The Best of Annapolis: A Complete Travel Guide for Tourists

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Annapolis, Maryland, located on the beautiful Chesapeake Bay, is a wonderful travel destination in the United States. It is known for its rich history, lively arts scene, and maritime heritage, making it a city that has something to offer for every traveler. Whether you are interested in visiting historical sites or exploring the waterfront, Annapolis guarantees an unforgettable experience.

Annapolis, Maryland, USA downtown view over Main Street with the State House at dawn
Photo 168727231 | Annapolis Maryland © Sean Pavone | Dreamstime.com

This travel guide aims to provide you with all the information you need to fully enjoy your time in Annapolis. From transportation options and top accommodations to must-visit attractions and delicious food recommendations, we have got you covered.

Get ready to discover the charm of Annapolis as you explore its streets and uncover its hidden gems, culinary delights, and cultural experiences. This guide will help you make the most out of your visit and ensure that you don’t miss out on anything worth seeing or doing.

So let’s begin our journey and dive into everything that Annapolis has to offer!

1. Getting to Annapolis

Reaching Annapolis, Maryland is convenient with multiple transportation options available. Whether you prefer traveling by air, road, or rail, you will find suitable choices that align with your preferences.

By Air

If you’re flying in, the closest major airport is Baltimore/Washington International Thurgood Marshall Airport (BWI), which is about 25 miles from downtown Annapolis.

This airport has a wide selection of domestic and international flights, making it a practical choice for travelers.

By Road

Driving to Annapolis is easy because of its well-connected roadways. Major highways such as U.S. Route 50 and Interstate 97 provide direct access to the city. If you’re coming from Washington D.C., it takes about an hour to drive via U.S. Route 50 East. From Baltimore, take I-97 South for a quick 40-minute drive.

By Rail

While there are no direct train services to Annapolis itself, nearby cities such as Baltimore and Washington D.C. have extensive rail networks. Amtrak serves these cities frequently, and from there, you can easily rent a car or use other public transportation options to reach Annapolis.

Public Transportation in Annapolis

Once you’ve arrived in Annapolis, getting around is hassle-free with several public transportation options:

  • Annapolis Transit: The city’s local bus service provides comprehensive routes covering key areas including historic sites and shopping districts.
  • Water Taxi: For a unique experience, consider using the water taxi service that connects various waterfront locations.
  • Ridesharing Services: Uber and Lyft are readily available and offer convenient rides around the city.

With these diverse transportation methods, visiting Annapolis becomes an accessible and enjoyable experience for all types of travelers.

2. Where to Stay in Annapolis

Finding the perfect place to stay can significantly enhance your visit to Annapolis, Maryland. The city offers a variety of neighborhoods, each with its own unique charm and appeal.

Best Neighborhoods to Stay in Annapolis

  • Historic District: Ideal for history buffs wanting to be close to landmarks such as the Maryland State House and the U.S. Naval Academy.
  • Eastport: A vibrant area known for its maritime culture and waterfront dining options.
  • West Annapolis: Offers a quieter atmosphere with quaint shops and less tourist traffic, perfect for a more relaxed stay.

Accommodation Options for Different Budgets

Luxury Hotels and Resorts

  • Annapolis Waterfront Hotel: Located right on the harbor, this hotel offers stunning views of Chesapeake Bay and is within walking distance of major attractions.
  • Graduate Annapolis: Known for its stylish decor and proximity to the U.S. Naval Academy.

Mid-Range Hotels

Budget-Friendly Options

  • Best Western Annapolis: Affordable rates without compromising on comfort, located just minutes from downtown.
  • Red Roof Inn Annapolis: Basic amenities at budget-friendly prices, ideal for travelers looking to save on accommodation costs.

Unique Stays

Bed & Breakfasts

  • Flag House Inn: A charming B&B located just steps from the U.S. Naval Academy, offering personalized service and a cozy atmosphere.

Vacation Rentals

Many homes and apartments are available through platforms like Airbnb or Vrbo, providing flexibility and a home-away-from-home experience.

