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Local Living Italy - Tuscany San Gimignano

If Tuscany has ever called your name, this is your chance to answer. For seven days, you’ll settle into a charming farmhouse in San Gimignano — your home for the week and your base for exploring the heart of central Italy. Wake up to vineyard views, stroll medieval streets, and soak up sunsets over rolling hills, all at a pace that feels truly local. With free days to embrace the countryside or head out on day trips to Florence, Siena, and Volterra, this isn’t just a visit — it’s living Tuscany, one unforgettable day at a time.

On Sale
7 DaysFlorence to Florence
Valid on May 5 2026Trip Code: EIFL
From $1451.67 USDIncluding taxes and fees

Is this tour for me?

Travel Style: Local Living

Intimate unpack-just-once adventures that bring out the best of the world’s best destinations.

Service Level: Standard

Comfortable tourist-class accommodations with character; mix of public and private transport.

Physical Grading: 2 - Light

Light walking and hiking suitable for most fitness levels. Nothing too challenging.

Merchandising: New Trips

Trip Type: Small Group

Group trips average 12 travellers per departure, depending on the adventure. The maximum is usually no more than 16, but some can be smaller or bigger, depending on the trip. Check individual trips for details.

Age requirements: 12+

All travellers under age 18 must be accompanied by an adult.

Check Your Visa Requirements

Before booking, use our handy entry requirements tool so you know which documents you need to enter and travel through the countries on your trip.

Local Living Italy - Tuscany San Gimignano - Itinerary

Trip Start: FlorenceTrip End: Florence

DAY 1

Florence

Arrive at any time.

Welcome Moment - Meet Your CEO and Group:
Your opportunity to meet your CEO and fellow travellers, and learn more about your tour. Opt to join the group for a local meal afterwards. Don't forget to see the notice in the lobby (or ask reception) for the official time and place to meet up with the group.

B&B Hotel Firenze City Center:
B&B Hotel Firenze City Center

Optional Activities

Local Living Italy - Tuscany San Gimignano - Itinerary

Trip Start: FlorenceTrip End: Florence
DAY 1
Florence

DAY 1

Florence

Arrive at any time.

Welcome Moment - Meet Your CEO and Group:
Your opportunity to meet your CEO and fellow travellers, and learn more about your tour. Opt to join the group for a local meal afterwards. Don't forget to see the notice in the lobby (or ask reception) for the official time and place to meet up with the group.

B&B Hotel Firenze City Center:
B&B Hotel Firenze City Center

Optional Activities

DAY 2
Florence/San Gimignano
+
DAY 3
San Gimignano
+
DAY 4
San Gimignano
+
DAY 5
San Gimignano
+
DAY 6
San Gimignano
+
DAY 7
San Gimignano/Florence
+

What’s Included

  • Your Welcome Moment: Welcome Moment - Meet Your CEO and Group
  • Your Local Living Moment: Home Cooked Dinner with Ugo, San Gimignano
  • Your Foodie Moment: Half-day Cooking Class, San Gimignano
  • Your Local Living Moment: Local Wine Tasting, San Gimignano
  • Orientation walk Florence
  • Welcome briefing with local host
  • Dinner at Ugo's
  • Cooking class in San Gimignano
  • Orientation walk San Gimignano
  • Orientation walk Volterra
  • Alabaster workshop tour and demonstration
  • Hike through the Tuscan Countryside
  • Free time to explore Siena
  • All transport between destinations and to/from included activities.
Accommodations
  • Hotel (1 nt), apartments in a locally owned home (5 nts).
Meals
  • 6 breakfasts, 1 dinner
Transportation
  • Local bus, train, walking
Staff & experts
  • CEO (Chief Experience Officer) throughout.

