Spring Sailing Weekend


Annapolis Spring Sailing Weekend 2018

A few years ago we decided to celebrate the weekend the Annapolis Spring Sailboat Show comes to town, this year April 20-22, as Spring Sailing Weekend in Annapolis. Apart from the boat show, there are all kinds of events around Annapolis designed to get you out on the water or at least get you in the sailing spirit. Get ready to start making room in your calendar, or better yet, leave that weekend wide open.


Ego Alley becomes Demo Alley during the Annapolis Spring Sailboat Show.

Cruisers University 

At Cruisers U, more than 50 classes are available for sailors and power boaters alike who have an interest in learning the fundamentals of blue water cruising, from individual courses to four days of study. Classes are held at the Naval Academy Club on the grounds of the United States Naval Academy, April 19-22. All packages include educational materials, breakfast and lunch, evening social activities, admission to the Boat Show, and complimentary one year basic BoatUS membership.


Annapolis Spring Sailboat Show

The seventh annual in-water show, April 20-22 at City Dock, Annapolis, will feature new and brokerage boats, including catamarans, monohulls, racing boats, family cruisers, daysailers, and inflatables, as well as more than 100 on-land exhibitors. There will be in-water demos in Demonstration Alley (Ego Alley) of various sailboats, the PropEle Electric Boat Motor, paddleboard yoga, a floating dock system, and the Hobie Mirage Eclipse stand-up-pedal board, among others. Stop by Entertainment Plaza for free food and drink tastings throughout the show. Beginner sailors will want to consider a First Sail Workshop where participants learn the basics of sailing in a 45-minute classroom session, followed by 90 minutes on the water on a Benteau First 22. Admission to the sailboat show is included; advance registration required. annapolisboatshows.com


Photo courtesy of the Woodwind

Sailor’s Delight Cocktail Cruise

Enjoy one of the first sunset sails of the season aboard the Schooner Woodwind Friday, April 20 or Saturday, April 21 from 5:30 to 7:30 p.m. out of the Annapolis Waterfront Hotel. Tickets cost $76 per adult and include delicious appetizers and two drink vouchers (beer, wine, cocktails). The menu features an assortment of savory dips, grilled vegetable crostini, grilled Asian shrimp and pineapple skewers, and a variety of local craft beers. During the day, the Woodwind will be offering two-hour public sails from 12:30-2:30 p.m. and 3-5 p.m. schoonerwoodwind.com


Get out on the water with CRAB on Sail Free Sunday. Photo courtesy of CRAB

SailFree Sunday

Chesapeake Region Accessible Boating (CRAB) will have a boat each day at the Boat Show to give sailing demos for persons with disabilities. On Sunday April 22 from 9:30 a.m. to 2:30 p.m., they will also be offering 45 minute sails for disabled sailors out of Sandy Point State Park. CRAB’s specially designed boats will provide full accessibility for anyone interested in learning more about the mental and physical therapeutic value of sailing. crabsailing.org

Annapolis Junior Keelboat Regatta

The fourth annual Annapolis Junior Keelboat Regatta will take place on April 21 at 12 p.m. The regatta brings together seven of the area’s top regional high school sailing teams to race in J/80s just off the docks of the Spring Sailboat Show in Annapolis Harbor. Teams will compete for a traveling cup designed by Weems and Plath, which will be presented immediately following the race in Susan Campbell Park.


Our Annapolis Crew Party at EYC April 22 is our largest.

Spinsheet Crew Parties

The Annapolis Crew Party, powered by Musto and Harken, will be held April 22 from 4-6 p.m. at Eastport Yacht Club, just across the bridge from the Boat Show. Free and open to the public, just bring cash for the bar and pen/paper or a smart phone to jot down sailor’s info. Register in advance at spinsheet.com/crew-parties for a chance to win a Musto MPX Gore-Tex PRO Coastal Jacket or Musto shoes. For more info on our other three crew parties in the month of April, click to our crew party registration page here.

NASS Spring Race 

The Naval Academy Sailing Squadron's annual spring race off Annapolis. April 21.