Schooner Woodwind

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Annaplis Harbor Cruise And US Naval Academy Tour

Annaplis Harbor Cruise And US Naval Academy Tour

Travel with the Pack to Maryland's state capital, Annapolis, for a walking tour of the prestigious United Sates Naval Academy, guided tour of the Maryland State House, a narrated Annapolis Harbor Cruise and free time to browse and explore the beautiful downtown. Also, enjoy a delightful lunch included at a local rstaurant.

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Package Includes:  Lunch, 1-Hour Guided Walking Tour of the United States Naval Academy, Guided Tour of the Maryland State House, Narrated Annapolis Harbor Cruise and Free Time to Browse and Explore Downtown Annapolis and Transportation

*Please Note:  Valid photo identification is required to enter the Maryland State House and the United States Naval Academy grounds. *

**Any cruise may be altered or cancelled by its Captain due to severe weather conditions**

***ALL WOLF’S TOURS – TIMES AND ITINERARY SUBJECT TO CHANGE***

Upon arrival in Annapolis, Maryland, the group meets our USNA certified guide for a 60-minute walking tour of the prestigious United States Naval Academy. Founded in 1845, the Naval Academy is home to 4,000 of our country's future naval leaders. As you stroll through the beautiful campus you will experience the sense of military tradition and heritage all around us. Your visit includes the Naval Chapel, the Crypt of John Paul Jones, Bancroft Hall, and various monuments that represent defining moments in the Academy's history. At the conclusion of the tour, you will walk to the Maryland State House for a guided walking tour of the building. Construction of the State House was begun in 1772 but was delayed by the outbreak of the American Revolution, and then completed in 1779. The interior of the original section of the State House was constructed of wood and plaster. The newer colonial revival section has matched veined Italian Marble walls and columns. A broad black line across the columned lobby marks the line between the two sections. The Maryland State House was the first peacetime capitol of the United Stated and is the only state house ever to have served as the nation's capitol. After your tour, lunch is included at an area restaurant. Next, you head to City Dock to take a 40-minute sightseeing cruise with spectacular views of the Annapolis Harbor and the banks of the US Naval Academy. Hear about the Annapolis' integral role as an historic seaport and even catch a glimpse of the Chesapeake Bay Bridge. Once back on land, you have free time to browse the downtown shops and get a bite of dinner on your own before departing for home.

Please Note: Valid photo identification is required to enter the Maryland State House and the United States Naval Academy grounds. * **Any cruise may be altered or cancelled by its Captain due to severe weather conditions** ***This tour involves a lot of walking*** ***ALL WOLF'S TOURS - TIMES AND ITINERARY SUBJECT TO CHANGE***

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200 Old US Rt. 15

York Springs, PA 17372

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Monday-Friday 8AM-5PM

Select Saturdays 8AM-1PM

Closed Sundays and Holidays

Annapolis and Anne Arundel County Conference & Visitors Bureau

Wine and Dinner Cruises on the Chesapeake

July can be steamy or dreamy – hot on land but much cooler on the water.  Watermark Cruises and the Schooner Woodwind offers a range of options for getting out on the scenic Severn River or the majestic Chesapeake Bay. These well- established local companies provide unique adventures of varying durations – from on-demand water taxis to foodie-favorite wine and dinner cruises.

Wine and Dinner Cruises

Watermark has a fleet of boats, ranging from the popular Harbor Queen , a replica of an old river boat that leaves City Dock every few hours for a 40-minute cruise around the Annapolis Harbor to round trip cruise on a catamaran motor boat named Lady Sarah that takes passengers on a glorious round trip from the City Dock to the picturesque town of St. Michael’s on Maryland’s Eastern Shore. This perfect “day on the bay” is a double-edged treat, with fare that includes a complimentary ticket to the Maryland Maritime Museum, the boat’s docking destination in St. Michael’s. Ticket holders for the cruise have a three-hour layover in St. Michael’s, a town with many good restaurants – among them the Crab Claw (super casual) and the elegant Inn at Perry Cabin.

