Where History
Hits the Road

Immersive journeys that blend scenic drives with authentic culture and insider access.

Explore Tours

la Corsa 1000 Siciliana

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.

Learn More

More than the Road

Legacy Road Tours blends the thrill of driving with the richness of authentic cultural encounters.

From private meals with local families to exclusive access at legendary races, we craft journeys you won’t find in a brochure.

Authentic Experiences

Dine with local families, taste regional cuisine, and explore hidden gems and artisan workshops.

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

Scenic Freedom

See each destination the way it was meant to be seen - by car.

Choose your own vehicle and enjoy the flexibility of exploring winding coastlines, mountain passes, and charming villages at your own pace.

Insider Access

Gain entry to events, people, and places that only comes through genuine relationships and local knowledge.

Turn each trip into an unforgettable experience no guidebook can offer.

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.

Ready to Start your Journey?

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

Ready to Start your Journey?

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

la Corsa 1000 Siciliana

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.

More than the Road

Legacy Road Tours blends the thrill of driving with the richness of authentic cultural encounters. From private meals with local families to exclusive access at legendary races, we craft journeys you won’t find in a brochure.

Legacy Road Tours blends the thrill of driving with the richness of authentic cultural encounters. From private meals with local families to exclusive access at legendary races, we craft journeys you won’t find in a brochure.

Authentic Experiences

Scenic Freedom

Insider Access

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?

Ready to Start your Journey?

Ready to Start your Journey?

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.

Legacy Road Tours blends the thrill of driving with the richness of authentic cultural encounters.

From private meals with local families to exclusive access at legendary races, we craft journeys you won’t find in a brochure.

Legacy Road Tours blends the thrill of driving with the richness of authentic cultural encounters.

From private meals with local families to exclusive access at legendary races, we craft journeys you won’t find in a brochure.