate, then explore the White City of Ostuni at leisure.
Walk baroque Lecce with a local expert, where every golden facade tells a different story.

8-Day Umbria Road Trip: Rome, Orvieto and the Hill Towns

From Rome's ancient piazzas to Umbria's hilltop abbeys, drive central Italy at your own pace

8 DAYS FROM$6,965per person

8-Day Umbria Road Trip: Rome, Orvieto and the Hill Towns

Drive from Rome's ancient piazzas into Umbria's hilltop roads and lake horizons, at your pace.
Drift above Umbria at dawn in a private hot air balloon, ending at a winery for breakfast.
Explore Assisi with a private guide and spend nights in a converted 11th-century abbey.

8 DAYS FROM$6,965per person

8-Day Umbria Road Trip: Rome, Orvieto and the Hill Towns

Drive from Rome's ancient piazzas into Umbria's hilltop roads and lake horizons, at your pace.
Drift above Umbria at dawn in a private hot air balloon, ending at a winery for breakfast.
Explore Assisi with a private guide and spend nights in a converted 11th-century abbey.

“I have had great experiences working with Kensington. Jenny planned a great trip and worked to meet all my requests. The drivers and guides were also great. This was my third trip with Kensington and not my last!”

– customer

“Thank you so much! Everything was fantastic. We want to go back again and again and see all the rest of Italy. Everyone was great and we could not have enjoyed our stays as much if you had not planned everything for us so perfectly!”

– Marybeth Durkin

“It was so easy to work with Kensington Tours...the experience was consistent, timely, and allowed us to have an amazing trip! The personalized experience was perfect and we are looking at doing another trip with Kensington in the near future.”

– Emese Nicholson

“This is our second time using Kensington. And again, it was a flawless, unforgettable and, at risk of being overly dramatic, life-affirming experience. Thanks to Courtney and the team for once again exceeding our expectations. ”

– Bob O.

“Coordinated trip options and transfers, wonderful hotel choices even when we had to opt for ‘different’ city. Great pre and post communication w advisor. Suggested side trips ( fiord speed boat cruise) campy but very fun”

– Debra

“From top to bottom all staff are knowledgeable with excellent customer service. Ownership looks out for you even when you are not with them through direct contact at all times ”

– Mitch

“Their attention to detail and the knowledge of the their home. My wife and I made a trip to Bali. Our guides Ardita and Pande were so amazing. On time, with the need to make anything possible for you! Thanks”

– G. Perentis

“What a trip of a lifetime. Gonzalo was an amazing guide. He was kind,caring, and very informative. Hosea is the best driver in Cusco. We appreciated the attention to detail and always having someone keeping us informed on what was going on next. ”

– sarah lake

Exclusive Perks When you Book with Kensington

Personalized Journeys, just for you

Every itinerary is designed to match your interests and pace.

Exclusive Skip-the-Line Access

Enjoy priority entry to the world’s most iconic sights.

Hidden Gems & Insider Experiences

Discover places and moments only locals know or experience.

24/7 Support

Travel with peace of mind knowing Kensington experts are just a call away throughout your journey.