SOUTHERN MARYLAND — The scenic views of the Chesapeake Bay are enough to make anyone wish for a day at sea. Southern Maryland is surrounded by beautiful bodies of water, and there are dozens of cruises throughout the area that’ll take you on an unforgettable day trip. We’ve compiled a handful of the best boat rides you can book near the Chesapeake Bay, so go get your captain’s hat and prepare to set sail!
Cruisin’ Tikis
For residents living near Solomons Island, Cruisin’ Tikis offers the perfect activity for a warm day. You can book a private vessel for a group or a single seat, which is a great way to mingle with other Marylanders. As a floating tiki bar, you’ll be able to enjoy a beverage while exploring a whole new side of Solomons Island. Plus, at $60 for a two-hour cruise, every tour is affordable.
Whether you’re looking for a family sail or a solo activity, Cruisin’ Tikis can accommodate your preferences, so book a tour this summer to set sail for adventure near Southern Maryland’s most famous island!
Address: Beacon Marina, 255 Lore Road, Solomons, MD 20688
Phone number: 888-406-1716
Smith Island Cruises
Running from May to October, Smith Island Cruises will take you around the nearby marsh isles. Smith Island has three communities to explore and is only accessible by water, so you’ll get to experience both the cultural and wildlife sides of this hidden gem. You can set sail from Point Lookout, a beloved state park, and you’ll have around two to three hours to explore the island. Adult tickets are typically $65, while children’s tickets are $33 each. If you want to see a new section of Maryland, then explore Smith Island Cruises today.
Address: Point Lookout Marina, 16244 Millers Wharf Road, Ridge, MD 20680
Phone number: 410-425-2771
Dinner & Cruise Series
If you’re seeking a date on an elegant vessel, then the Dinner & Cruise Series is for you! The St. Clement’s Island Water Taxi explores the local waters around Coltons Point, plus you’ll get to enjoy a delicious seafood feast. Couples can attend for $160, while single tickets are $85 each. Whether a first date or a night out with your spouse, the Dinner & Cruise Series will provide the ambiance you seek.
Address: 38370 Point Breeze Road, Coltons Point, MD 20626
Phone number: 301-769-2222
Big Kahuna Cruises
Big Kahuna Cruises offers boat rides out of Solomons and Hollywood, Md. At $50 per ticket, their first cruise will take you on a fantastical ride around Solomons Island, where you’ll learn about the local wildlife and explore the beautiful waters near the Chesapeake Bay. Party boats are also available for reservation in Solomons.
The second cruise in Hollywood offers a similarly scenic cruise through Cuckold Creek for $35. During the two-hour adventure, a full bar is available on the water. Whichever location you choose, you’ll find a fun time on Southern Maryland’s waves!
Address 1: 14426 Solomons Island Road, Solomons, MD 20688
Address 2: 24845 Marina Way, Hollywood, MD 20636
Phone number: 240-572-1440
Chesapeake Windsail Cruises
The Chesapeake Windsail Cruises Corporation is based in Calvert County, and they host a variety of different outings for avid sailors. Nature and sunset cruises are available, while they offer event tours for weddings or birthday parties. On certain holidays, the Chesapeake Windsail Cruises Corporation hosts a boat ride at night so that you can watch the dazzling fireworks. There’s something for everyone at Chesapeake Windsail Cruises, so booking a boat ride could lead to an exciting new experience!
Address: 4160 Mears Avenue, Dock X, Slip 15, Chesapeake Beach, MD 20732
Phone number: 855-561-8810
Chesapeake Bay Charters
Chesapeake Bay Charters offers an ideal family cruise for experienced and beginner sailors. USCG-licensed captains will accompany you on the voyage to ensure your safety, whether you’re sailing to the beach or local eateries. For private groups, Chesapeake Bay Charters is $200 per hour. You can schedule a personalized cruise around the Chesapeake Bay by filling out the form on their website. If you need a ride that accommodates the whole family, then perhaps Chesapeake Bay Charters can grant you the family fun you seek in Solomons this summer.
Address: 255 Lore Road, Solomons, MD 20688
Phone number: 443-963-9463
The Maryland Dove
The Maryland Dove is a detailed reconstruction of the historical boat, and it’s now offering sails to visitors. Explore the water in St. Mary’s County on this wooden ship to expand your knowledge of the state of Maryland. Sails are scheduled through October 2025, and there is a $60 general admission fee. If you like historical boats or summer sails, then the Dove offers a must-visit cruise in Southern Maryland!
Address: Historic St. Mary’s City, 47414 Old State House Road, St. Mary’s City, MD 20686
Phone numbers: 301-994-4371, 301-994-4372
Wm. B. Tennison Cruises
Yet another historic boat ride in Calvert County, the William B. Tennison was built in 1899 and now hosts tours at the Solomons Inner Harbor, taking visitors around the famous island. Adults spend $9 for an hour-long cruise, while children enter for only $5. At such a low price, Southern Marylanders should consider setting sail on the Tennison this summer for an affordable family activity that’ll let you explore the gorgeous Solomons Island.
Phone number: 410-326-2042
Calvert Marine Museum address: 14200 Solomons Island Road S, Solomons, MD 20688
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