Join us and ride the Tuscany hills to create an unforgettable memory. Stay at a high-end 4-star Villa on a scenic hill, explore local activities, meet the locals, and conquer a thrilling 100-kilometer ride through the Chianti Valley along with hundreds of other Vespas coming from all over Italy & Europe. Secure your spot now and get ready for the ride of a lifetime.

The only requirements?  Prior experience riding on a two-wheel vehicle, motorcycle, or scooter, and the desire to have a lot of fun!

Join us and ride the Tuscany hills to create an unforgettable memory. Stay at a high-end 4-star Villa on a scenic hill, explore local activities, meet the locals, and conquer a thrilling 100-kilometer ride through the Chianti Valley along with hundreds of other Vespas coming from all over Italy & Europe. Secure your spot now and get ready for the ride of a lifetime.

The only requirements?  Prior experience riding on a two-wheel vehicle, motorcycle, or scooter, and the desire to have a lot of fun!

ℹ️ This trip will have an optional additional day or 2 to attached at the end of the itinerary. This will be announced later on and you'll be able to enter your booking to adjust it, if so desired) ℹ️

Discover the soul of southern Puglia on a 5-day Vespa journey through Salento, a region where coastal beauty, ancient traditions, and relaxed Mediterranean living meet. Based at a beautiful masseria just outside Maglie, complete with a pool, spa, and in-house activities, each day invites you to explore a different slice of this sun-soaked land. You’ll take part in a cartapesta workshop in Lecce, ride through hidden villages of the Grecìa Salentina, and dive into quiet coves and sandy bays. One of the highlights? A boat excursion along the Ionian coast, where you’ll fish at sunset and enjoy a meal prepared with your catch, the perfect blend of adventure and local flavor. Each evening, return to your countryside retreat to unwind and savor the rhythms of Puglia.

Join us and ride the Tuscany hills to create an unforgettable memory. Stay at a high-end 4-star Villa on a scenic hill, explore local activities, meet the locals, and conquer a thrilling 100-kilometer ride through the Chianti Valley along with hundreds of other Vespas coming from all over Italy & Europe. Secure your spot now and get ready for the ride of a lifetime.

The only requirements?  Prior experience riding on a two-wheel vehicle, motorcycle, or scooter, and the desire to have a lot of fun!

Experience the magic of Italy’s Prosecco region on a 4-day Vespa adventure based in Vittorio Veneto, where each day blends scenic rides with rich cultural encounters and local flavors. From exploring the UNESCO-listed hills of Valdobbiadene and tasting world-class Prosecco, to visiting historic villas, medieval castles, and alpine malghe for hearty mountain meals, this itinerary captures the essence of slow travel. Evenings return you to the comfort of your boutique base for relaxed aperitivi and dinners in welcoming local osterie, making this the perfect journey for those seeking beauty, connection, and the real Italy—one ride, one bite, and one village at a time.

Discover the soul of southern Puglia on a 5-day Vespa journey through Salento, a region where coastal beauty, ancient traditions, and relaxed Mediterranean living meet. Based at a beautiful masseria just outside Maglie, complete with a pool, spa, and in-house activities, each day invites you to explore a different slice of this sun-soaked land. You’ll take part in a cartapesta workshop in Lecce, ride through hidden villages of the Grecìa Salentina, and dive into quiet coves and sandy bays. One of the highlights? A boat excursion along the Ionian coast, where you’ll fish at sunset and enjoy a meal prepared with your catch, the perfect blend of adventure and local flavor. Each evening, return to your countryside retreat to unwind and savor the rhythms of Puglia.

Join us and ride the Tuscany hills to create an unforgettable memory. Stay at a high-end 4-star Villa on a scenic hill, explore local activities, meet the locals, and conquer a thrilling 100-kilometer ride through the Chianti Valley along with hundreds of other Vespas coming from all over Italy & Europe. Secure your spot now and get ready for the ride of a lifetime.

The only requirements?  Prior experience riding on a two-wheel vehicle, motorcycle, or scooter, and the desire to have a lot of fun!

