Sunlit shores & clear water
Hand-picked resorts, private villas and custom journeys through quiet cays, reef-lined beaches, lively towns and islands rich in food, music and culture.
Why we love the Caribbean
Sun-drenched, salt-kissed, and moving to its own island rhythm, the Caribbean is so much more than a beach break. Stretching across more than 7,000 islands, islets and cays, every stop has a personality of its own – Dutch-colored waterfronts in Curaçao, nutmeg-scented hills in Grenada, and conch fritters served up at a shack with your toes in the water. Snorkel reefs swirling with parrotfish, or claim a hammock and let the turquoise do the talking. Island time starts now.
Perfect beaches
Island cultures with their own traditions
Intimate stays beside the sea
A starting point for your perfect escape
We're good company, and we give great advice
With more than 7,000 islands, islets and cays to choose from, we match the island to your vibe first, then find the hotel.
We keep a list of beaches that tend to stay clearer in sargassum season: Eagle Beach in Aruba, Grand Anse in Grenada, Grace Bay in Turks & Caicos and more.
We'll compare them honestly and help you decide when the extra privacy is worth it.
Adrienne and team were so easy to work with, and truly took the detailed logistical stress off of planning AND getting through our vacation. They worked to finalize the perfect itinerary and answered lots of questions and have the scoop on the best tours and best places to stay!
Perfect honeymoon
Adrienne planned the perfect honeymoon for us. We were overwhelmed with the thought of planning it ourselves and put it off for years. We found everyone informative, honest, and helpful.
A worry-free vacation
I loved our trip scheduled with [Osaviva] all of the activities and resorts were stunning. With vehicle transfers included it was truly a worry free vacation.
Two wonderful trips
We have travelled twice on trips organised by [Osaviva] and we have loved them both. Everything was planned exceptionally well, the hotels were beautiful and we had an amazing time! We look forward to our next adventure with [Osaviva]!
Our top picks
Providenciales
Amanyara occupies the remote northwest coast of Providenciales beside a marine national park and an 18,000-acre nature reserve. Standalone pavilions, a half-mile beach, and fully staffed three- to six-bedroom villas create one of the Caribbean’s most private full-service resort stays.
Caribbean
La Sagesse
Two quiet bays frame Six Senses La Sagesse on Grenada’s less-developed southern coast. Its 56 pool suites and 15 villas follow the hillside and lagoon, with private pools, extensive wellness facilities, and family programs built into the resort.
Caribbean
Mustique
Mustique’s only full-service hotel places 17 rooms, suites, and cottages across 13 acres of tropical gardens near Endeavour Bay. The historic Great House, island social calendar, and access to Mustique’s beaches make the destination itself the main attraction.
Caribbean
Maundays Bay
Cap Juluca stretches along Maundays Bay with 113 rooms and suites in low-rise whitewashed buildings. Every accommodation faces the beach, while four restaurants, a Guerlain spa, watersports, and larger villas make it equally strong for couples and families.
Caribbean
Anse de Toiny
Hotel Le Toiny has 22 villa suites spread across a protected 17-hectare hillside on St. Barth’s quieter southeast coast. Every suite has a heated private pool and ocean view, with a separate beach club below on rugged Toiny Bay.
Caribbean
Long Island
Jumby Bay is a car-free, 300-acre private island two miles from Antigua, reached by a 10-minute catamaran transfer. Forty oceanfront cottages anchor the hotel, while a changing collection of staffed villas and estates serves larger families and groups.
Caribbean
When we plan a trip
Island hopping
Cross clear channels by private boat, catamaran, or small ferry, stopping at quiet beaches and reef-lined cays along the way. The Grenadines are especially well suited to days that combine sailing, snorkeling, and lunch on a different island.
Rainforest & volcanoes
Follow rainforest trails to waterfalls, volcanic peaks, and high viewpoints in destinations such as Dominica, St. Lucia, and Guadeloupe. Routes range from short nature walks to full-day hikes through steep tropical terrain.
Reefs & marine life
Explore coral gardens, rocky coves, and offshore reefs inhabited by tropical fish, rays, turtles, and other marine life. Some islands have excellent snorkeling directly from the beach, while others are best explored by boat.
Beaches & coves
The Caribbean has everything from long, calm swimming beaches to small coves beneath rocky headlands. Spend the day in the water, stop at a beach restaurant, or travel by boat to a shoreline with few other visitors.
Historic towns
Explore cobblestone streets, colonial buildings, market squares, forts, and waterfront neighborhoods with a local guide. Havana, Trinidad, Santo Domingo, Willemstad, and San Juan each reveal a different part of Caribbean history.
Food, music & rum
Visit a market, cocoa estate, rum distillery, or family-run restaurant to learn how local ingredients and traditions differ across the region. Fresh seafood, Creole cooking, spices, live music, and regional rum give each island its own identity.
The things travelers ask us most about the Caribbean, from hurricane season to choosing the right island. Have a question we haven't covered? Send it to
June 1 to November 30, with the highest risk from August to October. Aruba, Bonaire and Curaçao sit south of the main hurricane belt.
Seaweed is mostly a spring and summer issue on Atlantic-facing beaches. Beaches that usually stay clear include Eagle Beach and Palm Beach in Aruba, Grand Anse in Grenada, Playa Porto Marie in Curaçao and Grace Bay in Turks & Caicos.
Yes, with planning. Direct flights between islands are limited, and some routes connect through hubs like San Juan or Miami. Ferries link a few close neighbors.
It depends on what you want: quiet beaches, diving, sailing, culture or a big resort. Islands differ a lot in size, pace and price.
It varies by island. Many use or accept US dollars, and cards are widely accepted.
For most islands, yes. US citizens can visit Puerto Rico and the US Virgin Islands with a government photo ID.