Wine and Dinner Cruises

Other members of the Watermark fleet are the Miss Anne , a cozy 22-seater that plies the coves of Carrol’s Creek and Cabaret II, a motorized craft whose route focuses on lighthouses on the bay. And there’s one more boat in the fleet – a water taxi . Call the Watermark Captain at 410-263-2033 if you need a water taxi to take you to and from the concentration of good restaurants on the Eastport side of the Annapolis Harbor.  This low-cost on-demand service originates at the City Dock, ferrying passengers to the docks of the Annapolis Chart House , Carrol’s Creek Café and O’Leary’s Seafood Restaurant and to walking-distance destinations like Ruth’s Chris, Boatyard Bar & Grill and Lewnes Steak House.  P.S. Watermark folks are pet friendly, welcoming leashed and well-behaved dogs on most cruises.

Call Katy 410-268-7601 for more information and go to www.cruisesonthebay.com for reservations and schedule.

Wine and Dinner Cruises

Schooner Woodwind & Woodwind II, a pair of gorgeous 74-foot wooden boats, offer a winning variety of on-the-water excursions ranging from daily two-hour cruises to Saturday night “Boat and Breakfast” accommodations that include a two-hour sunset sail and sunrise breakfast on the deck.  “Party Like a Sailor” events provide a taste of sailboat racing, with both schooners competing with each other during the popular Wednesday Night Races sponsored by the Annapolis Yacht Club. Reservation holders are entitled to a Cuzon Rum Punch beverage on board and another at the informal “after party” at the Boatyard Bar and Grill in Eastport.

Wine and Dinner Cruises

Schooner Woodwind owner and seasoned sailor Jen Kaye is also a “foodie,” who masterminds “Wine in the Wind” evenings.  Tickets are still available for August 27, a Spanish-themed two-hour sail featuring four wine samples “perfectly paired with magnificent morsels” provided by prime time Annapolis caterer Palate Pleasers.  Kaye will showcase the wines of Maryland’s Dodson Vineyards at a special dinner on August 20, when the menu will include a rose paired with a ceviche of scallops and shrimp, chardonnay with jumbo lump crab salad, red with beef medallions and a floral white with a dessert torte.  At this point, there are nine remaining reservations.

Captain Kaye will celebrate Schooner Woodwinds’ 25 th anniversary in 2018 – during which time Schooner II achieved international celebrity as the “star” of the movie “Wedding Crashers.” These two photogenic schooners are the setting for corporate team building sessions, wedding rehearsals and receptions and high-end social gatherings.  Scheduled cruises happen rain or shine or with only one person on board. Their home port is the dock at the Annapolis Waterfront Hotel , where they depart for two-hour cruises at 11 am and 1:30, 4 and 6:30 pm.  Join the crew with a call to 410-263-7837 for more information and go to www.schoonerwoodwind.com for reservations and schedule.

Photos courtesy of Cruises on the Bay by Watermark and Annapolis Sailing Cruises: Schooner Woodwind .

Mary Lou Baker

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Naptown Jazz Band AND the Harbor Queen... - Watermark Cruises and Tours

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Absolutely wonderful and relaxing cruise along the Severn River! Thank you for letting us bring our... read more

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Squire Richard was a knowledgeable tour guide with a great sense of humor. Visitors to Annapolis... read more

harbor cruise annapolis md

Naptown Jazz Band AND the Harbor Queen boat cruise!!

Wonderful trip on the Harbor Queen with the Naptown Band!! Staff was excellent however the lines for drinks at the bar was VERY long! Highly recommend any trip with this well run company!!

The Naptown Brass Band is so much fun! Thank you for your feedback, and we hope to see you again soon!

