Availability Search

It is time to experience the vacation of a lifetime aboard a luxury, all-inclusive, professionally crewed catamaran, sailing or power charter yacht in the Caribbean.

Escape from the icy winter to white sandy beaches, consistently light Caribbean trade winds, clear blue water, gourmet dining and fresh cocktails, islands close enough for day sailing, outstanding offshore game fishing, world-class dive sites, award winning yachts and crew, and sunshine every day of the year.

Sailing Directions® helps you find and reserve a crewed yacht charter in the Caribbean Virgin Islands, Leeward Islands and Grenadines. We can find you a charter yacht that best fits your budget and needs; from an all-inclusive family or couples group sailing vacation to a corporate party or an unforgettable honeymoon or anniversary charter. We provide a wealth of information and support throughout!

When you book a private crewed yacht through us you get all of our services as well as peace of mind that our advice is unbiased and your payments are held in a secure 3rd-party escrow account until the charter date.

Sailing Directions® is an independent crewed yacht charter brokerage with an extensive range of crewed yachts and a depth of expertise. We specialize in crewed catamaran charter vacations sailing the Virgin Islands. Let the experts match you with the perfect crew and yacht for your needs and price point. We know all of the boats and have extensive knowledge of the local cruising areas. Start your search now using our live online availability search form or contact us now for your unforgettable Caribbean crewed yacht charter vacation!

Specials and last minute Discounts:

> See all Specials and Discounts
$2,500 per week discount for any new charter sailing in 2017. Discount does not include one appetizer and dinner (you'd dine ashore for this).
Available for charters starting now through 15 December 2017
Reservations need to be confirmed before 1 November 2017
Save 10% off any new 6 night or longer reservation sailing by the end of August 2017 and take a bonus free sleep aboard the night before. Sleep aboard includes boarding after 4pm, welcome cocktails and canapes aboard then dinner ashore (dinner not included). Also included is breakfast the next morning before setting sail.
Available for charters starting now through 31 August 2017
Reservations need to be confirmed before 1 August 2017
Eclipse is offering 10% discount off the regular rates for new charter reservations taking place anywhere in the Caribbean from the Virgin Islands to Grenada now through 25 July 2017.
Available for charters starting now through 25 July 2017
Reservations need to be confirmed before 1 July 2017
Expires in 32 Days

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!

Latest crewed yacht charter Reviews

> See all of our crewed yacht charter Reviews

The trip was amazing, great times. Best family vacation ever.

Captain Magnus was fantastic with my kids, great personality and never stopped helping us find new places to explore. Chef Lindsey is awesome. World class chef in world class locations on a boat with only my family! It just doesn't get better.

Hypnautic was very clean, very comfortable and great atmosphere for a boat. I'd sail around the world on this boat if I could.

Lindsey is a great chef. Food was excellent. Dinners were first class, breakfast and lunch were outstanding. She did a great job at serving foods my whole family loved.

Our itinerary had 4-5 stops and we made 8-9. The beaches and adventures make my wife and I seriously consider changing careers to be closer to this lifestyle

John at Sailing Directions returned emails quickly which made decisions we needed to make much easier to process and decide. We even had a possible snag with the trip and John made the possibility of re-routing the trip easy. I'd highly recommend the service and attention he offered. Highly considering another charter and when the time is right again, I'll begin my vacation research the same way I did before, the only difference is I'll look at Sailing Directions first and only. It worked great.

Magnus and Lindsey are a GREAT team and I'd recommend anyone considering to sail with them with a million percent YES!! Both of my boys highly enjoyed their time with our crew.

Ryan L, aboard Catamaran Hypnautic, May 2017 sailing the Virgin Islands

This was our third catamaran trip, and by far the best, mainly because of our crew, Joseph and Britta Stiles. They were absolutely wonderful - friendly, accommodating, and very attentive. Britta seemed to anticipate our every need, and was patient and helpful to those of us who were first timers on this trip. We loved her!

