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Family Friendly
Family Friendly
Family Friendly

Regardless of when you visit or how old your family members are, everyone's certain to have a a great time.

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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...

EVENTS (10)

2017 SAP 5O5 World Championship

Severn Sailing Association (SSA) and Eastport Yacht Club (EYC) will jointly host the 2017 SAP 5O5 World Championship from September 20-29 in...

Acoustic Brunch Sail with Gareth Asher

An Intimate, Acoustic Show with GARETH ASHER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delic...

Annapolis Spring Sailboat Show

Enjoy the thrill of sailing from our show docks. Free sailboat rides provided by Annapolis Community Boating. Learn to sail at a FIrst Sail ...

Blue Angels Cruise

Watch the famous Blue Angels do their aero-acrobatics while sailing on the Bay. Tickets include box lunch, soda $103 per person, $66 per chi...

Brews in the Breeze Lunch Cruise

Sail on a lunchtime cruise of beer tasting on the Chesapeake Bay. After we raise all our sails, we will start the tasting with the lightest ...

Brews in the Breeze Lunch Cruise

Sail on a lunchtime cruise of beer tasting on the Chesapeake Bay. After we raise all our sails, we will start the tasting with the lightest ...

Brunch Sail Cruise with Ernie Halter

An Intimate, All Ages Acoustic Show with ERNIE HALTER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a ...

Christopher Cross

Christopher Cross was by far the biggest new star of 1980, virtually defining adult contemporary radio with a series of smoothly sophisticat...

Classic Wooden Boat Regtta

Participate in the National Sailing Hall of Fame Classic Wooden Boat Regatta. They have invited the Woodwinds’ to participate in the r...

Father’s Day Brunch Sailing Cruise

Our Father’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00am and returns at 1:00pm. Sailing cruise includes...

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....

Charter a Boat in Annapolis

Our area offers a variety of charter options ranging from fishing trips, overnight cruises, private parties, and more...

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....