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10 Reasons to Cruise to St. Michaels

On a Day on the Bay Cruise


Every Saturday -- plus select weekdays -- in season, we offer our memorable Day on the Bay to St. Michaels. A Watermark tradition for decades, this cruise should be on your summer bucket list every year. Read on for our 10 Reasons Why Day on the Bay to St. Michaels should be on your list:

#10: St. Michaels…the town that fooled the British (but not the rest of us!). Yes, it’s historic but that’s not all. Amazing restaurants (39 listed on Yelp), wonderful shopping (21 listed on St. Michaels Business Assoc site), walkable, quaint "seaport". Ice Cream! Show your Cruises on the Bay sticker for 10% off your order at Justine's Ice Cream Parlor. And the Cannonball House? It has its own Facebook Page.

#9: St. Michaels has a back side with a walking trail (free!) if you want to commune with nature rather than shop or eat. In fact, there are lots of parks to just, well, park it! Details here.

#8: The Water…and the Boats! There are plenty of places to sit and watch the boats come and go in St. Michaels harbor. And the Miles River Yacht Club hosts many regattas.

#7: The cruise over! You will probably see 2 lighthouses (Thomas Point Light at a distance and Bloody Point Light pretty close up). Fun fact: Bloody Point Bar Light was purchased by Michael Gabriel in 2006 and, in 2009, Mr. Gabriel (who owns other lighthouses around the U.S.) announced plans to dedicate each room in the Lighthouse to a brewery…cheers!

#6: The Cruise back! After a fun day of walking St. Michaels you can now sit back and relax on your 2-hour cruise home to Annapolis. No Bay Bridge Traffic. No Rush. No Worries. Enjoy a refreshing beverage from the River Run Bar aboard Lady Sarah as you reminisce about your day on the Shore.

#5: Free Tastings and Tours! St. Michaels opens its doors for delicious free tastings. From coffee in the morning (Olivin’s) to Wine (St. Michaels Winery 11am-5pm) to Beer (Eastern Shore Brewing Company 12-9pm) to Rum (Lyon Distilling Co. 11 am-6pm). Plan your day with free tastings and tours. Start your sample here:

#4: Dog Friendly! Not only is Watermark dog friendly but so is St. Michaels. Enjoy strolling the streets with your four legged friend, stopping many times for dog bowls of biscuits and water along the way. There are lots of outdoor-seating restaurants and the Chesapeake Bay Maritime Museum is also dog-friendly (except during festivals…too crowded!). See Tavish’s visit.

#3: The Chesapeake Bay Maritime Museum! This incredible place is included in your ticket for Day on the Bay…really! You’ll get a special sticker that shows “yes, I arrived by boat” and you can enjoy all the CBMM has to offer and there is a lot! You may need an entire 3 hours to explore (hmmm, another trip to St. Michaels??) with lighthouse exhibits, boat building, history, carvings, demonstrations, gift shop…there is a lot to see and th is year they celebrate 50 years!

#2: Events. There’s always something going on if you really needed another reason to take this Day on the Bay cruise to St. Michaels…like the Farmers Market, or the Museum at St. Mary’s Square…see the calendar before you cruise.

#1: This TripAdvisor review really says it all…thanks for sharing your experiences with us!