Elevated Escapes for Birds of a Feather.
Flights of Fancy
Elevated Escapes for Birds of a Feather.
Flights of Fancy
Flights of Fancy was born from a simple idea...
What if the same white-glove service and attention to detail our clients trust us to bring to their personal journeys could be shared, beautifully, with a small group? It’s our way of translating the seamless planning, insider access, and thoughtful touches we are already known for into experiences designed to be savored together.
Flights ofFancy
Flights of Fancy was born from a simple idea...
What if the same white-glove service and attention to detail our clients trust us to bring their personal journeys could be shared, beautifully, with a small group? It’s our way of translating the seamless planning, insider access, and thoughtful touches we are already known for into experiences designed to be savored together.
Below, you’ll find highlights from recent Flights of Fancy escapes.
They may be sold out, but they still serve as inspiration for what’s possible
when travel is designed with connection, ease, and style in mind.
We’re already curating the 2026 collection — and we’d love for you to be part of it. Reach out to plan your own Flight of Fancy, or join the list to
be the first to know when new journeys take flight.
Couples' Charleston Escape
Our inaugural Charleston Couples Trip was everything we hoped it would be: exploring cobblestone streets, alternating lobby bars with rooftop cocktails, savoring low country high cuisine, ...oh, and one epic yacht day! It was just the right balance of history and indulgence Every moment felt like it belonged on film — which is why we’ve gathered a highlight reel here, so you can glimpse the magic yourself.
Our Charleston escape was perfect for us but it’s only a glimpse of what’s possible for you! With Flights of Fancy, we can capture the same spirit — or create something entirely your own. Picture boutique hotels steeped in Southern charm, private chefs setting the table in historic homes, and curated experiences that reveal the city’s secrets. Every detail? Styled, seamless, and ready from arrival to farewell.
Three couples. One Grand Getaway.
Caftans & Confessions
Chic escapes, cheeky stories.
Every great series needs a dazzling femme fatale episode — and for Flights of Fancy, it begins in Palm Beach. Caftans & Confessions is our inaugural girls’ trip: a long weekend at the iconic Colony Hotel, where chinoiserie wallpaper meets poolside glamour and every corner feels like it was made for champagne toasts.
This escape is all about friendship, fun, and a touch of fabulous mischief. Think: vintage finds and curated shopping along Worth Avenue, yacht days on sparkling waters, Swifty’s bingo nights with cocktails in hand, and confessions whispered under striped umbrellas. The Colony becomes our pink paradise, and Palm Beach itself the stage for memories worth retelling.
Though this journey is already fully booked, the story is just beginning. Highlights are coming soon — but in the meantime, enjoy the teaser video we created to invite the group, and picture yourself in a flowing caftan, cocktail in hand, ready to join the next chapter.
Traveling side by side transforms a trip into something more — a shared story. Along the way, companions become friends, and friends become family. We design for those moments of connection, with just the right balance of landmark experiences and unhurried time to simply enjoy being together.
At Its Heart: Connection
What stays the same: our Virtuoso relationships and preferred partnerships, the upgrades and thoughtful touches, the seamless choreography you never have to see.
What’s distinct: the joy (and ease) of being a guest on your own group trip. You arrive; we handle the rest—hosted by a dedicated on-the-ground team who knows your names, notes your preferences, and anticipates the moment before you do.
And because groups deserve their own special touches and hand-holding, we even create custom what-to-wear style boards—head-to-toe outfit inspiration for every moment of the journey—along with curated branded swag that feels more like keepsakes than souvenirs. These aren’t just extras—they’re part of the storytelling, making each trip feel as styled and seamless as it is memorable.
Our Signature Touch with a Twist
Why It Matters for Businesses
Flights of Fancy is also built for corporate and small-business retreats. Not every company has an internal planner; so we become that partner. We translate your goals into an itinerary with purpose—time to connect, space to think, experiences that spark the conversations you actually want your team to have. Clear budgets, measured ROI, and the kind of hospitality that makes everyone feel looked after.
Want something to remind you of the epic story? We'll even design and deliver your branded swag. These aren’t just souvenirs; they’re keepsakes that connect everyone to something bigger, turning a group of travelers into part of a shared story
Who It’s For
A setting where every age finds joy, from grandparents to grandchildren, with details designed so everyone can simply enjoy the time together.
Connection redefined — a getaway for couples who love to travel together. Think shared adventures, laughter over long dinners, and every detail handled so you can simply show up and enjoy.
A chance for teams to connect beyond the boardroom, with thoughtful settings that inspire ideas, deepen relationships, and spark collaboration. Works for dreamy destinations requiring a boarding pass, and those short staycations closer to home.
An invitation into community — where individual travelers feel welcomed, included, and part of something larger from the very first hello.
Multi-Generational Families
Couples
Corporate and
Small-Business Retreats
Solo Travelers
Uninterrupted time together, filled with laughter, shared stories,
and the kind of memories that become lifelong touchstones.
START YOUR
FLIGHT OF FANCY