Great evening music cruise on the Harbor Queen with lots of friends. Lively and energetic crowd. Friendly and professional crew. A good time was had by everyone’

That is wonderful to hear! Our live music cruises are such a blast!

What a memorable part of our Annapolis experience! Captain Dean was amazing and put the biggest smiles on my son’s faces!

We're so glad to hear that you enjoyed your experience and hope to see you again soon!

The weather was perfect. The Captain and crew were amazing❤️ Very attentive and friendly. Our second time going. We live near Annapolis and always enjoy going on cruises. They are dog friendly. The special events I believe don’t allow dogs but that’s okay. Great tour information about your surroundings. I highly recommend it.

harbor cruise annapolis md

We're so glad to hear that you have enjoyed our cruises and hope to see you again soon! Thank you for sharing!

Had a wonderful experience this last weekend on the Lighthouse your, the boat was clean and relaxing and the staff was professional and so friendly. Great time!

harbor cruise annapolis md

We're so glad to hear that! Thank you for sharing, and we hope to see you again soon!

I've always wanted to go under the Chesapeake Bay Bridge by boat, ever since a failed attempt on a sailboat many years ago. This boat trip was relatively fast (90-minutes vs. the hours it takes to get to the bridge from Annapolis under sail), and even though I lived in Annapolis for many years, I learned some new things from the audio recording. The boat was CLEAN, inside and out! We left on time and returned on time. We talked to Colleen the bartender (great lady!), and my husband and I are already planning on doing the Baltimore cruise next weekend!

That is so wonderful to hear! Thank you for sharing, and we hope to see you in Baltimore next weekend!

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The Liberté

  • Annapolis: 410.263.8234
  • Cape Cod: 508.524.9121
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A Grand Experience for All

Custom built for sailing, comfort and fun. Our cruising grounds are some of the most beautiful and historic in the country

Corporate Events

Special occasions, adventure & entertainment.

Custom built for sailing, comfort and fun, the Liberte is a grand experience for all. Our cruising grounds are some of the most beautiful and historic in the country. The captain and crew are dedicated to your safety, comfort and enjoyment.

USCG certified for 49 passengers. Music. Full bar. Every Sail is Unique.

One Great boat, two great locations

About the boat.

harbor cruise annapolis md

The schooner, Liberté, is based on Spa Creek in Annapolis, Maryland. During the summer months, she’s docked at the Patriot Party Boats pier in Falmouth harbor in Cape Cod, Massachusetts. Captain Chris and Jane had this vessel built just for them.

The original hull design by Dudley Dix is a Hout Bay 70, a two-masted gaff-rigged schooner intended as a heavy but fast offshore cruiser. Many alterations were made to the design, including adding a spoon bow, scaling down the lines to meet U.S. Coast Guard parameters, redesigning the deck layout and adjusting the rig to a three-masted staysail design.

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Chronic Sailing

Annapolis Dinner Cruise

Dinner with an unbeatable view of the Maryland State House, Naval Academy, the Chesapeake Bay Bridge and the Annapolis skyline!  We’ll arrange for dinner from a downtown restaurant of your choice to be served onboard, as we cruise around the Annapolis harbor and the scenic Severn River.  With a variety of restaurants to choose from downtown Annapolis, we can help provide an elegant and romantic dinner for two, upscale fare for a group, crab cakes for all, or a casual meal to satisfy everyone in the family. Or have your cruise fully catered by April’s Table for the ultimate dining experience.

Some of our favorite Annapolis restaurants:

  • Dock Street Bar & Grill
  • Carrol’s Creek
  • Boatyard Bar & Grill
  • Iron Rooster
  • Chick & Ruth’s Deli
  • O’Leary’s Seafood Restaurant
  • Lewnes’ Steakhouse
  • Joss Café & Sushi Bar
  • Stan & Joe’s Saloon

Book this Cruise

Ready to sail with us? Submit the form below and we'll contact you to confirm & finalize your reservation based on availability.

