Sunlit shores, clear water, and islands shaped by culture and calm

Luxury Travel in the Caribbean

Warm turquoise water, palm-lined bays, and islands where the pace naturally slows.

The Caribbean is a mosaic of experiences, from volcanic peaks and rainforest trails to coral reefs, sailing routes, and powder-soft beaches. Days unfold with gentle ease: long swims, rum-soaked sunsets, fresh coastal cuisine, and lively island culture. Whether you’re dreaming of a private villa, a quiet cove, or a vibrant coastal town, the Caribbean offers a journey defined by color, warmth, and effortless beauty.

A starting point for your perfect escape

Caribbean Trip Inspiration

These are just a glimpse of what your journey could be. Get inspired, reach out and let's start planning your escape.

Why the Caribbean?

Our Top Picks

Where to Stay in the Caribbean

Island with a small building and lounge chairs on a grassy area, surrounded by turquoise water. Cap Juluca, Angullla, Caribbean.

Where will your island journey take you?

Follow the pull of sun & sand
Moments shaped by salt & sea

Caribbean Highlights

Island hopping across turquoise waters

The Caribbean is made for movement between islands. Sail or ferry across calm channels where the color of the water shifts with the light. Each stop brings a new shoreline, a different culture, and a fresh sense of discovery. It is an effortless way to experience the diversity of the region.
Aerial view of a tropical island with clear turquoise waters. Tobago Cays, St Vincent, Grenadines. Caribbean.

Lush rainforests & volcanic peaks

Some islands reveal a wilder side with dense forest, hot springs, and cloud-covered ridges. Trails lead to waterfalls, birdlife, and views that stretch beyond the coastline. These landscapes offer a refreshing contrast to the beaches and bring depth to any Caribbean journey.
Two people walking on a trail with scenic mountains and ocean view. St Lucia pitons, Caribbean.

Coral reefs and warm, clear seas

Under the surface lies one of the region’s greatest treasures. Coral gardens, gentle turtles, and schools of colorful fish thrive in warm, shallow water. Whether you prefer snorkeling from shore or diving deeper offshore, the Caribbean invites slow exploration and easy days in the sun.
Person snorkeling near a rocky cliff in clear blue water; Jamaica. Caribbean.

Quiet coves and boutique island stays

Small hotels and villas are tucked along hillsides, coves, and calm beaches. These stays offer privacy, thoughtful design, and settings shaped by light and sea breeze. They are ideal for travelers who value comfort, intimacy, and a sense of place.
Scenic view of a tropical beach with clear blue water and green mountains. Beach at Le Toiny, St Barts, Caribbean.

Hidden coves and soft sand beaches

Across the Caribbean you will find beaches in every shade of gold and white (and pink). Some are lively and sunlit, others quiet and tucked between rocky headlands. Clear water and gentle waves make these shores perfect for swimming, snorkeling, or simply settling into a slower pace. It is one of the region’s most iconic and restorative experiences.
Beach with pink sand and turquoise water under a blue sky. Antigua, Caribbean.

Caribbean culture and coastal cuisine

Island life is shaped by music, food, and stories passed between generations. Markets, beach cafés, and family-run restaurants bring local flavors to the forefront. Fresh seafood, tropical fruit, and warm hospitality create meals that feel connected to the land and sea.
Outdoor setting with plates of food on a table, including fried seafood and vegetables. Caribbean.
What sets us apart

Why Travel with Osaviva?

Tropical scene with palm trees, sunset, and birds on a beige background; Osaviva graphic when to go honeymoon

When to Go to the Caribbean

Dry season (high): December to April:

Sunniest weather, calm seas, peak travel

Shoulder season: May to early June

Warm with fewer crowds, good value

Wet season (low): June to November

Short showers & lush landscapes

Hurricane risk: August to October

Storms possible, insurance is recommended

Regatta season: January to April

World-class sailing events

Whale watching: January to March (Dominican Republic)

See humpbacks in their breeding season

Turtle nesting: May to October (Barbados, Grenada, St. Lucia)

WItness nesting and hatchlings