Are you planning a trip to Annapolis and wondering what to do in 5 days? Look no further! Our comprehensive guide will help you optimize your Annapolis itinerary and make the most of your trip. Whether you’re interested in history, sailing adventures, local cuisine, or cultural attractions, Annapolis has something for everyone.
Over the next few sections, we will take you on a journey through the best things to do, places to visit, and top attractions in Annapolis. Follow our itinerary, and you’ll leave with unforgettable memories and a newfound appreciation for this charming city.
So, grab a cup of coffee, sit back, and let’s plan your perfect 5-day Annapolis itinerary!
Exploring Annapolis’s Historic Sites
Discover the best things to do, places to visit, and top attractions in Annapolis by immersing yourself in the city’s rich history and exploring its fascinating historic sites. Start with the iconic United States Naval Academy, which serves as the home of the Navy’s undergraduate college and the Naval Academy Museum, showcasing over 150 years of naval history.
Visit the Maryland State House, which was built in 1772 and played a crucial role in the state’s history as the location of legislative and executive power. Learn about Annapolis’s colonial past by exploring the Historic Annapolis District, encompassing four lovely streets and providing a glimpse into the city’s 18th-century history.
Other notable historic sites in Annapolis include the William Paca House and Garden, a National Historic Landmark and former home of William Paca, a signer of the Declaration of Independence, and St. Anne’s Church, originally established in 1692 and one of the oldest churches in continuous use in the United States.
“Immerse yourself in Annapolis’s vibrant history and culture by exploring its historic sites and landmarks.”
Sailing Adventures in Annapolis
Take your Annapolis adventure to the next level by embarking on a sailing trip. The Chesapeake Bay boasts stunning vistas and picturesque coastline that you can discover on a sailing excursion or a chartered boat ride.
Enjoy breathtaking views of the water and the maritime life that thrives in the bay. Sailing is a very popular activity in Annapolis, so you shouldn’t miss the opportunity to experience it. Some of the best Annapolis day trips are sailing excursions that will offer you the chance to get closer to the water and witness its beauty.
Chartering a boat for a day trip is also a great way to explore and appreciate the rich offerings of Chesapeake Bay. You can choose to anchor at a quiet location, swim in crystal-clear water, or enjoy a picnic on your boat – it’s all possible with a chartered boat ride. Sailing is a fantastic activity for anyone looking for adventure and relaxation, and should be a top priority on your Annapolis travel itinerary.
Savoring Local Cuisine in Annapolis
Food lovers, this one’s for you. Annapolis has a thriving culinary scene, with a plethora of restaurants and eateries to explore. From fresh seafood to classic Maryland crab cakes, your taste buds are in for a treat.
For authentic Maryland cuisine, head to the Blackwall Hitch located in the heart of downtown Annapolis. Their crab and corn chowder and jumbo lump crab cakes are a must-try. Another popular destination is the iconic Cantler’s Riverside Inn, located on the shores of Mill Creek. Choose from live crabs, oysters, clams, and other fresh seafood, all while enjoying stunning waterfront views.
If you’re in the mood for upscale dining, visit the renowned Iron Rooster. Known for their all-day breakfast, homemade pop tarts, and chicken and waffles, this restaurant will not disappoint. For an intimate and cozy atmosphere, try the Level Small Plates Lounge. Their charcuterie board and craft cocktails are highly recommended.
Don’t miss out on the opportunity to explore Annapolis’s hidden gem eateries. Grumps Cafe, a local favorite, is known for its breakfast menu and homemade baked goods. Royal Karma offers Indian and Nepalese cuisine, with an extensive vegetarian menu. For something different, try the Phubs, an award-winning Vietnamese restaurant that offers large portions at affordable prices.
“Annapolis’s food scene is a tasty mix of seafood, classic Maryland cuisine, and hidden gem eateries. You won’t regret indulging in the culinary delights of this charming city.”
Day Trips from Annapolis
If you have more time to explore the area, take advantage of the exciting day trips from Annapolis. Discover some of the most beautiful and historic destinations in the region. Unleash your inner adventurer by exploring picturesque lighthouses, quaint towns like St. Michaels and Easton, or enjoy outdoor activities at the nearby parks and nature reserves. Don’t miss out on some of the most memorable experiences just a stone’s throw away from Annapolis.
| Destination | Distance from Annapolis | Highlights |
|---|---|---|
| St. Michaels | 31 miles | Visit the Chesapeake Bay Maritime Museum, explore the charming town, and enjoy a fresh seafood lunch by the waterfront. |
| Easton | 22 miles | Discover the legendary Avalon Theatre, stroll through historic neighborhoods, and enjoy the local cuisine at one of the culinary hotspots. |
| Patapsco Valley State Park | 35 miles | Explore the stunning waterfalls, hike the scenic trails, or enjoy a picnic in the beautiful park. |
| Great Falls Park | 43 miles | Marvel at the breathtaking waterfalls, go kayaking or rock climbing, and enjoy the unparalleled views of the Potomac River. |
| Assateague Island National Seashore | 126 miles | Spot the wild ponies, explore the sandy beaches, and go camping in the natural paradise. |
Take a break from the hustle and bustle of Annapolis and explore the hidden treasures nearby. You won’t regret it!
