Family Friendly

Family time is precious. There never seems to be enough of it! So, when you get together with loved ones, you want it to be special. Whether you’re traveling with toddlers, teenagers or ‘tweens, you can’t go wrong with Annapolis and Anne Arundel County! 

Day One

Welcome to Annapolis! If you’ve driven to town, park at Gotts Court Garage behind the 26 West Street Visitors Center. Be sure to stop in and talk with our information specialists. They’ll provide you with maps and information for a fun family getaway. Before you hit the streets, be sure to snap a picture – or two or three – of you and your crew at the Visit Annapolis photo booth. 

Pirate Adventures on the Chesapeake

Start your visit off with a bang – literally – with a cruise aboard the Sea Gypsy. Join in the excitement as your kids dress up as pirates and scour the Chesapeake in search of an ornery pirate to drench with a water cannon with Pirate Adventures on the Chesapeake. The best thing is, you’ll be there to celebrate their triumph! Never underestimate the power of a boatload of determined youngsters! If your kids are anxious to reel in their first catch, Family Fishing Adventures is just the ticket! They’ll teach your gang to fish and crab. If you’re lucky, your kids might reel in tonight’s dinner! 

Annapolis Maritime Museum

No family outing is complete without a visit to the Annapolis Maritime Museum. Housed in the last remaining oyster packing plant in Annapolis, the 2,500-square-foot museum is undergoing a major transformation. It will reopen in spring 2020 with a dynamic state-of-the-art, high tech, high touch gallery that focuses on the health of the Chesapeake Bay, the oyster economy and Annapolis-area waterways. The permanent exhibit is designed to help you and your family better understand the role everyone can play in helping to preserve and improve the natural environment. Before heading to lunch, treat yourself to a cruise aboard the Museum’s resident Chesapeake Bay Skipjack, the 47-foot Wilma Lee. Long used by watermen to harvest oysters on the Chesapeake Bay, wooden skipjacks are often referred to as the last commercial sailing fleet in the nation. Of the nearly 2,000 skipjacks that once plied the waters of the Chesapeake, only about thirty remain. 

Time For Lunch

If you’re hungry, you’re in the right place! You’re in Eastport, home of Annapolis’ famous Restaurant Row. Located on a four-block stretch of Severn Avenue between Sixth and Second Streets, Restaurant Row offers a spectrum of tempting indoor and outdoor dining possibilities. If you have young kids in tow, Boatyard Bar & Grill serves up crayons and paper along with its famous crab cakes. If you’re in the mood for waterfront dining, the outside deck at Carrol’s Creek offers a stellar view of Spa Creek and the Annapolis skyline. Rooftop dining at Blackwall Hitch provides a lay of the land perspective on the Maritime Republic of Eastport. If you’re traveling with your dog, consider snagging a picnic table outside of the legendary Davis’ Pub. Crab pretzel anyone? If no frills dining on fresh-from-the-Bay seafood is up your alley, Wild Country Seafood offers outside dining seasonally under tiki umbrellas one block from the Annapolis Maritime Museum. 

The Day’s Still Young  

After lunch, stroll back into downtown Annapolis or make like a local and enjoy a five-minute water taxi ride from Restaurant Row to City Dock

Clay Bakers

Chances are you have a budding artist or two in tow. If so, be sure to stop at The Clay Bakers near the foot of Main Street. There, your kids can pick the ceramic piece of their choice and turn it into a one-of-a-kind creation. Because the piece will need to be fired after it’s painted, it’s a great idea to stop by The Clay Bakers on the first day of your visit. That way, you’ll have time to circle back the following day to pick up the completed masterpiece.   

