Unwind aboard a luxurious catamaran on Chesapeake Bay with a private 8-hour charter from Annapolis. Perfect for sunset sails, romantic escapes, or fun with friends, this trip reveals the bay’s unmatched natural beauty and maritime charm.
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Difficulty
easy
Duration
8 hours
Fitness Level
Suitable for a wide range of fitness levels; minimal physical exertion required as sailing is mostly enjoyed seated or standing on deck.
Wildlife
History
Annapolis, established in 1649, has long been a maritime hub, home to the U.S. Naval Academy and a rich sailing tradition.
Conservation
The charters follow eco-friendly practices including minimizing fuel use and encouraging guests to respect wildlife habitats.
Chronic Sailing
Unwind aboard a luxurious catamaran on Chesapeake Bay with a private 8-hour charter from Annapolis. Perfect for sunset sails, romantic escapes, or fun with friends, this trip reveals the bay’s unmatched natural beauty and maritime charm.
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.
Bring Water and Snacks
Although some snacks may be offered, pack your own water and light bites to stay energized during the 8-hour sail.
Dress in Layers
Bay weather can shift quickly, so wear layered clothing to stay comfortable from warm afternoon sun to cooler evening breezes.
Apply Reef-Safe Sunscreen
Protect your skin and the Bay’s delicate ecosystem by using environmentally-friendly sunscreen during your sail.
Secure Your Belongings
Use waterproof bags or containers to keep personal items safe from spray and wind on the open water.
Sunglasses
Protect your eyes from glare off the water during daylight hours.
summer
Windbreaker Jacket
A light, windproof layer to block chilly breezes on the water.
spring
Non-Slip Footwear
Shoes with good traction help maintain stability on wet boat decks.
Reusable Water Bottle
Stay hydrated throughout the day without creating plastic waste.