Summer is the perfect time to explore, but I know my family is not the only one choosing to stay home. Plane tickets and gas prices have lots of families making different decisions with their budgets. But that doesn’t mean your only option is to stay at home. Instead of TSA lines and road trip traffic, you can have a vacation in your own backyard. There’s a reason tourists flock to downtown Annapolis. It’s beautiful, walkable, and entertaining for the whole family. Experience it for yourself with a weekend stay and check off all the quintessential Annapolis experiences. We have hotels, activities, and food to help you plan your close-by getaway.

Stay

A picturesque room on the water. A hotel with an indoor pool. A bed ‘n’ breakfast with modern upgrades. All of these lodgings come with convenience and charm. Most prices are based on the lowest-priced option for one room with two adults and two elementary-aged children (or older). If no children are allowed, we listed the price based on two adults (in case Mom and Dad want a staycation for themselves). 

Budget-Friendly

Hilton Garden Inn

Neighborhood/Address: Arts District, 174 West Street, Annapolis, MD 21401
Price Per Night: $165
Amenities: On-site restaurant, fitness center, pet-friendly, cribs, room service, parking for $35 per day, valet parking for $39. 

Graduate by Hilton

Neighborhood/Address: Arts District, 126 West Street, Annapolis, MD 21401
Price Per Night: $199
Amenities: On-site restaurant, fitness center, pet-friendly, cribs, parking for $35 per day, valet parking for $39. 

Residence Inn by Marriott

Neighborhood/Address: Taylor Avenue near the Naval Academy Stadium, 200 Taylor Avenue, Annapolis, MD 21401
Price Per Night: $222
Amenities: Laundry, in-room kitchen, free hot breakfast, on-site parking for $30 per day.

Annapolitan Experience

Luxury with Perks

The Westin 

Neighborhood/Address: Arts District, 100 Westgate Circle, Annapolis, MD 21401
Price Per Night: $363
Amenities: Indoor pool, on-site restaurant, fitness center, pet-friendly, parking for $37 per day, valet parking for $39. 

Annapolis Waterfront Hotel

Neighborhood/Address: City Dock, 80 Compromise Street, Annapolis, MD 21401
Price Per Night: $399, or $638 for a waterfront view
Amenities: Two on-site restaurants, fitness center, on-site laundry, marinas and boat slips, watercraft rental, pet-friendly, valet parking for $39. 

Leave the Kids at Home

The Annapolis Inn

Children’s Policy: “We do not host any children or guests under the age of 17 years.”
Neighborhood/Address: City Dock, 80 Compromise Street, Annapolis, MD 21401
Price Per Night: $379
Amenities: Each suite is on a separate floor. Complimentary breakfast. 

Reynolds Tavern

Children’s Policy: Overnight guests must be 12+.
Neighborhood/Address: Church Circle, 7 Church Circle, Annapolis, MD 21401
Price Per Night: $478 
Amenities: In-room coffee and tea, discounted parking at Gott’s Court Garage, complimentary full breakfast.

Inn at Horn Point

Children’s Policy: “We gladly welcome well-behaved children over the age of 13. Younger children are welcomed if the entire INN is reserved.”
Neighborhood/Address: Eastport, 534 Burnside Street, Annapolis, MD 21403
Price Per Night: $288
Amenities: There is a “No Breakfast” option for a discounted rate. 

Do

When you enter Annapolis, look at the architecture and streets of the historic district with new eyes. Then, when you embark on any of the activities you planned for the day, you can appreciate the hard work our community puts into the city. Here’s a list of hometown tourist experiences for you to check off.

Explore

• Start at the Visitor’s Center! Let the volunteers give you tips about their favorite things to do. And enjoy the exhibits about what makes Annapolis so special. The building has public restrooms for the kids to use (tell them they just need to try) before you get going to your next activity.
• Visit the ducks and watch the boats go by at City Dock (yes, even with the construction). Pay your respects at the Alex Haley memorial and learn about his life.
• See Annapolis from the water on the Harbor Queen. Wave to everyone out on their own boats and learn about the history of Annapolis and the Naval Academy. Or if you’d prefer, go for a ride on the Water Taxi to get from City Dock to Eastport.

• Check out the charming historic homes on Fleet Street, Pinkney Street, King George Street, and all over downtown.
• Have a family-bonding day as pirates with Pirate Adventures on the Chesapeake.
• Be sure to check out any (or all!) of our local museums, including the Annapolis Maritime Museum, the Banneker-Douglass-Tubman Museum, and the U.S. Naval Academy Museum. Also, check out any of the properties by Historic Annapolis, including the William Paca Home and Gardens, the Museum of Historic Annapolis, and the Hogshead Trade Museum. 

