Secure this trip with a 20% deposit
Tuscany: A journey through art, wine & culture
Tuscany in full pour – Chianti hills, vineyard feasts and Renaissance days steeped in sun
Overview
The lowdown
This is Italy in full colour – slow-sipped, sun-drenched and best shared with new friends. From vineyard e-bikes in Chianti to cooking pasta in the hills and roaming Florence’s Renaissance streets, this trip blends classic sights with soulful, off-script moments. It’s a curated small group tour for the younger, culturally curious traveller. No flag-following here, just spritz-fuelled connection.
Highlights
The best bits
Wine Tasting Among the Vines
Sip three locally produced wines at a farmhouse overlooking rolling Tuscan hills.
Itinerary
The day to day
Day 1
Rome Welcome & Aperitivo Vibes
Day 2
Orvieto Stop & Tuscan Roll-In
Day 3
Florence in Focus
Day 4
Pisa, Lucca & Tuscan Kitchen Secrets
Day 5
Chianti E-Bikes & Wine Country Magic
Day 6
Val d'Orcia Views & Montalcino Moments
Day 7
Rome Return & La Dolce Vita Finale
Day 8
Arrivederci, Amici
Host
The experts
WeRoad
WeRoad is travel collective born from the belief that strangers make the best stories. Their hosts aren’t just trip leaders; they’re vibe-setters, cultural translators and your in-the-know mates for the duration of the trip.
Accommodation
The quarters
Your stay in Rome is a boutique or four-star hotel, selected for its charm, central location and ease of access to the city’s iconic piazzas and trattorias. Twin-share rooms offer a comfortable welcome to the Eternal City.
Rome Stay
Rome, Città Metropolitana...
Settle into a four-star or boutique hotel in Montecatini Terme, your base in northern Tuscany. This spa town stay is chosen for its local character and easy access to nearby hilltowns. Twin-share comfort with Tuscan elegance.
Montecatini Stay
Montecatini Terme, Provin...
Tonight’s stay is in Chianciano Terme at a boutique or four-star hotel surrounded by rolling hills and vineyard views. Handpicked for its peaceful setting and proximity to wine country gems. Twin-share rooms with a Tuscan soul.
Chianti Stay
Via Cesare Battisti, Grev...
Your final night is spent back in Rome, in a centrally located four-star or boutique hotel. Close to historic streets and evening strolls, your twin-share room is a last taste of comfort before departure.
Rome Stay (Final Night)
Rome, Città Metropolitana...
Activities
The fun stuff
Skip the traffic and travel like a local with a 2nd-class roundtrip train ride from Montecatini Terme to Florence. It’s a scenic, no-fuss journey that drops you right in the heart of the city, ready to explore without the stress of parking or driving.
Scenic Train Ride – Montecatini to Florence
Florence, Metropolitan Ci...
Tick off the Leaning Tower in Pisa, then head to Lucca for a deeper dive. You’ll get time to explore the medieval centre, stroll or cycle its famed walls and grab a local bite. It’s a full day of landmarks, hidden gem and laid-back Tuscan charm.
Pisa & Lucca Day Trip
Lucca, Province of Lucca,...
Step into a local kitchen for a hands-on cooking class led by welcoming Tuscan hosts. Learn to craft regional dishes using fresh, seasonal ingredients—think handmade pasta and rustic sauces—then sit down together to enjoy your creations over a leisurely lunch.
Italian Cooking Class
Montecatini Terme, Provin...
Ride through the postcard-perfect hills of Chianti on an e-bike, making the climbs easy and the views unforgettable. Pedal past vineyards, olive groves and stone farmhouses on a moderate-level route designed for soaking in the scenery, not speed.
Chianti Cycling Trip
Via Cesare Battisti, Grev...
Visit a family-run Chianti estate for a guided tasting of three regional wines, each paired with simple, local snacks. Wander the vines, learn about production methods and sip your way through the flavours that define Tuscany’s world-famous wine country.
Tuscan Wine Tasting
Via Cesare Battisti, Grev...
Explore the rolling beauty of Val d’Orcia by road, stopping along the way in timeless hill towns like Pienza or Montalcino. You’ll have time to wander at your own pace – browse enotecas, snap cypress-lined vistas, or simply soak up the golden Tuscan light.
Val d’Orcia Drive
Via Dante Alighieri, San...
Fine Print
The small stuff
Cancel 65+ days from departure for a 80% refund. Within 64 days of departure, we’ve locked in logistics, so no refund can be offered. Thanks for understanding – it keeps things running smooth for everyone. Please make sure your dates are correct before booking, and we strongly recommend travel insurance for extra peace of mind.