Choosing where to stay based on your interests and budget can make your visit to Annapolis all the more enjoyable. Whether you’re seeking luxury or looking for budget-friendly options, there’s something for everyone in this historic city.

3. Must-See Attractions and Landmarks in Annapolis

U.S. Naval Academy

Annapolis is home to the prestigious U.S. Naval Academy, a cornerstone of the city’s maritime heritage. Founded in 1845, this institution trains officers for the Navy and Marine Corps and offers tours that provide an in-depth look at its historic campus.

Naval Dress Parade. U.S. Naval Academy Midshipmen in formal dress for parade, Annapolis, Maryland
Photo 23147754 | Annapolis Maryland © Joe Sohm | Dreamstime.com

Highlights include:

  • Bancroft Hall: The largest single dormitory in the world.
  • Naval Academy Chapel: Renowned for its striking architecture and the crypt of John Paul Jones, a Revolutionary War hero.
  • Armel-Leftwich Visitor Center: Start your visit here to schedule guided tours and explore interactive exhibits.

Maryland State House

The Maryland State House stands as a testament to American history.

Bladen street over Maryland State House capitol building and site of many historic events build in 1779 Annapolis MA, USA
Photo 182467092 | Annapolis Maryland © Sergey Novikov | Dreamstime.com

As the oldest state capitol still in continuous legislative use, it boasts several unique features:

  • Historic Significance: It was here that George Washington resigned his commission as commander-in-chief of the Continental Army.
  • Architectural Marvel: The wooden dome of the Maryland State House is a rare architectural feat.
  • Exhibits and Tours: Visitors can explore exhibits detailing the state’s political history and enjoy guided tours for deeper insights.

Smithsonian Environmental Research Center

For those seeking to connect with nature, the Smithsonian Environmental Research Center (SERC) offers a serene escape just outside Annapolis.

Smithsonian environmental research center and garden
Photo: Smithsonian Invironemtal Research Center

This lesser-known gem focuses on environmental studies and provides opportunities to explore diverse ecosystems:

  • Trails and Boardwalks: Wander through scenic trails and boardwalks that traverse wetlands, forests, and marshes.
  • Educational Programs: Participate in educational programs that highlight conservation efforts and environmental research.
  • Interactive Exhibits: Discover hands-on exhibits designed to engage visitors of all ages in understanding ecological systems.

These attractions offer a blend of history, culture, and natural beauty, making them essential stops on any trip to Annapolis.

4. Indulge in the Local Flavors: Where to Eat and Drink in Annapolis

Annapolis has a lively food scene that showcases its famous Chesapeake Bay seafood specialties. The city’s restaurants offer a wide variety of dishes, ensuring there’s something delicious for everyone.

Front of the Iron Rooster in Annapolis, Maryland, USA
Photo: Iron Rooster

Iron Rooster – Known for its comfort food with a twist, Iron Rooster serves up hearty dishes all day long. Their crab cakes and shrimp & grits are must-tries for seafood lovers. Website

Boatyard Bar & Grill – A local favorite, Boatyard Bar & Grill features a nautical theme and an extensive menu focusing on fresh seafood. Enjoy their famous crab cakes or the catch of the day while soaking in the maritime ambiance. Website

O’Learys Seafood Restaurant – For an upscale dining experience, O’Learys offers some of the finest seafood in town. Their menu includes exquisite dishes like lobster risotto and seared scallops, perfect for a special night out. Website

Seafood Specialties

The Chesapeake Bay is at the heart of Annapolis’s food culture. Here are some popular seafood dishes you should try:

  • Crab Cakes: Often considered Maryland’s signature dish, Annapolis crab cakes are made with fresh blue crabs from the bay.
  • Oysters: Enjoy freshly shucked oysters at many local restaurants, often served with classic mignonette or cocktail sauce.
  • Rockfish (Striped Bass): This local fish is commonly featured in various preparations, from grilled fillets to hearty stews.

