Heart of Italy
Nine days. Three regions. A decade of friendships with the people who feed, grow, make, and love this place — and who have been expecting us back.
→ Emilia-Romagna
Imagine yourself…
rolling pasta with a local chef, making mozzarella for lunch, sipping fresh limoncello in a family-owned lemon grove, and dining in a secret garden right off the main paths of Sorrento.
From the fields and the factories, all the way to the table.
Most food tours start at the plate. We start where the food does and follow it the whole way. Italy isn't one kind of meal, so we don't build one kind of trip. Here's what that range looks like:
The fields
Lemon groves in Sorrento, garden vegetables in Positano, vines in the Tuscan hills.
The makers
Inside a family-run acetaia where balsamic ages for decades in wooden barrels.
The hands
Market visits and cooking with Chef Alain.
The history
Walking tour around the city.
The table
A trattoria closed for the evening just for us.
Friends You Haven't Met Yet
Our dining experiences focus on eating fresh, seasonal, and local, guided by our friends who will share their stories as they invite you into their homes and kitchens. Our personal relationships in Italy with local chefs, guides and families open doors to experiences most travelers never have.
Marika & Family - Sorrento
Wander the market together, then step into her kitchen for a hands-on cooking class in the heart of Porto.
Gaia - Florence
Pick vegetables straight from the garden, then cook traditional Alentejo dishes together in her kitchen.
Gloria - Florence
Step into their home for dinner of traditional dishes and unhurried conversation.
Caterina - Emilia-Romagna
Wine tasting with Ines at her family's estate poured by someone who knows the vineyard by heart.
Be fully present. We’ve handled everything else.
✓ 4-5* Boutique Accommodations
✓ Airport meet and greet with private transfers
✓All ground transportation
✓ All meals listed in the itinerary
✓ Wine tastings 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: mandatory travel insurance, transportation or airfare to/from Portugal, hotel incidentals, and premium alcoholic beverages.
Just 6 – 12 travelers — small enough to fit inside a family kitchen.
"My standards are so much higher now."
"I've always had the travel bug, but after traveling with TTLT I know how unique a trip can be. Truly a life-changing experience."
"I loved not having to worry about one thing!"
"An amazing mix of interactive experiences."
"...dining in some of the smallest and best restaurants, and especially visits to small family businesses with amazing histories and stories."
Nine days, three regions, a friend waiting in each.
Benvenuto in Italia
A private driver whisks you from Naples past Mt. Vesuvius to Sorrento. In the evening, we meander to a tucked-away garden for dinner with Pia, fourth generation of a family of Sorrento gardeners.
Limoncello, mozzarella & a hillside table
Walk the lemon groves and learn to make limoncello, then make fresh mozzarella at a family farm. We drive to Positano to dine at Marika and Emanuele’s home, with vegetables picked from Marika’s own garden.
An islander’s Capri
Domenico — one of few guides born, raised, and still living on Capri — gives us his island. Lunch is on his and Maria’s back porch under the lemon trees, where Maria shares her nonna’s famous lemon cake.
Into the Renaissance
We take the train to Florence and feast on bistecca fiorentina and ribollita, then meet our friend Gaia for a relaxed walking tour through the city’s fascinating past and everyday charm.
The other side of the Arno
We wander a neighborhood across the river, tasting small bites from local artisans. At dinner, Gloria cooks her favorite Florentine dishes in her one-of-a-kind apartment overlooking the Duomo.
Pasta & Chianti in Pistoia
We gather market ingredients with our dear friend Alain, then he closes his restaurant just for us. An in-depth pasta lesson over Chianti, a Tuscan feast, and Alain’s tiramisu to re-create and eat.
Castles, wine & a family dinner
A leisurely drive to the countryside, stopping for wine tasting and lunch at a hillside castle. We settle into our final hotel, then drive to Francesca’s home to dine with her family on traditional Modenese dishes.
Cheese wheels & aged balsamic
A behind-the-scenes Parmigiano-Reggiano tour, then an inside look at a family acetaia where balsamic ages for decades. A farewell dinner of multi-course tasting celebrates the flavors of the region.
Arrivederci
An optional group breakfast at the resort before we say our goodbyes, with a private transfer arranged to your departure airport or train station.
Our itinerary is always evolving as we coordinate with our friends in Italy around their schedules. Consider it a vivid preview of what travel with us feels like.
Let's start with a conversation.
There's no commitment in asking. Whether you're wondering about the group dynamic, the activity level, or exactly what happens on day 7 — we're here. We'll reply within 24 hours.
Frequently Asked
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Travelers should be comfortable engaging in activities like walking tours (lasting up to 4 hours), walking over sometimes uneven terrain like cobblestone streets, climbing stairs, and standing for extended periods. This tour is appropriate for those who are comfortable with some longer and moderately active tour days. If you have any specific questions you’d like to discuss with the tour host, contact us!
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There are only 6 - 12 travelers on this group trip. With fewer travelers, we can explore unique, off-the-beaten-path spaces that larger groups can't access, such as family-owned kitchens, bustling markets, and private homes.
This small size also fosters meaningful connections - whether it’s sharing stories over a meal with a local host or bonding with fellow travelers, our trips feel more personal.
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The $9,950 per person price (double occupancy) includes 4–5 star boutique accommodations, airport meet-and-greet with private transfers, all ground transportation, all meals listed in the itinerary, wine tastings and select alcoholic beverages with most meals, all activities and tours, and all taxes and tips for drivers, guides, and restaurants. A 24/7 tour host travels with the group the entire trip. Not included: mandatory travel insurance, airfare to and from Portugal, hotel incidentals, and premium alcoholic beverages.