Find your
perfect charter
Every sailing vacation is different. So is every charter type.
Waypoints offers charter experiences across the world’s finest cruising destinations — from the British Virgin Islands and U.S. Virgin Islands, the Chesapeake Bay to the Bahamas, Belize, and San Diego.
Every yacht in our fleet is a new or late-model, privately owned, and professionally managed vessel, including models from world-class manufacturers Fountaine Pajot and Dufour. They are outfitted for comfort and performance, not mass-market charter — the difference is apparent from the moment you step aboard.
The right charter type depends on your experience, your group, and how you want to spend your time on the water. Here’s a straightforward guide to help you find the right fit.
Available Charter Types
Bareboat Charter
You're in Command
A bareboat charter puts the boat in your hands. Set your own itinerary, sail at your own pace, and wake up somewhere new each morning — entirely on your own terms. Bareboat charters are available on monohulls, catamarans, powerboats, and power catamarans across all Waypoints destinations.
Best for: experienced sailors with recent, relevant time on comparable vessels who want complete independence on the water.
Not quite ready to go fully solo? A professional captain can be added to any bareboat charter, giving you the freedom of having the boat to yourselves with an expert hand aboard for the sailing.
Captained Charters
All the adventure, without the sailing responsibility.
A captained charter pairs you with a professional skipper who handles all vessel operations — navigation, anchoring, weather, and docking — while you focus on enjoying the destination.
No sailing experience required. The boat is still yours; you simply have an expert at the helm.
Best for: guests who want the sailing vacation experience without the sailing responsibility, or groups that include a mix of sailors and non-sailors.
All-Inclusive Crewed Charters
The complete experience — every detail handled.
An all-inclusive crewed charter is the most immersive option in the Waypoints portfolio. A private captain and chef are aboard for the full charter, gourmet meals are prepared fresh daily to your preferences, the bar is open, and your itinerary is designed around your group before you arrive. All you do is show up.
Best for: guests who want a fully managed, resort-quality experience on the water — ideal for special occasions, honeymoons, family trips, and corporate groups.
Available on sailing catamarans, power yachts, and luxury yachts. Starting from approximately $40,000 per week for luxury vessels.
Learn To Sail
Come for the vacation. Leave with a certification.
Waypoints partners with accredited American Sailing Association (ASA) training facilities at select destinations, giving guests the opportunity to earn internationally recognized sailing certifications during their charter vacation. Learn on the water, in real conditions, at real destinations — then use those certifications to charter independently anywhere in the world.
ASA courses are available at Waypoints Annapolis and through our Newport, Rhode Island partner New England Sailing Center, with options ranging from introductory experiences through to offshore passage making.