Annapolis, MD

Travel Guide

A busy downtown street at dusk with historic buildings, a church steeple, and American flags.
A busy street with cars, pedestrians, and illuminated buildings at dusk.
A grand hall with high ceilings, ornate columns, chandeliers, and a polished floor.
A brick building with a white door and windows, surrounded by a black fence and trees.
A bustling street lined with shops and flags, including a prominent 'Go Navy' banner.

See sailing regattas, naval officers and red brick colonial mansions in the state of Maryland’s attractive capital city.

Annapolis is a laid-back place of narrow cobblestone streets, 18th-century brick buildings and colonial mansions and a proud naval heritage. Although now home to many high-tech industries, the city has retained its historic charm.

Situated on the south bank of the Severn River, the state capital of Maryland has been the center of marine activities for years. It’s a port and the site of the U.S. Naval Academy.

Annapolis was founded in 1649 by Puritan settlers and renamed Annapolis in 1694 after Princess Anne of Denmark and Norway. For 9 months between 1783 and 1784 it served as the nation’s first peacetime capital after the American Revolutionary War.

Make City Dock your first port of call. It’s the heart of the city’s waterfront. Walk along the promenade to view the boats, peruse the shops and dine in the restaurants and bars. Walk on the dock to see the memorial of Kunta Kinte’s arrival from Africa in 1767. His story was told in Alex Haley’s novel Roots.

The U.S. Naval Academy was founded here in 1845. Within its walls future naval officers undergo 4 years of training. Take a guided tour of the grounds where you’ll learn about the history of the academy and its traditions. Visit the U.S. Naval Academy History Museum and view medals, swords and multimedia presentations that chart the history of sea power and the development of the U.S. Navy.

Gain further insights into Annapolis’s history at Maryland State House, the oldest state house in the United States that’s still in legislative use. Stop by Chase-Lloyd House, the Georgian brick mansion that was constructed for Samuel Chase, one of the signatories to the Declaration of Independence.

Annapolis is the gateway to Chesapeake Bay, and its shoreline is dotted with marinas. Get out on the water with a day cruise or charter your own boat. You can also rent canoes, kayaks and pedal boats. If you don’t want to get on the water you can enjoy it from land by watching one of the sailing races. From the end of April to early September there are sailboat races every Wednesday night. More than 150 boats sail around several markers in the bay before heading for the finish in front of the Annapolis Yacht Club.

Annapolis is less than an hour’s drive from Washington D.C. and is a popular daytrip destination for visitors to the nation’s capital.

Where to stay in Annapolis

Find the best Annapolis areas and neighborhoods for the activities you enjoy most. Learn more about Annapolis
Learn more about Annapolis

Historic District

While visiting Historic District, you might make a stop by sights like Maryland State House and William Paca House.

Eastport

While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Annapolis Harbor.

West Annapolis

When in West Annapolis, you can plan a visit to Navy-Marine Corps Memorial Stadium and Maryland State House, some noteworthy sights in the nearby area.

Murray Hill

While visiting Murray Hill, you might make a stop by sights like Spa Creek and Ballet Theater of Maryland.

Hillsmere

If you're spending some time in Hillsmere, Maryland Quiet Waters Park and Great Frogs Winery are top sights worth seeing.

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
$147 nightly
The price is $167 total per night from Oct 26 to Oct 27
$167 total
Oct 26 - Oct 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
Graduate by Hilton Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
$106 nightly
The price is $121 total per night from Oct 18 to Oct 19
$121 total
Oct 18 - Oct 19
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
$110 nightly
The price is $125 total per night from Oct 25 to Oct 26
$125 total
Oct 25 - Oct 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,008 reviews)
"Clean room. Great breakfast."

Reviewed on Oct 13, 2026

Crowne Plaza Annapolis by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Annapolis MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Annapolis City Dock and Bay Ridge Beach are ...
9.6/10 Exceptional! (19 reviews)
"We had a lovely stay at this charming cottage on the bay. Everything was well maintained, the host provided strong communication, the grounds are beautiful, and our family found the hot tub to be a wonderful place to both relax amidst nature and reconnect . Also our 2 little dogs felt very much at ..."

