Cradled by turquoise waters and kissed by trade winds, the Caribbean is a mosaic of island escapes where culture, color, and luxury converge. Beyond its postcard-perfect beaches lies a world of refined adventure—sail into secluded coves in St. Lucia, dive vibrant reefs off Antigua, or hike Jamaica’s lush interior to hidden waterfalls. Each island hums with its own rhythm, from the French-Caribbean flair of St. Barts to the soulful reggae pulse of Negril. Whether indulging in private cliffside dinners, boutique villas perched above the sea, or bespoke cultural encounters, the Caribbean invites you to experience island life elevated—where every moment is as effortless as it is unforgettable.
Great for: Couples, Families, Groups
Trip Inspiration
Get inspired with our Costa Rica example trips and then get in touch to plan your own adventure
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How it Works
Browse our trip ideas. We specialize in creating custom trips centered around your special event, so this is a starting point - your trip will be unique! Then, we want to get to know you and your travel companions better. Once you send us your inquiry, our team will reach out to you within 48 hours to schedule an intake call.
We'll discuss your trip ideas, what matters to you, and your budget. We take your vision, and our ideas, and turn it into a tangible plan.
No idea what you want? No problem! Have as little or as much input as you want to. You can select your dream resorts and activities, or leave it to us. We've got you.
From here, the process is simple. We refine your itinerary until it's perfect, then you pay a deposit, and we get to work behind the scenes to prepare & arrange your trip.
We'll be here if you have any questions before your departure. Next thing you know, you're in paradise!
When to Go
The dry season (December to April) is peak travel time, with sunny skies, balmy temperatures (75°F-88°F / 24°C-31°C), and calm seas perfect for sailing, snorkeling, and beach time.
The wet season (May to November) brings short tropical downpours and increased humidity, with hurricane risk peaking in September and October. Travel insurance is a smart choice, but lush landscapes and thinner crowds during this time can be a draw.
For the best of both worlds, consider shoulder months (May and November) when the weather is generally pleasant & luxury resorts are quieter.
Caribbean Highlights
Jamaica: Waterfalls & Cliffside Views
Climb the terraced cascades of Dunn’s River Falls or hike to Reach Falls with a private guide. Unwind with cliffside cocktails in Negril at luxe hideaways like Rockhouse or the Caves, where sunsets steal the show.
St. Lucia: Piton Playground
Hike the majestic Gros Piton or snorkel beneath its shadow in warm turquoise waters. Stay in private infinity pool sanctuaries at Jade Mountain or Sugar Beach, where every vista is framed by volcanic drama.
Dominican Republic: Wide, White Sand Beaches
Unwind on the powdery white sands of Playa Esmeralda or the turquoise coves near Miches, far from the crowds. Stay at serene beachfront retreats like Temptation Miches or Zoëtry Agua Punta Cana, where oceanfront suites, spa rituals, and private cabanas set the tone for effortless indulgence.
Barbados: Adventure, Culture & Caves
Explore Harrison’s Cave by tram or paddleboard hidden coves along the Platinum Coast. Cap it off with a private rum tasting at Mount Gay or a cliffside dinner at The Cliff, staying at elegant beachfront spots like The Sandpiper.
St. Bart's: French Caribbean Indulgence
Charter a catamaran to remote beaches or dive into designer shopping in Gustavia. Sip rosé poolside at Cheval Blanc or Eden Rock, then dine barefoot in the sand—St. Barts is luxe living with a playful, Riviera twist.
