easy
2–4 hours
Suitable for all fitness levels; primarily seated and relaxed with occasional light walking on deck.
Discover Annapolis from the water aboard a private 50-foot catamaran. Enjoy panoramic Chesapeake Bay views, personalized service, and a uniquely immersive sailing experience tailored to your group’s pace and interests.
Age 18+ to book • 3-6 Hours • Private Catamaran Excursion • Up to 12 People
Embark on a luxurious charter experience where you and up to 12 guests can unwind in a secluded anchorage. Enjoy paddle boarding, swimming, and lounging on a floating dock or hammock chair. With a captain and crew at your service, bring your favorite food and drinks for an unforgettable day on the water.
$425/Hr Choose between 3-6 Hours Up to 12 Passengers
After onboarding, we set sail to a secluded anchorage where you'll be able to sit down for lunch, paddle board, float and swim for several hours. Guests are welcome to use all water toys which include 2 paddle boards, a large floating dock and a hammock chair. You are welcome to bring food and beverages of your choice. Captain and crew included (Gratuities not included), we cater to you!
*Gratuities not included
*This is a bareboat charter, payment to captain is separate. Must have a USCG licensed captain onboard to charter this boat. You will receive a list of approved captains to choose from or you can hire your own captain with the owners approval.
Reserve your private charter ahead of time, especially for weekends and holidays, to ensure availability on this popular Annapolis sailing excursion.
The open deck means ample sun exposure—bring sunscreen, hats, and sunglasses to stay comfortable during your cruise.
Deck surfaces can be slippery when wet, so sturdy, non-marking boat shoes help keep you safe while moving around the catamaran.
Chesapeake Bay conditions can change; confirm weather before your trip and dress in layers to stay comfortable on the water.
Annapolis is home to the historic U.S. Naval Academy, founded in 1845, influencing its enduring maritime culture.
The Chesapeake Bay faces ongoing conservation efforts to protect its delicate ecosystem and water quality, vital for local wildlife and recreation.
Spring waters can be cool, so a windbreaker helps keep warm without bulk.
spring specific
Protects skin from strong summer sun during open deck sailing.
summer specific
Keeps feet dry and secure as autumn moisture levels rise.
fall specific
Winters on the bay are brisk; layering enables adjustable warmth amid chilly winds.
winter specific