Discover a luxurious 3/4 day private catamaran charter on Chesapeake Bay departing from Annapolis, Maryland. Perfect for romantic sunsets or lively group outings, this 6-hour sailing adventure offers stunning views and intimate relaxation on iconic waters.
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Difficulty
easy
Duration
6 hours
Fitness Level
Suitable for individuals of all fitness levels; primarily a leisure sailing experience.
Wildlife
History
Annapolis has served as a key naval hub since the 18th century, deeply intertwined with maritime tradition.
Conservation
This charter emphasizes eco-friendly practices to minimize impact on the Chesapeake’s delicate aquatic ecosystems.
Chronic Sailing
Discover a luxurious 3/4 day private catamaran charter on Chesapeake Bay departing from Annapolis, Maryland. Perfect for romantic sunsets or lively group outings, this 6-hour sailing adventure offers stunning views and intimate relaxation on iconic waters.
Chronic Sailing offers curated private and multiday sailing charters based in Annapolis, Maryland, and specialized waterfront experiences across the Chesapeake Bay and beyond. The company operates a fleet that includes a Dufor 470, an Oceanis 45 and multiple luxury catamarans, and provides flexible private charters, bareboat options, and themed multiday itineraries like Slowdown, Dos Milagros, and Starz. Trips span half-day, three-quarter-day, full-day, and multiday formats, plus sunset sails of three, six, and eight hours, making options suitable for romantic evenings, corporate outings, family celebrations, and skill-building cruises.
Chronic Sailing combines professional captains and custom itineraries to prioritize safety, comfort, and memorable on-water moments. The fleet’s open-concept catamarans emphasize spacious deck areas and seamless interior-exterior flow for relaxed socializing and scenic viewing. Guests can expect departures from Annapolis for Chesapeake Bay adventures as well as specialized experiences such as private sunset charters and bareboat rentals for experienced sailors. The business highlights local knowledge of the Bay, tailored guest service, and vessel choice to match group size and trip goals. Bookings can be arranged for private groups and multiday voyages, and experiences are presented with clear duration options and vessel descriptions to help planners select the right charter. Chronic Sailing’s offerings are geared toward delivering professional, customizable sailing experiences that showcase Chesapeake Bay sunsets, cruising comfort, and safe, memorable time on the water.
Specialty itineraries include historical coastal routes, sunset photography opportunities, and family-friendly cruising plans designed to maximize sightseeing, relaxation, and on-deck comfort for every guest. on and off-board service excellence.
Home Port
Annapolis, MD
Departures from Annapolis
Vessels
Dufor 470, Oceanis 45, Catamarans
Multiple vessel types available
Tours Offered
17+
Private, sunset, multiday, bareboat
Trip Lengths
3–8 hours, multiday
Half-day to multiday options
Book private or bareboat charters from Annapolis today. Custom itineraries, experienced crews, and Chesapeake sunsets await.
Book Ahead for Sunset Cruises
Reserve your spot early to secure the best sunset sailing experience, especially during peak seasons.
Bring Layers for Evening Chill
Even summer evenings on the bay can get cool; packing a light jacket ensures comfort as the sun sets.
Sun Protection is Key
Wear sunscreen and hats to protect yourself during the daytime portion of your sailing trip.
Stay Hydrated Onboard
Even on the water, it’s important to drink plenty of water to stay refreshed throughout your 6-hour charter.
Light Jacket
Keeps you warm during cooler evening breezes on the bay.
summer
Sunglasses
Protects your eyes from sun glare reflecting off the water.
Water Bottle
Helps you stay hydrated during your sailing adventure.
Sunscreen
Crucial to protect your skin from UV rays while exposed to the sun.
spring