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Annapolis - Activities

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#1 of 26 attractions in Annapolis
Category: Tours
Owner description: Pirate Adventures on the Chesapeake is a unique, unforgettable experience for your child aboard a pirate ship in the... more » Owner description: Pirate Adventures on the Chesapeake is a unique, unforgettable experience for your child aboard a pirate ship in the Annapolis Harbor. You will be amazed as we tap into your child's imagination and transform him or her into a pirate, complete with face paint, tattoos, and pirate fashions. Time aboard our ship is filled with non-stop activity, including reading a treasure map, hauling loot aboard, and, of course, defending the ship with our famous water cannons. « less
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#2 of 26 attractions in Annapolis
Category: Tours
Owner description: The classic, wooden 74' Schooner Woodwind sails multiple cruises daily (in season) for public and private charters. Up to 48... more » Owner description: The classic, wooden 74' Schooner Woodwind sails multiple cruises daily (in season) for public and private charters. Up to 48 passengers on each of our twin schooners. Whether a couple, family, party or corporate, we can accommodate you. We also have a Boat & Breakfast available (in season) on Saturdays. Come Sail Away! « less
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#3 of 26 attractions in Annapolis
Category: Tours
Owner description: Annapolis Urban Adventures offers unique and authentic day tours around Annapolis. They range from 2 hour to 1 day adventures... more » Owner description: Annapolis Urban Adventures offers unique and authentic day tours around Annapolis. They range from 2 hour to 1 day adventures and uncover back streets, hidden gems, and fascinating sights. Step into the lives of locals, find out what makes the city tick, and get acquainted with the local food, culture, and traditions of Annapolis. A local expert guide will provide the knowledge and lead you through a fantastic urban experience. « less
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#4 of 26 attractions in Annapolis
Category: Boat Tours
Owner description: Enjoy your private sail charter with captain (up to 6 people) for a half day, full day, or sunset cruise in the Chesapeake... more » Owner description: Enjoy your private sail charter with captain (up to 6 people) for a half day, full day, or sunset cruise in the Chesapeake Bay. Sail under the Bay Bridge, tour the light houses, or sip wine with a special someone as the sun sets over Annapolis. « less
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#5 of 26 attractions in Annapolis
Category: Tours
Owner description: Harbor Queen is the well known tour boat docked at the end of Annapolis City Dock. Come enjoy a 40 minute cruise or take a... more » Owner description: Harbor Queen is the well known tour boat docked at the end of Annapolis City Dock. Come enjoy a 40 minute cruise or take a walking tour with our Colonial guides. With over 7 regular cruises and 4 walking tours in Annapolis to choose from, Watermark offers many ways to have fun in Annapolis! We also offer cruises of the Baltimore Inner Harbor, group tours, field trips and private events on our yachts. « less
Map | Visitor photos (44)
#6 of 26 attractions in Annapolis
Category: Tours
Owner description: Join us for an easygoing, educational and exciting guided kayak tour through one of America's oldest seaports. Annapolis... more » Owner description: Join us for an easygoing, educational and exciting guided kayak tour through one of America's oldest seaports. Annapolis harbor and the United States Naval Academy will be the backdrop for our 3-hour, "history rich" adventure. Our guided tour is designed for everyone and anyone can navigate the waters with our sit-on-top kayaks. « less
Map | Visitor photos (12)
#7 of 26 attractions in Annapolis
Category: Tours
Owner description: Food tasting and history await you. Our tours blends the best of past and present. Try our Historic District 101 Tour or the... more » Owner description: Food tasting and history await you. Our tours blends the best of past and present. Try our Historic District 101 Tour or the Annapolis Food & History tour. A colonial-clad guide leads you through the history of Annapolis while introducing you to 21st century culinary delights - a seamless blend of time and tastes. While walking this compact city, you eat where the founding fathers ate, and eat where the founding fathers wish they could have eaten. Enough food for lunch and history enough for continuing education credits. « less
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#8 of 26 attractions in Annapolis
Category: Tours
Map | Visitor photos (4)
#9 of 26 attractions in Annapolis
Category: Educational Sites; Historic Sites
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#10 of 26 attractions in Annapolis
Category: Tours
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#11 of 26 attractions in Annapolis
Owner description: Captained sailing cruises (2-2.5 hours) out of Annapolis, MD. Captain Kipp Vermeulen will be your skipper aboard this high... more » Owner description: Captained sailing cruises (2-2.5 hours) out of Annapolis, MD. Captain Kipp Vermeulen will be your skipper aboard this high performance open bridgedeck catamaran keeping you close to the water and passing all the boats in the bay. Relax and ghost around historic Annapolis passing the Naval Academy and exploring the shallows up the Severn River. « less
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#12 of 26 attractions in Annapolis
Owner description: Take a nighttime ghost walk through the historic downtown district on a spine-tingling journey into Annapolis’ dark and... more » Owner description: Take a nighttime ghost walk through the historic downtown district on a spine-tingling journey into Annapolis’ dark and troubled history! Meet some of our more spirited residents and visit our most horrific haunted sites! For the more daring, take a raucous romp through three of our most haunted pubs on our Haunted Pub Crawl. Filled with stories of resident ghosts, haunted taverns, and restless spirits; our tours will have you sleeping with one eye open! « less
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#13 of 26 attractions in Annapolis
Category: Tours
This is a self-guided tour of the city.
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#14 of 26 attractions in Annapolis
Owner description: City Running Tours (CRT) provides an opportunity to experience a city in an exciting way. Annapolis is an ideal town for... more » Owner description: City Running Tours (CRT) provides an opportunity to experience a city in an exciting way. Annapolis is an ideal town for runners and CRT is ideal for the traveler who is tired of the hotel treadmill, the runner who is training for a race or who wants to explore new and interesting routes. CRT offers both guided group and personalized runs to accommodate any athletic ability, pace, or style. « less
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#15 of 26 attractions in Annapolis
Category: Walking tours
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#16 of 26 attractions in Annapolis
Category: Tours

