The Caribbean spans dozens of islands with distinct character. The picks below are organized by island.
Anguilla
1. Belmond Cap Juluca
Maundays Bay. Moorish architecture and the long beach.
Best for: anniversary celebrations, design-conscious couples, multi-generational family.
2. Four Seasons Resort Anguilla
Barnes Bay. Contemporary alternative to Cap Juluca.
Best for: family travel, anniversary celebrations, business + leisure combinations.
Antigua
3. Jumby Bay Island (Oetker Collection)
Private island. 40 rooms across villas. Boat-only access.
Best for: privacy-focused trips, anniversary celebrations, multi-generational family.
4. Hermitage Bay
Boutique southwest coast. 25 suites.
Best for: anniversary celebrations, romantic getaway, value-conscious luxury.
Bahamas
5. The Cove Eleuthera
Boutique on Eleuthera's pink-sand coast.
Best for: design-led couples, repeat Bahamas visitors, weekend escape.
6. Atlantis Reef Atlantis (Royal Tower)
Theatrical luxury. Family-focused.
Best for: family travel, multi-generational family, group celebration.
Turks and Caicos
7. Como Parrot Cay
Private 1,000-acre island. Asian-style Caribbean luxury.
Best for: privacy-focused trips, anniversary celebrations, design-led couples.
8. Amanyara
The Caribbean Aman. Architecturally significant.
Best for: anniversary celebrations, design-led couples, formal occasions.
How to choose between islands
A specific framework:
- For elite small-island design: St Barths or Anguilla
- For private-island Caribbean: Antigua (Jumby Bay) or Turks and Caicos (Como Parrot Cay)
- For value Caribbean: Jamaica or Dominican Republic
- For family Caribbean: Bahamas (Atlantis) or Turks and Caicos
- For Asian-style Caribbean: Turks and Caicos (Como Parrot Cay or Amanyara)
When to visit
- December-April: peak Caribbean season
- May-June, November: shoulder seasons
- July-October: hurricane season
Five rules for Caribbean island hotel selection
- Match island character to trip type
- Smaller islands (St Barths, Anguilla) cost dramatically more than larger islands
- Hurricane season (June-October) is real weather risk
- Private-island properties require boat or seaplane transfers
- Caribbean-loyal travellers should rotate islands rather than repeat one
For more, see the Mexico/Caribbean pillar and Caribbean honeymoon hotels.