The small-group journeys I personally host are designed to be anintimate, beautifully paced travel experiences. Each itinerary is thoughtfully crafted with comfort, intention, and a touch of luxury, so you can fully immerse yourself in the destination while I handle every detail behind the scenes. This is travel that feels effortless, connected, and unforgettable.
it's all about
the group travel
process
the
Here’s how I create each experience:
- I begin with the destination. I choose places guests have expressed interest in or spots rich with culture, food, and beauty.
- Timing matters. I select dates when the region feels vibrant but not overwhelmed by crowds or extreme weather.
- The villa comes first. A luxurious, comfortable home base sets the tone and determines the number of guests who can join.
- Food + drink anchor the itinerary. Think vineyard tastings, chef-led dinners, markets, and culinary explorations.
- Cultural depth is essential. Museums, historical tours, artisans — experiences that help you understand the soul of a place.
- Transportation is a priority. Seamless, private, high-quality transportation so you never feel rushed or stressed.
Each trip is designed to feel elevated, intimate, and unforgettable.
explore our
Past trips
greece, Athens & Crete
Italy | lucca, tuscany
This 7-night stay in a private Lucca villa includes daily breakfast, hosted happy hours, hands-on cooking, vineyard dining, guided wine tastings, and curated trips to Florence and Cinque Terre. With luxurious accommodations, unforgettable meals, and seamless group travel, all you have to do is arrive and enjoy.
This 9-night journey begins in Athens with a private tour and welcome dinner, then moves to Crete for a week in a stunning seaside villa with a private beach, pool, spa amenities, and expansive outdoor living. Enjoy daily breakfast, hosted happy hours, wine, chef-curated meals, and three days of guided excursions—from olive oil tastings and cooking classes to sailing the Cretan coast. Seamless, indulgent, and unforgettable—Greece, the Chez Shay way.
