Book an unforgettable crewed yacht charter vacation.

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Book with the Caribbean specialists. For over 14 years we have been a leading yacht charter brokerage connecting groups like yours with the best crewed yachts available for charter in the Caribbean including the Virgin Islands & BVIs, Leewards, Grenadines and Bahamas.

Utilize out firsthand knowledge about available charter yachts, crews and locations to book the best yacht and crew for your budget and travel style.

Start planning your vacation today!

Sail away to white sand beaches, consistent Caribbean trade winds, clear blue water, sheltered island bays great for cruising, world-class dive sites, award winning yachts and crew, and sunshine every day of the year.

crewed catamaran charters


Catamarans offer stability and space, providing an excellent charter vacation platform. The accommodations are separated fore and aft and between hulls. The cockpit is wide and comfortable for dining with family and friends. Many catamarans feature a flybridge level, great for additional lounging and viewing.
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crewed sailboat charter


Monohulls offer a traditional sailing experience for active sailors. Monohulls are available in various sizes for various budgets and are generally ideal for smaller parties. They heel under sail and offer all the action of a true sailing vessel. Sail the Caribbean Tradewinds.
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crewed power yacht charter

Power Yachts

For the ultimate experience in luxury and comfort, a power yacht or super yacht offers a high crew to guest ratio, individually designed capacious interiors, highly customized, professionally prepared menus and the option to head to your next destination swiftly and style.
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Experience the vacation of a lifetime aboard a luxury, all-inclusive, professionally crewed charter catamaran, sailing, or power yacht in the Caribbean.

Specials and Last Minute Discounts:

These crewed catamaran specials are available for new reservations sailing from Tortola or St Thomas in the Virgin Islands or elsewhere in the Caribbean. Contact us now for further information and a no-obligation quote.

See all of the current crewed yacht charter specials and discounts.

Save 20% off all summer bookings aboard Luna sailing the Virgin Islands and Grenadines. Four night minimum charter.
Offer Dates:
1 Jun 2019 - 31 Aug 2019
Confirm before 16 Aug 2019
Santa Ana is offering 20% off new reservations for available dates sailing in June or July 2019 sailing the Virgin Islands. 5 night minimum, discount may not be combined with any other special.
Offer Dates:
1 Jun 2019 - 19 Jul 2019
Confirm before 3 Jul 2019 Expires in 42 Days
Save 15% off new reservations sailing now through 15 November 2019. Applies to new reservations 6 nights or longer.
Offer Dates:
Now - 15 Nov 2019
Confirm before 18 Oct 2019

Colleen and Matt were extremely professional and friendly. They were a lot of fun too. They took great care of us but they also took a lot of pride in the yacht, which we appreciated. They had all kinds of information and stories about the areas we visited and made recommendations for excursions, restaurants, shopping and hikes.

Colleen was an excellent captain and always went out of her way to ensure we had the best mooring spots and avoided cruise ship crowds.

Matt was very accommodating with our group of advanced divers and had plenty of equipment on board for us to use.

They were always asking if we needed anything, and at the end of the trip they planned a little surprise party for our 20th anniversary and our friend's birthday, complete with decorations, which was really nice. One night they even hosted a movie night complete with popcorn.

Firefly was very clean, comfortable and well ventilated. We appreciated having a shower/head in each room. The rooms were a great size and the beds were comfortable. The colors were really bright and fun which was beautiful when we sailed and they had comfortable bean bags on the trampoline. We booked this yacht because of the SCUBA tanks on board. Many boats did not have that. We enjoyed the transparent kayak, the lily pad and the paddle boards too.

Yes. The food was plentiful and exceeded our expectations and the presentation was lovely. Each day we had a menu with a "mood of the day" theme. That was really fun. Matt went out of his way to make special accommodations for specific requests. He made his own ice cream and it was fantastic. The bar was also very well stocked with everything we requested and some additional items we did not request but were pleased we could try like the local flavored rums and a themed cocktail each day.

Our favorites were the natural attractions such as trails on St. John (Annaberg) and the Baths on Virgin Gorda and the tour to Hog Heaven for the views. The two wreck dives (Rhone and Kodiak Queen) were really fun as was the dive near Scrub Island (I think it was the Dogs) because we saw the most wildlife there.

Lori R, aboard Catamaran Firefly, May 2019  sailing the Virgin Islands

We found Alli and Dan to be amazing! They were extremely knowledgeable and very attentive.

Kelea was clean, comfortable and well ventilated. My favorite aspect of the yacht was the bean bag chairs. As a group our favorite spot was sitting up top during the sails.

The chef made and presented the most amazing dishes. She used our preference sheet as a guide. She took great pride in her work and every meal was delicious!

The itinerary was perfect and every place we sailed was well worth seeing.

Sailing Directions provided a great service. They made it simple and easy to navigate through the process. We have had many people ask about our trip so we keep recommending your company.

Kristie R, aboard Catamaran Kelea, May 2019  sailing the Virgin Islands

Julia and Jos were so amazing! Our vacation experience was greatly improved by their knowledge about the islands, attentiveness, and their friendly nature!

Hypnautic was awesome. We slept so well! It was perfect amount of space for the 4 of us to spread out, yet interact with each other at will. I couldn't pick a favorite aspect of the yacht, because it was all so perfect!

Julia was an amazing chef! She worked so hard to give us such beautiful and delicious meals! The meals were above and beyond our best expectations!

We loved the ability to customize our itinerary to our preference. Jos was so good to give us all the options available for the day and let us decide when/where we wanted to go!

Sailing Directions was super helpful! Great service and easy to use website and payment. No issues whatsoever.

Great Boat for 2 couples or a small family! The boat was beautiful and clean. The crew was absolutely amazing!

We definitely will use your company in the future. I have recommended your company to a coworker for a similar charter!

Cailey K, aboard Catamaran Hypnautic, May 2019  sailing the Virgin Islands

> See all of our crewed yacht charter reviews

Caribbean Yacht Charter Vacations

A crewed Caribbean yacht charter offers you the freedom to explore this tropical paradise without limits and at your own pace.

With accommodation, a professional captain, a personal chef, all meals, cocktails, wine, beer, snacks, fuel, equipment, and water toys included, few other vacations offer such an extraordinary experience and value.

Itineraries are completely flexible within your cruising area. Sail the diverse US and British Virgin Islands, the undeveloped and resort islands of the Caribbean Grenadines, or charter a luxury power yacht to cruise St. Martin, St. Barts, and Antigua in the Caribbean Leeward Islands.

Sailing Direction's charter brokers help you book a private crewed yacht in the Caribbean for any group size and budget. Whether you're looking for a family sailing vacation, a couple's adventure holiday, a BVI yacht charter, or a honeymoon or anniversary celebration - we've got you covered for an unforgettable crewed yacht charter experience.