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Tuscany: From the Hills to the Sea

This tour combines “classic” Tuscany (Florence & San Gimignano) with three days along the Mediterranean coast, showing you parts of the region that most tourists don’t see. From sandy beaches to some of the best “Super Tuscan” wines in Italy, you’ll discover something surprising every day!

Duration: 7 nights / 8 days
Dates: Available upon request, contact us for details
Trip starts/ends: Florence / Grosseto train station
Activity level: 2+ easy to moderate walking (other activity options available) [more info]
Group size: min 4 - max 14


  • casual walk around Florence
  • 6 guided walks through the Tuscan Hills
  • visit of the medieval towers of San Gimignano
  • wine-pairing lunch at a local producer of Vernaccia
  • visit of the beautiful hilltop town of Volterra
  • lunch and visit at organic farm that produces essential oils and medicinal herbs
  • entrance to a natural thermal spa
  • wine-tasting in Bolgheri
  • 7 nights in charming accommodations

Trip price includes

  • 1 night Florence, 3 each in San Gimignano and Sassetta
  • 6 dinners & 2 lunches
  • wine tasting at a family-run winery
  • all other visits and transfers as per the itinerary

Not included

  • 5 lunches and 1 dinner
  • drinks other than water at meals
  • activities not listed in the itinerary


Day 1: Arrival in Florence
Independent arrival in Florence. We haven’t scheduled a meeting this evening to allow for relaxed arrivals, so you’re free to arrange your own dinner (we’re happy to provide suggestions!). Overnight Florence. Dinner not included.


Days 2-4: San Gimignano Area
Follow your guide this morning to explore the streets and highlights of Florence before heading south into the countryside. Spend the next 3 nights exploring “classic” Tuscany, including the famous town of San Gimignano, whose 14 Medieval towers still remain from an original 72. We also visit the nearby hilltop town of Volterra, which was an important Etruscan city 2,500 years ago. Then travel to fabulous Siena, which rivaled Florence for centuries in power, wealth, and the arts. Each day has a beautiful walk to accompany the cityscapes, though you could also do this tour as “light active” and add more cultural experiences in place of the walks. 3 nights near San Gimignano.


Day 5-7: Tuscan Coast
Transfer west today for 3 days along the Tuscan Coast. We explore more charming hilltop towns and also savor the powerful wines of the famous Bolgheri region, with views down over the glittering Mediterranean below you. We’ve done a lot of research in these past years to find special experiences for a brand-new itinerary that’s full of off-the-beaten-track surprises and unexpected visits. 3 nights near Sassetta. 

Day 8: Departures from the Grosseto train station
We offer one group transfer to the Grosseto train station this morning so you can hop a train back to Florence or down to Rome (or wherever your travel plans take you).


Getting there and away: You can fly directly into the Florence airport, which is well connected to a variety of European hubs, or take a train from Rome or Milan. Grosseto is also on a train line for easy onward connections.


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