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

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
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 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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Raven Yacht at Night

New Year's Eve Charm City Dinner & Fireworks Cruise on Raven
Wednesday, December 31st
9:30 p.m.-12:30 a.m.
$179/Adult or $214/Adult + Open Bar
Departs from Baltimore Finger Piers

Photo by The Susquhenna Photographic

Let Watermark plan the party! Ring in the New Year on an exclusive and FUN dinner cruise on Raven, the newest yacht in the Inner Harbor. Includes an excellent – and comfortable – view of the city of Baltimore’s impressive New Year’s Eve fireworks from the sparkling water. Top-rated Ken’s Creative Kitchen will serve a delicious gourmet meal including hors d’oeuvre station and buffet dinner. Our bartenders will mix up drinks from the fully stocked bar…open bar package is available! Festive decorations and party favors add to a perfect night out. Cruising Baltimore’s waterways and taking in the twinkling skyline at night sets the perfect tone for kicking off a new year.

Raven is an elegant vessel with enclosed climate controlled lower deck, open air top deck, two full bars and nicely appointed restrooms.

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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