Watermark Cruises on the Bay

Watermark Cruises has cruises leaving from Annapolis and Baltimore.

Cruises  leaving from the Annapolis City Dock range from 40-minute and 90-minute tours, to full day excursions. Special events include pirate cruises, music cruises and lighthouse cruises.

The Baltimore Inner Harbor Cruise. is a 45 minute tour by water of Federal Hill, Fells Point, the USS Constellation,and Ft. McHenry.

Annapolis, Maryland

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American Cruise Lines

The CrabFest cruise is one of the “theme cruises” offered by American Cruise Lines

American Cruise Lines operates 3 ships that offer 6 and 7 night cruises on the Chesapeake Bay, the American Glory, American Star, and Independence. All cruises depart from Baltimore.

Stops include historic locations such as Yorktown, Colonial Williamsburg, and Annapolis.  More information is available by calling 1-800-460-4518.

The cruises are available in October, November, May , and June.

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Captain Hogg’s Charter Fishing

Captain Chandler Hogg’s  charter boat, the “Smokin’ Gun,”  can carry 32 passengers on a fishing trip in the  lower Chesapeake Bay.  There are a number of unique  fish within a short boat ride from the dock in Hampton, Virginia.  Passengers should bring a cooler, drinks, food, camera, and suntan lotion.  Bait and tackle are provided.

Book here or call (757) 876-1590.

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Patriot Cruises

The PatriotThe Patriot is a 2 level cruise boat that can accommodate 149 passengers.  The main deck is climate controlled with heating and air conditioning. The top deck is partially covered by a canopy.

The Patriot leaves from St. Michael’s Maryland for a cruise up the Miles River.  The Miles is part of the Chesapeake Bay Estuary which is the largest estuary in the Western Hemisphere.  The boat has a full bar, and serves light snacks.

Patriot Cruises
P.O. 1206, St. Michaels, MD 21663

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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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59-alabama--shenandoah-croppedLiberté is a 74 foot schooner with a capacity of 49. She also has music, and a full bar. Liberté spend the summer off Cape Cod, but is available for private charters on the Cheasapeake Bay in the spring and fall.

Her berth is alongside the Chart House Restaurant in the Eastport section of Annapolis on Spa Creek. Her captain describes the sights you’ll see as follows: “After a very brief motor away from the dock, we’ll begin to hoist sail in the shadow of the Naval Academy. We can either sail up the protected waters of the Severn River, with riverside mansions and grand lawns gracing the shore, or out on to the Chesapeake Bay. Out there, we go north to the Bay Bridge or south to historic Thomas Point Lighthouse. Along the way we’ll pass many other boats of all sizes and shapes.”

Email TheLiberte@aol.com for more information

Captain Chris Tietje
Liberte, The Schooner
222 Severn Avenue Annapolis, MD 21403

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Reel Diamond Fishing Charters

Diamond Charters has a 42′ boat with a  cabin that seats 6, and a large deck roof, 15 minutes from downtown Baltimore and less than 1 hour from DC, Pennsylvania, Delaware and points north.

Rates include all licenses, bait, and equipment. The mate or captain will be able to provide fish cleaning services for an additional charge.

During the spring season (trophy rock fishing season) they depart from Deale, MD and fish Chesapeake Beach, Bloody Point, and other nearby areas.

In the summer and fall they departing from Baltimore/Sparrows Point, MD and fish between the Bay Bridge and Pooles Island. In the month of December they depart from Cape Charles, VA at Bay Creek Marina.

Anchor Bay East Marina
8500 Cove Road
Baltimore, MD 2122

Capt. Charlie Thrappas
P.O. Box 9673
Baltimore MD 21237

Phone: (443) 520-8977    E-mail: Capt. Charlie

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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 admin@cccharters.com

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 cvb@atlanticstars.com, 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, info@schoonerwoodwind.com.

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