Casual Eateries

If you prefer a more relaxed dining experience, check out these options:

Chick & Ruth’s Delly – This iconic deli offers generous portions and a wide menu that includes everything from sandwiches to seafood platters. It’s a great place for breakfast or lunch. Website

Cantler’s Riverside Inn – Tucked away from the main tourist areas, Cantler’s is ideal for enjoying steamed crabs by the water. It’s a quintessential Maryland experience that you shouldn’t miss. Website

Sweet Treats

Don’t forget to satisfy your sweet tooth while in Annapolis:

  • Annapolis Ice Cream Company: Treat yourself to homemade ice cream with flavors inspired by local ingredients. Website
  • Kilwins Annapolis: Indulge in a variety of chocolates, fudge, and other sweets that make perfect souvenirs or on-the-go snacks. Website

Exploring these top food spots will enhance your Annapolis experience, allowing you to savor the authentic flavors of Chesapeake Bay seafood right where it’s sourced.

5. Shopping Delights in Annapolis

Exploring the shopping options in Annapolis offers a diverse and delightful experience for visitors. From charming boutiques to expansive malls, this city caters to every shopper’s preferences.

Unique Boutiques

The historic city center is a treasure trove of unique boutiques. Here, you can find:

  • The Lucky Knot: Specializes in nautical-themed apparel and gifts, perfect for those looking to take a piece of Annapolis’s maritime heritage back home. Website

Expansive Malls

For those who prefer a more extensive shopping spree, Annapolis Town Centre and Arundel Mills outlet mall are must-visits:

  • Annapolis Town Centre: This upscale shopping area offers a mix of high-end retailers such as Anthropologie and Lululemon, along with popular dining options like Cooper’s Hawk Winery & Restaurant. Website
  • Arundel Mills Outlet Mall: Located just a short drive from Annapolis, this outlet mall features over 200 stores including Nike Factory Store and Saks Fifth Avenue OFF 5TH, making it a haven for bargain hunters.

Must-Visit Shopping Destinations

In addition to these prime locations:

  • City Dock & Ego Alley: A picturesque waterfront area where you can enjoy shopping at quaint shops while watching boats navigate the harbor.
  • Main Street: The heart of downtown Annapolis boasts an eclectic mix of shops ranging from antique stores to contemporary fashion boutiques.

Shopping in Annapolis is not just about buying items; it’s an immersive experience that lets you soak in the city’s charm and character while finding one-of-a-kind treasures.

Embracing the Culture: Tips for Immersion in Annapolis

Exploring Annapolis means diving into a rich tapestry of culture and history. Here are some essential cultural tips to enhance your experience:

  • Politeness and Respect: Annapolis locals value politeness and respect. Greet people with a smile, and don’t forget to say “please” and “thank you.”
  • Dress Code: While casual attire is common, certain places like the U.S. Naval Academy might require more formal dressing.

Exciting Cultural Events and Festivals

Annapolis hosts numerous cultural events throughout the year, offering a chance to immerse yourself in local traditions:

Black History 365 Collaborations

Understanding the importance of diverse narratives is crucial. The Black History 365 initiative collaborates with local organizations to preserve and celebrate African American heritage. Key highlights include:

  • Educational Tours: Guided tours focusing on significant African American landmarks in Annapolis.
  • Cultural Exhibits: Temporary exhibits showcasing African American art, history, and culture.

Authenticity and transparency are key when engaging with the local culture. Whether attending a festival or exploring historical sites, embracing these cultural tips will enrich your visit to Annapolis.

7. Explore More: Day Trips from Annapolis

Annapolis is surrounded by beautiful landscapes and thrilling activities waiting to be discovered. Here are some day trip ideas that combine outdoor wonders with shopping delights:

1. Quiet Waters Park: Nature Retreat

Located between the South River and Harness Creek, Quiet Waters Park is a paradise for nature lovers.

slides and deck chairs with lush grass at Quiet Waters Park in Annapolis, Maryland, United States
Photo: Quiet Waters Park

This expansive 340-acre park offers a range of attractions:

  • Scenic Trails: Explore six miles of well-maintained paths that wind through forests, meadows, and waterfront areas.
  • Art Gallery: Immerse yourself in the local art scene at the Quiet Waters Park Gallery, showcasing works by talented artists from the region.
  • Kayaking and Canoeing: Rent a kayak or canoe and glide along the peaceful waters of Harness Creek, taking in the serene surroundings.
  • Dog Park: Let your four-legged companion roam freely in one of the park’s two designated dog parks, designed for both small and large breeds.

