Across the Caribbean, each island has its own rhythm. One day you might sail into the Tobago Cays where sea turtles drift through coral gardens, the next you are sipping aged rum on a breezy veranda as steelpan notes drift on the air. In St. Lucia, rainforest-cloaked peaks give way to secluded bays. In the Bahamas, sandbars stretch into turquoise infinity.
Boutique hideaways perch above crashing surf or nestle in lush hillsides, their infinity pools mirroring the sea. Private villas open onto quiet beaches, while yachts glide between islets that can be yours for a day. On shore, markets brim with tropical fruit and the scent of jerk spices, and evenings bring candlelit dinners under the palms.
Here, culture and nature intertwine. French, Creole, African, Spanish, and English influences shape the flavors on your plate, the music in the air, and the warmth of a welcome. Luxury travel in the Caribbean means choice, contrast, and connection, whether you seek adventure, romance, or stillness.
Which Caribbean Island speaks to you?
- St. Lucia: For lovers of dramatic scenery and a touch of indulgence. Hike or sail beneath the Pitons, soak in warm mineral baths at the Sulphur Springs, and end the day with a sunset toast on a private terrace.
- Bahamas: For those who crave endless shades of blue. Charter a boat through the Exuma Cays, swim with gentle pigs, and picnic on sandbars that appear and vanish with the tide.
- Barbados: For travelers who want flavor with their sunshine. Tour a historic rum distillery, sample bold island spices, and dine on a private chef’s tasting menu beside the sea.
- Dominica: For nature lovers who prefer their beaches wild and their forests lush. Trek to hidden waterfalls, float in hot pools under the canopy, and listen for parrots in the treetops.
- Grenada: For the romantics and explorers. Wander spice plantations rich with nutmeg and cocoa, then snorkel the world’s first underwater sculpture park where art and coral thrive together.
- Antigua: For beach seekers who love variety. With 365 stretches of sand, you can find a quiet cove one day and join the sailing scene the next.
Sugar-soft sands, hidden coves, and sunsets that linger. Each island has its own rhythm, from sailing into the Tobago Cays to sipping aged rum on a breezy veranda. Boutique hideaways overlook turquoise bays, private villas open to quiet beaches, and yachts glide between islets that can be yours for a day. Culture and nature meet in every flavor, every song, and every welcome.
- St. Lucia
Pitons & Sea
- Discover St. Lucia’s volcanic peaks, coral reefs, rooftop plunge pools, and cliffside sunset sails.
- 7 days
- from $8,700 pp
- Antigua
Island Hopping Adventure
- An all-inclusive escape with catamaran sailing, pink-sand beaches, and private dinners on Antigua’s coast.
- 8 days
- from $5,500 pp
- St. Lucia
Pitons & Sea
- Discover St. Lucia’s volcanic peaks, coral reefs, rooftop plunge pools, and cliffside sunset sails.
- 7 days
- from $8,700 pp
- Antigua
Island Hopping Adventure
- An all-inclusive escape with catamaran sailing, pink-sand beaches, and private dinners on Antigua’s coast.
- 8 days
- from $5,500 pp
- Grenada
Spice Island Escape
- Snorkel sculpture gardens, savor island spices, and sail to secret beaches on this romantic Grenadian retreat.
- 9 days
- from $5,500 pp
- Barbados
Art of Island Time
- A chic escape with catamaran sails, rum tastings, garden strolls, and beachfront dining on the Platinum Coast.
- 8 days
- from $5,500 pp
- St. Barts
French Caribbean Romance
- A chic French-Caribbean escape with yacht sails, designer shops, rooftop dinners, and secluded ocean-view suites.
- 8 days
- from $5,400 pp
Cap Maison, St. Lucia
Tucked atop a cliff on St. Lucia’s northern coast, Cap Maison blends Mediterranean charm with Caribbean soul. With lush gardens, oceanview suites, and a private beach below, this intimate hideaway invites slow mornings, sunset toasts, and elevated island living.
Le Toiny, St. Barts
Perched above the waves on St. Barts’ Anse de Toiny, Hotel Le Toiny pairs French-Caribbean charm with serene luxury. Oceanview suites come with private terraces and plunge pools, offering uninterrupted sea views and complete privacy. Relais & Châteaux service, a chic beach club, and seasonal cuisine set the tone for romance, relaxation, and elevated island living.
