Schooner silhouette at sunset in the harbor when you visit Annapolis, Chesapeake Bay.
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Set Sail for Adventure: Water Tours of Annapolis

Annapolis, cradled by the Severn River, Spa Creek, and College Creek, is a jewel surrounded by enchanting waterways. As the gateway to the majestic Chesapeake Bay—the largest estuary in the United States—Annapolis rightfully claims the title of the world’s “sailing capital.” From our Annapolis bed and breakfast’s charming downtown location, you are merely moments away from an array of water tour options. Whether it’s sailing on a magnificent schooner at sunset, embarking on boat outings focused on Annapolis Harbor or the Chesapeake Bay Bridge, enjoying a private party with friends aboard a “tiki” cruise, or experiencing an exhilarating guided paddleboard tour along Spa Creek, you can plan an unforgettable day on the water when you visit Annapolis.

Schooner Woodwind – Exploring the Chesapeake on a World-Class Sailboat

The impressive 74-foot schooners operated by Schooner Woodwind offer an extraordinary opportunity to spend an afternoon aboard a world-class vessel. These boats, crafted from beautiful cedar and Douglas fir planks by a renowned New York boat builder in the early 1990s, are helmed by a dedicated family-run crew. Retired teachers Ken and Ellen Kaye, alongside their daughter Captain Jen, have been sailing these splendid racing schooners along the Chesapeake for over 25 years, sharing their wealth of experience and local knowledge. Their two identical schooners, Woodwind and Woodwind II, are as stable as they are magnificent, thanks to their heavily ballasted keels—ideal for guests prone to seasickness.

A mere five-minute stroll from your luxurious suite at The Annapolis Inn brings you to the dock on Spa Creek from which these beautiful schooners set sail. With multiple daily departures, including popular two-hour public cruises at 11 a.m., 1:30 p.m., 4:40 p.m., and 6:30 p.m. during the vibrant summer season, there is ample opportunity to embark on a memorable journey. Priced affordably, this experience offers exceptional value as you sail past iconic landmarks like the Chesapeake Bay Bridge and the Thomas Point Lighthouse. Each public tour is limited to 30 guests, ensuring ample space to relax, mingle, and capture stunning photos of the picturesque scenery.

In addition to their regular public cruises, Schooner Woodwind offers enchanting sunset sails with nightly themed experiences. On “Historic Mondays,” experts in oceanography and maritime history join the cruise, offering fascinating insights. Upcoming themes include “What Swims Beneath Us” on June 10th, 2024, featuring a local fishing guide, and “Birds of Chesapeake” on July 1st, led by an environmental scientist. Beer enthusiasts can revel in the Beer-Tasting tours on Tuesday nights, with June highlighting Port City Brewing and July featuring DC Brau. For an extra thrill, join the Wednesday night racing series, where the prize-winning crew competes in the weekly regatta—a spectacle that may inspire you to pursue sailing lessons at one of Annapolis’s esteemed sailing schools.

visit annapolis' Quiet Cove on the Chesapeake Bay

Watermark – Setting a High Bar for Boat Tours When You Visit Annapolis

Watermark Tours, an iconic presence on the Annapolis waterfront, offers a variety of themed cruises departing from the central slips at City Dock. Their Annapolis Harbor and USNA tour is highly rated and always packed, providing an up-close view of the picturesque landscape that makes up Annapolis and the USNA campus (worth touring on foot, too). This 40-minute cruise departs six times a day, on the hour, between 11 a.m. and 4 p.m. on weekdays, with additional 5 p.m., 6 p.m., and 7 p.m. options added on weekends. If you visit Annapolis during the Naval Academy commissioning week, this tour becomes a festive prelude to graduation day.

For a more extensive exploration, the Chesapeake Bay Bridge cruise offers a 90-minute voyage under the awe-inspiring Bay Bridge. Available Fridays through Sundays, this tour highlights the engineering marvel that spans over four miles. For a shorter yet equally enchanting experience, the Spa Creek cruise offers multiple daily departures, navigating the tranquil waters and showcasing the beautiful marinas and yachts of Eastport.

Watermark’s all-day adventure, “Day on the Bay to St. Michael’s,” is a Saturday delight. Departing at 10 a.m., this tour takes you to the charming fishing village of St. Michael’s, founded in 1677. With three hours to explore the historic downtown, classic architecture, and quaint shops, this tour is a perfect blend of history and leisure before returning to Annapolis by 5:30 p.m.

While walk-up tickets are often available at City Dock, weekend cruises tend to sell out, so it’s advisable to book in advance. Arrive 30 minutes before departure to ensure a seamless boarding process.

Watermark Water Taxi – Convenient and Scenic Transportation

Experience Annapolis with ease using Watermark’s Water Taxi service, offering continuous, on-demand transit throughout Annapolis Harbor, including Spa Creek and Back Creek. With fares vary in price depending where you are going and start at around $4.00, this service provides a delightful alternative to driving, eliminating parking hassles while offering scenic views. The knowledgeable captains are always ready to share local tips and recommendations, enhancing your journey. Whether heading to a favorite restaurant or exploring the city, the Water Taxi ensures a memorable and convenient way to travel when you visit Annapolis.

Seas the Bay Sailing – Bespoke Charters on the Chesapeake

For those seeking a truly personalized sailing experience, Seas the Bay Sailing offers an unparalleled adventure on their exquisite 54-foot Irwin, Southerly. This family-owned company, based in the heart of Annapolis, provides bespoke charters perfect for any occasion. Whether it’s a serene sunset cruise, a romantic dinner sail, or a festive family outing, each voyage is tailored to create unforgettable memories.

With options for three-hour day cruises, sunset dinner sails, and special event photo shoots, Seas the Bay ensures every detail is meticulously planned for your enjoyment. Embrace the magic of Annapolis and the Chesapeake Bay with a customized sailing experience that promises both elegance and excitement.

Visit Annapolis: Tropical Tiki Ambiance and Paddle Tours on Spa Creek

For a unique and festive experience, the Naptown Tiki Club offers Annapolis’s only Tiki Boat Booze Cruise. Perfect for a spirited outing, these cruises accommodate up to 16 guests and feature personalized music and BYOB beverages. The 90-minute journey departs from Nautilus Point Marina and takes you through scenic routes around Annapolis Harbor and the USNA campus.

For those seeking an active adventure, Paddle Annapolis offers guided paddleboard and kayak tours. Departing daily from the Eastport Yacht Club, these two-hour excursions provide a thorough tutorial before embarking on a scenic paddle along Spa Creek, navigating charming coves and picturesque waterways.

Visit Annapolis and Stay at The Annapolis Inn, where history and luxury converge, and your next water adventure is just minutes away.