Last-Minute Summer Escape
THIS AUGUST ONLY!
30% OFF Your Chesapeake Bay Charter
Got a free week before summer slips away? The Chesapeake Bay isn’t just a sailing destination – it’s the sailing capital of the world, and your front door to it is right here at Waypoints Annapolis.
⛵️Catamarans, Monohulls, and Power Yachts
📍Departing from our Annapolis base
🦀 Book today, August is going fast!
*New and direct bookings only. Blackout dates may apply. May not be combined with any other promotion.
FALL SPECIAL
Save 15% on Charters Booked October 1 – December 15
Stretch out your escape in the Caribbean and let the days unfold at their own pace.
Waypoints is excited to welcome to our 2026 fleet a stunning lineup of Fountaine Pajot catamarans now sailing the BVI and USVI. From the nimble FP41 Maestro to the breathtaking Aura 51, these boats were built for the trip you’ve always imagined.
Intimate escapes or family adventure, there’s a perfect yacht waiting for you. New boats, fewer crowds, trade winds – the BVI and USVI don’t have an off season — just better deals.
BOOK NOW!
*New and direct bookings only. Blackout dates may apply. May not be combined with any other promotion.
Waypoints Wanderer Yacht Charter Reward Program
Save 10% on future charters, earn free upgrades, and receive special discounts and offers along with the latest cruising news.
