Annapolis trips and vacations

With a rich maritime heritage, Annapolis proudly calls itself ‘America's Sailing Capital.’ It's home to the United States Naval Academy and Chesapeake Bay, a sailing playground. Maryland is one of the original 13 colonies, so your vacation in Annapolis will give you a glimpse into America's storied past. And when the history lesson is over? Indulge in the bay’s famous blue crabs and unwind on sandy beaches.

Annapolis: Know before you go

Language

English

Currency

United States dollar ($)

Time zone

UTC-5 (EST) and UTC-4 (EDT)

High season

June – August

Low season

January – February

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The best neighborhoods in Annapolis

Downtown

Experience the city’s history in Downtown Annapolis. Step out of your hotel and stroll down streets lined with 300-year-old red-brick buildings. Visit the Maryland State House, the oldest US state capitol still in use. Check out the United States Naval Academy, which is open to the public, before exploring historic ships in Annapolis Harbour. You can even stay in inns that were once regular stops for signers of the Declaration of Independence.

Good for: History, architecture, harbor

Eastport

Take a water taxi across Annapolis Harbour and you’ll find yourself among the waterfront developments of Eastport. Dine out with a view of Chesapeake Bay from the marina, where you can try Eastport’s renowned oysters in some of the city’s best seafood restaurants. Rent a canoe or kayak, or learn to sail at the Eastport Yacht Club. The area is also home to Annapolis Maritime Museum & Park.

Good for: Waterside dining, seafood, water sports

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West Annapolis

To the northwest of the historic city center, West Annapolis is an oasis of leafy streets and beautiful scenery. There aren’t many big hotels in this neighborhood, so it’s a great place to stay if you’re looking for a more local experience. You’ll find suburban vacation homes to rent in this quiet and exclusive part of the city overlooking the River Severn.

Good for: Riverside views, community feel, vacation homes

Things to do in Annapolis

Annapolis

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Places to eat

From blue crab to rockfish, Chesapeake Bay serves up a seafood bounty and Annapolis restaurants proudly present it. Head to Severn Avenue in Eastport (also known as ‘Restaurant Row’) to feast on crab cakes, lobster rolls and freshly shucked oysters. Rather a juicy piece of ribeye? This popular waterfront strip has steakhouses too.

Shopping

Main Street was graced in centuries past by legendary American figures like George Washington and Benjamin Franklin. These days, the city’s most historic thoroughfare is where you’ll find some of the best shopping. Browse for your next yachting outfit in boutiques, pick up nautical-inspired art or grab a souvenir from a gift shop. Annapolis Harbour Center also has a good mix of shopping.

Beaches

Annapolis isn’t directly on the coast, so it doesn't have beaches in the traditional sense. However, Chesapeake Bay and its tributaries have some great spots for swimming and water sports. Sprawl out on the beach of Sandy Point State Park, across the Chesapeake Bay Bridge. Mayo Beach Park on the South River also has a sandy stretch that’s popular with families.

FAQs about Annapolis vacations

How much is it to go on vacation to Annapolis?

Your city break in Annapolis can vary in price based on anything from where you stay to your travel dates. To find the best deals on Annapolis flights and hotels, try to have flexible departure dates and look out for sales and discounts.

What language is spoken in Annapolis?

English is what you'll hear the most while you're here. Learn a few local expressions or greetings during your city break in Annapolis and you'll blend right in.

What is the hottest month in Annapolis?

With temperatures hitting a maximum of 86ºF, July is the warmest month in Annapolis.

What is the rainiest month in Annapolis?

With around 5.5 inches of rainfall, July is the rainiest month. If you're taking your Annapolis vacation then, it's a good idea to have a few indoor activities in mind. Dine at one of the best spots in town, check out an art gallery, or indulge in a shopping spree.

What is the coldest month in Annapolis?

Plan your Annapolis vacation for January and you'll be there when the weather is at its coolest. 25ºF is as cold as the city gets.

Is Annapolis a good vacation destination?

No matter how many times you visit, this city always has something new to offer. If sightseeing is on your list of things to do in Annapolis, be sure to include ARTFX Gallery of Fine Crafts and Arts and Annapolis Collection Gallery.

What currency is used in Annapolis?

While on your trip to Annapolis, you'll be using the United States dollar (USD) for all your expenses. You may want to carry a mix of cards and cash to avoid any issues with paying.

When is the best time to visit for a vacation in Annapolis?

Many sailing events and races take place during the peak sailing season, making it a great time for an Annapolis vacation. The season kicks off in April with the Spring Sailboat Show and continues through summer.

How many days do you need for a trip to Annapolis?

That depends on where you're arriving from and the types of activities you plan to fill your trip to Annapolis with. Three to five days is plenty of time to visit the leading sights if you live close by. If you're traveling from farther afield, you'll want to make the most of every day. Stay at least a week to take in the highlights and then venture beyond the city.

Is it safe to travel to Annapolis on a vacation?

The city is generally considered a safe destination for travelers, so you can plan a trip to Annapolis without any particular concern. The city has a low crime rate for Maryland.

Are vacations in Annapolis good value?

For the best value on your Annapolis holiday, aim to visit outside of the peak summer season and major events. These include the Naval Academy’s Commissioning Week, which involves graduation and swearing-in ceremonies held in late spring, and the country’s biggest boat shows in October.