Flag House Inn

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10 Ways to Play on the Bay

Find Your Way to Get Out on the Bay

(cover photo courtesy of David Sites – @motoxdms on Instagram)
(March 29, 2022) Mandatory short commercial: this blog can start your planning for a great visit to Annapolis, especially from April to November which is our prime boating season…. Book your stay with us, we include on site parking and breakfast in our rates, which the large and luxury hotels don’t include if they even have it…. Also, check out our 1000+ reviews in Google and Trip Advisor, and see why our guests love us!
Ok, let’s get out on the water!
We wrapped up an amazing 2021 and are making several improvements around the house for 2022 including
  • Exposing and refinishing the original 1879 pine floors in sitting room and dining room
  • New towels, mattresses, refreshed decor and room amenities
  • Certification and approval for membership in Select Registry, a collection of ~300 premier properties in the US
We were busy hosting so many great guests, serving up yummy breakfasts and managing rooms… but we still had plenty of play time too, especially out on the Chesapeake Bay!…..While we didn’t get out quite as much as noted area photographers David Sites and Jeff Norman, we still did pretty well!
That got us to thinking about our biggest highlight this past summer which was the variety of ways we got out on the Chesapeake Bay!
Here is our list of the best ways to get out and play on the Bay: (note, we experienced just about ALL of these this past year.). This will be a long-ish list as we drop in a pic or two for each option… All pics owned by Flag House Inn (we took ’em!) unless noted.
  1. Woodwind Sailing – Our single favorite Bay outing. Two 74’ schooners, max capacity 32 people, sailing 3-4 times a day. They motor out into the harbor, put up the sails, and go where the wind takes them! If the wind is right, which is quite often, they will sail under the Bay Bridge! On Wednesday night it’s Race Night when the yacht clubs have their weekly races with over 100 sailboats out on the harbor, including the 2 Woodwind yachts racing again each other (see pic below). Even better, when you stay with us, Captain Jenn (owner) has given us a voucher good for a little treat on board …. Book your stay here. Tickets go on sale 6 days before the day you want to sail.
    Sialboat on water

    The Woodwind I and II can take you out on a 2 hour sail into Annapolis Harbor and the Bay

    sailboats on water

    Wednesday night is race night for the yacht clubs – see it up close from the Woodwind

  2. Watermark cruise to Thomas Point Lighthouse – Most weekends, once a day. Enjoy a 90 minute cruise down the Bay to the iconic Thomas Point Lighthouse, the last original lighthouse still in place in the Bay. Built in the 1875, it has protected large freighters from the shoals nearly a mile offshore. The cruise usually offers bar service and both deck and cabin seating. Other cruises will take you under the Bay Bridge or up the Severn River or even a day trip to St Michael’s. Buy tickets in advance here or walk up. We love doing this tour with friends and family.
    flag and lighthouse on Bay

    Watermark has a number of tours to get you out on the Bay: 40 min harbor cruises, 90 min Bay cruises or the all day cruise to St Michaels

    lighthouse on Bay

    The iconic, 1875 built Thomas Point lighthouse is best viewed by boat since it’s a mile offshore!

  3. History cruise on the Wilma Lee, a restored 1940 skipjack – We’ve done this cruise twice, and will probably do it a 3rd and fourth time. Each cruise includes narration by a docent, who will give you a real appreciation for what a difficult life it was for the watermen who made a living on the Bay harvesting oysters and crabs. The Wilma Lee was a working boat for decades…. Cruises usually depart from the Annapolis Maritime Museum in Eastport, you can make an afternoon of it, exploring the museum (housed in a former oyster packing house), stopping at Forward Brewing, Davis’ Pub, Boatyard or our fave nautical home goods shop, Lat Long… buy your outing here.

