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.

2014 Seasonal and Holiday Special Event Cruises & Tours

Battle of Baltimore Cruise Watermark

Battle of Baltimore Cruise

Tuesday, October 14th
10:30 a.m.-12:30 p.m.
$42/Adults, $19/Children 3-11, Free 2 & Under
Departing from Baltimore Finger Piers

A special extended version of our National Anthem Tour by Sea featuring the unique opportunity to watch the Battle of Baltimore demonstration - a special Bicentennial event! - by Fort McHenry.  Our Francis Scott Key re-enactor will guide you into the battle as you witness schooners representing the British fleet re-enact the bombardment of Ft.McHenry during the Battle of Baltimore. The Pride of Baltimore, The Virginia, The Norfolk and the Lady Maryland are a few of the schooners who will be on site for this special reenactment. Step back into history with us and enjoy unparalleled views of this special War of 1812 event.

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Chesapeake Schooner Race Cruise

Chesapeake Schooner Race Cruise

Thursday, October 16th
11:30 a.m.-2:30 p.m.
$49/Adults, $29/Children 3-11, Free 2 & Under
Departing from Annapolis City Dock

Schooners join up once a year for a week’s worth of activities on the Chesapeake Bay. Cruise out to the start of the race south of the Chesapeake Bay Bridge with Watermark. Join us as we watch the start of the race and even briefly follow the Schooners down the Bay. A Sailor will provide live narration about the origin of the race and call the start. Cash bar on board. 

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Fall Foliage Cruise Annapolis

Fall Foliage Cruise

Saturday, October 25th
11:15 a.m.-2:45 p.m.
$42/Adults, $20/Children 3-11, Free 2 & Under
Departing from Annapolis City Dock

Enjoy the crisp fall air and lovely reds, yellows and oranges of the foliage along the river as you cruise out onto the Bay on a special Fall Foliage Cruise. Welcome Fall 2013 from the water! This beautiful cruise includes three Chesapeake Bay Lighthouses and also gives guests a spectacular view of the lovely fall foliage along the waterfront. Our Fall Foliage Cruise is a favorite event amongst our guests and it sells out every year. Advanced reservations recommended.  

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Annapolis Ghost Tour Paca House

Special Historic Hauntings

Fridays & Saturdays in October
7:30-9:00 p.m.
$20/Adults, $14/Children 3-11, Free 2 & Under
Departing from Historic Annapolis Museum Store

Includes spooky interior tour of the William Paca House! An exclusive opportunity to step foot inside this haunted mansion at night. As the sun sets and darkness wraps the streets of historic, and many say, haunted Annapolis, a 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.

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holiday tour annapolis

Holiday Candlelight Stroll

Fridays & Saturdays in December
Details TBA
Departing from City Dock Information Booth in Annapolis

Enjoy an evening stroll during the holidays. Your period dressed guide will lead the tour by candlelight and share stories of holiday traditions. The historic district is beautiful during the holiday season. New for 2014! Your walking tour will end at the historic Hammond Harwood House where you'll tour the interior of this beautiful home decorated for the holidays.

More details TBA including online ticket sales.


Jolly Express Annapolis

Jolly Express Cruises

December 5-28 & December 31
Fridays, Saturdays* & Sundays
6, 7, 8 p.m.
$23/Adults, $13/Children Under 12 *Except December 13
Departing from Annapolis City Dock

Ho, ho, ho! The Jolly Express will cruise Spa Creek during the holiday season. This festive evening cruise includes hot cocoa, holiday music and a wintry 45-minute cruise of the Annapolis Harbor and scenic Spa Creek. Captain Santa is at the helm. Advanced reservations recommended.


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Parade of Lights Cruise

Parade of Lights Cruise

Saturday, December 13th
Departing from The Severn Inn Restaurant, Annapolis

A holiday tradition! Enjoy a delicious dinner at the Severn Inn, a beautiful waterfront restaurant Annapolis. After your meal step on board Catherine Marie -- our most elegant vessel -- for a 1.5 hour dessert cruise and watch the annual Eastport Yacht Club Parade of Lights. This event always sells out. We recommend booking early.

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View our entire 2014 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