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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

Highlights

  • 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

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 stationWe 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.

from €2,850
[info on prices]

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Activity Levels

Some tours have a range of activity levels through the week, where some walks may be more challenging than others, but this will give you a general idea of the type of walking/hiking involved on your tour.

1 – EASY: City walking, all or mostly paved, minimal climbing
2 – GENTLE: Moderate hills & easy terrain
3 – MODERATE: Some sustained hills with occasional steep grades on a mix of terrains
4 – HIKE: Classic hiking with rough/rocky terrain, sustained hills, and longer mileage
5 – CHALLENGING: Challenging hiking with steep climbs and descents over rocky terrain and some longer mileage

See below for more detail:

1 – EASY: City walking, all or mostly paved, with minimal climbing (though some cities may have steeper inclines). Archaeological sites may be unpaved but the grades and difficulty level is easy. TOURS: Sicily Coast-to-Coast and any “light active” version of a tour

2 – GENTLE: Moderate hills & easy terrain
The terrain is easy to navigate with packed earth or gravel roads. There are some climbs but nothing too challenging. TOURS: Tuscany, Puglia, Provence
[2+ The “plus” indicates more challenging terrain though the walks are gentle].

3 – MODERATE: Some sustained hills with occasional steep grades and rocky terrain
Here you find a mix of terrain with some steep stretches.
TOURS: Corsica, Sardinia, some of the Dolomites tours, and some hikes on the Greek Islands
[3+ The plus indicates rockier terrain or lots of stone steps (Amalfi, the Cinque Terre) or greater elevation gain/loss (the Dolomites)].

4 — HIKE: Classical hiking with rough terrain, sustained hills, and more mileage. These hikes are on a mix of rough terrain, sometimes involving steep stretches and difficult footing. TOURS: some of our hikes in Sardinia, some of the days in the Cinque Terre, some of the variants of our Dolomites tours.

5 – CHALLENGING: Longer days, challenging climbs, rocky terrain. We don’t do a lot of seriously challenging tours but we do have a Dolomites trip where we hike from hut to hut, so that’s probably the closest we get to a 5.

Info on prices

The price indicated is for a minimum of 6 people and our basic itinerary based on double occupancy (a “single supplement” covers hotel prices only, we apply no extra fees). Departures with fewer people or with upgraded hotels will have a higher price. We can organize private departures for any number of people but prices vary depending on number of participants. Please contact us for details!