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Rome. San Gimignano . Siena . Florence

If you’ve ever wanted to forge a deeper bond with Tuscay, this is your chance. Centred in San Gimignano, this Local Living experience places you in the heart of central Tuscany.


You’re free to explore the town, visit vineyards, discover medieval highlights, or embrace your inner artist wandering the Tuscan countryside.


If you’re looking for a deeper dive into Italian cities, there’ll be day trips to visit Siena and Florence.


You’ll share accommodation with like-minded travelers and a bilingual guide there to point you in the right direction.


Prepare to fall in love with Italy.

Your giveback on this journey is Co-op Casba.

7 days / 6 nights


From $1749 per person sharing


Transportation by local bus and train
Bilingual guide throughout
1 night Rome hotel accommodation 
Walking tour of Rome
5 nights San Gimignano guesthouse accommodation
Walking tour of San Gimignano

Italian cooking class
Wine tasting
Walking tour of Siena

Short hike through the Tuscan countryside to Montauto

6 breakfasts, 2 dinners

Weekly, April - October          

Rome Skyline

Day 1 Rome

Make your way to the Rome hotel to meet your guide and group, and opt to join for a welcome dinner and maybe a glass of local wine. 
Stay: Hotel Stella (or similar) (B)


Day 2  San Gimignano

Enjoy a morning orientation walk in Rome, then travel in the afternoon via train and bus to your home for the week which is located just outside the beautiful medieval hill town of San Gimignano. The property owner, Ugo, is a San Gimignano native and is a fountain of information about the area. He lives in one of the apartments in his remodeled medieval house. Take an orientation stroll with your guide for a first glance at San Gimignano.

Stay: Agriturismo Casa Florelia (or similar) (B)


Day 3 San Gimignano

Take a walk with your guide around San Gimignano's medieval walls dating back to the 13th century and enjoy sweeping views both outside the walls and down little backstreets within the town. Walk all 4.3 miles or opt out partway.
Expand your culinary skills with a cooking class. Learn how to prepare typical Tuscan dishes and enjoy the fruits of your labor for dinner.

Stay: Agriturismo Casa Florelia (or similar) (B,D)


Day 4 Siena

Head to nearby Siena and wander this medieval walled city. Options abound! Visit the gorgeous Duomo and the Piazza del Campo, where the famous Palio horse race is held each summer. Climb the Torre del Mangia for fantastic views of the Tuscan landscape.

Back in San Gimi, enjoy a dinner prepared by your host. Sit back, relax and take in the aromas and flavors of delicious Italian home-cooking.

Stay: Agriturismo Casa Florelia (or similar) (B,D)

Wine Tasting Events

Day 5 San Gimignano

Enjoy free time to visit the San Gimignano market in the morning, then take the ancient Via Francigena path, and walk through some woods, across a stream, and then through vineyards up to Montauto, which offers outstanding views of San Gimignano. The Via Francigena, a historical path in use approximately 1,000 years ago by those making pilgrimage between Canterbury, England, and Rome, runs very close to Casa Florelia and is great path for those who wish to explore the Tuscan countryside by foot
Sample local wine varieties upon returning to our rustic farmhouse for the night.

Stay: Agriturismo Casa Florelia (or similar) (B)

Cityscape of Florence

Day 6  Florence

Enjoy a day trip to beautiful Florence with plenty of free time to check out local museums and plazas. Your return train ticket is open; you are free to enjoy this magnificent city for as long as you wish. Advance bookings at museums are recommended.
Stay: Agriturismo Casa Florelia  (or similar) (B)

Saint Peter's Basilica

Day 7  Depart Rome

Transfer by bus and train to Rome. Depart in the early afternoon from the Rome train station (Termini).


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