Experience the magic of Italy’s Prosecco region on a 4-day Vespa adventure based in Vittorio Veneto, where each day blends scenic rides with rich cultural encounters and local flavors. From exploring the UNESCO-listed hills of Valdobbiadene and tasting world-class Prosecco, to visiting historic villas, medieval castles, and alpine malghe for hearty mountain meals, this itinerary captures the essence of slow travel. Evenings return you to the comfort of your boutique base for relaxed aperitivi and dinners in welcoming local osterie, making this the perfect journey for those seeking beauty, connection, and the real Italy—one ride, one bite, and one village at a time.

FLASH PROMO: use code TUSCANYSPRING25 to get a 25% rebate at checkout until Feb 15. (applies only to package, doesn't apply to add-ons)

Join us and ride the Tuscany hills to create an unforgettable memory. Stay at a high-end 4-star Villa on a scenic hill, explore local activities, meet the locals, and conquer a thrilling 100-kilometer ride through the Chianti Valley along with hundreds of other Vespas coming from all over Italy & Europe. Secure your spot now and get ready for the ride of a lifetime.

The only requirements?  Prior experience riding on a two-wheel vehicle, motorcycle, or scooter, and the desire to have a lot of fun!

Join us and ride the Tuscany hills to create an unforgettable memory. Stay at a high-end 4-star Villa on a scenic hill, explore local activities, meet the locals, and conquer a thrilling 100-kilometer ride through the Chianti Valley along with hundreds of other Vespas coming from all over Italy & Europe. Secure your spot now and get ready for the ride of a lifetime.

The only requirements?  Prior experience riding on a two-wheel vehicle, motorcycle, or scooter, and the desire to have a lot of fun!

 This curated 5-day Vespa adventure is based just outside Taormina, blending the thrill of open-road riding with the charm of Sicily’s coastlines, volcanoes, and hilltop villages. Each day invites you into a new story: cooking with nonnas, sunset aperitivos in Castelmola, vineyard tastings on the slopes of Mount Etna, hidden canyons and river trails, seaside lunches along the Riviera dei Ciclopi, and cinematic experiences such as the Godfather villages nd the White Lotus hotel. With a boutique stay as your home base, you’ll enjoy scenic daily rides (never over 70 km), hands-on local experiences, and plenty of time to savor Sicilian food, culture.

 This curated 5-day Vespa adventure is based just outside Taormina, blending the thrill of open-road riding with the charm of Sicily’s coastlines, volcanoes, and hilltop villages. Each day invites you into a new story: cooking with nonnas, sunset aperitivos in Castelmola, vineyard tastings on the slopes of Mount Etna, hidden canyons and river trails, seaside lunches along the Riviera dei Ciclopi, and cinematic experiences such as the Godfather villages nd the White Lotus hotel. With a boutique stay as your home base, you’ll enjoy scenic daily rides (never over 70 km), hands-on local experiences, and plenty of time to savor Sicilian food, culture.

Join us and ride the Tuscany hills to create an unforgettable memory. Stay at a high-end 4-star Villa on a scenic hill, explore local activities, meet the locals, and conquer a thrilling 100-kilometer ride through the Chianti Valley along with hundreds of other Vespas coming from all over Italy & Europe. Secure your spot now and get ready for the ride of a lifetime.

The only requirements?  Prior experience riding on a two-wheel vehicle, motorcycle, or scooter, and the desire to have a lot of fun!

Imagine yourself zipping through Puglia on a classic Vespa. Ride past endless olive groves to the whitewashed town of Ostuni, where narrow alleyways and panoramic views await. Journey through the scenic Valle d'Itria, dotted with unique trullo houses, and towards the baroque splendor of Lecce, experiencing the rustic charm of local villages and the vibrant city life. Along the way, meet local Vespisti from nearby clubs, sharing stories and a passion for the ride. Continue to the ancient town of Alberobello and the picturesque coastal city of Otranto. Visit the world-famous and charming fishing village of Polignano a Mare, where the sun sets over stunning cliffside vistas. Each twist of the road offers new breathtaking scenes, immersing you in the rich history, culture, and flavors of Puglia.

The only requirements?  The desire to have a lot of fun!

Join us and ride the Tuscany hills to create an unforgettable memory. Stay at a high-end 4-star Villa on a scenic hill, explore local activities, meet the locals, and conquer a thrilling 100-kilometer ride through the Chianti Valley along with hundreds of other Vespas coming from all over Italy & Europe. Secure your spot now and get ready for the ride of a lifetime.

