Annapolis

Day Trips

Begin your day with a visit to the Maryland State House, the oldest state capitol still in continuous legislative use. After exploring the impressive architecture and historical exhibits, stroll down Main Street to soak in the charming atmosphere of the historic district. Stop by a local café for a delicious breakfast featuring freshly baked pastries and locally brewed coffee.

Head to the United States Naval Academy, where you can take a guided tour to learn about the history and traditions of this prestigious institution. Marvel at the stunning Chapel and the beautiful grounds while absorbing the rich maritime history of Annapolis. For lunch, enjoy seafood at a waterfront restaurant overlooking the harbor, where you can taste the local specialty of crab cakes.

As the sun sets, take a leisurely stroll along the City Dock, watching the boats gliding in and out of the harbor. Enjoy dinner at a quaint eatery, where you can indulge in fresh catches and Maryland-style dishes. Conclude your evening with a ghost tour that delves into the spooky tales and legends of Annapolis, making for an unforgettable night.

Kick off the day with a hearty breakfast at a popular waterside café, enjoying views of the Chesapeake Bay. Afterward, rent a kayak or paddleboard and explore the tranquil waters, taking in the serene beauty of the surrounding landscape. Keep an eye out for local wildlife, including herons and osprey, as you navigate the calm waters.

Spend the afternoon at the Annapolis Maritime Museum, where you can learn about the region's rich maritime heritage and its connection to the Bay. Participate in interactive exhibits and watch a film about the local ecology while enjoying the scenic views from the museum's waterfront location. For lunch, grab a casual bite at a nearby food truck offering fresh seafood and local fare.

As evening approaches, take a sunset cruise on the Chesapeake Bay, where you can witness the vibrant colors of the sky reflecting on the water. Enjoy a relaxing dinner on board, complete with local seafood dishes and a selection of Maryland wines. After the cruise, unwind at a cozy bar with live music, experiencing the lively nightlife of Annapolis.

Begin your morning at the Banneker-Douglass Museum, where you can learn about the African American heritage of Maryland through engaging exhibits and artifacts. After immersing yourself in history, take a short walk to the nearby St. John's College, known for its beautiful campus and unique curriculum. Grab a coffee at a nearby café, where you can enjoy the buzz of student life.

In the afternoon, visit the historic William Paca House and Garden, where you can explore the beautifully restored 18th-century home and its stunning gardens. Participate in a guided tour to learn about the life of the signatory of the Declaration of Independence and enjoy the serene landscape. For lunch, indulge in a picnic in the gardens, surrounded by blooming flowers and lush greenery.

After a day filled with culture, head to a local theater for an evening performance, whether it be a play, concert, or dance show. Experience the vibrant arts scene of Annapolis while enjoying snacks or drinks from the venue's café. Cap off your night with a leisurely walk back to your accommodation, taking in the sights and sounds of the city at night.

Start your day with a delicious breakfast at a historic inn, where you can savor homemade dishes in a charming setting. Following breakfast, embark on a walking tour of Annapolis, visiting key landmarks such as the Hammond-Harwood House and the Chase-Lloyd House. Take time to admire the exquisite architecture and learn about the stories behind these historic homes.

In the afternoon, head to the Maryland State House for a deeper exploration of its history and significance. Join a guided tour to appreciate its role in American history and the stunning views from its dome. For lunch, stop by a local deli for a classic sandwich paired with a refreshing drink, perfect for recharging after your morning of exploration.

As the evening sets in, enjoy dinner at a renowned restaurant specializing in Maryland cuisine. Savor local dishes while enjoying the cozy ambiance and friendly service. After dinner, take a leisurely stroll along the waterfront, perhaps stopping to listen to live music at one of the outdoor venues.

Breathe in the fresh air as you start your day with breakfast at a local farm-to-table restaurant. Afterward, head to Sandy Point State Park, where you can hike along scenic trails and enjoy views of the Chesapeake Bay. Keep your camera ready to capture the stunning vistas and wildlife that inhabit the park.

