June 17, 2024
Dylan Roche
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Did you know Anne Arundel County has more than 500 miles of shoreline? (It’s true. You can look it up.) But if you don’t have a boat of your own — and let’s face it, a lot of us don’t — it can leave you feeling a little landlocked. That is unless you take advantage of some of the opportunities to charter a cruise, rent a paddleboard, or any of the other adventurous ways of getting out on the water on offer around Annapolis. Here are 20+ options to get out on our beautiful waterways without owning your own boat:
Boat clubs like the Chesapeake Boat Club let you sidestep the time and expense of maintaining a personal boat. For a one-time initiation fee and an annual rate, you can reserve one of Chesapeake Boat Club’s sailboats or powerboats for a waterfront outing. You even have a choice between two levels of membership to customize the perks.
Promoting “all the fun without the hassles of ownership,” Annapolis Boat Club has a monthly membership rate instead of an annual one. Once you join, you can choose from the many boats in its fleet, get training from licensed captains, and make friends with other people who love the water.
Operating boat clubs all over the country, SailTime specializes in sailing, whether you’re looking for a catamaran or a monohull, making it a great fit for a membership base here in Annapolis. SailTime also offers training with a network of 30 professional sailing schools, plus you can join the Ownership Program.
With 35 years of experience, Freedom Boat Club has become a leader in the boat club model, operating at marinas all over the country. Your membership gets you access to unlimited training from licensed captains as well as your choice from a fleet of pontoons, deck boats, center consoles, wake boats, and more. Local marinas include Nautilus Point Marina, Annapolis Landing Marina, Podickory Point, and Fairwinds Marina.
With these options, you can buy individual tickets for unique experiences or charter the whole boat for your private party.
Chronic's fleet offers private charters or sailing lessons (private groups or individuals can join a group.) Some options for charter itineraries include sunset cruise, dinner cruise, half-day, full-day, or overnight.
Tour Boat Annapolis can accommodate small (up to 6) and large (up to 32) groups for their sightseeing charters. You can also join the fun on one of their public cruises like the sunset cruises with live entertainment and special occasion cruises like the July 4th Fireworks Cruise.
Sometimes sailing feels more exciting when you do it in historic style. The Wilma Lee is a 1940s authentic Chesapeake Bay Skipjack, one of the few remaining boats designed for oyster dredging on our local waterways and an icon of maritime history. The Annapolis Maritime Museum offers 2-hour Heritage Tours aboard the Wilma Lee where you can learn the history of our waterways. Private charters are also available.
You’ve probably seen the Harbor Queen cruising around the Annapolis waterways with its bright red trim and yellow crown on top. You can drop in for a 40-minute cruise around Annapolis and USNA any day of the week, or you can book tickets for one of the specialty cruises, such as a trip to St. Michael’s or the Thomas Point Lighthouse. Beyond the Harbor Queen, Watermark has an impressive fleet available for private charters of up to 200 guests.
It’s up to you whether you want a hands-on sailing experience or you just want to sit back and relax when you set sail aboard one of these two wooden 74-foot Schooners, the Woodwind or the Woodwind II. 2-hour public sailing cruises are available, or you can book a private sailing cruise for you and a group of friends.
During this unique experience, guests will depart from the dock behind the Annapolis Maritime Museum located at 723 2nd St Annapolis, MD. The tour not only includes a pleasant boat ride around the bay, but also a tour of the iconic Thomas Point Shoal Lighthouse. Built in 1875 and now a National Historic Landmark, it is the last intact lighthouse of its kind still in its original location.
Want to cruise with only your own guests? Try one of these private charter options.
This classic lobster yacht built on Martha’s Vineyard accommodates up to 6 guests, and you can book it for a private cruise that is elegant and stylish.
Cruise around Annapolis in this 6-passenger charter option. A Forward beer package (12 beers) and Snackle box is included. Sally IVth is conveniently docked by Chart House Prime Restaurant and the Captain will meet you there to show you onboard.
Fish with Weaver specializes in light tackle, fast-action fun for all levels, giving tips on technique, tackle, and fish behavior. Some of the fish you might encounter are Bluefish, Speckled Trout, Spanish Mackerel, and Red Drum. Charter for a half-day or full-day of fun. Or consider a two-day fishing trip with their unique Lighthouse Adventure.
You get to plan your ultimate day on the water with Cap’n Mike, whose custom-built Markley 46 Full Moon can take you on an unforgettable adventure. You can even rent kayaks or paddleboards for closer-to-the-water exploration once you dock at your destination.
This two-masted gaff-rigged schooner is yours when you book a private sailing charter — the day, the time, and the number of hours are all yours to choose. The Liberté takes you either along the Severn River or the Chesapeake Bay, accommodating up to 49 passengers who can enjoy music and a full bar during the trip.
Annapolis Canoe and Kayak sells and rents canoes, kayaks, and paddle boards, plus all the related gear and equipment you need to spend a day — or a lifetime — out on the water.
In case you’ve ever wondered, “SUP” stands for “standup paddleboard,” and Capital SUP offers rentals and lessons for anyone who has ever been curious to try this popular way of exploring the water. Want to paddle while sitting down? They also rent out kayaks!
Visit Paddle Annapolis in Eastport for kayak and SUP rentals, as well as guided tours, great for families and people of all ages.
Boating is super user-friendly with these electric boats, which are easy to operate (no experience necessary), quiet, and safe. Plus, they’re environmentally friendly. Book one for just 1-2 hours and you and your crew can explore the local waterways all around Annapolis.
Annapolis Sailing School was founded in 1959 and is the first sailing school for adults in the nation. There are lots of options for all ages including basic sailing courses, private sailing and powerboat instruction, youth camps, Family TrySail, KeelBoat club, sailboat rentals, and social events.
Boating is truly for everyone with CRAB. This fleet offers adaptive boating opportunities to people with disabilities, recovering warriors, and youth from underserved communities.
Why get a road taxi when you can get a water taxi? Get anywhere on the Annapolis Harbor, including Spa Creek and Back Creek, in the most Annapolitan way possible — via the water.
Any maritime adventure is better with pirates! This great option for a family outing is an interactive experience where you get to sail aboard a pirate ship and team up with the pirates to follow a map, find treasure, and defeat the stinky pirate enemy.
You’ll feel like you’re on the South Seas when you sail around the Severn River on this private floating tiki bar. You and 15 of your fellow partygoers can BYOB and hop aboard at Nautilus Point Marina. The boats have USB charging stations and Bluetooth speakers, so it’s easy to blast your favorite music while you sail around.
Yes, that's right. Fido can get in on the boating action here. Whoof provides opportunities for people to get out on the South River with their pups, whether it be in personal or Whoof kayak rentals. Other fun activities include summer camps for kids, training opportunities, yoga, and pet-focused art classes.
If you've ever wanted to try parasailing, here is your chance. ZFlight's USCG-licensed Master Captain has over 30 years in the boating industry and over 15,000 flights. You will see Annapolis from a whole new perspective with this one!
We hope you have a great time exploring Annapolis' beautiful waterways ... even without your own boat.
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