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

Lady Sarah

St. Michaels Wine Festival Cruise

Saturday, April 25th & Sunday, April 26th
9:30 a.m.-7 p.m.
$142/person on Saturday; $129/person on Sunday
Departing from Annapolis City Dock

Travel in luxury to the St. Michaels Wine Festival. 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. Skip the admission lines when you arrive by water! 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. All inclusive.


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Blue Angels
Blue Angels Demonstration Cruises
Tuesday, May 19 & Wednesday, May 20

1-3 p.m.
$53/Adults, $27/Children under 12
Departing from Annapolis City Dock

The Blue Angels return to Annapolis in 2015! Watching the Blue Angels perform is a spectacular and unique experience. Join us for a Blue Angels Demonstration cruise to experience this elite team of Navy pilots as they streak across the Annapolis sky to celebrate Naval Academy graduates. There is no better way to see these elite Navy pilots perform than being on the water. Enjoy an unobstructed view and watch the air show on a comfortable Watermark yacht. Full cash bar and snacks available for purchase on board. Practice Day and Demonstration Day Cruises.

Tuesday, May 19: Tickets Still Available

Wednesday, May 20: Sold Out!

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Fireworks Cruise Annapolis

Independence Day Fireworks Cruises
Friday, July 3rd & Saturday, July 4th
7:30-10:30 p.m.
July 3rd: $48/Adults, $25/Children under 12
July 4th: $53/Adults, $25/Children under 12
Departing from Annapolis City Dock

July 3rd Fireworks Cruise: Get an early start on Independence Day festivities this year by taking in a local Annapolis community's fireworks display aboard the Harbor Queen, the best place in Annapolis to watch fireworks.

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July 4th Fireworks Cruise: 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.

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Light snacks will be served. Cash bar. 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.


Independence Day Fireworks Cruise
Friday, July 3rd & Saturday, July 4th
8:00-11:00 p.m.
July 4th: $59/Adults, $39/Children under 12
Departing from Baltimore Finger Piers

Enjoy an unobstructed view of the July 4th fireworks display in Baltimore's Inner Harbor. Step aboard a Watermark yacht for an enjoyable evening cruise of the Harbor capped off by the city's spectacular fireworks show. The cruise will include light snacks and a cash bar.

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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 William Paca 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