Enjoying Annapolis’s Water Activities
Make the most out of your Annapolis day trips by exploring the water-related activities in the Chesapeake Bay. Annapolis has a lot of water-based recreational activities, perfect for a family day out or an adventure with friends. Kayaking, paddleboarding, sailing, and boating are some of the top attractions in Annapolis that you can enjoy.
If you are feeling adventurous and want to explore the waters, rent a boat and discover the hidden gems along the coastline. Head to the stunning beaches and soak up some sun while enjoying the picturesque views of the Chesapeake Bay. If you love fishing and crabbing, try your luck and reel in some delicious seafood for a fresh and local meal.
For those who love water sports, kayaking and paddleboarding are excellent options. Glide across the sparkling waters while enjoying the stunning views of the shoreline. Exciting and challenging, these activities promise an unforgettable experience for water enthusiasts.
Whether you want to relax, soak up some sun, or go on an adventure, Annapolis’s water activities have something for everyone.
Exploring Annapolis’s Cultural Scene
Immerse yourself in Annapolis’s vibrant cultural scene. Visit art galleries, museums, and theaters that showcase local talent and historical artifacts. Attend live performances, art exhibitions, or explore the rich heritage of Annapolis.
Take a stroll through the Historic Annapolis District, where you’ll find charming boutiques, specialty shops, and historic landmarks. Shop for unique souvenirs and handmade crafts while admiring the colonial architecture of the buildings.
| Place | Details |
|---|---|
| Maryland Hall for the Creative Arts | Address: 801 Chase St, Annapolis, MD Details: This venue showcases a variety of performances, including concerts, dance performances, and theater productions. Visitors can also take art classes and workshops. |
| Banneker-Douglass Museum | Address: 84 Franklin St, Annapolis, MD Details: This museum is dedicated to preserving the history and achievements of African Americans in Maryland. Visitors can explore permanent and rotating exhibits that showcase the contributions of African American leaders, artists, and activists. |
| Chesapeake Bay Maritime Museum | Address: 213 N Talbot St, St Michaels, MD Details: Take a day trip to St. Michaels and visit this museum that celebrates the maritime heritage of Chesapeake Bay. The museum features exhibits on boat building, navigation, and the ecology of the Bay. Visitors can take boat tours and watch boatbuilding demonstrations. |
Whether you’re interested in history, art, or live performances, Annapolis has something to offer for everyone. Take a break from your Annapolis vacation itinerary and explore the city’s cultural scene.
Shopping and Entertainment in Annapolis
As your 5-day trip to Annapolis wraps up, take some time to enjoy the city’s vibrant shopping and entertainment scene. Annapolis offers an eclectic mix of unique boutiques, shops, and galleries that are perfect for souvenir hunting or gift shopping. Explore the Annapolis City Dock, a picturesque area filled with shops and eateries that offer a breathtaking view of the Chesapeake Bay.
If you’re looking for some entertainment after a long day of sightseeing, Annapolis has plenty to offer. The city is home to a variety of live music venues and theaters that host performances ranging from jazz to classical music. Don’t miss out on the opportunity to catch a show at the Maryland Hall for the Creative Arts or Rams Head On Stage.
With so many options to choose from, it can be hard to decide where to go first. Luckily, Annapolis is a compact city, and most of the attractions are within easy walking distance of one another.
“The Annapolis Arts and Entertainment District is a great place to explore the local arts scene. You’ll find everything from art galleries and studios to theaters and dance companies.”
– Visit Annapolis
Conclusion
Congratulations, you have successfully optimized your 5-day Annapolis itinerary with our comprehensive guide. By exploring the historic sites, indulging in local cuisine, and enjoying various water activities, you have experienced the best of Annapolis. Day trips to nearby attractions, exploring the cultural scene, shopping, and entertainment options have made your trip even more memorable.
We hope our guide has helped you create unforgettable memories on your vacation. Annapolis has a lot to offer, and we hope you have fallen in love with the city’s charms. Don’t forget to share your experience with your friends and family, and don’t hesitate to visit Annapolis again for new adventures.
