Book with the Caribbean specialists. For over 18 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.
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.
Melody D, aboard Catamaran Excess, January 2023 sailing the British Virgin Islands
Mathieu C, aboard Catamaran Sea Dragon, December 2022 sailing the Caribbean Leeward Islands
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
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.