Maryland State House

No matter how old your kids are, you’ll want to visit the oldest State House in continuous legislative use in the nation. Pre-schoolers may enjoy just how beautiful it is. ‘Tweens learning about the American Revolution may be impressed by the Old Senate Chamber where George Washington resigned his commission as commander-in-chief of the continental army and where the Treaty of Paris was ratified, officially ending the Revolutionary War. Chances are you’ll be impressed by the building’s Tiffany windows and by the House and Senate chambers where Maryland legislators debate and pass laws annually during a 90-day session that runs from January until Easter. 


You’ve had a busy first day! Now’s the perfect time to check into your accommodations. With a host of full- and select-service hotels and bed and breakfasts to choose from, rest assured you’ll find the place that’s right for you! 

Dinner on the Town

Trying to find a restaurant that will satisfy the whole family for dinner? If so, the Annapolis Market House might be just the ticket. You and the kids can stroll past the various eateries and order from the counter. From hamburgers, to salads, to seafood, to vegan options and desserts, the Market House has you covered. Then, pick your favorite spot to sit – from high tops, to traditional tables, to seats with a view of City Dock. Market House even has loaner games to keep young minds engaged while you dine. Other nearby eateries, including Iron RoosterMangiaBuddy’s Crabs and Ribs and Mission BBQ are all family friendly. After dinner, top your evening off with a visit to Iron Rooster’s General Store and/or a trek to Annapolis Ice Cream Company for some of the best homemade ice cream you’ve ever had! 

City Dock

If you want to hang out with the locals, take that ice cream cone of yours and head to City Dock. After finding a favorite spot along the seawall, sit back, relax and watch the people and boats go by. You’ll soon discover why the Annapolis Harbor is nicknamed Ego Alley! If you’re in the mood for a quick bite to eat when the people-watching is through, head to Sofi’s crepes. It’s right outside the U.S. Naval Academy’s John Barry Gate and just steps away from City Dock.

Day Two

With little ones in the mix, chances are you’re rising and shining with the sun. That means you’ll have plenty of time to cover a lot of turf today! 

Your kids may get a kick out of reciting the Pledge of Allegiance at Chick & Ruth’s Delly. The staff recites it every weekday morning at 8:30 a.m. and on weekends at 9:30 a.m. Add to that fresh baked doughnuts and pies and some of the best milkshakes around, and you’re bound to have some pretty happy campers! Of course, mom and dad are likely to get hooked on the crab eggs benedict and a host of other specialties – all of which are named after Maryland legislators and elected officials. Nearby, the Iron Rooster serves up homemade pop tarts of the day that are real crowd pleasers. Hearty appetites may want to opt for the chicken and waffles – a best seller. Have a sweet tooth? Baker’s & Co is bound to satisfy. Be sure to arrive early. After selling out, the popular eatery closes for the day. 

Tour Annapolis

If little feet feel like they got a real workout yesterday, you might want to begin day two with a Discover Annapolis Trolley Tour. It provides a great overview of downtown Annapolis and will help you map out a game plan for the rest of your stay. Tours depart daily from the 26 West Street Visitors Center.

U.S. Naval Academy

Since the one and only U.S. Naval Academy is in Annapolis, it’s a must stop on your visit. Guided tours of the “Yard” depart daily from the Armel-Leftwich Visitor Center. If you visit the Naval Academy during the academic year, you may want to time your tour to coincide with noon formation. Weather permitting, 4000+ midshipmen line up before heading into Bancroft Hall for lunch – complete with color guard and the Navy band. Want to buy some Navy memorabilia? Head to the gift shop at the Armel-Leftwich Visitor Center. Your tax-free purchases will be a big hit back home. 

Time for Lunch

Since you’re already at the Naval Academy, you may want to grab lunch at the Drydock.  Located in Dahlgren Hall, it’s an affordable, cafeteria-style restaurant that’s perfect for families with young kids. If you go on a weekend, you’re likely to bump into some midshipmen as you indulge in fries, pizza, milk shakes, hamburgers and more. If you’re traveling with teenagers, you might want to check out the Naval Academy’s Alley restaurant. Also located on the “Yard,” chances are you’ll see some Navy brass there.  

