Waypoints Yacht Charters

🍂 Fall Special — Save 15% on charters booked October 1 through December 15. And this year, you'll be stepping aboard something brand new.

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 adventures — 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.

📅 Valid for charters October 1 – December 15, 2026
💰 Save 15% when you book today
⛵ New fleet additions now available
👉 Book now at waypoints.com or call 443.225.4355

Link in comments to book now!

*New and direct bookings only. Blackout dates may apply. May not be combined with any other promotion.

💡 Did You Know?

After your first charter, you're automatically enrolled as a Waypoints Wanderer — unlocking perks like 10% off future charters, exclusive gifts, special partner discounts, sailing course savings, and more.

The more you sail, the more rewards you enjoy. Learn what it means to be a Waypoints Wanderer at the link in comments!

⚓ Give Dad a Day He’ll Never Forget ⚓️

This Father’s Day, skip the tie and give him the open water instead.

Book a summer charter on Rosie, our stunning Nimbus, or one of our exquisite Fountaine Pajot catamarans or Dufour monohulls, for a charter on the Chesapeake Bay — sun on his face, wind in his hair, and not a single chore in sight.

Whether he’s at the helm or just kicking back with a cold drink in hand, this is the kind of gift Dad will be talking about all summer.

🛥️ Charter Weeks Now Available�📍 Annapolis, MD�👨‍✈️ Captain-led or Bareboat
🎁 Gift Cards Available

Reserve Rosie — because Dad deserves more than another pair of socks this year.

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Nothing means more to us than helping guests create unforgettable memories on the water. Thank you for choosing Waypoints — we can't wait to welcome you aboard again! 🌴

Experience America's 250th celebration from your own private yacht! 🇺🇸⚓

The Tall Ships are coming to Baltimore June 24–July 5, and the best view is from the water with Waypoints. 🌊

Enjoy front-row luxury sailing aboard Fountaine Pajot catamarans Amajen or Zensation, or a fun day on the water with Nimbus powerboat Rosie.

Skip the crowds for exclusive on-water access to all the action:
⛵ Tall Ships
✈️ Airshows (including the U.S. Navy Blue Angels)
🎪 Festivals
🎆 Fireworks

Available captained or bareboat, our Annapolis fleet offers a unique way to celebrate this historic event with friends, family, or colleagues.

🎉 Reserve your charter today for a once-in-a-lifetime celebration!

🌊 This summer, give your kids an adventure they'll never forget.

A family sailing charter is more than a vacation — it's a chance to learn sailing, discover marine life, explore new destinations, and make lifelong memories along the way. ⚓🐢

From Annapolis to the Caribbean, we've rounded up 7 incredible destinations where every day on the water becomes a new lesson and a new adventure.

📖 Read the blog and start planning your family's summer escape. Link in comments.

With ASA-certified sailing courses from Waypoints, you can build your skills, gain confidence on the water, and learn to sail in some of the world’s best cruising destinations.

From beginner basics to advanced cruising certifications, courses are available across Waypoints bases — including Annapolis, the Bahamas, Belize, the USVI, and more. 🌊

Your sailing journey starts here. Link in bio to learn more and book your course.

Introducing Our Newest BVI Fleet Additions! ☀️ ✨

Now available in the British Virgin Islands:

🔹 2026 Fountaine Pajot Aura 51
• Last Mango
• Peace Out

The Aura 51 delivers exceptional space, luxury, and comfort for the ultimate Caribbean sailing experience.

Your dream BVI charter starts here. Only a 25% deposit required for all January-March 2027 bookings in the Virgin Islands! Link in comments for more details.

🌴 More time in the Caribbean just got even better.

For a limited time, save up to 30% on 7+ night charters booked within six weeks of departure.*

Because the best island escapes are the ones you don’t have to rush. ✨

📅 Offer valid through the end of the season

Ready to plan your escape? Link in comments.

*Applies to new, direct bookings only. Blackout dates may apply. Cannot be combined with other offers.