Destinations
Each Vesping Around journey is more than just a tour—it’s an invitation to experience Italy the way it was meant to be savored: slowly, intimately, and with all five senses engaged. Our handcrafted itineraries take you off the beaten path and into the heart of five stunning regions, each with its own personality, flavors, and rhythms. From the vineyard-laced hills of Tuscany to the sun-drenched coastlines of Sicily, you’ll ride classic Vespas through landscapes rich in history, cuisine, and local culture.
Whether you’re sipping Prosecco in Veneto, wandering the cliffside villages of Liguria, or sharing a meal with locals in Puglia, every stop is designed to connect you to the land—and the people who call it home. Discover our featured destinations below and find the ride that speaks to your soul.
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Val D'Itria
PUGLIA
Puglia offers a raw, soulful Italy—sun-baked and full of character. With its ancient olive trees, whitewashed villages, and dry-stone walls stretching endlessly across the landscape, it feels like time slows here. Riding through the Itria Valley or along the Adriatic coast, you’ll discover trulli houses, underground wine cellars, and towns carved from limestone.
Vesping Around in Puglia is an invitation to discover three of its most distinct regions: the fairytale trulli of Valle d’Itria, the forested coastline of the Gargano promontory, and the sun-drenched beaches and Baroque towns of Salento. You’ll cruise scenic routes that shift from quiet inland roads to panoramic sea views, stopping to taste freshly baked focaccia, visit centuries-old olive presses, and meet artisans keeping traditions alive. Every turn uncovers a new layer of Puglia’s soulful charm.
LAST 3 ROOMS
Chianti & Val D'Orcia
TUSCANY
Tuscany is the classic postcard of Italy—but riding through it on a Vespa takes that image and breathes life into it. Cypress-lined roads lead you through golden fields, medieval villages, and vineyard-covered hills as you explore Chianti, Val d’Orcia, and lesser-known gems tucked between Siena and Florence. The Tuscan sun casts a warm glow over every day of exploration.
With Vesping Around, you won’t just see Tuscany—you’ll live it through the winding roads of Chianti and the cinematic landscapes of Val d’Orcia. You’ll visit world-class wineries nestled between Greve and Gaiole, ride past wheat fields and poppy-lined trails near Pienza, and enjoy leisurely meals in sun-drenched farmhouses. Each day is a celebration of the senses—where history, food, and natural beauty combine into unforgettable moments on two wheels.
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Prosecco & Dolomites
VENETO
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Veneto offers a captivating mix of elegant landscapes and vibrant traditions, making it an ideal setting for a Vespa adventure. Riding through the rolling Prosecco Hills, a UNESCO World Heritage site, you’ll weave past ancient vineyards, rustic trattorias, and noble villas perched above the vines. The charming towns of Bassano del Grappa and Asolo welcome you with cobblestone streets, artisan grappa distilleries, and breathtaking views of the Dolomites in the distance.
The Vesping Around experience in Veneto blends refined beauty with countryside authenticity. You’ll sip your way through the lush Prosecco Hills, ride into the grappa capital of Bassano del Grappa for tastings and artisan encounters, and venture toward the foothills of the Dolomites where alpine culture meets vineyard elegance. Each day is carefully curated to balance leisurely rides with immersive stops—whether it’s a family-run winery, a mountain-view picnic, or a stroll through charming medieval villages that time forgot.
Cinque Terre & Portofino
LIGURIA
In Liguria, Vespa riding becomes an art form as you hug dramatic coastal roads and wind your way through terraced hillsides filled with olive groves and lemon trees. This narrow, mountainous region offers a unique blend of seaside charm and rugged inland exploration. From pastel-hued fishing villages to secluded mountain hamlets, Liguria surprises you at every curve.
The Vesping Around journey here follows the most enchanting coastline in Italy, with curated routes between the glittering harbor of Portofino and the colorful cliffs of Cinque Terre. You’ll ride narrow roads perched above the sea, take coastal detours to beachside trattorias, and hop off to explore ancient villages like Vernazza and Manarola. With every curve, Liguria reveals its unique rhythm—a place where seaside glamour and rural simplicity coexist in perfect harmony.
White Lotus's Taormina & Etna
SICILY
Sicily is a land of myth, mountains, and Mediterranean flair—perfectly suited for Vespa exploration. From Mount Etna’s lava-scarred slopes to the baroque towns of the Val di Noto, every ride is a sensory overload. The scent of orange blossoms, the taste of fresh cannoli, and the feel of coastal winds all converge to create an unforgettable experience.
The Vesping Around journey in Sicily centers on two iconic landscapes—Taormina’s glamorous hilltop beauty and Mount Etna’s raw volcanic power. You’ll ride through fertile valleys where citrus trees grow in black volcanic soil, explore ancient amphitheaters overlooking the Ionian Sea, and stop in small mountain towns for arancini and espresso. This itinerary fuses cultural depth and natural drama, giving you a front-row seat to Sicily’s layered history and larger-than-life personality.
Why Vesping Around
Vesping Around offers immersive, all-inclusive, multi-day trips that is perfect for those seeking.a bit of adventure along with comfort and curated experience. It’s not just a ride—it’s a journey you’ll never forget.
24/7 Guided
Vesping Around provides expert, native guides available 24/7 to ensure a smooth, informative, and worry-free experience throughout your journey.
Small Groups
With small groups, you’ll enjoy a more intimate, personalized experience, allowing for deeper connections and a truly impactful adventure.
Multi-Day
Our multi-day itineraries let you fully immerse yourself in the culture and landscapes, giving you ample time to explore and savor each destination.
All-Inclusive
Every Vesping Around tour is all-inclusive, covering everything from Vespa rentals and accommodations to meals and guided excursions, so you can relax and enjoy the ride. Oh, and you get the sought after Vesping Around Travel Kit!
Hands-On
Engage in hands-on food and cultural experiences like cooking classes, workshops, local museums, and more, allowing you to actively connect with local culture.
Off Beaten Path
We take you off the beaten path, exploring hidden gems and quiet spots away from the tourist crowds for a truly authentic experience.
What Other Travelers Say
"Experiencing Tuscany on a Vespa versus a prior trip om a rental car is s a totally different, the smells, the flowers, It's much better investment...the groups are smalls. If you are even thinking about it, you need to sign up for the trip, because there might not be a seat for you. You don't want to miss the opportunity 'cause it's really fun!"
Andy M., Tom M. - Miami