Find Sailing Charters Near You

Local Sailing Reviews

1. ML

   Martha

   50ft Catamaran Charter with Water Toys - Annapolis, MD

   We intentionally booked a late afternoon cruise around the Chesapeake so we would return around sunset to get great views and photos. Kristal was super responsive in preparing us and Captain Wayne and his 'first mate' Mish were super helpful with capturing the perfect photos. We would definitely book again!

2. CR

   Chawin

   38-ft Hunter 376 Sailing Adventure in Annapolis

   Captain Alberto and Grace are wonderful hosts and guides. They have a wealth of sailing and life experience to share during your trip. They were very flexible with us during a proposal event.

3. AP

   Andrea

   38-ft Hunter 376 Sailing Adventure in Annapolis

   This was our crew’s second trip with Capt Alberto and was a second great experience. Capt Alberto shares his passion for sailing and teaching sailing! Capt and Grace are incredibly kind and make a great day spent out on the bay!

4. 

   Elisabeth

   Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese

   Charles & Renee were amazing! We booked last minute and enjoyed an awesome afternoon on The Optimystic in Chesapeake Bay!! We can’t wait to sail again!! Charles is an excellent Captain and host. A good teacher as well! Have an awesome winter!! See you in the Spring!! Charlie, Beth and Sam (Class of 2026) ⚓️⚓️⚓️

5. 

   Lisa

   38-ft Hunter 376 Sailing Adventure in Annapolis

   Thank you so much Captain Alberto & Grace. We had a fabulous time and enjoyed learning about sailing. Thanks for trusting us to help steer and tack the boat. We had so much fun. You are a great teacher. We wish we could have stayed out longer.

6. JW

   Jessica

   Captained Charter 30' Sailboat in Milwaukee, Wisconsin

   Our group of six women celebrating girl's weekend had the most memorable and special outting on Scott's boat. He is very friendly, accomodating, generous, and easy going. His background as a Navy search and rescue swimmer coupled with his confident sailing abilites assured the group that safety was never an issue. He perfectly integrated into or out of our conversations, highlighting is flexible nature. We all highly recommend!