FLORENCE + PUGLIA, ITALY | June 9-17, 2026
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Overview
This journey invites couples, friends, and solo travelers to experience Italy with curiosity, energy, and a sense of discovery that is not your traditional trip to Italy. From the art and architecture of Florence to the vineyards and olive groves of Tuscany, the dramatic Adriatic coastline of Polignano a Mare, and the baroque soul of Lecce, this trip blends culture, food, movement, and connection—designed to feel immersive, dynamic, and anything but ordinary.
We travel intentionally, guided by locals who open doors to places and experiences that go beyond the expected. Each day balances exploration and ease—city walks and coastal boat rides, hands-on food and wine experiences, time outdoors, and evenings that unfold naturally over great meals and conversation. Expect lesser-known wineries, producers, and artisans alongside iconic moments, creating a journey that feels authentic, surprising, and deeply memorable. This isn’t a checklist tour or a slow retreat—it’s a shared experience built around curiosity, connection, and the joy of discovering Italy together.
Accommodations
Our accommodations are chosen for their character, sense of place, and the feeling of being genuinely well cared for. In Florence, we stay in a modern, locally inspired boutique hotel that puts us right in the rhythm of the city—ideal for wandering historic streets, slipping into aperitivo spots, and ending the night in lively conversation.
In Tuscany, our countryside stay offers a front-row seat to the landscape, surrounded by vineyards and olive groves. These thoughtfully selected properties create a natural gathering place—perfect for recharging between immersive days of winery visits, hands-on experiences, and long meals shared around the table.
Along the coast in Polignano a Mare and onward to Lecce, accommodations capture southern Italy’s sunlit elegance, with sea views, historic details, and inviting spaces to unwind after days of exploration. Whether perched above the Adriatic or tucked into the heart of the old town, each stay deepens your connection to the place—and to the people you’re traveling with.
Food & Wine
In Tuscany, our countryside stay places us at the crossroads of refined wine, exceptional food, and Italian craftsmanship. Days unfold with curated tastings at standout wineries, including time at Grignano, a historic House of Medici property where heritage and elegance shape every glass. Between vineyard visits, there’s time to explore Italy’s effortless sense of style—high-end Italian fashion, artisanal boutiques, and timeless design that mirrors the intention behind the wines.
Meals are a highlight in their own right, with thoughtfully chosen restaurants showcasing Tuscan ingredients at their best—seasonal, regional, and deeply rooted in place. Evenings gather naturally around long tables, where beautifully prepared dishes, great bottles, and glowing conversation carry the night.
Energize & Connect
This journey is designed to energize your senses and strengthen connection through shared experiences and inspiring settings. Days are engaging and dynamic—walking historic streets, tasting wines in the countryside, cruising along the coast by boat, and moving naturally between exploration and ease.
There’s space to discover together and reconnect along the way—morning coffees in sunlit piazzas, post-adventure moments to refresh at the hotel or spa, and evenings that unfold over great food, wine, and conversation. Connection here feels effortless and genuine—sparked by curiosity, shared discovery, and the simple joy of experiencing Italy side by side.
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Details
Duration: 9 days / 8 nights
Single Supplement: $1,200
Deposit: 25% non-refundable deposit to confirm your reservation
Group Size: Limited to 14 guests
This journey is intentionally intimate and thoughtfully curated, allowing you to fully immerse yourself without worrying about logistics. From arrival to departure, every detail is handled so you can focus on connection, discovery, and enjoyment.
What’s Included
- Expert Hosts – Guided by experienced trip leaders with deep local relationships and cultural insight
- Boutique Accommodations – Thoughtfully selected hotels rooted in comfort and place
- All Meals – Daily breakfast, lunch, and dinner at notable restaurants, wineries, and local favorites
- Food & Wine Experiences – Olive oil and truffle experiences, vineyard visits, tastings, and cooking classes
- Cultural Immersion – Art, history, walking tours, and hands-on local traditions
- Transportation – High-speed trains, private transfers, and all in-country transportation
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Retreat Gifts – Special welcome gifts curated for the journey
What’s Not Included
- International Airfare – Flights to and from US/Italy
- Optional Purchases – Wine, souvenirs, or personal shopping
- Hotel Incidentals – Room service, laundry, minibar, and personal tabs
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