Waypoints Yacht Charters

Shotskis at Willie T, sunset dinners, morning swims, and island-hopping through paradise. Playful understood the assignment. 🍹⛵🌴 It’s hard to imagine a better way to experience the BVI than aboard Playful. For 9 days, this beautiful 47-foot catamaran was our home, our transportation, our…

Greg R · 2026-08-18 · sailed May 2026 · From Tripadvisor

We loved everything about this vacation. Best vacation ever. Really hope to be able to do it again. Kimmy and Anthony and the entire team were easy to work with. When a pipe leaked, Waypoints had a mechanic out to fix it where we were within hours. They brought us two bags of ice and took our trash…

Danae n · 2026-08-11 · sailed July 2026 · From Tripadvisor

Rented a catamaran . Great boat everyone was very helpful competitive prices have done a lot of boat rentals … they are the best

lisa w · 2026-08-08 · sailed June 2026 · From Tripadvisor

This is our 2nd time with Waypoints BVI. I would give them, their service, their willingness to go above and beyond, a 6 star rating. Trip advisor only allows me to give them a 5. They are the "Gold Standard" for customer service and charters in the BVI. Nanny Cay where they operate out of is…

William J · 2026-07-28 · sailed July 2026 · From Tripadvisor

This was my third bareboat charter with Waypoints in the BVI’s and once again they provided a top class 5-star service from start to finish! I have grown to be particularly appreciative of the team – it’s the same professionals each year, Kimmy & Sayula in the office, helping with all aspects of…

Roving53477572253 · 2026-07-28 · sailed July 2026 · From Tripadvisor

What an amazing experience and I can't speak highly enough about Waypoint Chaters and every member of their staff. My wife and I just returned from a 10 day honeymoon in July 2026 on a 40' Fountain Pajot. This was my first time chartering a bareboat myself and from the initial booking until our…

WhalerBob · 2026-07-22 · sailed July 2026 · From Tripadvisor

Staff was amazing. Answered every question. Boat was excellent with no issues. Looking forward to next year!

Michael D · 2026-07-19 · sailed July 2026 · From Tripadvisor

We bareboat chartered the 47’ Fountain Pajout caterman “Playful” through Waypoints. Amazing experience. The boat was incredible, the Waypoints staff pampered us and the islands did not disappoint. If you’re looking at a BVI charter, you most likely already recognize the BVI is an unparalleled…

Blueteej1997 · 2026-07-13 · sailed May 2026 · From Tripadvisor

I've chartered in the BVI for years and have used several different companies, but none of them compare to Waypoints. The boats, the service, the people, and the base location are all top notch. They tend to be a bit more expensive, but it is well worth it.

Ian W · 2026-07-10 · sailed June 2026 · From Tripadvisor

I had previously been chartering with another company in Tortola and decided to try Waypoints. From the moment I booked the charter to after the charter ended, the service I received was above and beyond. The catamaran I chartered was immaculate, no problems, best rigging I've seen, outfitted with…

verenarobinson · 2026-07-07 · sailed June 2026 · From Tripadvisor

We have been chartering in the BVI for twenty years. We like small companies that give you great service and provide very clean, well maintained boats. Waypoints ticks all the boxes. We, 3 couples, chose to charter Aboat Time, which is an FP Elba 45 and is an owner's version with 3 cabins from…

Passport52980388092 · 2026-06-27 · sailed June 2026 · From Tripadvisor

We recently returned from our 28th bareboat charter to the BVI. Having previously always booked with the same large charter company, after yet another trip constantly marred by mostly preventable issues, we finally decided to charter with a different company. After extensive research and…

Louise1262 · 2026-06-23 · sailed May 2026 · From Tripadvisor

We just returned from an unforgettable week in the British Virgin Islands with our family of six, and Waypoint Yacht Charters made the entire experience absolutely exceptional from start to finish. From the moment we arrived, the staff was organized, welcoming, and incredibly helpful. They took the…

Departure23031564533 · 2026-06-22 · sailed May 2026 · From Tripadvisor

Waypoints is a tremendous team from top to bottom. Prior reviews of Waypoints reveal a consistent pattern of superior service and immaculate vessels. My review is based on over 15 years of interaction with Anthony and multiple weeks of sailing at their various locations across the globe. The level…

andrewtduane · 2026-06-18 · sailed May 2026 · From Tripadvisor

If you’d love an incredible, stress-free adventure on the water, Playful, a 47-foot catamaran at Waypoints Marina in Nanny Cay in Tortola, is the way to go! We recently chose Playful for a week-long friends trip. It was glorious! That boat. Oh my goodness. The owners have done wonderful things to…

Ann M · 2026-06-16 · sailed May 2026 · From Tripadvisor

Waypoints Yacht Charters in the BVI is hands down the best charter company in the BVI. We have chartered with 3 other charter companies in the past and we will only be using Waypoints from here on out. We have done 2 bareboat charters with them, just completed a 10 day charter and just booked our…

jennifer y · 2026-06-15 · sailed June 2026 · From Tripadvisor

My wife and I just finished the 2nd charter with WayPoints, the first with a monohull vs a cat on the prior charter. The customer experience with the BVI base staff is as the first time, fantastic. They are extremely helpful, experienced and friendly. Kudos to Sayula, Kimmy and Anthony. First rate…

