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Naptown Tiki Club is the first and only tiki boat bar in Annapolis! Passengers will embark and disembark from our slip at Nautilus Point Marina, just 4 minutes from the heart of downtown. The marina has free parking available for our passengers.
The Couple’s Waterfront Elopement Included a Private Sunset Boat Cruise - Washingtonian
The Couple’s Waterfront Elopement Included a Private Sunset Boat Cruise.
Posted: Thu, 11 Mar 2021 08:00:00 GMT [source]
A Grand Experience for All
Woodwind is a replica of the classic, fast wooden schooners that were built as yachts in the early 1900s. Her handsome mahogany brightwork, gleaming chrome, and roomy cockpit distinguish her from cargo-carrying work vessels. Our bar is stocked with wine and beer, including a nice selection of local craft beer. Woodwind sails up to four times daily throughout our summer season from the Annapolis Waterfront Hotel.
Around Town
Docks are home to a surge of drinking vessels designed for every occasion, vibe, and price point. A returning line of retro motor boats are apparently the ticket to getting engaged, with seven proposals out on the water last year. Want to watch dolphins give birth on the Chesapeake this summer? And a fancy sailboat manned by a fine-dining chef pairs tasting menus with French wines.
Weekday sunset sails include the following events or entertainment:
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. Each month we feature a different brewery from the Chesapeake area. A representative from the brewery comes aboard and teaches you about beer.
Adventure & Entertainment
As it turns out, dolphins use the Potomac and Bay as a nursery to birth their calves — a rare event that happens from mid-June to mid-August when the water is warmest. Kicking it up at full speed (35-40 knots), hat-holding patrons will jet downstream through Old Town, Fort Washington, and Mt. Vernon and (hopefully) see the annual occurrence. Chef and sommelier Troy Knapp makes Michelin-level menus on his luxury sailboat Cru Classé. Knapp also mans other Wharf vessels for parties of six or more, partnering with Nautiste to offer dining excursions with his catering company Curated. Passengers will embark and disembark from our slip at Nautilus Point Marina. Custom built for sailing, comfort and fun, the Liberte is a grand experience for all.

We will contact you via text on the cell phone number provided. Cruises are subject to cancellation due to weather and unforeseen conditions and are fully refundable. Let our captain and crew make your trip an enjoyable and memorable experience. Our bar is stocked with wine, beer and bubbly, including a nice selection of local, independent craft beers available for purchase.
The sunset over the Annapolis skyline is breathtaking. The golden glow reflecting off the sails as the sun descends near the horizon is an unforgettable sight. Here in Annapolis, we claim the Chesapeake Bay, the nation's largest estuary, as our very own playground. With countless rivers, streams, and coves spanning over five hundred miles of the shoreline - there are plenty of ways to play on the water. Spend the afternoon paddle boarding through the areas winding inlets, take a sunset tour through the Harbor, or learn to sail on your own! There is something for everyone, no matter the age.
Paddle Club Cruises
Schooner Woodwind owner and seasoned sailor Jen Kaye is also a “foodie,” who masterminds “Wine in the Wind” evenings. At this point, there are nine remaining reservations. 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. The 74-foot schooner Woodwind and Woodwind II were custom designed and built specifically for sailing on the Chesapeake Bay.

You will taste 3 samples of beer and then you can purchase full beers from the brews that you enjoyed the most. A guided tour exploring the history of the Chesapeake area, and the sights you see while on a sail. Soak up monumental views along the Potomac River, drink in tow, with this running list of bookable boats. Everyone has loved having more room, so we are staying at just 30 people per cruise (instead of 48). 2024 marks the 60th anniversary of the Civil Rights Act of 1964, a historic law making discrimination based on race, color, religion, sex, and national origin illegal.
Each four-top fiberglass beauty sports a different color and name (Gladys, Bonnie, and Violet). Passengers will be picked up and dropped at the T Head of B Dock at Nautilus Point Marina. One of our crew members will meet you on the dock and escort your party to the boat. Each month we feature a different brewery from the Mid-Atlantic Region, and their representative comes aboard and teaches you about beer. 3 samples of beer come with the cruise, and then order full beers from the brews that you enjoyed the most. Sunset is a favorite time for a sail on the Woodwinds.
We’ll cruise for an hour and a half on this private boat tour of Annapolis. The route begins at Nautilus Point, and we’ll cruise up Back Creek, around Horn Point, and into the Annapolis Harbor. Soak in the iconic sights and sounds of the sailing capital of the world as we cruise past the US Naval Academy, Ego Alley, and Eastport before cruising back around Horn Point and down Back Creek. The cruise concludes back at Nautilus Point Marina, where your licensed captain and deckhand will safely return you to the dock. 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. Be the envy of Maryland’s capital city as you sip on your favorite drinks, snack on your favorite foods, dance to your favorite music, and celebrate with your favorite people on a private boat charter. “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.
Let our captains and crew make your trip most enjoyable and memorable. Help hoist the sails (all 4 of them) or take a turn at the wheel. We cruise rain or shine, but we will cancel two hours prior to departure for high winds or thunderstorms.
In light of this significant milestone, Governor Wes Moore of Maryland declared 2024 as Maryland's Year of Civil Rights. To honor this occasion, the state has planned various events, exhibits, and commemorations throughout the year. Sign up today and we'll keep you in the loop on upcoming deals, specials, and happenings in and around Annapolis.
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. The Annapolis Spring Sailboat Show rings in the new season by bringing together sailing enthusiasts from around the Mid-Atlantic. Every April, guests experience an in-water show boasting the sailing industry’s latest boats, gear, and tech....
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