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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

St Michaels Harbor

St. Michaels Wine Festival Cruise

Saturday and Sunday, April 26 & 27
10 a.m.-7 p.m.
$142/person All Inclusive
Departing from Annapolis City Dock

Take a cruise on a luxurious Watermark Yacht from Annapolis to St. Michaels. On board you'll enjoy a continental breakfast. The cruise is an enjoyable 2-hour ride across the Chesapeake Bay. Once on land in St. Michaels, you'll attend the St. Michaels Wine Festival featuring wine samplings, chef demos, gourmet food, crafts and more. Spend the day at the wine festival and take some time to enjoy this quaint Eastern Shore town at your leisure if you choose. On the return cruise to Annapolis, a complimentary boxed meal will be provided. One of our most popular cruises in 2013!


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Blue Angels Annapolis

Blue Angels Demonstration Cruise

May 20 & 21
1-3 p.m.
$50/Adult & $27/Children 12 & Under
Departing from Annapolis City Dock

The Blue Angels are Back! Join us for Blue Angels Practice Day and Demonstration Day Cruises in Annapolis. These elite Navy air pilots will streak through the sky to celebrate Commissioning Week at the United States Naval Academy. Practice Day Demonstration on Tuesday. Demonstration Day on Wednesday.

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yoga cruise annapolis

Yoga and Pilates Cruise with Ridgely Retreat
Saturday, May 31

8:30-10:30 a.m.
Departing from Annapolis City Dock

Cruise the lovely Chesapeake Bay while nourishing and strengthening your body. After we leave the dock, enjoy the beautiful sites and mingle with friends. Then, choose between an hour long yoga level 1&2 class or an hour long yogalates (yoga and pilates) class. Classes will be led by Andrea Lichtenstein, RN, RYT200, Peak Pilates Cerftified, and Laura Seal, Peak Pilates Certified.

Please register directly with Ridgely Retreat by May 10th to hold your spot.

SPCA Dog Cruise

Dog Days of Summer Cruise to Benefit the SPCA

June 12, 2014
5:30-7:00 p.m.
$30/Adult & $15/Children 12 & Under
Departing from Annapolis City Dock

Join us on Harbor Queen for our second annual special 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, adoptable dogs from the SPCA and refreshments for Fido. The top deck of Harbor Queen will even feature doggie pools so "hot dogs" can cool off! Friendly on leash dogs welcome. Dogs cruise free! This is a special fundraiser to benefit the SPCA while enjoying getting out on the water with our furry friends. Spend the first half hour dockside then cruise for one hour.

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wednesday night races annapolis

Wednesday Night Races Cruise

June 18, July 16, August 20
6-8:30 p.m.
Departing from Annapolis City Dock

A new special event cruise for 2014! 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. Guests will be dockside from 6:00 to 6:30p.m. from Harbor Queen's slip at the end of City Dock, cruise to the race course to view the races until 7:45 and then return dockside until 8:30 to catch the thrilling finish. The cruise includes Happy Hour Appetizers. Full cash bar on board. Advanced reservations recommended. Cruise will take place even if the race is canceled.

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annapolis fireworks

Pre-Independence Day Fireworks Cruise in Annapolis

Thursday, July 3rd
7:30-10:30 p.m.
$28/Adults, $25/Children Under 12
Departs from Annapolis City Dock

Get an early start on your Fourth of July celebrations with a Pre-Independence Day Fireworks Cruise on July 3rd. We'll cruise the Severn River and watch a local community's fireworks display. Harbor Queen is the best place in town to watch fireworks! Light snacks will be served. Cash bar on board.

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Annapolis Fireworks Cruise

Independence Day Fireworks Cruise in Annapolis

Friday, July 4th
7:30-10:30 p.m.
$52/Adults, $30/Children Under 12
Departing from Annapolis City Dock

Step aboard a Watermark Yacht for the annual Annapolis Fireworks Cruise. Enjoy the city of Annapolis' spectacular Fourth of July fireworks from the best seat in town as you cruise the Harbor. Light snacks will be served. Full cash bar on board. Reservations are recommended for all Fireworks Cruises. We always sell out. Beer, Wine, mixed drinks and non-alcoholic beverages plus other snacks available for purchase.

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Baltimore Fireworks Cruise

Independence Day Fireworks Cruise in Baltimore

Friday, July 4th
8-11 p.m.
$59/Adults, $39 Children Under 12
Departing from Baltimore Finger Piers

Watch Baltimore City's Inner Harbor Fireworks display from a Watermark yacht. Watching this impressive display from the water is a treat! This cruise around the Inner Harbor includes light snacks and great views of the fireworks. Advanced reservations recommended. Our fireworks cruises sell out early. Restrooms and full cash bar on board. Our vessels feature a climate controlled lower deck and open air top deck.

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Star-Spangled Spectactular Schooner

Star-Spangled Spectacular Cruises

September 11-15
Throughout the Day
$20/Adults, $9 Children Under 12 for 45 minute cruies
$25/Adults, $15/Children Under 12 for 60 minute cruises
Departing from Baltimore Finger Piers

The tall ships are making their return! The Star-Spangled Spectacular is the culmination of two years of celebrating the bicentennial of our National Anthem and the War of 1812. This one-time event is an impressive maritime and air festival featuring tall ships from around the world, demonstrations and more. Cruises include live narration by experienced period dressed tour guides. Learn about the War of 1812, why we're celebrating the Bicentennial and hear about the ships in for the event. This festival is not to be missed! 

Choose from 45-minute and 60-minute cruises. Learn more about the Star-Spangled Spectacular in Baltimore's Inner Harbor.

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Blue Angels in Baltimore

Star-Spangled Spectacular Blue Angels Cruises

September 11-14th
12:30-3:30 p.m.
$52/Adults, $33/Children Under 12 Practice Days;
$57/Adults, $35/Children Under 12 Demonstration Days
Departing from Baltimore Finger Piers

The Star-Spangled Spectacular in Baltimore features Blue Angels demonstrations. This elite team of Navy pilots will streak across the Baltimore sky dazzling spectators during this unique and impressive one-time event. Public viewing areas for the Star-Spangled Air Show are limited so join Watermark for a comfortable seat to view the show from the water. Practice Day and Demonstration Day cruises available. Tickets are already selling fast! Book your seat before we sell out.

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Baltimore Fireworks Cruise

Star-Spangled Spectacular Fireworks Cruise

Saturday, September 13th
8-11 p.m.
$77/Adults, $57/Children Under 12
Departing from Baltimore Finger Piers

A featured event of the Star-Spangled Spectacular! Watch the show from the best seat in town, a Watermark yacht. This three-hour cruise around the Inner Harbor shows off Baltimore at night and includes great views of this special fireworks display. Includes a light snack. Full cash bar on board including beer, wine, sodas and mixed drinks. Restrooms on board. Advanced reservations recommended. Our Fireworks Cruises sell out early.

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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

Weekends in December
Details TBA
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. Full schedule and online ticket sales TBA.

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