And Joseph's cooking - I can't say enough about it. Definitely a foodie's paradise on the Dianna Rose! It was like sailing on a 5 star restaurant, only better. His attention to detail in every meal was astounding. If he wasn't being captain and sailing the boat, he was Chef Joseph, prepping and preparing every meal. I don't think he ever sat still.

Between the two of them, they managed to find the perfect balance between relaxing time and keeping us busy. It was the perfect itinerary; we saw and did all we wanted to and still spent wonderful hours cruising the Caribbean. It was by far the trip of a lifetime.

We loved the boat - Dianna Rose was clean and comfortable, the perfect size for 6 passengers & crew. There is plenty of space to stretch out, front and back. I love the layout of the Lagoon 500.

I have always been very pleased with the service from Sailing Directions, and would recommend them to anyone considering this type of vacation. I hope we can do this again - with the same boat and crew!

Thanks for helping me put together this vacation. It was hard to come home!

Carol M, aboard Catamaran Dianna Rose, May 2017 sailing the British Virgin Islands

The trip surpassed all our expectations and dreams. It was beyond beyond!

The boat was beyond beautiful, comfortable and immaculate and totally comfortable. Her size was a step above the norm which is what we wanted. It felt totally spacious. I love the teak wood throughout, the dining table that had two chairs and I loved the aft teak swim platforms. We also loved the bow with really comfie seating areas, trampoline and forward seats to stretch out over the water.

The bedrooms were amazing. There is one cabin that seems smaller due to the bed configuration but it never bothered anyone. The shower and bathrooms were incredible and made you feel like home. It was all amazing and so comfortable.

Jade and Pete are extraordinary with their culinary experience. They work together like a well-oiled machine to present the most decadent meals, decor, tastes and experience. Jades food was out of this world and Pete worked with her every step of the way with his grilling and many items he made himself. Every single meal whether breakfast, lunch or dinner was an event and everyone raved over each course. Everything was custom made for each guest.

There was nothing that fazed either of them and there was nothing that was too much trouble.

Jade worked tirelessly in the galley but she made it look effortless. It was the highlight of the day to have her dinner presentation and have her describe what she set in front of us. Rave reviews on everything.

Pete and I designed the itinerary together as this was a very unique sailing for 3 weeks and I had a very specific vision of what I wanted for routing and activities and site seeing. We sat down each week and designed together and Pete directed me to all the right things and extra things to do. He listened and really tried to accommodate my requests and learned the things that I loved. It was important to him. It made the trip so much better and we saw every single thing on my researched list except one and I made the call to skip it. I like his idea better to see some remote islands - he knew I would love them more.He was spot on.

Could’nt have been happier with Sailing Directions. John was incredible and always had answers for me. He always got back to me really quickly and answered everything very thoroughly.

The payment web site was really great and very easy to use. John was flexible and genuinely wanted to assist me.

Everything surpassed our expectations. Pete and Jade went out of their way to make is a trip of a lifetime. It is certainly a 5 star service level all the way. They are incredible and I highly recommend Xenia 50.

Barb B, aboard Catamaran Xenia 50, April 2017 sailing the Virgin Islands

> See all of our crewed yacht charter Reviews!

Crewed yacht charter vacations in the Caribbean

Yacht Charter Virgin Islands Leeward Islands Grenadines Ask Us - Caribbean Charters
Charter the Caribbean

A crewed Caribbean yacht charter offers you freedom to explore paradise at your own pace, choose your itinerary, activities and have a personalized menu unlike any cruise ship, resort or beach side hotel.

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

We offer a large selection of Caribbean charter yacht rentals including a fleet of luxury crewed catamarans based from St Thomas & Tortola, as well as full range of crewed power yachts, monohulls and catamarans based throughout the Caribbean to suit every budget.

Unlimited options include sailing the many and varied US and British Virgin Islands, sailing and diving in the undeveloped Grenadines or chartering a luxury power yacht in Antigua, St Martin & fabulous St Barts. See more information about the team at Sailing Directions.