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

holiday tour annapolis

Holiday Candlelight Stroll

Fridays & Saturdays in December
December 5, 6, 12, 19, 20
$18/Adults, $10/Children 3-11, Free 2 & Under 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.

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Jolly Express Annapolis

Jolly Express Cruises

December 5-28 & December 24, 25, 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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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