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Special & Seasonal Cruises

Annapolis & Baltimore

Climb on board for special & seasonal cruises!

Looking for fun things to do in Annapolis and Baltimore? Look no further! We plan special and seasonal cruises for holidays, city celebrations, area partnerships, and just for fun.

Don’t forget to check this page often, as we regularly add new events.

Available Now

harbor cruise annapolis md

Critter Cruise

-annapolis-.

April 13 & May 3, 2024

Climb on board to explore the unique ecosystem of the Chesapeake Bay through this hands-on learning cruise ideal for grades 1-5.

Thomas Pt Lighthouse and Bay Bridge

Bay Lighthouses Cruise

April 22, 2024

Pass under the twin spans of the Bay Bridge and past three Chesapeake lighthouses on this award-winning 3- to 3½-hour cruise.

harbor cruise annapolis md

Rock the Harbor with Tranzfusion

April 26, 2024

Tranzfusion is back by popular demand for a 2½-hour live music cruise in Annapolis!

harbor cruise annapolis md

Chesapeake Bay Trio

May 13, 2024

Join our live interpreter for an enjoyable 3-hour cruise from Annapolis’ historic harbor, up the scenic Severn River, then into the Chesapeake Bay.

Live music cruise aboard the Harbor Queen in Annapolis.

Annapolis Sunset Cruise with Live Music

Select Fridays and Saturdays May through September

Enjoy live music and beautiful scenery as you relax with a cool drink on this 90-minute sunset cruise in Annapolis.

harbor cruise annapolis md

Yoga on a Yacht

-baltimore-.

May 11, 2024

We’re teaming up with Baltimore yoga instructor Marissa Walch for Yoga on a Yacht! Grab your mat and climb on board for a morning flow.

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Mother’s Day Cruise

May 12, 2024

Treat the moms in your life to a lovely brunch cruise this Mother’s Day featuring live music and an open mom-osa and champagne bar!

harbor cruise annapolis md

Spirits & Spirits

May-September 2024

During this walking tour and cruise combination experience, you’ll brave the Historic District by foot and then continue on through the haunted waterways.

harbor cruise annapolis md

Naptown Brass Band Cruise

June 27, 2024

Enjoy a 2-hour cruise with live music by The Naptown Brass Band, a New Orleans style street band that is taking Annapolis, Baltimore and Washington by storm.

Coming Soon

Dog days of summer cruise.

Join us on Harbor Queen for a dog-friendly party on the water with our friends at the Anne Arundel County SPCA in support of their work.

harbor cruise annapolis md

Full Moon Cruise

Climb aboard to watch the sun set and the full moon rise over the water as you sip a cool cocktail and relax to live music.

harbor cruise annapolis md

Fireworks Cruises on July 3rd & 4th

-annapolis & baltimore-.

Enjoy the spectacular fireworks displays from the best seat in town!

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Fall Foliage Bay Lighthouses Cruise

This beautiful cruise includes three Chesapeake Bay lighthouses in addition to a spectacular view of the lovely fall foliage along the Annapolis waterfront.

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Jolly Express Cruise

November & December 2024

Annapolis’ favorite holiday activity makes its return. Enjoy hot cocoa, holiday music, and good cheer!

harbor cruise annapolis md

Lights Parade Dinner Cruise

December 2024

Join Watermark for a holiday dinner cruise aboard our luxury yacht.

harbor cruise annapolis md

New Year’s Eve Yacht Parties

December 31, 2023

Make your New Year’s Eve memorable with a cruise aboard a luxury yacht! Enjoy a DJ, dancing, desserts, a complimentary glass of bubbly, and fireworks!

