Did This Survey Get the Most Charming Caribbean Small Towns Right?

by Holly Riddle

Feb 17, 2019
Trends / Top Trends

A survey of more than 300 travel writers, social media influencers and in-the-know travel professionals voted for their favorite charming Caribbean destinations as part of a survey conducted by TravelMag.com.


The digital travel provider compiled the top 20 destinations with the most votes and published them to the press. Destinations ranged from luxury hideaways in Jamaica to locals-only spots in the Bahamas. Several island countries also landed more than one destination on the top 20 list, including Trinidad & Tobago, Saint Kitts & Nevis, Barbados and Guadeloupe.


Many of the destinations chosen have strong cultural histories, food scenes and art communities.


The top 20 most charming Caribbean small towns are listed below, as chosen by the 300 travel writers, influencers and professionals surveyed. Destinations are presented alphabetically by island, not by number of votes received.


  1. West End Village, Anguilla
  2. Savaneta, Aruba
  3. Governor’s Harbour, Bahamas
  4. Oistins, Barbados
  5. Speighstown, Barbados
  6. Trinidad, Cuba
  7. George’s, Grenada
  8. Deshaies, Guadeloupe
  9. Saint Anne, Guadeloupe
  10. Negril, Jamaica
  11. Le Carbet, Martinique
  12. Rincón, Puerto Rico
  13. Gustavia, Saint Barths
  14. Basseterre, Saint Kitts & Nevis
  15. Charlestown, Saint Kitts & Nevis
  16. Port Elizabeth, Saint Vincent & the Grenadines
  17. Castara, Trinidad & Tobago
  18. Maracas, Trinidad & Tobago
  19. Cockburn Town, Turks & Caicos
  20. Cruz Bay, U.S. Virgin Islands
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