Private Yacht Vacations,
Designed Around You
We help you plan a private, all-inclusive yacht vacation tailored perfectly to your group.
A better way to travel
We help you choose the right yacht and design a fully personalized vacation from start to finish.
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Why Sail Play Dine
Curated selection of top crewed yachts- Independent recommendations based on your trip
- Personalized planning from start to finish
- Access to the best destinations in the Caribbean and Mediterranean
- Dedicated planning support from first inquiry to departure
What our Guests Say
Everything is taken care of so you can simply relax and enjoy the experience
This was one of the very best trips we’ve ever taken and by far the best vacation we’ve taken in the Caribbean. We have been to many islands and resorts over the last 30 years; all wonderful experiences, but pale in comparison to this vacation.
Kelly M.
Beatriz was great in assisting us to choose the right catamaran for 8 of us including two kids on relative short notice and very helpful In answering all kinds of question about the boat, the crew , contract and the possible route.Definitely recommend you use their expertise in choosing your boat and crew as I will also do the next time I do a charter in the islands.
Jorge Canellas
Fabiola took all the time I needed to choose the perfect yacht vacation for my friends and I for my special birthday. In the end, all of my needs were met and we had the vacation of a lifetime. She was extremely patient in explaining all the ins and outs and what to look for as I was choosing the perfect yacht and I so appreciate that. She also made all the paperwork and pre-vacation planning a breeze. Thank you Sail Play Dine Yacht Charters!
Esther Kuznetz
Choose Your Experience
We’ll match you with the right yacht for your trip
How it Works
- 1Tell us about your trip
- 2We match you with the perfect yacht and handle all the details
- 3You enjoy your vacation
Explore Destinations
From the Caribbean to the Mediterranean, discover where your journey can take you
Yachts We Recommend
The best crewed yachts carefully vetted by our team
Special Offer
Plus Expenses
Plus Expenses Charters generally don't include food and beverages as well as fuel for the yacht. Inclusions and exclusions vary by yacht, please contact us for a custom proposal.
All Inclusive
All Inclusive Charters typically include food and beverages you consume in the yacht. Inclusions and exclusions vary by yacht, please contact us for a custom proposal.
Special Offer
Plus Expenses
Plus Expenses Charters generally don't include food and beverages as well as fuel for the yacht. Inclusions and exclusions vary by yacht, please contact us for a custom proposal.
All Inclusive
All Inclusive Charters typically include food and beverages you consume in the yacht. Inclusions and exclusions vary by yacht, please contact us for a custom proposal.
Special Offer
Plus Expenses
Plus Expenses Charters generally don't include food and beverages as well as fuel for the yacht. Inclusions and exclusions vary by yacht, please contact us for a custom proposal.
All Inclusive
All Inclusive Charters typically include food and beverages you consume in the yacht. Inclusions and exclusions vary by yacht, please contact us for a custom proposal.
Frequently Asked Questions
Your yacht, professional crew, all meals, open bar, and all water activities — everything taken care of.
Most of our yachts accommodate 2 to 10 guests. We’ll match you to the right size for your group.
None at all. Your professional crew handles everything — you just show up and enjoy.
Primarily in the British Virgin Islands and wider Caribbean, with Mediterranean destinations also available.
Our yachts start from $25,000 per week for the entire yacht — not per person. For a group of six, that’s around $600 per person per night, fully all-inclusive. We’ll share options that fit your group and budget when you reach out.
We recommend reaching out at least 3–6 months before your preferred dates. Popular seasons and peak weeks fill quickly.
Still have questions? Tell us about your trip and we’ll answer everything.
Download Your Guide to Planning a Private Yacht Vacation
Learn how private yacht vacations work, what to expect onboard, and how to plan the perfect trip for your group.
Download the Free Guide
Start Planning Your Yacht Vacation
Tell us about your trip and we’ll help you create the perfect experience
We typically respond within a few hours. No commitment required.
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