Schooner_Sara_B_sailingHave a sailing adventure in Annapolis, the capital city of Maryland!  The city is located right smack in the middle of two metropolitan areas, Baltimore and Washington DC.  We’ve created an itinerary of experiences you just can’t miss when you are in Annapolis.  Known as a beautiful colonial seaport with picturesque sail boats dotting on the inner harbor, Annapolis is historic and surprisingly still a small and quaint little town.  The town surrounds itself around the waterfront and typical things to experience in Annapolis are a sail boat ride and a good old-fashioned crab feast!  Since it is the fall season, we included a Haunted Pub Tour to end the day on a fun spooky Halloween note.

Stop 1 –  Windschooner Sailing Cruise

Why not have the time of your life onboard the Woodwind and Woodwind II for a true sailing experience on the Chesapeake Bay.  Two-hour public sailing cruises are available during the day.  In your  experience you will assist the captain and crew hoist the sails and take a turn at the wheel.   Private cruises  are available for special occasion parties and group instructional tours are available for those who want to learn more about how to sail.  Also check out their Specialty Cruises calendar as you might want to plan your trip around one of their special events.

All cruises sail by the United States Naval Academy, into the Severn River and typically into the Chesapeake Bay.  Sunset cruises are available in the evenings at 5:30 pm.  Check the schedule for special sunset cruise events on Mondays-Thursdays where a cash bar of wine, beer and local microbrews will be provided, along with Beer Tasting Tuesdays and Wednesday Night Races.   All cruises run through Sept. and October.

PicMonkey Collage buddysStop 2 – Crab Feast at Buddy’s Crabs & Ribs

No experience on the Chesapeake Bay is complete without tasting some crab and old bay seasoning!  Have the ultimate Maryland Crab feast experience at Buddy’s Crabs & Ribs.  The menu has a wide range of options from All You Can Eat Buffets to Crab Meat Heaven and Land and Sea entrees.  The freshest local Chesapeake Bay seafood are used for their Steamer & Raw Bar of oysters, crab, mussels, clams and shrimp.  Steamed crabs are sold by the dozen!   Alaskan Snow crabs, soft shell crabs, lobster, rockfish and traditional English fish & chips are all offered in this scrumptious seafood heaven.

Stop 3 – Walk on Ego Alley

Ego Alley is a small waterway on the Annapolis City Dock that leads into the heart of the city.  It is named for the expensive boats and private yachts that go in and out of the channel.  Take a walk on Dock Street and find a bench to sit down.  This is the best place to sit and watch the boats and people go by.  You might want to get some ice cream at Storm Brothers Ice Cream Factory on Dock Street while you are relaxing there.  You will see lots of people going to and from the boat slips and water taxi stands that are located there.  On the opposite side of the dock there is the Annapolis Yacht Club and Pusser’s Caribbean Grille Restaurant, the only waterfront restaurant that has outdoor seating on Ego’s Alley.   There are lots of other sites and landmarks  that  you can walk to from there, so check our list of Nearby Attractions below and take a walk around the downtown.

Annapolis Ghost Tours2Stop 4 – Haunted Pub Crawl

Our last stop is a Haunted Pub Crawl by Annapolis Ghost Tours and Crawls.  The tour starts at 9:00 pm at 13 Francis Street, just a few short blocks from Ego’s Alley.  On the tour you will find out about the 300 year history of the town and hear the ghost stories of the spirits that still live there.  Your tour guide will take you to three different pubs for about 30 minutes each stay.  Total tour time takes about 2 to 2 1/2 hours.  Ticket prices are $20 for the tour but that doesn’t include drinks, so bring some extra money for that.  Also available are 7:00 pm Walking Ghost Tours and 8:00 pm Twisted History Tavern Tours that you might prefer instead.  Check out more information about all the tours on their FAQ page.


Other Attractions


Photo Credits

Wind Schooner Collage:

Buddy’s Crabs & Ribs Collage: Buddy’s Crabs & Ribs

Ego Alley: Google

Haunted Pub Crawl: Haunted Pub Crawl


Interested in taking your own experiential tour to Annapolis, MD without worrying about driving? We have vehicles ranging in size from sedans to motorcoaches and can accommodate any size group. Booking your vehicle is as easy as 1-2-3!

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