Annapolis harbor

The historic and charming city of Annapolis is located on the Chesapeake Bay 30 miles east of Washington, D.C. In addition to a vibrant waterfront setting with a wide range of outdoor recreational opportunities, Annapolis offers visitors a glimpse into early American culture and life as well as a rich history dating back to the 17th century.

For visitors to Annapolis who plan to spend 36 hours in the city, there is plenty to see and do. Visitors can tour historic sites such as the Maryland State House and the William Paca House and Garden, stroll along the waterfront, and indulge in local seafood. In addition, visitors to the city may explore the city’s shops and boutiques, attend a festival or event, or take a short drive to nearby attractions such as Washington, D.C., Maryland’s Eastern Shore, or the city’s museums. A weekend getaway or a quick day trip to Annapolis is the perfect destination with so much to see and do.

Planning your visit

Getting the most out of a 36-hour visit to any destination requires advance planning, and Annapolis, Maryland is no exception. A well-planned itinerary can help ensure that travelers make the most of their time and do not miss out on any must-see attractions or experiences while in the city.

Annapolis harbor

Travelers can make informed decisions about what to see and do, as well as where to eat and stay, by conducting research and planning in advance. In this way, you can save time and avoid the stress associated with figuring everything out on the spot. Additionally, planning ahead can enable visitors to secure reservations or tickets for popular attractions or events, which may be difficult to obtain during peak times.

Travelers can make the most of their time in Annapolis by planning an itinerary in advance, allowing them to see and do more, and creating a more enjoyable and memorable visit. You should conduct thorough research before planning a 36-hour visit to Annapolis to ensure that you make the most of your time in this historic and charming city.

Accessibility by foot, car, or public transport

Annapolis is a small and walkable city, so visitors can easily explore many of the top attractions on foot. However, for those who prefer to use a car or public transport, there are options available.

By foot: Visitors can easily explore the historic district of Annapolis on foot. The downtown area is compact and walkable, and visitors can easily access many of the top attractions, restaurants, and shops in the area. The waterfront is also within walking distance of downtown, and visitors can enjoy scenic walks along the harbor and take in the views of the Chesapeake Bay.

By car: While the downtown area of Annapolis is walkable (one of America’s top walkable towns in fact), a car may be necessary for visitors who wish to explore attractions outside the city center, such as the Westfield Annapolis Mall, which is located about 3 miles west of downtown. There are also several parking garages and metered parking spaces available in the downtown area for those who wish to drive.

By public transport: The Annapolis Transit bus system is available for visitors who prefer to use public transportation. The bus system operates several routes throughout the city, including stops at the Navy-Marine Corps Memorial Stadium, the Westfield Annapolis Mall, and the Anne Arundel Medical Center. There is also a free Circulator Trolley that operates downtown, with stops at many of the top attractions and restaurants in the area. Additionally, visitors can take the water taxi from downtown Annapolis to nearby attractions such as the Chesapeake Bay Bridge, the Bay Bridge Marina, and the Kent Island area.

Sample 36-hour itinerary

Day 1:

  • 9:00am: Start the day with breakfast at Chick & Ruth’s Delly, a local favorite that has been serving up classic breakfast fare since 1965.
  • 10:00am: Take a guided tour of the Maryland State House, which served as the nation’s capital from 1783-1784, and see the room where George Washington resigned his commission as Commander-in-Chief of the Continental Army.
  • 12:00pm: Walk over to the Naval Academy and take a guided tour of the stunning campus, including the impressive Chapel, the Crypt of John Paul Jones, and the USNA Museum.
  • 2:00pm: Grab a quick bite to eat at Annapolis Market House, a historic building that houses a variety of food vendors serving everything from sandwiches to sushi.
  • 3:00pm: Head over to the William Paca House and Garden, a beautifully restored Georgian mansion and National Historic Landmark that dates back to the 18th century.
  • 5:00pm: Stroll along the waterfront and enjoy the views of the Chesapeake Bay, then grab a drink and some fresh seafood at one of the many waterfront restaurants and bars.
  • 7:00pm: Take in a show at the Rams Head On Stage, a popular venue that hosts a wide variety of live music and comedy acts.
Annapolis by night.

