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Dining
Dining
Dining

Thanks to an incredibly picturesque waterfront backdrop, plentiful access to the bounty of the Chesapeake Bay, and an energetic, happy-to-be here pulse, Annapolis has quickly become a foodie's paradise.

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BUSINESSES (8)

Annapolis Sailing Cruises: Schooner Woodwind
Boating

Sail the Chesapeake on a 74-foot schooner! Raise the sails, steer the boat, or sit back and relax on a two-hour sail. Special, longer event ...

Annapolis Sailing Cruises: Schooner Woodwind
Music Venue

Sail away on a 74-foot wooden, schooner with terrific local musicians performing while under full sail on the Chesapeake Bay. Schooner Wood...

Annapolis Sailing Cruises: Schooner Woodwind
Tours

Sail the Chesapeake on one of two, 74-foot wooden, schooners that offer a real Chesapeake Bay sailing experience for 2-hour public cruises, ...

Annapolis Sailing School
Boating

America's oldest sailing school and Annapolis' largest sailing school. Learn to sail the "Annapolis Way" from beginner to advanced. KidShip ...

Annapolis Sailing School
Kayaking & Paddleboarding

The Annapolis Sailing School now hosts Annapolis Water Experiences which has Annapolis Stand-up paddle boarding and Kayaking off Bembe Beach...

Sailing Lessons with Cruise Annapolis
Boating

Learn to sail on the boat you ultimately want to own. Catamaran sailing schools are our specialty. Go out at any time, for any length of tim...

National Sailing Hall of Fame
Attractions

The National Sailing Hall of Fame is a not-for-profit educational institution dedicated to preserving America's sailing legacy....

Chesapeake Sailing School & Charter Company
Boating

Putting the Fun in Sailing since 1980!  Offering Basic through Advanced sailing programs for adults, families and groups – including 2 ho...

ARTICLES (10)

Annapolis Boat Shows

Known as America's Sailing Capital, it's no wonder Annapolis is home to the largest in-water boat shows in the world....

Autumn in Annapolis

Autumn in Annapolis...there's nothing quite like it. It comes with a snap in the air and an energy that permeates the region....

Family Friendly Activities by Season

Annapolis is known for its colonial history and sailing tradition, but it’s also a great place to spend time with the family. ...

Five Fabulous Ways to Spend an Evening in Annapolis

Whether meeting up with friends, planning a date, or bringing the whole family, prepare for a great evening....

Five Overnight Ideas in Annapolis

For those of us that love our job but are looking for some much-needed time off, Annapolis offers the perfect night, or weekend, getaway. ...

Five Super Fun, Out-of-the Ordinary Ways to Spend Time on the Water in Annapolis

Here are five fun ways to enjoy being on the water during your time in Annapolis....

Maryland Avenue: a Historical Hub of Commercial Activity Boasting 20-plus Independent Shops

In this historic, walkable town, you don’t have to make a special trip to go shopping....

Nightlife in Downtown Annapolis

Check out downtown Annapolis for personality, old world charm, authenticity and a whole lot of fun....

Outdoor Adventure in Annapolis

No matter what your idea of adventure is, there's a little something for everyone in Annapolis....

Paddle Your Way through Annapolis’ Scenic Tributaries

There’s nothing quite like getting acquainted with an area by paddling through its waterways....