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The Annapolis Sailboat show combines local flavor and the international boating community.

Eight Things You Won’t Want To Miss at the Annapolis Sailboat Show

This year’s Annapolis Sailboat Show will feature a fleet of 155 boats, fun family activities, hands-on learning, and more. Come stroll the docks and enjoy historic downtown Annapolis. Here are eight things you won’t want to miss.

Tall Ship Tour

The Pride of Baltimore II, a 105-foot reproduction of a War of 1812-era privateer, will be at the show and open for deck tours for attendees. In the midst of all these new vessels, immerse yourself in the region’s sailing history. Pride II will be at Dock K3. 

Family Activities 

Your whole family is welcome at the Annapolis Sailboat Show. Children are encouraged to board the boats with adult supervision. Youth lifejackets may be borrowed at no cost from the BoatUS booth. 

Stop by the SpinSheet booth for fun stickers and temporary tattoos. In the same spot you’ll find the EWE Spirit Foundation, which has a kids’ scavenger hunt; finishers win a small bag of prizes. Find both at land space 19A.

Be sure to tour the Pride of Baltimore II (see above). You may be inspired to take the whole family sailing aboard the Schooner Woodwind, which you’ll find at Dock F2.

Right outside the show, pick up an ice cream cone at Storm Brothers (the colorful Superman flavor is a hit with kids), and shake out their wiggles on the playground at the corner of Newman and Compromise Streets. From there, it’s easy for most families to catch the water taxi at the stop near the Annapolis Waterfront Hotel. Ride across Spa Creek and hop off at the Chart House Restaurant. A 10-minute, half-mile walk down Second Street will take you to the Annapolis Maritime Museum, which has exhibits for all ages to enjoy.

There’s plenty to do in downtown Annapolis, just outside the boat show.

Tastings Tent

Indulge in complimentary wine and fine spirits tastings. Located in the Yacht Basin, the Wine & Spirits Tasting Tent is for show-goers ages 21 years and older. Here you’ll find a premium selection of spirits and wine and an opportunity to learn more about the drinks. Samplings include Oak Ridge Winery, Baltimore Spirits Company, and Old Line Spirits.

Meet Sailing’s Social Media Influencers

The Cruisers Creating Content Booth will host a rotating schedule of cruisers who share their adventures through video and other mediums. Stop in to hear their stories and snap your photo with them. Parlay Revival, Captain Glenn Shephard from Below Deck, SV Delos, and many more of your favorites are on the schedule. Located in the Yacht Basin.

Free Seminars and Beginner Sailing Workshops

Every day the show offers free seminars to all attendees. There’s something for everyone, from beginners who are curious to seasoned sailors who aim to expand their horizons. Topics include useful knots for sailors, cruising tips and destinations, an introduction to sailboat racing, and many more. There are even seminars about fishing from a sailboat.

If you’re interested in learning to sail, check out the First Sail Workshop, a hands-on learning experience with 45 minutes in the classroom followed by 90 minutes of instruction on the water. Workshops are held each day and include show admission. Registration is required at annapolisboatshows.com. The workshop costs $85.

Meet the Author – Book Signing

Chesapeake sailor, SpinSheet co-founder, and author David Gendell will discuss and sign his latest book, “The Last Days of the Schooner America,” an account of the iconic yacht for which the famous yacht race, America’s Cup, is named. Learn about the boat’s special ties to Annapolis, Saturday, October 12 from 4:30 to 5:30 p.m. in the southeast corner of the show, next to Tent YB.

Amazing Door Prizes

Incredible and fun door prizes include a six-night, seven-day charter in the British Virgin Islands aboard a Moorings 4500 sailing catamaran, airfare for two included. Among the other prizes are a Helly Hansen jacket, an inflatable catamaran by Further Customs, and a Colby Davis Compass Rose pendant. 

Boats… and Much More

With more than 500 show vendors, you’ll find outdoor gear designed to be used on and off the water. Look for sunglasses, sun hats, UV protective clothing, rain jackets, rain boats, coolers, nautical jewelry, and much more. All this is in addition to the latest sailing gear, boat electronics, and other sailing necessities. 

Multihulls are popular at this in-water boat show.

Of course, the boats are still the stars of the show, and they range from dinghies to luxury yachts. This year, 16 stunning vessels will make their North American debut in Annapolis. Be among the first to see and board them!

Map out your day at the Annapolis Sailboat Show ahead of time with the show program, produced by Chesapeake Bay Magazine!