Drive Sicily exceptionally.

Curated, small-group driving journeys through Sicily featuring legendary roads, authenic local connection, memorable dining, and efforless planning.

Not a tour, an Entry Point.

More than a Road trip

More than A Road Trip

Drive roads most travelers never find.
Meet people most visitors never meet.
Experience a Sicily most itineraries miss.

Drive roads most travelers never find.
Meet people most visitors never meet.
Experience a Sicily most itineraries miss.

Legendary roads, real access

Legendary roads, real access

Travel routes shaped by history, taste regional cuisine, and discover hidden gems.

Every stop is designed to immerse you in the real culture, not the tourist version.

Travel routes shaped by history, taste regional cuisine, and discover hidden gems.

Every stop is designed to immerse you in the real culture, not the tourist version.

Drive what moves you

Drive what moves you

Rent the vehicle that matches your taste — comfortable cruiser or performance machine — and experience Sicily with true independence.

Rent the vehicle that matches your taste — comfortable cruiser or performance machine — and experience Sicily with true independence.

Seamless from start to finish

Seamless from start to finish

Thoughtfully planned routes, curated stops, and expert guidance — without the stress of figuring it out alone.

Thoughtfully planned routes, curated stops, and expert guidance — without the stress of figuring it out alone.

la Corsa 1000 Siciliana

la Corsa 1000 Siciliana

October 14-21, 2025

October 14-21, 2025

Designed for driving enthusiasts who crave winding roads, authentic local experiences, and killer cuisine.

Spend seven days exploring Sicily, Italy's coastal towns and attend (or participate in!) the Targa Florio, Italy's oldest race.

Designed for driving enthusiasts who crave winding roads, authentic local experiences, and killer cuisine.

Spend seven days exploring Sicily, Italy's coastal towns and attend (or participate in!) the Targa Florio, Italy's oldest race.

Designed for driving enthusiasts who crave winding roads, authentic local experiences, and killer cuisine.

Spend seven days exploring Sicily, Italy's coastal towns and attend (or participate in!) the Targa Florio, Italy's oldest race.

Coach explaining stuff to an athlete

Frequently Asked Questions

What kind of cars can I drive?

Do I need to be an experienced driver?

What’s included in the trip?

How many people are in each group?

Frequently Asked Questions

What kind of cars can I drive?

Do I need to be an experienced driver?

What’s included in the trip?

How many people are in each group?

Frequently Asked Questions

What kind of cars can I drive?

Do I need to be an experienced driver?

What’s included in the trip?

How many people are in each group?

Ready to Start your Journey?

Join a small group of travelers who share your love for the road, culture, and authentic experiences.

Drone shot of a running track at night

Ready to Start your Journey?

Join a small group of travelers who share your love for the road, culture, and authentic experiences.

Drone shot of a running track at night

Ready to Start your Journey?

Join a small group of travelers who share your love for the road, culture, and authentic experiences.

Drone shot of a running track at night

Legacy Road Tours are curated cultural road journeys — immersive small-group trips that combine the freedom of driving with insider access to authentic local food, culture, and heritage events.

Copyright Legacy Road Tours, 2025. All Rights Reserved.

Legacy Road Tours are curated cultural road journeys — immersive small-group trips that combine the freedom of driving with insider access to authentic local food, culture, and heritage events.

Copyright Legacy Road Tours, 2025. All Rights Reserved.

Legacy Road Tours are curated cultural road journeys — immersive small-group trips that combine the freedom of driving with insider access to authentic local food, culture, and heritage events.

Copyright Legacy Road Tours, 2025. All Rights Reserved.