Round Hill Hotel, Jamaica
Set on a lush estate just outside Montego Bay, Round Hill Villas blend timeless Caribbean elegance with a private, residential feel. Each villa is uniquely designed, with ocean views, a private pool, and dedicated staff. Guests enjoy refined comfort, five-star service, and access to the resort’s secluded beach, tennis courts, and award-winning dining.
The Sandpiper, Barbados
On Barbados’ Platinum Coast, The Sandpiper is a family-owned hideaway where barefoot luxury meets timeless elegance. Ocean Suites sit just steps from the sea, surrounded by tropical gardens and calm, swimmable waters. Refined dining captures the island’s freshest flavors, while the intimate setting makes every moment feel unhurried and personal.
Calabash Boutique Hotel, Grenada
Between tropical gardens and the curve of Grand Anse Beach, Calabash Luxury Boutique Hotel offers barefoot elegance with a distinctly Grenadian soul. Oceanview suites open to sea-kissed breezes, while thoughtful touches—from breakfast served on your private patio to candlelit dinners under the stars—make every moment feel deeply personal.
Hemitage Bay, Antigua
Tucked into a secluded bay on Antigua’s quiet west coast, Hermitage Bay blends barefoot luxury with natural elegance. This adults-only, all-inclusive retreat offers private hillside and beachfront suites with plunge pools, open-air showers, and sweeping sea views. With farm-to-table dining, personalized service, and a setting that feels both wild and refined, it’s a sanctuary for romance and rest.
Regional Expertise
With deep roots across Central and South America, we’ve traveled every terrain, by road, air, and river. Our team curates bespoke journeys grounded in personal insight, from secluded island retreats to sunrise hot air balloon rides above the rainforest. Every itinerary is handpicked, perfectly paced, and thoughtfully tailored to you.
Seamless & Personalized
From the first conversation to your final day abroad, we design each trip around your style, interests, and rhythm. You’ll receive curated options, stress-free planning, and no-pressure guidance, along with 24/7 support throughout your journey. With thoughtful extras along the way, your experience feels as smooth as it is unforgettable.
Responsible Travel
We believe indulgence and impact belong together. Our journeys support local communities, cultural preservation, and conservation across the region. There are no added fees for doing good. Our partners fund our work, so your investment stays where it matters most. Travel with Osaviva and experience luxury that gives back.
St. Lucia & the Pitons
St. Lucia’s twin volcanic peaks, the Pitons, rise from the sea in a dramatic display. Spend the morning sailing beneath them, then soak in warm mineral baths at the Sulphur Springs. In the evening, watch the sun dip below the horizon from a private terrace surrounded by lush tropical gardens.
The Bahamas & the Exuma Cays
The Bahamas offer a kaleidoscope of turquoise waters and white-sand islands. Charter a boat through the Exuma Cays, stopping to snorkel coral reefs, swim with gentle pigs, and picnic on sandbars that appear and vanish with the tide.
Barbados' Culinary Heritage
Barbados blends golden beaches with a rich food culture. Visit a historic rum distillery, wander lively markets filled with tropical produce, and enjoy a private tasting menu where a chef reimagines Bajan flavors into fine dining perfection.
Dominica's Rainforest Adventures
Known as the “Nature Island,” Dominica offers lush rainforest trails, hidden waterfalls, and volcanic hot springs. Hike to Boiling Lake with a private guide, then unwind in a natural hot pool beneath the canopy, listening to the calls of tropical birds.
Antigua's 365 Beaches
Antigua claims a beach for every day of the year. Spend mornings discovering secluded coves by kayak, afternoons enjoying the vibrant sailing scene, and evenings on a quiet stretch of sand with nothing but the sound of the waves.
Grenada's Spice Plantations
Grenada’s spice-scented hillsides invite exploration. Tour nutmeg and cocoa plantations, then head offshore to snorkel the world’s first underwater sculpture park, where coral and marine life weave through submerged works of art.
Each island is unique
Customs, currency, language, and vibe vary. Check local norms before you go.
Island time is real
Life moves slower here. Embrace the relaxed pace and enjoy the moment.
Mind the mosquitos
Bring repellent for evenings, especially in lush or undeveloped areas.
US Dollars & local currency
Most islands accept US dollars, but having local currency is helpful for taxis and tips.
Book ahead for high season
Book early for winter escapes. Shoulder season (May–June) can offer great value.
Hurricane season awareness
Officially June through November. Travel insurance and flexibility are recommended.