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  2. Annapolis Harbor & USNA Cruise

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  3. Visit Annapolis

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  4. Things to do in Annapolis

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  5. Watermark Cruises and Tours (Annapolis)

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  6. Annapolis Cruises

    harbor cruise annapolis md

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  1. Spring Boat Show comes to Annapolis this weekend

  2. Sunset Boat Ride in Annapolis, A Summer Night Cruise. #zachbryan #lyrics #song #annapolis

  3. Buddy's Crabs and Ribs Annapolis Maryland Ep 106

  4. Mega Yacht in Annapolis harbor #annapolis #boat #music #djidrone #visitannapolis #drone

COMMENTS

  1. Annapolis Cruises

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  2. Annapolis Harbor & USNA Cruise

    Step aboard the classic Harbor Queen for a narrated cruise of the Annapolis Harbor and the banks of the U.S. Naval Academy. Watermark. Directions & Parking 410-268-7601 Search. Close Toggle navigation. ... 1 Dock Street, Annapolis, MD, 21401. Get Directions. Share This Event. Watermark.

  3. Climb Aboard the Harbor Queen by Watermark

    One of the best ways to truly experience Annapolis' beautiful historic seaport is aboard Watermark Cruises signature tour boat, the Harbor Queen. Sit back and relax during a 40-minute informative cruise along the Annapolis Harbor and the banks of the U.S. Naval Academy. ... ANNAPOLIS, MD 21401 [email protected] PHONE: 410-280-0445 TOLL ...

  4. Watermark Journey

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  5. Sailing Cruises in Annapolis, Maryland on the Schooner Woodwind on the

    Welcome Aboard! Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II, for a true sailing experience in Annapolis, Maryland. Located in the heart of the Chesapeake Bay, Annapolis is "America's Sailing Capital.". Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the ...

  6. Cruises on the Bay by Watermark

    Cruises on the Bay by Watermark has been sharing the history, culture, and fun of the Chesapeake area with visitors and residents alike since 1972! Cruises run daily from early spring through fall with special event cruises all year long. Climb aboard for 40-minute narrated Annapolis Harbor & USNA Cruise, a must-do Annapolis activity and a local tradition ...

  7. THE 10 BEST Annapolis Boat Rides & Cruises

    These are the best places for groups seeking boat tours & water sports in Annapolis: Schooner Woodwind Annapolis Sailing Cruises; Watermark Cruises and Tours; Family Fishing Adventures; Annapolis Electric Boat Rentals; Capital SUP - Quiet Waters Park; See more boat tours & water sports for groups in Annapolis on Tripadvisor

  8. TOP 10 BEST Harbor Cruise near you in Annapolis, MD

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  9. Watermark Cruises and Tours

    Watermark is your destination for fun on land and sea in Annapolis through sightseeing cruises and walking tours. Come enjoy a 40 minute cruise on the iconic Harbor Queen or take a walking tour with our Colonial guides. Choose from our variety of regularly offered cruises, walking tours and special events. ... Annapolis, MD 1 contribution ...

  10. Annapolis Sailing Cruises around the Chesapeake Bay aboard the Schooner

    Rates and Schedule. Buy Tickets. 410-263-7837. × Close Panel. Annapolis sailing cruises aboard the 74-foot Schooner Woodwind featuring sightseeing tours, sunset sails, multi-day cruises, special event specialty cruises and entertainment cruises on the Chesapeake Bay.

  11. Annapolis Harbor Cruise, Naval Academy Walking Tour & Guided MD State

    Travel with the Pack to Maryland's state capital, Annapolis, for a walking tour of the prestigious United Sates Naval Academy, guided tour of the Maryland State House, a narrated Annapolis Harbor Cruise and free time to browse and explore the beautiful downtown. Also, enjoy a delightful lunch included at a local rstaurant. Package Includes ...

  12. Watermark

    16 reviews and 22 photos of Watermark "Annapolis Seaport: This was a good way to take a break from walking around the waterfront. Watermark offers over nine different cruises providing history & culture lessons of the Chesapeake Bay area. They also have a location at the Baltimore Inner Harbor. We were on the Harbor Queen boat ($19 per adult) that provided us with a 45-minute narrated cruise ...

