Special Event Holiday Cruises & Tours

Seasonal and Holiday Tours • Annapolis Holiday Activities

Watermark offers a variety of specially crafted tours and cruises in Annapolis and Baltimore throughout the year. Our special events get you right in the middle of the action of city and holiday celebrations. Visit this page often as new events are added throughout the year.


2015 Seasonal and Holiday Special Event Cruises & Tours

Chesapeake bay Cruise

Time & Tide: Tales of Annapolis & the Chesapeake Bay
August 12, September 9, September 17, October 1

11:15 a.m.-2:15 p.m.
$45/Adults, $25/Children 3-11, Free 2 & Under
Departing from Annapolis City Dock

New for 2015! A live interpreter delivers a connection with the waters of Annapolis, the crown jewel of the Bay through rich and diverse legends and lore. We suggest guests bring a bagged lunch on the cruise. No beverages please. Full cash bar on board. Reservations recommended. 

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Rock N River Cruise

WRNR Rock 'N River Cruise with Kopecky
Friday, September 11th
7:30-10:30 p.m.
$28/person
Departing from Annapolis City Dock

The most fun you can have in Annapolis! In partnership with WRNR 103.1 FM, enjoy a rockin' 3-hour cruise on Harbor Queen. The third of the 2015 season, Kopecky will perform. Food and drinks available for purchase on the boat. We suggest purchasing tickets early.

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Wednesday Night Races CruiseWednesday Night Races Cruises
August 19

6-8 p.m.
$32/Adults, $18/Children 3-11, Free 2 & Under
Departing from Annapolis City Dock

Wednesday Night Sailboat Races are an Annapolis staple. Every Wednesday night during the boating season, 150 sailboats must quickly race around several markers in the bay before speeding towards the finish line in Spa Creek. Watermark provides a great opportunity to get out on the water onboard Harbor Queen for the best view in town of the Wednesday Night Races.The cruise includes Happy Hour Appetizers. Full bar on board including beer, wine, soda, mixed drinks and additional snacks available for purchase.

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dog days cruise

Dogtober Fest Cruise
October 1st

6-7:30 p.m.
$30/Adults, $15/Children 3-11, Free 2 & Under
Departing from Annapolis City Dock

Annapolis is one dog friendly town! Join us on Harbor Queen for a specially added dog friendly cruise with our friends at the Anne Arundel County SPCA. This event will include food donated by Graul's Market, music, a silent auction, cash bar and refreshments for Fido.

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Annapolis Ghost Tour
Special Historic Hauntings
Fridays & Saturdays in October

7:30 p.m.
$22/Adults, $14/Children 3-11
Departs from Museum Store at 99 Main Street

As the sun sets and darkness wraps the streets of historic, and many say, haunted Annapolis, a period dressed guide will lead you on a journey sharing tales by candlelight of the spirits who dwell in the town's 18th century buildings and may still linger in the mist. Learn about drowned watermen, men who fell to their doom and women who still haunt their former residences. Special for October, includes an interior tour of the haunted Big Brice House.

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Cabaret II
Fall Foliage Cruise
Saturday, October 24th

11:15 a.m.-2:15 p.m.
$45/Adults, $25/Children 3-11
Departs from Annapolis City Dock

Our popular Bay Lighthouses Cruise takes on a Fall twist. Enjoy the fall foliage along the water and crisp air on this relaxing cruise. Pass under the twin spans of the Bay Bridges and by Sandy Point Shoal, Baltimore Harbor, and Thomas Point lighthouses. During your Chesapeake Bay Cruise and into the history of these three historic Chesapeake Bay lighthouses, our characterization of a turn of the century lighthouse keeper will keep guests entertained and engaged throughout the duration of the trip.

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View our entire 2015 schedule of special event cruises and tours in Annapolis and cruises in Baltimore.

*Any Event may be canceled due to severe weather, lack of participation or mechanical breakdown