Custom Caribbean Luxury Travel

Turquoise Seas & White Sand Beaches

Caribbean

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.
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What Our Clients Say

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★★★★★

Our trip went off flawlessly. We enjoyed every venue, excursion, every minute. We went from the jungle in Belize to a private island and felt so comfortable throughout our stay. It was truly an adventure!!

Charles McMath
★★★★★

We are are so glad we booked with ROAM Wild. They were wonderful to deal with and accommodated a lengthy list of requests on our honeymoon. We had so many fun surprises along the way which made our honeymoon special!

Jenna
★★★★★

An absolutely unreal experience. Attention to detail was exceptional. Every activity was planned to perfection, transportation was arranged, and we didn’t have to worry about a thing. I do not have enough good things to say about this trip. The service ROAM provides is worth every penny and more.

Mike Tweedie
★★★★★

You planned the perfect trip, the accommodations were first class and the guides were very good and knowledgeable. I will be spreading the word.

Laura Lym-Murphy
★★★★★

ROAM was fantastic! Their communication was superb also- that’s critical while you’re in another country! They listened to our wants and desires for what we wanted our trip to look like, and exceeded our expectations!

Kristen Morse

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.

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