The only requirements?  Prior experience riding on a two-wheel vehicle, motorcycle, or scooter, and the desire to have a lot of fun!

Join us and ride the Tuscany hills to create an unforgettable memory. Stay at a high-end 4-star Villa on a scenic hill, explore local activities, meet the locals, and conquer a thrilling 100-kilometer ride through the Chianti Valley along with hundreds of other Vespas coming from all over Italy & Europe. Secure your spot now and get ready for the ride of a lifetime.

The only requirements?  Prior experience riding on a two-wheel vehicle, motorcycle, or scooter, and the desire to have a lot of fun!

Join us and ride the Tuscany hills to create an unforgettable memory. Stay at a high-end 4-star Villa on a scenic hill, explore local activities, meet the locals, and conquer a thrilling 100-kilometer ride through the Chianti Valley along with hundreds of other Vespas coming from all over Italy & Europe. Secure your spot now and get ready for the ride of a lifetime.

The only requirements?  Prior experience riding on a two-wheel vehicle, motorcycle, or scooter, and the desire to have a lot of fun!

 This curated 5-day Vespa adventure is based just outside Taormina, blending the thrill of open-road riding with the charm of Sicily’s coastlines, volcanoes, and hilltop villages. Each day invites you into a new story: cooking with nonnas, sunset aperitivos in Castelmola, vineyard tastings on the slopes of Mount Etna, hidden canyons and river trails, seaside lunches along the Riviera dei Ciclopi, and cinematic experiences such as the Godfather villages and the White Lotus hotel. With a boutique stay as your home base, you’ll enjoy scenic daily rides (never over 70 km), hands-on local experiences, and plenty of time to savor Sicilian food, culture.

Imagine yourself zipping through Puglia on a classic Vespa. Ride past endless olive groves to the whitewashed town of Ostuni, where narrow alleyways and panoramic views await. Journey through the scenic Valle d'Itria, dotted with unique trullo houses, and towards the baroque splendor of Lecce, experiencing the rustic charm of local villages and the vibrant city life. Along the way, meet local Vespisti from nearby clubs, sharing stories and a passion for the ride. Continue to the ancient town of Alberobello and the picturesque coastal city of Otranto. Visit the world-famous and charming fishing village of Polignano a Mare, where the sun sets over stunning cliffside vistas. Each twist of the road offers new breathtaking scenes, immersing you in the rich history, culture, and flavors of Puglia.

The only requirements?  The desire to have a lot of fun!

A digital gift card that loads credit into a pre-paid Vesping Around wallet. Guests can use this credit toward any scheduled departure of their choice. Easy to gift, easy to redeem, impossible not to love.

How it works

• You (the purchaser) choose the amount and complete the payment.

• We generate a unique digital gift card code and send it directly to the recipient with you on cc.

• The recipient applies the code at checkout on their chosen Vespa experience.

• Credit can be used toward the trip deposit or the full balance of the chosen trip.

ℹ️ An extra optional day will be added later on for those who want to extend their ride.

Discover the soul of southern Puglia on a 5-day Vespa journey through Salento, a region where coastal beauty, ancient traditions, and relaxed Mediterranean living meet. Based at a beautiful masseria just outside Maglie, complete with a pool, spa, and in-house activities, each day invites you to explore a different slice of this sun-soaked land. You’ll take part in a cartapesta (paper mache) workshop in Lecce, ride through hidden villages of the Grecìa Salentina, and dive into quiet coves and sandy bays. One of the highlights? A boat excursion along the Ionian coast, where you’ll fish at sunset and enjoy a meal prepared with your catch, the perfect blend of adventure and local flavor. Each evening, return to your countryside retreat to unwind and savor the rhythms of Puglia.

ℹ️ This trip will have an optional additional day or 2 to attached at the end of the itinerary. This will be announced later on and you'll be able to enter your booking to adjust it, if so desired) ℹ️

Discover the soul of southern Puglia on a 5-day Vespa journey through Salento, a region where coastal beauty, ancient traditions, and relaxed Mediterranean living meet. Based at a beautiful masseria just outside Maglie, complete with a pool, spa, and in-house activities, each day invites you to explore a different slice of this sun-soaked land. You’ll take part in a cartapesta workshop in Lecce, ride through hidden villages of the Grecìa Salentina, and dive into quiet coves and sandy bays. One of the highlights? A boat excursion along the Ionian coast, where you’ll fish at sunset and enjoy a meal prepared with your catch, the perfect blend of adventure and local flavor. Each evening, return to your countryside retreat to unwind and savor the rhythms of Puglia.

