Book an unforgettable crewed yacht charter vacation.

View Available Yachts:

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 / USVIs, 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

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.
View catamarans
crewed sailboat charter

Monohulls

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.
View monohulls
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.
View power yachts
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 charter specials are available for new reservations sailing from St Thomas or Tortola 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.

Offering 10% off new charters for 6+ nights taking place by 15 July 2020. May not be combined with any other special.
Offer Dates:
Now - 15 Jul 2020
Confirm before 1 Jul 2020
Save $1,000 on new charters starting in November 2020, December 2020 and January 2021 booked by 01 July 2020. Does not include Christmas or New Years. This may not be combined with half board options or children discounts.
Offer Dates:
1 Nov 2020 - 31 Jan 2021
Confirm before 1 Jul 2020
Save $1,000 on new charters starting in November 2020, December 2020 and January 2021 booked by 01 July 2020. Does not include Christmas or New Years. This may not be combined with half board options or children discounts.
Offer Dates:
1 Nov 2020 - 31 Jan 2021
Confirm before 1 Jul 2020

We are among one of the five couples that were recently in the BVIs on a sailing adventure aboard the Blue Pepper. You must know that The Blue Pepper experience, in EVERY way, was impeccable! The crew of Taylor, Denise and Liz were top notch. Together, they created a magical experience for us all. They worked tirelessly to make our sailing adventure relaxing and no detail was overlooked.

The boat was immaculately clean and beautiful! Denise’s absolute gift for preparing and serving delicious food was truly spectacular. We were blown away by her creativity and culinary skill. The crew were engaging, caring and their respect for the boat and their craft was most commendable.

I will most certainly recommend the Blue Pepper to our friends who are looking for an outstanding sailing adventure.

***

I just wanted to let you know how very impressed we were with Captain Taylor, Chef Denise and Liz. They absolutely MADE the trip for us.

The boat was immaculate and the attention to detail throughout the trip was amazing.

Denise's meals were spectacular - they were fresh, healthy and delicious - and the presentation was beautiful.

We felt like every meal came from a top tier restaurant - which was not something we expected.

Captain Taylor's easy-going Texas style made it seem like nothing was a problem - he put us at ease the entire trip - while we know he was in constant motion making sure that everything was perfect. And we LOVED Denise - so fun and personable! Liz was always there to make sure everything was presented just so.

The crew was fun - but also extremely professional and thorough. The Blue Pepper hosted 10 of us for a week - and it always looked like we had just stepped on board. I don't know how they did it. They set the bar for hospitality and service for any future vacations for us.

Larry N, aboard Catamaran Blue Pepper, January 2020  sailing the Virgin Islands

Jason and Dana were fantastic! They were very friendly and welcoming. They took great care to make sure that we were always enjoying ourselves, doing things we wanted to do, and that we had everything we needed. We left the week feeling like friends.

Island R&R was great for our group. Everything was very clean and comfortable.

The food was terrific. We enjoyed all the meals that Dana planned. She had taken care to make sure we didn’t have anything we didn’t want, and she made a few modifications as we went based on our comments and feedback.

We loved the itinerary that we ended up with. We had to make some changes along the way because of weather, but the alternative spots didn’t leave us feeling like we missed out on something. Jason and Dana took us to some places that really hit our personality and our goals for the trip.

Sailing Directions was great to work with. The process of finding and booking a yacht was so simple. And all our questions were thoroughly answered leading up to the trip. We found everything we really needed on the web site. It was great to see sample itineraries and menus. The information about the yachts was thorough and clear.

We will be doing this trip again in the future and we will not hesitate to come back to Sailing Directions when we do. We’ve also already shared your web site and information with other friends that were interested in our trip, and we’ll continue to do so.

Rachel A, aboard Catamaran Island R&R, January 2020  sailing the Virgin Islands

Everything was wonderful. Really enjoyed the wave runners. Kayaks and paddle boards were used almost daily and were in excellent condition. The dive sites were amazing and probably the best ones we have been to.

We did get introduced to all the new crew and spent our orientation time getting to know them. As the crew got to know us they would often have drinks ready without even having to ask for it.

I can’t offer enough praise for the cuisine this charter. Being our third time aboard the Lady J this year’s food was far superior then our previous charters. Everyone was very happy with every meal. There were no disappointments. The chef even was willing to make items off menu when requested. The plating was beautifully done and each dish was described so the children with allergies knew which dishes were safe for them to eat. Also, the table decorations were beautiful.

We love the Lady J and always have an amazing experience on each charter.

Special thanks to Captain John for another amazing charter and finding Chef Mark. The food blew everyone away. I would also like to thank the crew for taking such great care of everyone. We had a wonderful time!

Heather H, aboard Power Yacht Lady J, January 2020  sailing the Caribbean Grenadines

> 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.