Reviewed on Aug 3, 2026

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital

Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital

Annapolis MD
Stay at this vacation home in Annapolis. Enjoy a fitness center, laundry facilities, and air conditioning. Popular attractions Annapolis City Dock and Annapolis ...
Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital
Annapolis Condominium in the heart of the historic center

Annapolis Condominium in the heart of the historic center

Annapolis MD
Stay at this condo in Annapolis. Enjoy a garden, laundry facilities, and patios. Our guests praise the helpful staff in our reviews. Popular attractions Annapolis ...
9.8/10 Exceptional! (313 reviews)
"This condo was centrally located in downtown historic Annapolis. It was clean and had all the amenities you’d want - flat screen smart tv; wonderful deck overlooking the city; parking close by; full kitchen and quiet neighborhood."

Reviewed on Sep 27, 2026

Annapolis Condominium in the heart of the historic center
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Annapolis attractions

Things to do

Frequently asked questions

Is Annapolis worth visiting?
Annapolis is worth visiting for its unique attractions, including the historic U.S. Naval Academy and the scenic Sandy Point State Park. Travelers can explore the distinct Historic District, and enjoy diverse dining experiences with options spanning North American and Asian cuisines.
When is the best time to visit Annapolis?
The best time to visit Annapolis is from May through September, when the weather is warm and pleasant, ideal for exploring. For fewer crowds and better value, consider the quieter months of November through February, which offer cooler temperatures and a more relaxed atmosphere.
Where are the best neighborhoods to explore in Annapolis?
The best neighborhoods to explore in Annapolis depend on what you want to see:

  • Historic District is where you can find attractions like Ego Alley, Spa Creek, and the Maryland State House.

What is Annapolis known for?
Annapolis is known for being a UNESCO World Heritage site and home to the U.S. Naval Academy. This riverside city on the Severn River also features Sandy Point State Park and the Chesapeake Bay Bridge. Travelers can experience North American food culture here, in a city named after Anne of Great Britain.
What is a good itinerary length for Annapolis?
A good itinerary length for Annapolis is two to three days to explore the U.S. Naval Academy, the Historic District, and take a walking tour. An extended stay of four to five days allows travelers to also visit Sandy Point State Park, see the Chesapeake Bay Bridge, or enjoy a haunted pub crawl. See Annapolis Activities.
What are the top things to do in and around Annapolis?
Annapolis offers a rich blend of history, natural beauty, and unique local experiences for travelers:

  • Visit the U.S. Naval Academy, a prominent area of interest
  • Take an America 250 Historic Walking Tour of Annapolis to explore its past
  • Explore Sandy Point State Park for outdoor activities and nature
  • Join an Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl for a spooky evening
  • See the Chesapeake Bay Bridge, an iconic landmark.

How do I plan a trip to Annapolis?
To plan your Annapolis trip, focus on the Historic District, including Ego Alley and Spa Creek. Book flights, hotels, and activities like a walking tour or visiting the U.S. Naval Academy in advance. For outdoor plans, such as Sandy Point State Park, have indoor backups ready for weather flexibility.
What cuisines can you find in Annapolis?
In Annapolis, travelers can find New American cuisine, featuring dishes like gourmet burgers, creative small plates, and seasonal entrees. Travelers can also enjoy North American options such as Cajun Creole, alongside Asian (Japanese, Chinese, Thai), Italian, Latin American (Mexican), and European (Mediterranean, French) cuisines.
Can I book a refundable hotel in Annapolis?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Annapolis by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Annapolis with Expedia?
Expedia makes it easier to plan your Annapolis trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Annapolis?
The best choice depends on your travel style. Hotels in Annapolis can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Annapolis trip on Expedia?
Once you've booked your Annapolis trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Annapolis trip?
Expedia offers customer support before, during, and after your Annapolis trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Annapolis?
If it's your first trip to Annapolis, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Annapolis hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Annapolis hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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