Private Family
Yacht Vacations

Disconnect from the busy world and spend meaningful time together exploring beautiful islands as a family.

An ocean surrounded by nature with two yachts sailing

Why Choose
Sail Play Dine?

  • Curated selection of top crewed yachts
  • Independent recommendations tailored to your tripe full of ideas
  • Personalized planning from start to finish
  • Access to the best destinations
  • We handle every detail

Preserved Land.
Open Water

The Experience, Designed for Families

Spend Meaningful Time Together

Swim, snorkel, paddle, or try fishing together. Each day offers simple, memorable experiences that everyone can enjoy.

Fun for All Ages

Swim, snorkel, paddle, or try fishing together. Each day offers simple, memorable experiences that everyone can enjoy.

Discover New Places

Visit quiet beaches, explore island towns, and experience something new every day, at your own pace.

Relax Without the Stress

With everything handled for you, parents can relax and enjoy the experience just as much as the kids.

Everything included for families

Whats Included

Everything is taken care of so you can simply relax and enjoy the experience

Private yacht exclusively for your group
Professional captain and crew
All meals prepared onboard
Open bar and beverages
Fully personalized itinerary
Snorkeling gear
Paddle boards and kayaks
Fishing gear
Floating water toysn of top crewed yachts
Fuel and all operating expenses

How it Works

  • 1
    Tell us about your trip
  • 2
    We recommend the right yachts and plan everything
  • 3
    You enjoy your vacation
A view from above of a blue ocean and a yacht

What our Clients are Saying

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

Frequently Asked Questions

Can I book now for a charter that is taking place in 6 months?

Absolutely! In fact, we recommend it. This type of vacation is typically booked 12-18 months in advance, especially when booking during school vacation (Spring Break) and holidays (Christmas and NYE).

Can I book a Charter Yacht for less than a week?

Yes, you can! While most charter yacht pricing is based on a weeklong charter, some yachts offer daily rates, allowing you to customize the duration of your trip. However, please note that some yachts may apply a surcharge for charters shorter than 6 nights. The flexibility of charter durations varies by yacht. We’ll discuss your specific needs and give you recommendations.

When is the best time to visit?

The Caribbean is a great destination year-round. Temperatures range from around 79°F in December to March to around 84°F from May to October. Winds are slightly higher in winter, and rates may be higher during holiday weeks, particularly from Thanksgiving through Easter. Christmas and New Year's charters are often booked well in advance.

Can I get a better rate by contacting the charter yacht directly?

It's unlikely. The rates on Sail Play Dine are provided directly by the charter yacht management. We are promptly informed of any discounts or special offers. Our team at Sail Play Dine maintains strong relationships with all yacht agents. If you're looking for a better rate, contact us, and we'll work with the agents on your behalf to explore available options.

What is the cost of crewed yacht charters?

Crewed yacht charters range from $20,000 to $100,000 per week, depending on the yacht's size, age, and capacity. Fees may be all-inclusive or include additional running expenses and APA (Advanced Provisioning Allowance) for luxury motor yachts.

View all FAQ

Start Planning Your Yacht Vacation

Tell us about your trip and we’ll help you create the perfect experience