  13. Wine and Dinner Cruises on the Chesapeake

    Scheduled cruises happen rain or shine or with only one person on board. Their home port is the dock at the Annapolis Waterfront Hotel, where they depart for two-hour cruises at 11 am and 1:30, 4 and 6:30 pm. Join the crew with a call to 410-263-7837 for more information and go to www.schoonerwoodwind.com for reservations and schedule.

  14. Harbor Queen

    Watermark Cruises and Tours: Harbor Queen - See 1,123 traveler reviews, 518 candid photos, and great deals for Annapolis, MD, at Tripadvisor.

  15. Public Cruises & Water Taxi

    Cruises on the Bay by Watermark Cruises offers public Annapolis cruises, Annapolis boat tours, Baltimore Inner Harbor cruise and things to do in Baltimore. Watermark. Directions & Parking 410-268-7601 Search. Close Toggle navigation. Watermark. Public Cruises & Water Taxi;

  16. Naptown Jazz Band AND the Harbor Queen boat cruise!!

    Watermark Cruises and Tours: Naptown Jazz Band AND the Harbor Queen boat cruise!! - See 1,123 traveler reviews, 518 candid photos, and great deals for Annapolis, MD, at Tripadvisor. Skip to main content. Discover. Trips. Review. ... 1 Dock St, Annapolis, MD 21401-1818. Open today: 8:30 AM - 5:00 PM.

  17. Sailboat Cruises on The Liberte

    The schooner, Liberté, is based on Spa Creek in Annapolis, Maryland. During the summer months, she's docked at the Patriot Party Boats pier in Falmouth harbor in Cape Cod, Massachusetts. Captain Chris and Jane had this vessel built just for them. The original hull design by Dudley Dix is a Hout Bay 70, a two-masted gaff-rigged schooner ...

  18. Annapolis Dinner Cruise

    3 hours. Capacity. 2 - 12 people. Availability. Dinner with an unbeatable view of the Maryland State House, Naval Academy, the Chesapeake Bay Bridge and the Annapolis skyline! We'll arrange for dinner from a downtown restaurant of your choice to be served onboard, as we cruise around the Annapolis harbor and the scenic Severn River.

  19. Annapolis Lighthouse Cruise

    This morning board your deluxe Starr Tours motorcoach and travel to to Annapolis, MD. Here you enjoy a three-hour Bay Lighthouse Cruise. Pass under the twin spans of the Bay Bridges and by Sandy Point Shoal, Baltimore Harbor, and Thomas Point lighthouses on this award-winning cruise. A historically attired lighthouse keeper will entertain you ...

  20. Annapolis Sunset Cruise

    Our Annapolis Sunset Cruise takes you out on the water to watch the sunset and see the lights of the Annapolis Harbor. Watermark. Directions & Parking 410-268-7601 Search. Close Toggle navigation. ... Annapolis MD, 21401. Get Directions. Share This Event.

  21. Annapolis Harbormaster

    Hours of Operation. Monday - Friday 8:00 am to 5:00 pm . Saturday and Sunday 8:00 to 6:00 pm **OFF SEASON HOURS MAY VARY, PLEASE EMAIL US AT [email protected] FOR ASSITANCE.. Contact Our Office . 410-263-7973 or VHF 17

  22. Annapolis Harbor Boat Yard

    Annapolis Harbor Boat Yard, Annapolis, Maryland. 1,471 likes · 18 talking about this · 2,564 were here. The boat yard that does it all!

  23. Special or Seasonal Cruises

    Join us for a 90-minute solar eclipse cruise! Annapolis is expected to see the moon cover 88% of the sun at the peak of the eclipse. Book Now. Critter Cruise-Annapolis- ... Join our live interpreter for an enjoyable 3-hour cruise from Annapolis' historic harbor, up the scenic Severn River, then into the Chesapeake Bay. Book Now.