Imagine yourself zipping through Puglia on a classic Vespa. Ride past endless olive groves to the whitewashed town of Ostuni, where narrow alleyways and panoramic views await. Journey through the scenic Valle d'Itria, dotted with unique trullo houses, and towards the baroque splendor of Lecce, experiencing the rustic charm of local villages and the vibrant city life. Along the way, meet local Vespisti from nearby clubs, sharing stories and a passion for the ride. Continue to the ancient town of Alberobello and the picturesque coastal city of Otranto. Visit the world-famous and charming fishing village of Polignano a Mare, where the sun sets over stunning cliffside vistas. Each twist of the road offers new breathtaking scenes, immersing you in the rich history, culture, and flavors of Puglia.

The only requirements?  The desire to have a lot of fun!

Click here to consult full itinerary

This tour is part of a broader initiative to bridge American and Italian Vespa culture celebrating the scooter lifestyle not just as a means of travel, but as a vehicle for connection. Each itinerary is carefully curated to explore local traditions, cuisine, and people while creating opportunities to meet and ride with passionate Vespa clubs across Italy. A new region will be spotlighted each year, offering participants a deeper cultural immersion and a unique way to experience Italy—from the saddle of a classic scooter.

Embark on an unforgettable 10-day Vespa journey through the heart of Sicily, designed in collaboration with the local Vespa Clubs which will be meeting the itinerary group. This itinerant adventure begins and ends in Taormina, weaving through iconic landscapes and historic towns like Bronte, Enna, Caltagirone, Modica, Noto, and Catania. Along the way, riders will experience the raw beauty of Mount Etna’s slopes, the baroque splendor of southeast Sicily, and the warm hospitality of local Vespa clubs joining for scenic rides, meet-ups, and shared dinners.

Each day is crafted to blend cultural immersion with the joy of riding. Highlights include a boat tour of Isola Bella, pistachio tastings in Bronte, a ceramic workshop in Caltagirone, a hands-on ricotta-making experience near Ragusa, and a chocolate tour in Modica. The tour also features select culinary stops, coastal detours, and charming village visits—all culminating in a coastal ride back to Taormina. With a perfect balance of adventure, tradition, and local connection, this journey captures the spirit of Sicily one winding road at a time.

For experienced riders ready for a challenge.

These routes include narrow mountain roads, switchbacks, steeper climbs, and busier traffic zones—often with fast-moving cars and assertive local drivers. You must be able to confidently share the road with multiple forms of transport and respond quickly to changing conditions.

Ideal for riders who are agile, alert, and used to adapting to dynamic environments.

(Vespa is a Piaggio trademark, Vesping Around is not associated or affiliated in any way)

October 20 -> 24 + 2 optional add-on days

This curated 5-day Vespa adventure is based just outside Taormina, blending the thrill of open-road riding with the charm of Sicily’s coastlines, volcanoes, and hilltop villages. Each day invites you into a new story: cooking with nonnas, sunset aperitivos in Castelmola, vineyard tastings on the slopes of Mount Etna, hidden canyons and river trails, seaside lunches along the Riviera dei Ciclopi, and cinematic experiences such as the Godfather villages and the White Lotus hotel. With a boutique stay as your home base, you’ll enjoy scenic daily rides (never over 70 km), hands-on local experiences, and plenty of time to savor Sicilian food, culture.

Imagine yourself zipping through Puglia on a classic Vespa. Ride past endless olive groves to the whitewashed town of Ostuni, where narrow alleyways and panoramic views await. Journey through the scenic Valle d'Itria, dotted with unique trullo houses, and towards the baroque splendor of Lecce, experiencing the rustic charm of local villages and the vibrant city life. Along the way, meet local Vespisti from nearby clubs, sharing stories and a passion for the ride. Continue to the ancient town of Alberobello and the picturesque coastal city of Otranto. Visit the world-famous and charming fishing village of Polignano a Mare, where the sun sets over stunning cliffside vistas. Each twist of the road offers new breathtaking scenes, immersing you in the rich history, culture, and flavors of Puglia.

