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Annapolis Bay Charters

At Port Annapolis Marina. ABC offers Quality Sailing Yachts from 30' to 48' Monohulls and Catamarans for bareboat and captained sailing. We will customize your cruise for you. It's as easy as ABC.

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Chesapeake Boating Club

Chesapeake Boating Club is the #1 flexible boat sharing program on the Chesapeake Bay. Let us help you experience the thrill of boating at a fraction of the cost of ownership. We offer annual memberships to meet every boater's need. Choose Sail, Power, or a combination - and have unlimited use of our fleet of boats ranging from 19'-35'. Low annual fee, we take care of maintenance, repairs, and slip expenses. You get rid of the hassles and keep all of the fun! Training available for all levels.

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Cruise Annapolis

Cruise Annapolis, a Waypoints Destination, is a boutique charter company in the heart of Annapolis offering luxury bareboat charters, crewed yacht charters, & ASA sailing instruction on the Chesapeake Bay. Our world-class fleet consists of new model Fountaine Pajot sailing catamarans and motor yachts, and Jeanneau sailing monohulls and powerboats. All of our yachts are well equipped, privately owned, and meticulously maintained. Whether you are looking for a short sailing getaway or a longer trip to explore the historic locations on the Bay, we're here to help you make the most out of your excursion. Additionally, if you love chartering so much that you'd like to own your own vessel, we have yachts available for ownership! Contact your Cruise Annapolis Charter Concierge to learn how it is possible to offset 80-100% of new yacht costs with tax advantages and income.

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Herrington Harbour North

Herrington Harbour North combines an award winning yacht yard and marina resort in one location. We have the largest service and sales Yacht Center on the Chesapeake located on Herring Bay. We balance our property with many resort amenities along the waterfront overlooking our protected 600 slip marina. Annual and transient dockage is available. Amenities include private salt water pool, pool side bar, fitness center, WiFi, vending and customer lounges, Dockside Restaurant, and clean bathhouses. Complimentary weekend events include evening socials, seminars, breakfast buffets, parties at the pool, exercise programs and outdoor music/movies. Bikes, kayaks, and paddle boards available to explore local areas. Herrington North is annually recognized as the Best of the Bay yacht yard and marina resort. Land storage is available for over 1,200 boats. Virtually every contractor service on site including: bottom painting, engine service, electronics, fiberglass, sail construction and repairs, rigging, canvas, detailing, A/C service, woodworking, prop shop, shrink wrapping, and welding. 4 travel lifts 25 to 85 ton capacity, West Marine, The Sailing Academy and Boat brokers are located on our property.

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Herrington Harbour South

Herrington Harbour South is centrally located on the Bay with a multitude of exciting destinations within easy reach. The 1,500' Entrance Channel, maintained at 7' MLW, quickly takes you from the protected harbour to deep open water. Lounge on the private beaches, swim in the Olympic-size pool, dine at Ketch 22, enjoy breakfast, lunch or dinner at Chesapeake Market & Deli, grill in the picnic areas, play tennis/pickleball, and relax on your boat. We have a host of events for slipholders such as bonfires on the beach with drinks and live entertainment, a 4th of July Fireworks Celebration, free kayak/paddleboard use, and more. Everything you need is on-siteluding a full-service Fuel Dock, free WiFi, Cable TV, pump-outs, Private Bathhouses, Fitness Room and Sauna. Naturally preserved shorelines around the marina basin are home to an array of wildlife. Annual and transient dockage available. Only 20-minutes from the beltway to the bay. The Marina Office is open daily from 9am - 5pm.

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Port Annapolis Marina

Port Annapolis Marina is a deep water 245-slip marina, with a full-service boatyard facility. Ample dry storage for self-service customers and winter storage. 50 & 75-ton travelift with haulout capacity to 65 ft and 26 ft wide. Pumpout station. Service includes: carpentry, engine work, installations, rigging, repairs and maintenance, f/glass repair, Imron spray painting. Large brokerage display area. Newly remodeled clubhouse facility, cafe, laundry and pool house areas. Swimming pool, playground, store, and ice for marina patrons. Transients and clubs welcome.