On the Water

As you may have guessed, America’s Sailing Capital is all about getting on the water. If your family’s in the mood for a leisurely afternoon on the Chesapeake, a two-hour public cruise aboard the 74’ Schooner Woodwind that was featured in the movie, The Wedding Crashers, could be just the ticket. If the wind is right, you just may find yourself sailing beneath the twin-spans of the Chesapeake Bay Bridge! If a shorter cruise better suits your schedule, a 40-minute narrated cruise of the Annapolis Harbor aboard the Harbor Queen promises fun for all. If you’d like to see some beautiful waterfront homes, opt for a 40-minute cruise up Spa Creek aboard the Miss Anne. If dad and mom are feeling adventurous, put on your captain hats, load the kids aboard a Duffy Electric Boat and treat them to a green cruise a la Annapolis Electric Boat Rentals

Shopping, Anyone?

As you make your way to The Clay Bakers to pick up yesterday’s creation, be sure to check out other downtown Annapolis shops for mementos of your visit. There’s a host of possibilities for mom and dad to choose from – from spices and olive oils, to handmade purses and wallets from Hobo Leather, to handcrafted, one-of-a-kind artisan creations at Local by Design and the Annapolis Pottery. As you stroll along Main StreetMaryland Avenue, State Circle and West Street, you’ll also come across fun keepsakes for the kids. 

Dinner Already?

In the mood for Irish tonight? If so, head to Galway Bay, where fish and chips are their number one best seller. You may have seen the restaurant on Diners, Drive-ins and Dives. Now’s your chance to experience it for yourself. Be sure to ask for a taste of their famous eggnog – while supplies last! Light House Bistro is another fun eatery the whole family will enjoy. If you want to dine on the water, Pusser’s Caribbean Grille sits right on Ego Alley.  

Theatre Under the Stars

If you want to top off your last night in Annapolis with a special something, consider theatre under the stars at Annapolis Summer Garden Theatre. Be sure to check out the show ratings – as not all performances are appropriate for young children. 

Day Three

Where has the time gone? It’s hard to believe it’s your final day in Annapolis – at least for this go ‘round! If you haven’t yet ventured to Miss Shirley’s for one of their famous breakfasts, today’s the perfect day!  

Banneker-Douglass Museum

If you want to learn about Annapolis’ rich African American history, head to the Banneker-Douglass Museum. With hands on activities for the kids, the museum appeals to all ages. It’s Deep Roots, Rising Waters exhibit documents African American history in Maryland from 1633 to the present day. 

Old Fox Book Store

Before you head home, be sure to stop by Old Fox Book Store and Coffeehouse at 35 Maryland Avenue. Your little ones will like the kids’ section and the fairy garden out back – complete with its kid-size house made of books. Grownups will enjoy the relaxed, casual feel of the store, the wide selection of books, and the comfortable chair that’s calling your name. Go ahead, indulge! Buy that second cup of coffee and a mouth-watering dessert and sink into that inviting chair, book in hand. 

William Paca House and Garden

You’re in the zone now. So, before you leave town, make a quick stop at the William Paca House and Garden. You and the kids will enjoy strolling the reconstructed two-acre 18th century pleasure garden – once the pride and joy of Declaration of Independence signer William Paca. 

Quiet Waters Park

If you want to give the kids a workout before you head for home, drive to the nearby Quiet Waters Park for a hike along their 5.1-mile trail. The 340-acre park is the perfect place to run off some excess energy before the long drive ahead!

Safe Journey

You did a great job of squeezing as much into your Annapolis visit as possible. Still, you’ve only scratched the surface of all that awaits you here! It’s not too early to begin mapping out plans for your next visit. As you pile the kids into the car and set the GPS for home, we invite you linger longer with us in spirit – imagining the many possibilities repeat visits would hold for you and your family! We look forward to welcoming you to the shores of the Chesapeake soon again. In the meantime, safe journey!