• Don’t forget to visit the Maryland State House! You don’t need tickets to enter and explore early American history.
• For art lovers, check out The Circle Gallery, operated by the Maryland Federation of Art. Then visit galleries including Gallery 57 West, The Annapolis Collection Gallery, or the McBride Gallery. You can also buy from local makers at Annapolis Pottery and Woodcraft Artisans.
• Do some antiquing and vintage shopping at Annapolis Maritime Antiques, All the Rage Vintage, Silk Road Antiques, and Evergreen Antiques & True Vintage.
• There’s plenty of boutique shopping at HERE., Mango & Main, Mantovani Moda, and Stardust Deluxe Boutique.
• And take a break at Old Fox Books to relax and read with a drink from their café. The kids will love their children’s section.
• Don’t be above grabbing some souvenirs at Eagle Souvenirs, A.L. Goodies General Store, and Annapolis Essentials. Wear your Annapolis heart on your sleeve, your mug, or your refrigerator magnet! 
• Later, check out a performance at Annapolis Garden Theatre, The Colonial Players, Maryland Hall, or Rams Head on Stage. 

Eat

The food in Annapolis is world-class (and not just for the crabs). Yes, seafood devotees will want to have some crab cakes, oysters, or rockfish. But there are menus inspired by cuisines from across the U.S. and around the world. Our list prioritizes places that only exist right here in downtown Annapolis. You’re sure to find something to satisfy you here.

Start the Day Off Right

Before you get going with the day’s itinerary, fuel up with breakfast. There are coffee shops, including 49 West Coffeehouse and Curate Annapolis on West Street, and the Eastport-based Oscar’s Coffee. They all have food options, but if you want a bigger breakfast, try Sofi’s Crepes on Dock Street, Bread and Butter Kitchen in Eastport (with lots of vegan options), or locally beloved Lighthouse Bistro on West Street.

Eat Iconic Maryland Seafood

For lunch, stop by Boatyard Bar & Grille in Eastport for some classic seafood options, especially its crab cakes (“All Killer, No Filler”). Unsurprisingly, Sailor Oyster Bar has excellent raw oysters for those who are so inclined. Or just get some seafood appetizers to share at Latitude 38º, such as calamari, crab dip, or steamed mussels. Finally, I’ll recommend Buddy’s Crabs & Ribs. Locals say it’s a tourist trap, but I’ve enjoyed the food and the family-friendly atmosphere. If you’re going to be a tourist, you might as well go for it!

Have a Casual Meal

If you want comfort food for lunch, you can’t go wrong with hometown landmark Chick & Ruth’s Deli. You’re bound to find something you want on their extensive menu, and finish off with a milkshake—which could be normal-sized or one of their six-pound Colossal shakes. Or you can head over to Pip’s Hot Dogs on Dock Street or Potato Valley Café on State Circle.

At the end of the day, relax with dinner outside in the fresh air. Restaurants such as Federal House and Red Red Wine Bar & Bistro have sidewalk seating perfect for people-watching. Or you can head up to Metropolitan Kitchen & Lounge’s rooftop for an intimate, easygoing evening.

Dress Up for a Five-Star Dinner

Enjoy Ice Cream at City Dock

For the kids especially, a trip to Annapolis isn’t complete without grabbing a cone to eat while watching the water. Head to Storm Bros. Ice Cream on Dock Street or to Main Street spots such as Annapolis Ice Cream Company and The Red Bean. 

Finish with a Nightcap

For a parents-only staycation, drinks with a side of music or even just warm conversation will be a perfect way to end an evening in Annapolis. Parley Room and Harold Black have excellent cocktails. Fox’s Den and Forward Brewing serve filling food alongside craft beer. And visit Middleton Tavern for piano tunes on Thursday evenings, and The 1747 Pub has music in its beautiful courtyard. These places offer a chance to relax and enjoy your time together before you get back to the kids.

You don’t have to drive far to get into vacation mode. Unpack your weekend bag in a historic inn, take a walk along the brick streets, and let yourself embrace being a tourist. Spend your time this summer exploring Annapolis, cracking open some crabs, and simply relaxing by the water. You and your family will have a new appreciation and pride for our town. And the best part? You can do it again any time!