    Sailboat with people on it

    The Wilma Lee, built in 1940, is a fine example of a skipjack, a working boat built by local waterman to use in dredging oysters

  4. Curated tour inside Thomas Point Lighthouse – This is a really special treat! The Annapolis Maritime Museum is your departure spot – take a short cruise down the Bay, dock up at the lighthouse, and a docent will lead you around the interior levels. The Lighthouse is maintained similar to what existed in the 1960’s . The views are spectacular and again you get a sense of the lonely and occasionally dangerous life living on the Bay. Tours run on weekends June to October, buy tickets here 

    Thomas Point Lighthouse, a mile offshore, built 1875. The most iconic and oldest operating lighthouse on the Bay

    looking out window to sailboat and chesapeake Bay

    You will get a really unique perspective on the Bay from inside Thomas Pt Lighthouse

  5. Private sail – How does a small (max 6 people plus crew) sail outing sound? If you plan ahead, buy some drinks and snacks (you can always stash in our guest fridge) and drive over to a marina, then we really have a treat for you!  We know of at least 3 boats who will take you on a 2 – 4 hour sail, some will even cater a meal on board! The most accessible is Capt. Paul and his 38’ Non-Seaquitter, he will give you a great private sail, also try Seas the Bay and Annapolis Sailing Adventures.  (photo courtesy of Capt. Paul)
    little girl steering a sailboat

    Capt Paul will give you a great private sail outing

    view from sailboat out to chesapeake bay

    Relaxing with Capt Paul on the Nonseaquitter

  6. Charter fishing on the Bay – We went out for a half day fishing with the My Girl, a 20 minute drive to Edgewater.  We didn’t hook much, but we enjoyed a great, relaxing afternoon trolling and soaking up the pleasant October sun with friends and family. The captain also runs crabbing tours and we can see that in our future this year. There are a number of charters in the area, we can help advise on booking.
    girl pointing out fishing rods

    Charter fishing boats are stocked with gear

    Girl fishing from boat

    Hoping to hook a rockfish…

  7. Harbor Tour on Harbor Queen (Watermark) – The venerable Harbor Queen has givens thousands of visitors an informative and pleasant cruise around Annapolis harbor. The tour runs about 40 minutes and goes out every day in the season (which as of this writing has already started in March!). Sit out on the deck or in the cabin with bar service. Really great for those not feeling as seaworthy or limited on time. Advance purchase usually not needed, more info here.  (photo courtesy of Watermark)

    large boat on water

    Get a great 40 minute, narrated cruise around Annapolis harbor and US Naval Academy on the Harbor Queen

  8. Powerboat rental – ok this usually requires “friends with boats” or previous experience but we wanted to include. There are many boat share options around the area and a few places that will rent you a power or sailboat. After that it’s your trip! Hire boats here
    view of harbor and sky from boat

    Experience the freedom of taking a boat wherever you want to go (prior experience required)

    view of waterfront homes

    When you have your own boat rental, you can explore all the small creeks around the area

  9. Kayak / Canoe/ SUP rental – The best way to get up close with the Bay, there are several options : – Annapolis Canoe & Kayak, you can water taxi over to Eastport. Explore Spa Creek and paddle down Ego Alley!  – Capital SUP on Back Creek, 15 minute drive, plus Quiet Waters Park, also 15 min drive. Offers canoes & kayaks and innovative classes. Also, Paddle Annapolis in Eastport, also accessible by water taxi  Woman with hat sitting in a kayak on sun-kissed waters
  10. (And don’t forget) The Water Taxi! Hey a 5 minute ride counts too! The quickest, cheapest and easiest way to get out on the Bay! The short ride across the harbor puts you in a relaxed frame of mind…. If not busy the captain will gladly take you on a longer ride around Spa Creek and the harbor… (photo courtesy of Watermark)
So there it is, 10 ways to get out on the Bay, really it’s closer to 20 when you itemize the different vessels and destinations! Like we always say, there is always something happening in Annapolis
Wait, there’s more!  We only talked about getting ON the Bay – we’ve also got 4, FOUR beaches within 30 minute drive of Annapolis as well! That’s a blog for another day, but we can always advise you once you book a stay with us….
We’d be happy to further advise you once you book your stay with us. See YOU this summer out on the Bay!
man and woman on a boat

Our boat models always enjoy a day out on the Bay!

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