Local Living Italy - Tuscany San Gimignano Departure Dates

All Years

StartEndingAvailabilityPrices from
Sun, Apr 12 2026Sat, Apr 18 2026Open (3)$1,451.67 USD
(price includes taxes and fees)
Sun, Apr 19 2026Sat, Apr 25 2026Open (2)$1,451.67 USD
(price includes taxes and fees)
Sun, Apr 26 2026Sat, May 02 2026Open (3)$1,451.67 USD
(price includes taxes and fees)
Sun, May 03 2026Sat, May 09 2026Open (3)$1,534.67 USD
(price includes taxes and fees)
Sun, May 17 2026Sat, May 23 2026Open (5)$1,534.67 USD
(price includes taxes and fees)
Sun, May 31 2026Sat, Jun 06 2026Open (4)$1,534.67 USD
(price includes taxes and fees)
Sun, Jun 07 2026Sat, Jun 13 2026Open (7)$1,534.67 USD
(price includes taxes and fees)

USEFUL INFO

Your Welcome Moment: Welcome Moment - Meet Your CEO and Group
Your Local Living Moment: Home Cooked Dinner with Ugo, San Gimignano
Your Foodie Moment: Half-day Cooking Class, San Gimignano
Your Local Living Moment: Local Wine Tasting, San Gimignano. Orientation walk Florence. Welcome briefing with local host. Dinner at Ugo's. Cooking class in San Gimignano. Orientation walk San Gimignano. Orientation walk Volterra. Alabaster workshop tour and demonstration. Hike through the Tuscan Countryside. Free time to explore Siena. All transport between destinations and to/from included activities.

Share an apartment in our local friend Ugo's home, eat delicious Tuscan cuisine and sample regional wines, stroll the lanes of medieval San Gimignano, walk along the beautiful Tuscan countryside, make new friends at your home away from home.

The information in this trip details document has been compiled with care and is provided in good faith. However it is subject to change, and does not form part of the contract between the client and the operator. The itinerary featured is correct at time of printing. It may differ slightly to the one in the brochure. Occasionally our itineraries change as we make improvements that stem from past travellers, comments and our own research. Sometimes it can be a small change like adding an extra meal along the itinerary. Sometimes the change may result in us altering the tour for the coming year. Ultimately, our goal is to provide you with the most rewarding experience. Please note that our brochure is usually released in November each year. If you have booked from the previous brochure you may find there have been some changes to the itinerary.

VERY IMPORTANT: Please ensure that you view a final copy of your Trip Details a couple of days prior to travel, in case there have been changes that affect your plans.

While it is our intention to adhere to the route described below, there is a certain amount of flexibility built into the itinerary and on occasion it may be necessary, or desirable to make alterations. The itinerary is brief, as we never know exactly where our journey will take us. Due to our style of travel and the regions we visit, travel can be unpredictable. The Trip Details document is a general guide to the tour and region and any mention of specific destinations or wildlife is by no means a guarantee that they will be visited or encountered. Aboard expedition trips visits to research stations depend on final permission.

Additionally, any travel times listed are approximations only and subject to vary due to local circumstances.

1. AIR CONDITIONING NOTE: Please be aware that the rooms at Agriturismo Casa Florelia do not have air conditioning.

2. It is important to note that in Europe, all guiding is based around local guides all of whom are licensed to work only in a particular city. As such, our leaders are able to provide orientation walks which will show you the layout of each town and city as well as the location of local services such as post offices and laundromats, but are unable to legally share historical facts and figures in public places.

3. In Europe it is very rare to find elevators in train stations, hotels or other public places. We use public transport on this trip, which means you will need to carry your luggage from platform to platform, in and out of trains and buses etc. and also possibly up several flights of stairs. You will also need to be able to stow your luggage safely on trains and buses. It is therefore essential that you pack light and bring luggage which is compact and lightweight, and which you can easily transport. The carrying of your luggage remains your responsibility at all times.

4. Please note that if during your visit to Italy you wish to visit popular museums such as the Uffizi or Accademia Galleries in Florence, to avoid waiting in line for a long time (especially in high season May-September when it could be a question of hours!), it is advisable to reserve tickets in advance. Tickets can be reserved online at various websites including www.florenceart.it or www.virtualuffizi.com for Florence and www.tickitaly.com for all.

5. OPTIONAL ACTIVITIES NOTE:
During high season in Europe (May-October) we highly recommend booking reservations for any popular optional activities/museum tickets etc. in advance to avoid encountering sold-out activities on the ground while on tour.

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