Day 2:

  • 9:00am: Start the day with a cup of coffee and a pastry at City Dock Coffee, a cozy spot with great views of the harbor.
  • 10:00am: Explore the charming streets and shops of downtown Annapolis, stopping in at the Annapolis Maritime Museum to learn more about the city’s seafaring history.
  • 12:00pm: Grab a casual lunch at Pusser’s Caribbean Grille, a waterfront restaurant that serves up delicious Caribbean-inspired cuisine.
  • 1:00pm: Take a sailboat tour of the Chesapeake Bay, enjoying the views of the city and the bay from the water.
  • 3:00pm: Visit the Banneker-Douglass Museum, a museum that highlights the African American experience in Maryland.
  • 5:00pm: Walk through the Arts District and browse the galleries and shops, then stop in at the Chesapeake Brewing Company for a local craft beer.
  • 7:00pm: End the day with a romantic dinner at Osteria 177, an upscale Italian restaurant that offers a fine dining experience in a cozy atmosphere.

Accommodations in Annapolis


Annapolis has a wide range of hotels, from luxury properties to more affordable options. Many of these hotels are located in or near the downtown area, making them convenient for visitors who want to explore the city’s top attractions.

Bed and Breakfasts

Annapolis is home to several charming bed and breakfasts, many of which are located in historic homes and buildings. Bed and breakfasts offer a more personalized experience than traditional hotels, and are a great option for visitors who want to immerse themselves in the local culture.

Vacation Rentals

Annapolis has a variety of vacation rentals available, including apartments, condos, and homes. These are a great option for visitors who prefer more space and privacy, and who want to feel more like a local during their stay.


Annapolis has a few hostels that offer affordable accommodations for budget-minded travelers. Hostels typically offer shared dormitory-style rooms and common areas for socializing and cooking.


There are several campgrounds located near Annapolis, including state parks and private campgrounds. These are great options for visitors who want to experience the outdoors and enjoy activities such as hiking and kayaking.

Make the most of your 36 hours in Annapolis

  1. If you have only 36 hours in Annapolis, it is imperative that you plan ahead. This will ensure that you will be able to see all the top attractions and experiences. Plan your itinerary based on the things you wish to see and do.

  2. Because much of Annapolis is walkable, it is wise to wear comfortable shoes and clothing. The summer months can be hot and humid, so lightweight and breathable fabrics are recommended. The weather can get chilly in the fall and winter, so it is advisable to dress in layers.

  3. Taste local cuisine: Annapolis is renowned for its delicious seafood and local cuisine, so be sure to try some of the city’s specialties. During their visit, visitors should try regional favorites such as crab cakes, oysters, and rockfish.

  4. Taking a boat tour or water taxi is a great way to experience Annapolis from a different perspective since it is located on Chesapeake Bay. Views of the city and bay can be enjoyed from the water, as well as views of the United States Naval Academy.

  5. During the peak tourist season, some of Annapolis’ top attractions, including the Naval Academy and the State House, may become crowded. Visiting these attractions early in the morning will help you avoid the crowds.

  6. You can enjoy several free activities and attractions in Annapolis, including the Historic District, the Arts District, and the Annapolis City Dock. Visitors who wish to experience the city on a budget should consider these options.

  7. Be sure to stay hydrated: During the summer months, Annapolis can get hot and humid, so you should drink plenty of water to stay hydrated. Sunscreen and a hat should also be worn to for sun protection.


A 36-hour visit to Annapolis, Maryland is a wonderful way to experience the best that this historic city has to offer. During such a visit, visitors can expect to enjoy a wide range of attractions, experiences, and local cuisine even just for a brief period of time.