Travel to Tuscany on a crafted trip that is anything but ordinary.

 

“What really delighted us was all of the very personal experiences with artisans that were not your standard tourist activities. I highly recommend this trip if you want to really experience Italy.”
- Michelle B.

 
 
 
 
 

 

Pricing

$6,885 per person based on double occupancy
$8,810 per person based on single occupancy

Dates - 6 days/5 nights

April 28 - May 3, 2025 - Call to book
June 16 - 21, 2025
September 1 - 6, 2025
October 13 - 18, 2025

Destinations

Cortona
Montalcino
Anghiari
The Tuscan Countryside

 

Join an all-inclusive trip to Tuscany!

From family-owned vineyards to a generations-old family-run textile business, you'll savor the region's finest foods and handcrafts while learning the age-old techniques behind their creations.

 
 

✓ 4-5* Boutique Accommodations

✓ Airport meet and greet with private transfers

✓All ground transportation logistics

✓ All meals listed in the itinerary

✓ Wine tasting and select alcoholic beverages with most meals

✓ All activities, experiences, tours and sightseeing

✓ All taxes and tips for all drivers, guides, restaurants, and more

✓ 24/7 Tour Host

Exclusions: transportation or airfare to/from Tuscany, travel protection and trip cancellation protection, hotel room incidentals, and premium alcoholic beverages

 
 
 
 

Imagine yourself…

exploring picturesque villages, cooking in a local’s home, walking through rolling vineyards, touring family-run factories, and learning from local artists.

 
 
 

From Fine Dining to Family Tables

Our personal relationships in Tuscany with local chefs, guides, artisans, and families open doors to experiences most travelers never have - a home cook teaching traditional Tuscan cuisine, a local painter sharing their skills, or a warm invitation to visit a family-run textile factory. These connections turn every experience into a story, immersing you in Tuscany’s rich culture and leaving you with memories you’ll cherish forever.

 

Valeria

Antonella

Giovanni

Lisa


 
 
 
 
 

“The TTLT team shows incredible dedication to making the trip go smoothly and had incredible attention to detail - very impressed!” - Annie G.

 
 
 
 

“Visiting the Busatti Factory was the highlight of the trip. This felt like a treat and to have [the owner] Giovanni give us the tour was a humbling experience.” - Kerri L.

 
 

Trip to Tuscany Itinerary

This trip to Tuscany promises an unforgettable blend of culture, cuisine, and craftsmanship for those seeking an authentic taste of Tuscany's rich heritage.

 
 

Day One - Cortona

Welcome to Italy! Upon arrival at the Florence Airport (FLR), our driver will take you through the Tuscan countryside to the town of Cortona to our group hotel.

We will have a short introduction and welcome before heading off on a walking tour of Cortona led by our friend Valeria, whose family has lived in the village for generations. After getting more familiar with the area, we’ll head to a local restaurant for our welcome dinner.

Included meals: dinner

 
 
 

Day Two - Cortona

This morning, we'll explore the local market with our friend, Antonella, and purchase ingredients for our cooking class and dinner. After the market tour, lunch and the afternoon are on your own to explore.

We'll meet back together in the late afternoon and take a short drive to Antonella's home where she will teach us how to prepare traditional Tuscan dishes. For dinner, we'll feast on the fruits of our labor on her patio.

Included meals: breakfast, dinner

 
 
 

Day Three - Montalcino

Today we’ll visit a “full-circle” farm. The owner will give us a private tour and share the farm’s unique history, and we’ll taste the unforgettable cheese made on site. During lunch, we’ll savor the farm’s fresh produce, cheeses, and hand-made pastas.

Then we’ll make our way to Montalcino, home to the famous Brunello wine, to visit a biodynamic wine estate. We’ll tour the vineyard and taste the estate’s best wines served directly by their makers.

Included meals: breakfast, lunch

 
 
 

Day Four - Anghiari

In the morning we’ll depart Cortona and travel to Anghiari. In this picturesque town we’ll enjoy a special visit to the Busatti factory with the owners of this beloved textile brand. Walk through the looms from the 1800’s that are still in use, and learn why the family has maintained their production in the same way it’s been done for generations. After our tour, Giovanni the owner will host us in his private villa for a morning aperitivo while he shares with us his personal collection of artwork.

We’ll have lunch in town and then continue on to our hotel. We will end the evening with a delicious dinner outdoors.

Included meals: breakfast, lunch, dinner

 
 
 

Day Five - Tuscan Countryside

Today we enjoy a leisurely morning before visiting one of our favorite wineries tucked away in the rolling Tuscan hills. We’ll spend the morning sipping local wines and hearing stories from winemakers.

After our tasting, we’ll have a relaxed lunch then head back to the hotel where we’ll have a bit of free time before our final activity together - Sip & Paint with Lisa! Sip on local Tuscan wine as Lisa guides you through a watercolor class.

At our farewell dinner, we’ll enjoy a multiple-course menu showcasing local ingredients sourced from surrounding areas.

Included meals: breakfast, lunch, dinner

 
 
 

Day Six - Tuscan Countryside

On our day of departure, we will have an optional group breakfast at the hotel. Then you will have a private driver take you to the airport in Florence (FLR) or the train station if you have an onward destination in Italy.

 
 
 

Our itinerary is always subject to change as we constantly research, update our trip, and coordinate with our friends in Italy to work with their schedules. This itinerary is a great resource for getting an idea of what kind of experiences you’ll have when you travel with us to Italy.

 
 
 

 

Meet your tour host, Kathryn! Send her a message if you have any questions about the trip.

Questions? Ask me anything!

 

 
 

Frequently Asked Questions

 
 

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