The only requirements?  The desire to have a lot of fun!

Join us and ride the Tuscany hills to create an unforgettable memory. Stay at a high-end 4-star Villa on a scenic hill, explore local activities, meet the locals, and conquer a thrilling 100-kilometer ride through the Chianti Valley along with hundreds of other Vespas coming from all over Italy & Europe. Secure your spot now and get ready for the ride of a lifetime.

The only requirements?  Prior experience riding on a two-wheel vehicle, motorcycle, or scooter, and the desire to have a lot of fun!

Trip Riding Skill Level: Intermediate to Advanced

Experience the magic of Italy’s Prosecco region on a 4-day Vespa adventure based in Vittorio Veneto, where each day blends scenic rides with rich cultural encounters and local flavors. From exploring the UNESCO-listed hills of Valdobbiadene and tasting world-class Prosecco, to visiting historic villas, medieval castles, and alpine malghe for hearty mountain meals, this itinerary captures the essence of slow travel. Evenings return you to the comfort of your boutique base for relaxed aperitivi and dinners in welcoming local osterie, making this the perfect journey for those seeking beauty, connection, and the real Italy—one ride, one bite, and one village at a time.

 This curated 5-day Vespa adventure is based just outside Taormina, blending the thrill of open-road riding with the charm of Sicily’s coastlines, volcanoes, and hilltop villages. Each day invites you into a new story: cooking with nonnas, sunset aperitivos in Castelmola, vineyard tastings on the slopes of Mount Etna, hidden canyons and river trails, seaside lunches along the Riviera dei Ciclopi, and cinematic experiences such as the Godfather villages nd the White Lotus hotel. With a boutique stay as your home base, you’ll enjoy scenic daily rides (never over 70 km), hands-on local experiences, and plenty of time to savor Sicilian food, culture.

Imagine yourself zipping through Puglia on a classic Vespa. Ride past endless olive groves to the whitewashed town of Ostuni, where narrow alleyways and panoramic views await. Journey through the scenic Valle d'Itria, dotted with unique trullo houses, and towards the baroque splendor of Lecce, experiencing the rustic charm of local villages and the vibrant city life. Along the way, meet local Vespisti from nearby clubs, sharing stories and a passion for the ride. Continue to the ancient town of Alberobello and the picturesque coastal city of Otranto. Visit the world-famous and charming fishing village of Polignano a Mare, where the sun sets over stunning cliffside vistas. Each twist of the road offers new breathtaking scenes, immersing you in the rich history, culture, and flavors of Puglia.

The only requirements?  The desire to have a lot of fun!

Imagine yourself zipping through Puglia on a classic Vespa. Ride past endless olive groves to the whitewashed town of Ostuni, where narrow alleyways and panoramic views await. Journey through the scenic Valle d'Itria, dotted with unique trullo houses, and towards the baroque splendor of Lecce, experiencing the rustic charm of local villages and the vibrant city life. Along the way, meet local Vespisti from nearby clubs, sharing stories and a passion for the ride. Continue to the ancient town of Alberobello and the picturesque coastal city of Otranto. Visit the world-famous and charming fishing village of Polignano a Mare, where the sun sets over stunning cliffside vistas. Each twist of the road offers new breathtaking scenes, immersing you in the rich history, culture, and flavors of Puglia.

The only requirements?  The desire to have a lot of fun!

Imagine yourself zipping through Puglia on a classic Vespa. Ride past endless olive groves to the whitewashed town of Ostuni, where narrow alleyways and panoramic views await. Journey through the scenic Valle d'Itria, dotted with unique trullo houses, and towards the baroque splendor of Lecce, experiencing the rustic charm of local villages and the vibrant city life. Along the way, meet local Vespisti from nearby clubs, sharing stories and a passion for the ride. Continue to the ancient town of Alberobello and the picturesque coastal city of Otranto. Visit the world-famous and charming fishing village of Polignano a Mare, where the sun sets over stunning cliffside vistas. Each twist of the road offers new breathtaking scenes, immersing you in the rich history, culture, and flavors of Puglia.

The only requirements?  The desire to have a lot of fun!