8 days

Tuscan Trails

Tuscan Trails

Trip rating
  • Why we love it

    • Private tour of the cellars of a wine estate in Chianti as well as tastings of their acclaimed wines
    • Enjoy a picnic lunch overlooking the Sant’Antimo, one of the most beautiful monasteries in Tuscany
    • Learn about and taste regional cuisines while exploring the city’s small alleyways on a tasting trail through Florence
    • Visit the stunning Abbey of San Fruttuoso - an 11th century 'jewel' that is set in a secluded cove and reachable only by boat


    Day 1 - Florence

    You will be met by your tour leader and transferred to your hotel in the heart of Florence. Freshen up then wander in any direction to uncover the city’s delights. Come together for dinner at one of the oldest and most renowned trattorias in Florence. 

    Firenze Number Nine Hotel & Spa
    Breakfast | Dinner

    Day 2 - Florence

    The best way to explore Florence is on foot. See Michelangelo’s David at the Academia Gallery of Florence, the Bargello, the Piazza del Duomo, the Basilica di Santa Maria del Fiore and climb the 414 steps of Giotto’s Campanile for breathtaking views. Taste regional delicacies including truffle panini, artisan chocolate, olive oil, prosecco, chianti and gelato. 

    Firenze Number Nine Hotel & Spa
    Breakfast | Dinner

    Day 3 - Chianti

    Drive towards the Chianti countryside, stopping en route at the medieval village of Volpai and the home of one of Chianti’s great wineries. Tonight you’ll sleep in a castle dating back to 1077, which has been part of the Ricasoli family since the 1400s. 

    Castello la Leccia
    Breakfast | Lunch

    Day 4 - Colle Val d’Elsa ~ San Gimignano ~ Siena

    In Colle Val d’Elsa you’ll meet one of the town’s oldest glass blowers, an art which has been practised here for centuries. Enjoy a short stroll before continuing to San Gimignano and then Siena, one of the best-preserved medieval towns in Europe. Stop for lunch at Monteriggioni, the most spectacular fortified village in all of Tuscany before returning to the hotel. 

    Castello la Leccia

    Day 5 - Into the Val d'Orcia: Montalcino, San Quirico, Pienza & Montepulciano

    Continue immersing yourself in the charms of Tuscany, with visits to the iconic landscapes, rolling hills and famed vineyards of Montalcino and San Quirico ~ a town that expresses the spirit of Tuscany. The rest of the evening is free to relax. 

    Castello la Leccia

    Day 6 - Lucca ~ Camogli

    Walk through the town of Lucca, which boasts 16th century Renaissance walls, a spectacular white marble duomo, Roman amphitheatre and cobblestone streets. Drive along the Apuane Mountains to your hotel in the heart of the Italian Riviera. Walk from Camogli to the small peninsula of Punta Chiappa then take a boat towards the Abbey of San Fruttuoso for a swim. 

    Hotel Cenobio dei Dogi
    Breakfast | Dinner

    Day 7 - Cinque Terre villages

    Hop on the little coastal train to Riomaggiore and start the Sentiero dell’Amore (Lover’s Walk). Walk through olive groves and along cliffs to the sister villages: Manarola, Corniglia, Vernazza and finally Monterosso. There is time for a swim at the end of your walk before a seafood dinner on the shores of the Mediterranean. This is a challenging walk and if you don't wish to participate an alternative activity can be arranged. 

    Hotel Cenobio dei Dogi
    Breakfast | Lunch

    Day 8 - Portofino ~ Florence

    Take a short train ride to Santa Margherita Ligure and reach Portofino by late morning with time to explore. Make the return journey to Florence this afternoon where your tour ends on arrival. If travelling out of Florence today you will be transferred to the airport or train station.

  • What to Know

    What's Included

    • Breakfast daily, 3 lunches and 3 dinners.
    • Private sightseeing (including all entrance fees) as outlined in the itinerary.
    • Comfortable private transportation with driver. Other modes of transportation include a boat, coastal train & ferry.
    • Snacks and refreshments along the way.
    • Tipping & porterage taken care of by tour leader along the way.
    • Airport meet and greet service.
    • Departure transfer.

    Not Included

    • International flights
    • Visas
    • Airport taxes
    • Laundry
    • Gratuities for the tour leader
  • Map Itinerary

  • Past Travellers' Ratings & Comments

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Trip at a glance

Trip Code RETT
Group size 4 - 16
Start City: Florence
End City: Santa Margherita
Style: Small Group

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