Quiet Waters Park is an ideal destination for a leisurely picnic or an active day spent outdoors.

2. Westfield Annapolis Mall: Retail Therapy Haven

If you’re in need of some retail therapy, look no further than Westfield Annapolis Mall.

Entrance to the Annapolis mall Westfield in Annapolis Maryland, United States
Photo: Westfield Annapolis Mall

Here’s what you can expect at this bustling shopping center:

  • Wide Range of Retailers: Browse through more than 200 stores featuring popular brands like Apple, Nordstrom, and Anthropologie.
  • Dining Variety: Treat yourself to a delicious meal at one of the mall’s numerous dining options, catering to all tastes and budgets.
  • Entertainment Choices: Catch a movie at Bow Tie Cinemas or engage in friendly competition with arcade games at Dave & Buster’s.

With its diverse offerings, Westfield Annapolis Mall promises an enjoyable experience for shoppers of all kinds.

3. Sandy Point State Park: Beach Bliss

Just a short drive away from downtown Annapolis lies Sandy Point State Park, a haven for beach enthusiasts.

The beach at Sandy Point State Park, in Annapolis, Maryland.
Photo 147462876 | Annapolis Maryland © Jon Bilous | Dreamstime.com

Here’s what awaits you there:

  • Direct Beach Access: Bask in the sun or take a refreshing dip along the sandy shores overlooking the majestic Chesapeake Bay Bridge.
  • Fishing and Boating Opportunities: Bring your fishing gear or launch a boat from one of the park’s ramps to enjoy a day out on the water.
  • Picnic Spots: Make use of the well-equipped picnic areas, complete with grills and tables, for a delightful outdoor meal.

Sandy Point State Park offers the perfect blend of relaxation and recreational activities, accompanied by breathtaking waterfront views.

Exploring these nearby attractions from Annapolis ensures that you get to immerse yourself in both natural wonders and modern conveniences. Each destination has its own charm and provides opportunities for creating unforgettable memories during your visit.

8. Essential Travel Tips for a Seamless Annapolis Experience

Best Time to Visit

Spring and fall are ideal seasons to explore Annapolis. The weather is mild, and the city hosts numerous festivals and events. Cherry blossoms in spring and vibrant foliage in fall enhance the scenic beauty.

Top Tourist Activities

  • Sailing on the Chesapeake Bay: Experience the maritime heritage firsthand with a sailing tour.
  • Historic Tours: Walk through history with tours of the U.S. Naval Academy and Maryland State House.
  • Outdoor Adventures: Kayaking or paddleboarding on the Severn River offers a more active way to enjoy nature.
  • Cultural Immersion: Participate in local events such as the Annapolis Film Festival or arts exhibits at Maryland Hall.

Practical Advice

  1. Getting Around: Use public transportation or rent bikes for an eco-friendly way to explore.
  2. Pack Accordingly: Lightweight clothing and comfortable shoes are essential for walking tours.
  3. Local Etiquette: Engage with locals respectfully; they offer valuable insights into hidden gems.

Annapolis offers a blend of activities catering to diverse interests, ensuring every visitor finds something memorable.

Conclusion

Annapolis, Maryland is an unforgettable destination that seamlessly blends history, culture, and natural beauty. Nestled on the Chesapeake Bay, this charming maritime city offers a rich tapestry of experiences from the historic U.S. Naval Academy to the vibrant Arts District.

  • Historic Charm: Walk the cobblestone streets and explore landmarks like the Maryland State House.
  • Maritime Heritage: Enjoy waterfront views and partake in sailing or kayaking adventures.
  • Culinary Delights: Indulge in Chesapeake Bay seafood at renowned local eateries.
  • Cultural Events: Immerse yourself in local traditions and festivals, celebrating diverse narratives.

Annapolis beckons you to plan your own adventure. Create lasting memories as you uncover the hidden gems and iconic sites in this captivating city. Start your journey today and discover why Annapolis is a must-visit travel destination in the United States.

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