Sail Away In The Maritime City of Annapolis

 Sail Away In The Maritime City of Annapolis


sailing in annapolis









Visitors from all over the world head to Annapolis because of its historic charm, colonial architecture, culture, and of course its obsession with all things sailing. Given its unique location on the Chesapeake Bay, and being quite accessible from both Baltimore and Washington, DC, Annapolis is a dream destination for sailing. Maryland enjoys four seasons a year, making sailing available almost year round (with the exception of winter). From sailboat races and boat-building workshops, to the spring and fall U.S. Sailboat shows and private sailing charters, there is no lack of sailing opportunity for the novice or enthusiast.

U.S. Sailboat Shows

Annapolis Sailboat Show
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Every spring and summer, Annapolis hosts the annual U.S. Sailboat show, an event for which the area is well known. The fall Annapolis Sailboat Show is the most popular of the two, and takes place within a week of the also popular U.S. Powerboat Show. People from all over the world come to attend one of the most spectacular sailboat events, some of whom are expert sailors and some of whom who have never stepped on a boat, but wish to learn more about sailing. The 2015 Annapolis US Sailboat show takes place from October 8 – 12.

Private Sailing Charters

Many leisure travelers want to enjoy a sailing experience during their visit to Annapolis. The Granmar sailing charter offers a half-day Annapolis sailing package for 1-6 guests, includes light snacks, non-alcoholic beverages, wine and beer. Groups leave from the Annapolis Yacht Club and head out to popular spots in the Chesapeake Bay like the Thomas Point Lighthouse and the Chesapeake Bay Bridge. The Granmar sailing package is popular for romantic sunset trip for two, as a unique way to celebrate a bachelorette party or girlfriend getaway or just as a fun, group recreational activity. Another popular option is to take a sail on the Schooner Woodwind, a 72 foot boat that offers public and private cruises.

Wednesday Night Sailboat Races at the Annapolis Yacht Club

For visitors and locals alike, the famous “Wednesday Night Sailboat Races” always attract quite a crowd. The races started in 1959 at the Annapolis Yacht Club thanks to Past Commodore Gaither Scott, who modeled them after “Wednesday Night Races” at East Greenwich Yacht Club in Rhode Island. Today, the races run every Wednesday from April to August, and include more than 125 yachts total. Click below for a taste of the Wednesday Night Sailboat Races are all about.


Looking for accommodations close to Annapolis sailing activities? The Annapolitan Bed and Breakfast offers nautically inspired Annapolis accommodations, gourmet breakfast and more! And John Holt, the Innkeeper happens to be quite an experienced sailor himself, so if you have a sailing question, he is all ears! Call 410-990-1234 for more information or to book now.

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