SegZone Tours of Annapolis (formerly Annapolis Segway Tours) is the original Segway tour of Annapolis. SegZone offers a new twist on old vacation favorites by offering... more »

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#17 of 26 attractions in Annapolis
Owner description: We are walking guides and colonial entertainers, offering tours in the Historic District of Annapolis. Our goal is for you to... more » Owner description: We are walking guides and colonial entertainers, offering tours in the Historic District of Annapolis. Our goal is for you to enjoy and experiene History. « less
Map | Visitor photos (1)
#18 of 26 attractions in Annapolis
Category: Other
The school offers classes in sailing.
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#19 of 26 attractions in Annapolis
Category: Spas
Owner description: Annapolis Boutique Spa is located in lovely West Annapolis behind the Grauls Supermarket. Plenty of street parking and a... more » Owner description: Annapolis Boutique Spa is located in lovely West Annapolis behind the Grauls Supermarket. Plenty of street parking and a parking lot for your convenience.Not only do we offer relaxation through massages, facials, body wraps, body waxing, hair & nails but acupuncture, permanent make up, teeth whitening and much more. A very friendly group of true caregivers.Our month to month memberships allow for a great selection of services at a great savings of $65 reg $90-$125. No long term contract. Family & friends can enjoy the same value. Can be gifted as well. « less
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#20 of 26 attractions in Annapolis
Category: Tours
This company rents kayaks at Quiet Waters Park in Annapolis.
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Category: Boat Tours
Owner description: Tour Annapolis by water on your own private yacht. Five Star is a well appointed 50ft Chris Craft motoryacht that is... more » Owner description: Tour Annapolis by water on your own private yacht. Five Star is a well appointed 50ft Chris Craft motoryacht that is available for 3-10 hour charters on the Chesapeake Bay. « less
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Owner description: Take a haunted walking tour through Annapolis with a local historian as he reveals terrifying town lore. You need to hear... more » Owner description: Take a haunted walking tour through Annapolis with a local historian as he reveals terrifying town lore. You need to hear about his personal experiences living with ghosts at one of the oldest houses in town. See for yourself why this city of cemeteries and ancient houses has the most ghosts around. Annapolis is haunted! « less
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Category: Tours
The company offers lessons in kayaking.
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