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Whether you are feeling adventurous or lazy, the sparkling waters of the Chesapeake Bay await. These cruises on the Chesapeake Bay have it all: from sailing on a majestic schooner to motoring in a leisurely fashion to St. Michaels for lunch to fishing and crabbing on a 26-foot skiff captained by a waterman. Please connect with each organization directly to plan your trip, as times and pricing may change.
1. Schooner Woodwind Sailing Cruises
A two-masted staysail schooner sails from the historic Annapolis waterfront past the Naval Academy and cruises into the Chesapeake Bay.
PRICE: Approximately $75 per person for public cruises
AHM SUGGESTION: Wednesday Night Racing Tour
FUN FACT: Her hull was made of Port Orford Cedar ribs and then strip-planked with the same material.
80 Compromise Street, Annapolis, MD 21401 • 410.263.7837 • schoonerwoodwind.com
2. Watermark Tours, Charters, Cruises
Locally owned and family-operated since 1972, Watermark has over 15 tours that range from day trips to St. Michaels to the Annapolis Fireworks Display.
PRICE: From $25 for a short cruise of the harbor and Naval Academy to $118 for a day cruise to St. Michaels
AHM SUGGESTION: Day Trip to St. Michaels
1 Dock Street, Annapolis, MD 21401 • 410.268.7601 • watermarkjourney.com
3. Annapolis Water Taxi Service
Watermark also operates Annapolis’ water taxi, where you can catch a ride and/or tour the Annapolis Harbor, including Spa Creek and Back Creek. A fun and fast way to sightsee!
PRICE: $4.00 to $9.00 per person, depending on destination
AHM SUGGESTION: Tour of Spa and Back Creeks
Call the Water Taxi: 410.263.0033 or VHF 68 • watermarkjourney.com/public-cruises-water-taxi/water-taxi/
4. Chesapeake Skipjack Sailing Tour, St. Michaels
Sail on the H.M. Krentz, an authentic working skipjack captained by an experienced waterman.
PRICE: $75 per person, with discounts for seniors
AHM SUGGESTION: Conversations with Captain Ed ensure a salty time!
FUN FACT: The H.M. Krentz is an authentic working skipjack, one of the newer vessels built for the rigors of Maryland’s wintertime commercial oyster dredging.
Departs from the Chesapeake Bay Maritime Museum: 213 North Talbot Street, St. Michaels, MD 21663 • 410.745.6080 • oystercatcher.com
5. Sail Selina II Tours and Charters
Captain Iris will take six guests on a two-hour day sail aboard Selina II, a rare vintage catboat. Her discussion includes a history of the Miles River and the surrounding area.
PRICE: $95-$125
AHM SUGGESTION: Moonlight Tour
Docks across from the Harbour Inn: 101 N Harbor Road, St. Michaels, MD 21663 • 410.726.9400 • sailselina.com
6. River Paddleboat Cruise
On the lower Eastern Shore, cruise on one of the Choptank Riverboat Company’s authentic 80-foot turn-of-the-century paddle wheelers, the Dorothy & Megan and the Choptank River Queen. Choose from a variety of cruises that include sightseeing, lunch, dinner, a crab feast, and a Murder Mystery.
PRICE: Pricing varies; check website
AHM SUGGESTION: Crab Feast
6304 Suicide Bridge Road, Hurlock, MD 21643 • 410.943.4689 • suicide-bridge-restaurant.com/choptank-riverboats
7. Solomons Island Heritage Tours
Rachel and Simon Dean captain a 26-foot Carolina Skiff and welcome those with an adventurous spirit, kids, and dogs. Their offerings include a historical tour to the site of a decisive battle on Leonardtown Creek during the War of 1812.
PRICE: The cost of one boat holding up to six guests is $150 per hour, with a two-hour minimum.
AHM SUGGESTION: Watermen’s Crew for a Day
Solomons Boardwalk, Solomons, MD 20688 • 301.672.3509 • solomonsislandheritagetours.com
8. Sultana Schooner Educational Tours
Take a two-hour trip on the Chester River aboard the replica 1768 schooner Sultana. Passengers are encouraged to help raise sail, steer, and explore the authentically reproduced crew quarters below decks.
PRICE: $40/$20 under 12
AHM SUGGESTION: It’s worth the drive for this museum-quality tour and exquisite ship.
Sails from the Chestertown Marina: 207 S. Water Street, Chestertown, MD • 410.778.5954 • sultanaeducation.org
© Annapolis Home Magazine
The Faces of Annapolis 2025