Annapolis, MD


Smart Family Travel Tips: Traveling Annapolis, Maryland


Annapolis, Maryland is a water-lover’s dream town and a great place to bring the kiddos! Known as the “Sailing Capital of the World,” Annapolis is home to the U.S. Naval Academy, the United States Sailboat Show, and the historic Maryland State House. Annapolis served as the capital of the United States from November 26, 1783 to August 13, 1784 and was supposedly under consideration as the capital before Washington D. C. was built.

Annapolis Harbor featuring sailboats, a pirate ship, and historical buildings.


Annapolis Harbor

The town features beautiful architecture, old cottage style homes, and lots of water activities. Of course, there’s no shortage of great food, shopping, and cool attractions.

Things to see & do

US Naval Academy

One of the most popular things to see in Annapolis is the US Naval Academy. This service academy features a free museum and guided tours. Entry to the grounds is free. The Naval Academy music program offers numerous shows throughout the year. Check the schedule here to purchase tickets.

The Naval Academy Visitor Center is conveniently located inside USNA Gate 1 at the Annapolis Harbor.

Pedestrian entrances are on Prince George and Randall Streets. Expect to have your packages and bags inspected at the entrance and remember that anyone 18 years of age or older must present a valid, unexpired original REAL ID Act-compliant government photo ID card (e.g. state-issued driver’s license or identification card); or an original, unexpired passport. If your state or territory ID cards are not REAL ID Act compliant, you must present additional acceptable identification such as an SSN card, unexpired passport (book or card), birth certificate, or voter registration card. 

Sailing schol boats tied up to the docks.


So many boats!

Visit Historic Annapolis

Historic Annapolis is the area of restaurants, galleries, and shops that fill the converted row houses on Main Street and spills all the way down to the harbor. You’ll find everything from fancy boutiques to ice cream and fudge shops. On warm summer days, many cafes set tables outdoors so patrons can enjoy the beauty the area has to offer.

Ego Alley

Ego Alley is a narrow waterway at the tip of the harbor. The name refers to the queue of expensive boats that parade through the waterway nearly every day. The benches along Dock Street are the perfect place to sit, relax with some ice cream and watch the boats and people go by. The weeks leading up to Christmas also make for an interesting experience in this area as many of the boats are decorated for Christmas and all lit up at night.


Take a boat tour

Take a boat tour along the Chesapeake Bay. Depending on your tastes and budgets, you can get on the water and tour the area around Annapolis by boat around the Chesapeake Bay.  

If touring by sailboat is your thing, check out Schooner Woodwind. We’ve ridden with them and they love having kids on board. You and your kids may even get a chance to drive their very large sailboats!

If you’d prefer to tour the bay and extend your trip a little further, Watermark Cruises and Tours are a great option. The lighthouse cruise will take you all along to Thomas Point Lighthouse, Sandy Shoal, and Baltimore Harbor Light.  


Heather enjoying the view at Thomas Shoal Lighthouse

Families with young children may wish to check out Pirate Adventures. You can take the kids out on a pirate ship and watch as the crew and children live life as a pirate as they search for sunken treasure and fire the water cannons. 

The United States Sailboat Show

Visit The United States Sailboat Show as each October sailors from around the globe gather on miles of docks in beautiful downtown historic Annapolis for the United States Sailboat Show. This internationally acclaimed sailboat show is recognized as the world’s largest and most prestigious sailboat show and is a great way to explore lots of beautiful boats. A smaller sailboat show is held each spring – check out our visit!

Take a Ghost Tour

Take a Ghost Tour or a pub crawl or just a guided walking tour! The good folks at Annapolis Tours and Crawls offer all sorts of fun trips around the town.

Getting There
Annapolis is conveniently located about an hour and 15 minutes east of Washington DC off US route 50 and about 45 minutes south of Baltimore off I-97. It’s also easily approachable from the water as it is a major harbor on the west side of the Chesapeake Bay.

Getting Around
Getting around in the downtown and historic areas is all by foot. Make sure you wear good shoes, comfortable clothing, and be prepared to be awed by your surroundings! If you’re going out on the water, be sure to bring sunscreen and be prepared for the air temps to be a lot different out in the Bay. 


Smart Family Travel Tips

  • Give yourself plenty of time. You can tour the downtown and harbor areas of Annapolis in just a few hours if you hurry – but you really shouldn’t do that. Take some time to experience the calm of the harbor, the beauty of the yachts in the basin, and the many shops that line the streets in this historic town.  

  • Parking can be a chore in the downtown area and it’s usually best to just park in one of the main parking garages. Check out this site for up to date info. If you happen to possess US military ID, it’s a great idea to park at the Naval Academy and walk into the harbor area. If you park in one of the four parking garages, the city offers a free trolley service to get you into the downtown area. Check out this page for more info (including links to an app that will allow you to track the trolley!).  

  • Take that boat tour! Annapolis is all about the water – so take the time to get out there. There are a number of sailing schools in the area as well that offer basic sailing instruction. It’s a blast! 

  •  Drive around through some of the residential neighborhoods. Many of the homes in the area date from the 1700s.