What Does Your Dream Caribbean Vacation Look Like?

Explore the possibilities aboard a luxury crewed yacht.

Charter the Caribbean
Specializing 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.

Sailing in Greece vs. Sailing in Croatia

Do you need clarification about choosing the right Mediterranean destination for a vacation? Or is it confusing for you to sail in Greece or Croatia? Greece and Croatia are the two most popular yachting locations. The biggest Sailboat Charter fleets in the world enable you to take advantage of your time at sea, and their […]

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 […]

View All