Meet Wes,

Island Matchmaker

I specialize in Caribbean travel, using nearly a decade of firsthand experience to match travelers with islands that truly fit their vibe, goals, and travel style. My expertise includes St. Lucia, St. Kitts & Nevis, Antigua & Barbuda, Aruba, British Virgin Islands, US Virgin Islands, Barbados, Curaçao, Cuba, Grenada, St. Martin, Anguilla, St. Barts, Guadeloupe, Turks & Caicos, Abaco Island in the Bahamas and more - with insight into each destination’s culture, pace, and experience.

Caribbean Island Matchmaking Questionnaire

I’m excited to get started on your Caribbean Island Matchmaking experience!

The questionnaire below helps me understand your travel style, preferences, and trip goals so I can accurately match you with the right island and design your itinerary.

Please answer based on what you truly enjoy (not what sounds nice) and be as specific as you can - especially about past trips you loved or didn’t. There are no right or wrong answers.

  • It takes about 10–15 minutes

  • Please complete within 48 hours so I can stay on schedule

Once submitted, I’ll begin building your personalized Match Report and itinerary.