What does your dream Caribbean vacation look like?

Explore the possibilities aboard a luxury crewed yacht.

Charter the Caribbean specializes in unique cruising vacations that you’ll remember for the rest of your life.

What you’ll get when you plan a trip with Charter the Caribbean:
  • • Attentive, first-class service provided by your dedicated captain and crew.

  • • Input into the planning of the itinerary, menu, and onshore activities.

  • • Delicious, gourmet meals prepared by your personal chef.

  • • Open bar for beer, wine, and spirits with our all-inclusive charters.

  • • Sailing, snorkeling, windsurfing, and kayaking instruction on many of our crewed yachts.

  • • Ability to make your crew selection the priority when choosing a yacht.

  • • Access to pristine beaches and secluded coves that large cruise ships can’t reach.

  • • Complete privacy

  • • Highest safety standards.

  • • Expert assistance with all aspects of planning your cruising vacation.

Why Charter the Caribbean?

50+ years sailing experience
10+ years as licensed boat captain
Nearly 30 years charter yacht broker experience

Tips & Articles Browse the latest articles from our blog.

Meet Charter Yacht Chef Stacy Ulmer

    Chef Stacy Ulmer Stacy Ulmer, the charter chef onboard LET’S PLAY TWO, believes that a dinner is more than just a collection of ingredients that have been expertly prepared. It is opportunity to tell a story. It is impossible for even the most memorable meal you’ve ever had in a restaurant to match […]

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