Waypoints Yacht Charters

06/01/2026

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.

05/28/2026

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

The USVI is one of those places.

Ready to experience it for yourself?

05/26/2026

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.

05/25/2026

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. 🇺🇸⚓

05/23/2026

05/20/2026

Fair winds and following seas, Class of 2026 ⚓

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

05/19/2026

Busy day on the Waypoints docks today!

Summer is calling… and the Chesapeake Bay is waiting. ☀️⚓

From waterfront towns and quiet anchorages to sunset cruises and weekends on the Bay, there’s no better way to experience summer than from the deck of a yacht.

Whether you’re planning a family getaway, a couples escape, or a trip with friends, Waypoints Annapolis has the perfect yacht for your next adventure.

Book your charter today and make this the summer you spend more time on the water.

Link in bio.

05/18/2026

Belize might be the Caribbean’s best-kept secret… 🤫

Sail along the world’s second-largest barrier reef, anchor in places that feel completely untouched, and experience a side of the Caribbean that’s still off the map.

For those looking to explore something different — this is your waypoint. 🧭

Reach out to get started on your next charter.

05/15/2026

Why summer might be the best time to sail the Caribbean:

✔ Fewer crowds.
✔ More availability.
✔ Incredible value.
✔ Same turquoise water. Same steady winds.

If you’ve been waiting for the “perfect time”… this might be it.

Would you sail the Caribbean in summer? Book today with Waypoints.

05/14/2026

This is what a week in the USVI actually feels like…

Morning swims. 🌊 Afternoons under sail. ⛅ Evenings you wish you could replay forever. 🔁

Our guests don’t just visit — they experience it.

Is the USVI on your bucket list?