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

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
Lush rainforests & volcanic peaks
Coral reefs and warm, clear seas
Quiet coves and boutique island stays
Hidden coves and soft sand beaches
Caribbean culture and coastal cuisine
What sets us apart
Why Travel with Osaviva?

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