Waypoints Yacht Charters

From seamless planning to unforgettable days on the water, this BVI charter experience says it all. 🌴

Thank you to this amazing group for the incredible review and for trusting Waypoints with your adventure aboard Scarlet Ibis II. We can’t wait to welcome you back to the islands.

⬇️ Full review below:

"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 (and afterwards) I encountered the most lovely people who had a true passion for their work. The document process was straightforward with everything well laid out. We showed up 3 days early to rent a VRBO in Tortola and have a look around. They were gracious enough to allow us to load the provisions on the boat the evening before (we shopped locally rather than did the online provision list). The FP44, Scarlet Ibis II was new, beautiful, clean and perfect. Anthony went through the most thorough boat brief I have experienced and never rushed us, answering whatever questions we had and stopped for an urgent call from a group that had just left. His knowledge and patience are exemplary. At the reception, Sayula is simply an angel. Genuinely a sweet person and will do whatever is in her powers to assist and enhance your experience. We sailed for 8 days and the check-in process was just as efficient and straightforward. I have indeed found a home for charter in the BVI and, soon, we'll try their base in the USVI. I cannot recommend Waypoints highly enough. Cheers and many thanks to everyone at Waypoints."

DRESS CODE: NO SHOES REQUIRED 🌴

Imagine waking up next winter anchored in crystal-clear Caribbean waters, coffee in hand, with nowhere to be and nothing on the agenda except deciding which beautiful island to explore next.

January, February, and March 2027 dates are NOW OPEN in the USVI and BVI — your dream yacht charter vacation awaits — reserve it today with just a 25% deposit.

Peak season in the Virgin Islands is everything they say it is — and so much more!

📍 US Virgin Islands & British Virgin Islands

📅 January · February · March 2027

🔗 waypoints.com

✨ New Fleet Additions Have Arrived in the USVI! ⚓🌴

We're excited to welcome a lineup of brand-new 2026 Fountaine Pajot catamarans to our U.S. Virgin Islands fleet:

🔹 2026 Fountaine Pajot FP41 Maestro 3
• Zefiro
• Moonlight

🔹 2026 Fountaine Pajot FP44 Maestro – 3 Cabin
• Ripple
• Cat-O-Caster

🔹 2026 Fountaine Pajot FP44 – 4 Cabin
• Selah Vie

🔹 2026 Fountaine Pajot FP48 – Quintet 5
• Long Layover

🌊 More choices. More luxury. More unforgettable memories.

Secure your Caribbean charter today with only a 25% deposit required during January-March 2027 bookings in the Virgin Islands! Link in comments for more info.

Summer on the Chesapeake starts with Waypoints ⚓️☀️

Set sail from Waypoints’ Annapolis base and explore charming waterfront towns, quiet anchorages, historic landmarks, and unforgettable sunsets along the Chesapeake Bay.

From Annapolis to St. Michaels and beyond, your perfect summer charter adventure is waiting.

Book now at the link in the comments.

Some trips are memorable. Others change how you see travel entirely.

The USVI is one of those places.

Ready to experience it for yourself?

Take the Helm!

Take advantage of your time aboard by learning the ropes, sign up for American Sailing Association courses with your charter and gain certifications as you go! Our sailing classes will have you learning hands on with a licensed Captain who is a ASA-Certified Sailing Instructor.

Throughout a typical week, charter guests can complete up to three courses gaining ASA certifications.

Ready to sail? Learn more at the link in comments.

This Memorial Day, as we gather with family and friends and spend time on the water, we pause to honor the brave men and women whose sacrifice made our freedom possible.

May we remember those who gave all — and carry their legacy forward with gratitude. 🇺🇸⚓

Fair winds and following seas, Class of 2026 ⚓

Congratulations to the newest graduates of the United States Naval Academy.