Sail Annapolis: Explore Chesapeake Bay Aboard a Cruising Catamaran
Difficulty
moderate
Duration
4–6 hours
Fitness Level
Participants should have moderate physical fitness; basic agility and balance are needed to move safely on deck.
Overview
Set sail from Annapolis aboard a stable cruising catamaran and experience Chesapeake Bay like never before. Learn the ropes and feel the thrill of commanding a twin-hulled vessel in one of America's top sailing destinations.
Cruising Catamaran (ASA 114)
3 Days, 2 Nights, Liveaboard • Cruise and learn on a luxurious 40-foot catamaran
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About This Adventure
Embark on an exhilarating three-day sailing adventure aboard a catamaran, mastering essential skills like advanced sail trim and emergency operations. Set sail from Annapolis, exploring scenic anchorages while earning your ASA 114 certification. This unique experience combines hands-on learning with the thrill of navigating coastal waters in diverse conditions.
Charter that Cat!
Duration
3 Days, 2 nights liveaboard
About
Learn how to sail a sloop-rigged, auxiliary powered 30'-45' catamaran during a multi-day cruise upon inland/coastal waters in moderate/heavy winds and sea conditions.
Learn about boat systems, auxiliary engines, advanced sail trim, anchoring / mooring, docking, emergency operations and more.
What's Included
- Textbook and materials
- ASA 114 certification
- Fuel and docking fees
Additional costs for provisions (about $200).
More Information
This cruise departs from Annapolis, Maryland. We return to Annapolis after three days with possible overnights in Rock Hall, Baltimore, Kent Island or other anchorages.
Ages
18+
Prerequisites
Certification: ASA 104 Bareboat Chartering
Adventure Tips
Check Weather Before Sailing
Chesapeake Bay conditions can change quickly; always verify weather forecasts before setting out to ensure a safe voyage.
Wear Non-Slip Footwear
The catamaran deck can be slippery when wet; shoes with good grip will help maintain stability on board.
Hydrate and Protect from Sun
Bring water and wear sunscreen—even on cloudy days, reflected light from water increases UV exposure.
Arrive Early for Briefing
Plan to arrive at least 30 minutes ahead of your scheduled time to complete safety briefings and get comfortable with the boat.
Local Insights
Wildlife
- Osprey
- Great blue heron
History
Annapolis has served as an important naval center since the 18th century, hosting the U.S. Naval Academy established in 1845.
Conservation
Local operators follow Chesapeake Bay stewardship practices to minimize environmental impact and preserve water quality.
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Adventure Hotspots in Annapolis
Frequently Asked Questions
Recommended Gear
Non-slip Deck Shoes
Provides safety and stability when moving around the wet catamaran deck.
Sailing Gloves
Protects hands when handling ropes and sails.
Light Waterproof Jacket
spring specific
Polarized Sunglasses
Reduces glare reflecting off the water, enhancing visibility and comfort.
summer specific