The Sailing Capital of the U.S. Is a Perfect East Coast Getaway — With Historic Charm, Tasty Seafood, and Scenic Harbor Views

Maryland brims with charm and history. Nestled on the East Coast, it’s known for its stunning waterfronts and delicious seafood. Crabbing and sailing are local pastimes, thanks to the Chesapeake Bay.

As one of the original 13 colonies, Maryland played a key role in the nation’s early days. In 1791, it donated land to form Washington, D.C. This gesture highlights its historical significance.

Annapolis, Maryland’s capital, captures the state’s essence perfectly. This city hosts the prestigious U.S. Naval Academy and features a delightful, walkable downtown. Its cobblestone streets and historic buildings transport visitors back in time.

Sailing is central to Annapolis life, with regattas and boat shows filling the calendar. The city’s vibrant waterfront is perfect for a leisurely stroll or dining on fresh seafood.

Annapolis blends history, culture, and maritime adventure. Whether you’re exploring historic sites or enjoying a day on the bay, it offers a rich and engaging experience.

Best Things to Do in Annapolis

Annapolis, with its rich history, tasty seafood, and scenic harbor views, is a perfect East Coast getaway. Whether exploring historic sites or enjoying a day on the water, there’s something for everyone.

Explore the U.S. Naval Academy: Visit the prestigious U.S. Naval Academy. Take a guided tour to learn about its history and significance. Marvel at the impressive architecture and serene grounds.

Stroll through Historic Downtown: Walk along the cobblestone streets of downtown Annapolis. Enjoy the charming colonial buildings and vibrant shops. Stop by cafes and boutiques for a unique experience.

Visit the Maryland State House: Step into history at the Maryland State House. It’s the oldest state capitol in continuous legislative use. Admire its beautiful dome and learn about its role in American history.

Enjoy the Waterfront: Annapolis is known for its scenic harbor views. Take a leisurely stroll along the waterfront. Watch boats sail by and soak in the picturesque scenery.

Go Sailing: Annapolis is the sailing capital of the U.S. Charter a boat or join a sailing tour. Experience the thrill of sailing on the Chesapeake Bay.

Tour the Banneker-Douglass Museum: Learn about African American history at this museum. Discover inspiring stories and significant artifacts. It’s a must-visit for history enthusiasts.

Attend a Festival: Annapolis hosts numerous festivals throughout the year. Enjoy the Annapolis Boat Shows, seafood festivals, and more. These events offer fun and entertainment for all ages.

Best Time to Visit Annapolis

Spring and fall are the best times to visit Annapolis. In spring, the city blooms with vibrant flowers. The weather is mild, perfect for outdoor activities. You can enjoy the annual Annapolis Spring Sailboat Show in April.

Fall offers crisp air and beautiful foliage. The Annapolis Boat Shows in October attract sailing enthusiasts. Fall is also great for exploring historic sites and enjoying waterfront dining.

Summer is lively with festivals and events. However, it can be hot and crowded. Winter is quieter but offers holiday charm and off-season rates.

Overall, Annapolis shines year-round. Whether you’re sailing, exploring history, or savoring seafood, there’s always something to enjoy. Plan your visit around the activities you love for the best experience.

Where To Stay in Annapolis

Annapolis offers a variety of accommodations to suit every traveler. From waterfront luxury to historic charm, there’s a perfect place for everyone. Whether you prefer a room with a view of the harbor or a cozy historic inn, you’ll find comfort and hospitality in Annapolis.

The Annapolis Waterfront Hotel

The Annapolis Waterfront Hotel offers stunning harbor views. Located right on the waterfront, it provides easy access to downtown attractions. Guests enjoy luxurious rooms, a fitness center, and an on-site restaurant. The hotel’s nautical decor and friendly staff make for a memorable stay.

Historic Inns of Annapolis

Historic Inns of Annapolis combines three charming properties: the Maryland Inn, the Governor Calvert House, and the Robert Johnson House. These inns offer a unique blend of historic charm and modern amenities. Each property features beautifully restored rooms, elegant furnishings, and convenient locations near key attractions. Guests appreciate the cozy atmosphere and personalized service.

The Westin Annapolis

The Westin Annapolis is perfect for those seeking comfort and convenience. Located in the heart of the city, it’s close to shopping, dining, and the U.S. Naval Academy. The hotel features spacious rooms, a fitness center, and an indoor pool. The on-site restaurant serves delicious local cuisine. Guests love the Westin’s modern amenities and attentive service.

Where to Eat and Drink in Annapolis

Annapolis offers a diverse culinary scene. From hearty breakfasts to fresh seafood and fine wines, there’s something for everyone. Enjoy the local flavors and warm hospitality at these top spots.

Iron Rooster

Iron Rooster is a must-visit for breakfast lovers. This cozy spot serves breakfast all day, with a menu full of comfort food. Try their famous homemade Pop-Tarts and delicious chicken and waffles. The friendly atmosphere and hearty meals make it a favorite among locals and visitors.

Cantler’s Riverside Inn

For a true taste of Maryland, head to Cantler’s Riverside Inn. Located by the water, it’s famous for its fresh seafood. Enjoy steamed crabs, oysters, and other seafood delights. The rustic setting and waterfront views provide an authentic and relaxed dining experience.

Vin 909 Winecafe

Vin 909 Winecafe is perfect for a casual yet refined meal. This charming eatery offers a seasonal menu with local ingredients. Pair your meal with a selection from their extensive wine list. The wood-fired pizzas and creative small plates are a hit with guests. The cozy atmosphere and excellent service ensure a delightful dining experience.

Getting There

Reaching Annapolis is easy and convenient. Fly into Baltimore/Washington International (BWI) Airport, just 30 minutes away. Rent a car or take a shuttle from the airport. Annapolis is also accessible by car via US Route 50.

For a scenic arrival, consider coming by boat. The city’s harbor welcomes sailors with open arms. Once in Annapolis, use local transit or explore on foot. The city is compact and walkable. Enjoy the charming streets and historic sites as you stroll. Annapolis is the perfect blend of accessibility and adventure.

Final Thoughts

Annapolis, the Sailing Capital of the U.S., captivates visitors year-round. Whether you’re exploring cobblestone streets, enjoying fresh crab cakes, or sailing the Chesapeake Bay, Annapolis promises memorable experiences. Its rich history, vibrant culture, and welcoming atmosphere make it an ideal destination. Plan your visit and discover why this charming city is a beloved destination for both relaxation and adventure.