Spend the afternoon relaxing on the beach or swimming in the bay, soaking up the sun and enjoying the refreshing waters. Pack a picnic lunch to enjoy at one of the park's scenic picnic areas, surrounded by nature. If you're feeling adventurous, rent a bike and explore the park's extensive trails further.

As dusk approaches, return to Annapolis for dinner at a seafood shack, where you can indulge in steamed crabs and corn on the cob. Experience the local culture as you dine outdoors and listen to the sounds of the Bay. After dinner, head to a nearby rooftop bar for a nightcap, enjoying panoramic views of the city skyline.

Start your day with breakfast at a cozy café known for its artisanal pastries and locally sourced ingredients. After fueling up, visit the ArtWalk in downtown Annapolis, where you can explore galleries featuring local artists and their works. Take your time to appreciate the creativity and talent on display while chatting with the artists themselves.

In the afternoon, attend a hands-on workshop at a local art studio, where you can create your own masterpiece under the guidance of an experienced instructor. Choose from various mediums, including painting, pottery, or photography, to unleash your inner artist. For lunch, enjoy a quick bite at a trendy eatery nearby, featuring dishes made with seasonal ingredients.

As the sun sets, head to a local art gallery for an evening opening reception, where you can mingle with other art enthusiasts and enjoy refreshments. Immerse yourself in the local art scene while appreciating new works and perhaps even purchasing a piece to take home. End your night with a stroll through the illuminated streets of Annapolis, reflecting on the creative experiences of the day.

Kick off your culinary adventure with a brunch at a popular restaurant known for its innovative takes on classic dishes. After brunch, join a guided food tour that will take you through the best eateries and specialty shops in Annapolis. Sample local treats, from fresh seafood to artisan chocolates, as you learn about the culinary history of the area.

Continue your food exploration in the afternoon by visiting local markets, picking up fresh ingredients and handmade goods to take home. Discover unique spices and specialty items that can add a taste of Annapolis to your own kitchen. For lunch, enjoy a gourmet sandwich or salad from a food stall while mingling with locals at the market.

As evening falls, treat yourself to a special dinner at one of Annapolis's renowned fine dining establishments, where you can savor multi-course meals crafted from local ingredients. Pair your meal with exquisite wine selections to enhance the flavors of your dishes. After dinner, consider joining a dessert tour, stopping at various bakeries for sweet treats to conclude your culinary experience.

Begin your day with a hearty breakfast at a local diner, filling up on classic American fare. After breakfast, head to a sailing school where you can take a lesson or rent a sailboat to explore the beautiful Chesapeake Bay. Feel the wind in your hair as you learn the basics of sailing while enjoying the stunning views of the water and coastline.

Spend the afternoon sailing at your leisure, taking in the picturesque scenery and perhaps even spotting some dolphins or other wildlife. Anchor at one of the nearby islands for a picnic lunch on the beach, surrounded by nature and serenity. After your meal, take a dip in the refreshing waters or simply relax on the sand.

As the sun sets, make your way back to Annapolis, returning your sailboat and reflecting on the day’s adventures. Treat yourself to dinner at a restaurant known for its seafood, celebrating your successful day on the water. Finish off with a nightcap at a cozy bar overlooking the harbor, relishing the peaceful ambiance.

Start your morning with breakfast at a historic inn, enjoying the charm of the past. Head to the Annapolis Historic District to witness a reenactment of a significant historical event, immersing yourself in the stories of the people who shaped the city. Engage with actors in period costumes, gaining a deeper understanding of life in colonial America.

In the afternoon, visit a local festival or artisan market if your visit coincides with one, filled with handmade crafts, local food vendors, and live entertainment. Explore the stalls and interact with local artisans, learning about their crafts and the inspiration behind their work. Enjoy lunch at one of the food stalls, sampling various regional dishes.

As the day winds down, enjoy dinner at a restaurant that hosts live music, allowing you to unwind with good food and entertainment. Savor dishes inspired by local ingredients, soaking in the lively atmosphere. After dinner, take one last stroll through the streets of Annapolis, enjoying the blend of history and modern charm before your trip concludes.