Expats-Living-Abroad · 2026-06-14 · sailed June 2026 · From Tripadvisor

I never write reviews but here I go. Everything about my charter with Waypoints BVI was top notch. Beth was a joy to work with arranging the right vessel for us, a nearly new FP44. Stefan gave me a thorough walk-thru of the boat’s systems with expert patience and professionalism. That’s when you…

Fearless22647926032 · 2026-06-14 · sailed June 2026 · From Tripadvisor

We had a fantastic week with our family of four (kids are college students) and our captain. I love working with boutique companies. They were fantastic from start to finish. My husband and i have sailed twice before with a different outfit and this was by far our best experience and our first with…

SueBW · 2026-06-06 · sailed May 2026 · From Tripadvisor

We took our adult children for a week on their first sailing adventure (and our first charter as captain). Our FP42 Unsupervised was perfect for the 6 of us. The boat was in wonderful condition and everything worked well. The staff at Waypoints were so helpful from the beginning, booking, planning…

Wander64367725624 · 2026-06-01 · sailed May 2026 · From Tripadvisor

Waypoints managed the cleanliness and operational excellence of their boats like no others. I have really high expectations and all were hit. We sailed the Runny Babbit. Perfect catamaran. Our captain was KHADIN, he was friendly, instructed those who wanted to learn how to sail in such a patient…

elgonz123 · 2026-05-30 · sailed May 2026 · From Tripadvisor

Waypoints is a great charter company. Way better boats and service than Moorings or some of the other big companies. We hired Captain Khadin directly and he was first rate. He is a top rate captain and his local knowledge is insane, he is quick with a smile and was in just flipping amazing. Someone…

patrick c · 2026-05-30 · sailed May 2026 · From Tripadvisor

Top notch charter company, from the checkout, to the support while we were on the water, to the final fueling and check/in. Everything went smoothly, professionally and they were very thorough. This also reflects on the quality/ condition of our boat “Shandy Breeze”. We were concerned that it would…

Brian M · 2026-05-28 · sailed May 2026 · From Tripadvisor

We had an absolute wonderful time. The boat was amazing and we were treated sooo incredibly wonderful by the staff. Everyone was extremely professional and tailored our experience so well!! We are already in talks to reserve our next trip.

coastieflyboy · 2026-05-28 · sailed April 2026 · From Tripadvisor

Oh man, where do I start. I've been to the BVI doing bareboat charters since 2001 and had all good experiences. We used several charter companies and have nothing negative but until we tried Waypoints, I never knew what exceptional meant with respect to the bareboat process. From start to finish…

kaweeka · 2026-05-19 · sailed May 2026 · From Tripadvisor

We had a wonderful week in the BVI’s in April 2026. There were eight of us on a 45 foot catamaran. We bareboated around the islands there. Before we left, we received two detailed briefings about the boat, which was a brilliant idea. The boat was built in 2025 and had very sophisticated features…

tinkerbell0706 · 2026-05-19 · sailed April 2026 · From Tripadvisor

This was our 2nd BVI trip with Waypoints for bar boat charter out of Nanny Cay. Very professional and helpful. They have a great system. Chartered 51 foot Cat. Boat was well maintained. Service is excellent. Kimmy is very kind and helpful, great snorkeling tips. She recommended the bubble pools…

roy u · 2026-05-17 · sailed April 2026 · From Tripadvisor

We chartered a brand new Elba 45. The boat is beautiful and incredibly equipped. The staff was very helpful and always available. I would heartily recommend Waypoint charters.

cdpmichaelp · 2026-05-15 · sailed April 2026 · From Tripadvisor

A++++! we had an amazing time and everything was well taken care of. Anthony specifically was so incredibly patient and helpful, even going above and beyond to help us track down missing luggage at 9pm before our charter started! We will definitely be back.

Theresa P · 2026-05-15 · sailed May 2026 · From Tripadvisor

We were highly impressed with the quality of service and knowledge of the vessels from Waypoints staff. The boat was in tiptop shape and even had a water maker which was a game changer.

marie t · 2026-05-14 · sailed April 2026 · From Tripadvisor

We rented a 47 foot bareboat catamaran for 4 couples for a week and sailed around the BVIs. What a fantastic trip! Beth was fantastic in helping us choose the right boat for our group, suggesting the perfect itinerary, recommending provisioning tips, and all around ensuring we had the most amazing…

Vacationer691786 · 2026-05-14 · sailed May 2026 · From Tripadvisor

Sailing in the BVIs and chartering through Waypoints makes for an exceptional vacation. We have sailed in the Virgin Islands eight times, four in the US and four in the BVIs. This trip we chartered a 40 ft FP for one week where we sailed with family. The following 10 days we chartered a 50 ft FP…

Carl P · 2026-05-14 · sailed April 2026 · From Tripadvisor

Our bareboat charter with Waypoints was amazing! Beth couldn’t have been more helpful and kind. She gave great recommendations and first class service throughout the entire charter. The boat exceeded our expectations! We can’t wait to come back.

Michelle S · 2026-05-12 · sailed May 2026 · From Tripadvisor