Liberty Clipper: Chesapeake Windjammer Cruises.

Chesapeake Bay Tall Ship Sailing Vacation…

Liberty Clipper sailing vacations start from Fells Point in Baltimore’s Inner Harbor. You’re invited to board tChesapeake Bay Sailing Cruise Crab Boil Feasthe ship anytime after 4pm on the day before the scheduled departure. The ship will set sail the following morning reaching out towards the Chesapeake sailing under the battlements of Fort McHenry, which inspired Francis Scott Key’s composition of our National Anthem, and cruise down the bay before stopping at any number of our ports of call on your sailing cruise.

While on your windjammer cruise, you’ll have the opportunity to explore ashore each day on a different island.  You may avail yourself of

  • Rowing and sailing boats
  • Inflatable sea kayaks
  • Rope swing off the masts
  • Hammocks
  • Beach towels

The Liberty Fleet of Tall Ships
67 Long Wharf
Boston, MA 02110

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Whether you want to have fun on a special event cruise or simply relax on the water, Chesapeake Bay cruises have something for everyone. Enjoy the bounty of the bay on a fishing trip with your family and friends. If family fun is what you seek, consider an exciting pirate cruise. You can also give your family a truly educational experience aboard a nearly exact replica of a British schooner.

Experienced sailors can book a bareboat charter, while those who wish someone else to do all the work can sail in comfort with a captain and crew.  There are many options to choose from, all of which result in a great time on the water.

Spending a day, an evening, or even a week, on the Chesapeake Bay is a unique experience. There are historical areas to visit, spectacular scenery to enjoy, and local cuisine to be savored. There is nowhere quite like the Bay!

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The Moorings

This  yacht charter company offers bareboat sailing, power and skippered charters on the Chesapeake Bay. The fleet  includes monohulls built by Beneteau as well as  catamarans from Robertson & Caine. All cruises depart from the Annapolis Landing Marina, 980 Awald Rd.

The Moorings’ season runs from March 2 through October 31.


Phone: 888-952-8420

93 North Park Place Boulevard
Clearwater, FL 33759

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Pirate Adventures on the Chesapeake

Photos of Pirate Adventures on the Chesapeake, Annapolis

This photo of Pirate Adventures on the Chesapeake is courtesy of TripAdvisor

Pirate Adventures on the Chesapeake is a cruise geared to kids- and kids at heart.  The company describes the cruise this way:

“Come aboard our pirate ship and get caught up in this real life adventure and be amazed as our crew taps into the wonder of a child’s imagination. This is not a typical pirate cruise, before you know it your child will be painted with a curly mustache or a beautiful mermaid, dressed up as a pirate and marching off to the ship.

Once aboard, the young pirates will learn the rules at sea aboard their pirate ship and read a treasure map to find sunken treasure. A message in a bottle floats by and the children discover that Pirate Pete, the smelliest most rotten pirate on the seven seas, is lurking nearby. He has something our brave crew needs. Off we go into battle with our famous water cannons! Will the crew defeat Pirate Pete and find the sunken treasure?”

Information about discounts for Pirate Adventures on the Chesapeake can be found at Best Free Stuff Guide

Pirate Adventures on the Chesapeake
311 Third Street
Annapolis MD 21403

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C&C Charters

C&C Charters offers excursions on both sail and power boats. The fleet includes

  • Motor Yachts
  • Express Cruisers
  • Trawlers
  • Sailboats
  • Catamarans

Experienced mariners can rent “bareboat” without a crew.

Each trip is customized to the needs and preferences of the customer – no two trips are the same.

C & C Charters is located next to to Annie’s Paramount Steak House, on the water side, in Mears Point Marina in Grasonville.

For more information, contact

office: 800-733-7245
local: 410-827-7888
fax: 410-827-5341

C & C Charters Maryland
506 Kent Narrows Way North
Grasonville, MD 21638


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Arabella Cruise WindjammerThe windjammer Arabella is a 160′ tri-mast with 20 cabins, which feature private bathrooms, satellite TV, and individual climate control. She has teak decks , a hot water spa, and shaded cabana seating.

The Arabella winters in the Caribbean and summers in New England, but is available for 5 and 6 night cruises on the Chesapeake with stops in Annapolis, Cambridge and St. Michael’s.

She is available for private & corporate charters,  group outings, family reunions, weddings, and other special occasions.  Reservations may be made by telephone only: 800-395-1343. You may email mailing address, cell number, and food allergies to, then call with credit card number.

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Schooner Woodwind

File:Annapolis Harbor (7315901278).jpg

Annapolis Sailing Cruises features two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II that provide a variety of cruise options, including:

The company states, “Located in the heart of the Chesapeake Bay, Annapolis is ‘America’s  Sailing Capital.’ Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay.  As a family business, we take great pride in making your sailing experience a memorable one. Our captains and crew are engaging and enthusiastic. Sail away with us!”

All cruises leave from the Annapolis Marriott Waterfront Hotel

For more information, contact the Schooner Woodwind at 80 Compromise Street, Annapolis, MD 21401,  410-263-7837,

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Rebecca T. Ruark

Sail aboard the oldest working skipjack on the Chesapeake Bay, built in 1886. Enjoy nautical tales and ecology stories from 5th-generation and world-renown Capt. Wade H. Murphy, Jr.  Capt. Wade personally takes you on a 2-hour sail 7 days a week. Saturday and Sunday (11-1, 2-4, 6-8 sunset) and Monday through Friday (11-1, 6-8 sunset).

Private group charters available. Best comparison rates available: $30 per adult , $15 per child under 12, tiny ones free! BYOB (wine, beer, champagne, soda, picnic). Wade guarantees that you have a good time!

The Rebecca T Ruark is U.S. Coast Guard certified for 49 passengers.

The Rebecca T. Ruark is docked in Dogwood Harbor on Tilghman, Maryland and the mailing address is 21308 Phillips Road, Tilghman, Maryland 21671. Call Captain Wade at 410-829-3976 for more information..

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