Waypoints Yacht Charters

🌴 Leave the planning behind and enjoy a truly effortless getaway.

With a Waypoints All-Inclusive Crewed Charter, every detail is taken care of:

• Professional captain
• Private chef
• Customized itineraries
• Gourmet meals & open bar
• Access to water toys
• and more!

Our crewed charters let you relax, reconnect, and make the most of every moment.

Book yours at Waypoints.com

Reviews like this are why we do what we do. 💙

Thank you for trusting Waypoints with your BVI honeymoon! 🔔 We're honored to be part of such unforgettable adventures and can't wait to welcome you back on the water.

One of the best perks of being a Waypoints Wanderer? Exclusive local discounts. ⚓

🍽️ In Annapolis, enjoy 15% off your meal or catering order at Bread and Butter Kitchen (retail excluded).

Complete your first Waypoints charter and you're automatically enrolled in the Waypoints Wanderers program, unlocking member-only perks in our charter destinations.

Check out our other community partners & perks at the 🔗 in comments!

☀️ Summer isn't over yet!

There's still plenty of time to get out on the water in Annapolis before the kids head back to school. Better yet, you can even earn your American Sailing Association certification while you're on your charter.

Make the most of the season — your next Chesapeake Bay adventure is waiting with Waypoints.

⚓ What does it take to name a boat?

From sailor superstitions 🌊 to personal stories 💙, every yacht in our fleet has a name with meaning behind it.

Ever heard it's bad luck to rename a boat? 👀

Read the full blog to discover the stories behind some of our newest fleet additions. ⛵✨

🔗 Link in comments.

⚓ Last-Minute Summer Escape: 30% Off Your Chesapeake Bay Charter — August Only!

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.

Picture this: over 11,000 miles of shoreline, 200 miles of open Bay, and a whole summer's worth of adventure packed into whatever days you've got left. Duck into a quiet cove one afternoon, tie up in historic St. Michaels or Oxford the next, then swap it for the buzz of Annapolis or Baltimore before you head home.

And the best part? You don't need a whole summer to do it right. A long weekend, a week, a spontaneous escape — the Chesapeake delivers no matter how much time you have.

Save 30% on your August Chesapeake Bay charter.

⛵️Catamarans, Monohulls and Power Yachts
📍Departing from our Annapolis base
👉 https://waypoints.com/charter-specials/

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

Welcome aboard, Erica! ⚓

We're excited to welcome Erica to the Waypoints team as our new Charter Experience Specialist! Erica will be working closely with our guests to make sure every charter — from first inquiry to final sunset — is smooth, memorable, and exactly what they're dreaming of.

Whether you're planning a week in the Caribbean, chartering out of Annapolis, or exploring the Bahamas, Erica will be one of the friendly faces helping bring your dream charter trip to life.

Just 11 miles off the coast of Placencia lies one of Belize's most beautiful hidden gems — Laughing Bird Caye. 🦜🌴🌊

This pristine 1.4-acre national park and protected marine sanctuary is surrounded by crystal-clear waters and vibrant coral reefs, making it a must-visit stop for charter guests exploring Belize.

Spend the day:
🤿 Snorkeling among marine life
🪸 Diving the reef
⛱️ Picnicking on the beach

Accessible only by boat, it's the kind of destination that makes a yacht charter unforgettable.

Some destinations are worth protecting — and visiting. Let Waypoints help you get there.