Annapolis Neck

Day Trips

Make the most of your day with our curated plans, packed with Annapolis Neck's hidden gems and unique experiences!

day 1
Exploring the Historic Charm
morning
:

Begin your journey by strolling through the historic district, admiring the colonial architecture and vibrant storefronts. Visit the Maryland State House, with its stunning dome and rich history, and take a guided tour to learn about the state's past. Don't forget to stop at a local café for a delicious breakfast featuring fresh, local ingredients.

afternoon
:

After exploring the State House, head to the U.S. Naval Academy for a fascinating tour where you can see cadets in action and visit the beautiful Chapel. For lunch, enjoy seafood at one of the harbor-side restaurants, taking in views of the Chesapeake Bay. Later, take a leisurely walk along the waterfront, soaking up the picturesque scenes of sailboats and historic ships.

evening
:

As the sun sets, enjoy a dinner cruise on the Chesapeake Bay, where you can savor local cuisine while taking in the stunning views and gentle breeze off the water. After dinner, explore the vibrant nightlife around West Street, filled with bars, live music venues, and charming shops. Finish the evening with a relaxing stroll along the docks as the stars begin to sparkle over the bay.

day 2
Nature and Relaxation
morning
:

Start your day with a refreshing hike at Broadneck Park, where you can enjoy serene trails surrounded by lush greenery and wildlife. Bring a packed breakfast to enjoy on the trail or nearby picnic spots, allowing you to embrace nature's beauty. Alternatively, take a leisurely kayak trip around the nearby creeks and coves, offering a unique perspective of the area.

afternoon
:

After your morning adventures, visit Sandy Point State Park for lunch and relaxation on the sandy shores of the Chesapeake Bay. Spend the afternoon swimming, picnicking, or hiking one of the park's many nature trails while enjoying breathtaking views of the bay and the city skyline. Engage in some birdwatching—the park is home to several species of migratory birds.

evening
:

As the day winds down, head to a local seafood restaurant to taste freshly caught crabs and other Bay-inspired dishes. Enjoy live music at a waterfront bar or watch the sunset over the water, providing a perfect backdrop for a memorable evening. Conclude the night with a cozy bonfire on the beach, mingling with fellow travelers and locals under the stars.

day 3
Cultural Immersion
morning
:

Begin your cultural journey by visiting the Hammond-Harwood House, an exemplary colonial home that showcases beautiful architecture and period furnishings. Enjoy a guided tour to appreciate the finer details and historical significance of the house. Afterward, have a leisurely breakfast at a nearby bakery known for its artisanal pastries and freshly brewed coffee.

afternoon
:

Spend your afternoon at the Banneker-Douglass Museum, where you can delve into African American heritage in Maryland through engaging exhibits and displays. Take time to reflect on the significance of the history presented before heading out to a local market for lunch, sampling fresh produce and artisan goods. Visit the nearby galleries and studios, supporting local artists and perhaps picking up a unique souvenir.

evening
:

As the evening approaches, enjoy dinner at one of Annapolis's fine dining establishments known for their innovative cuisine. Afterward, catch a theatrical performance or live show at the Annapolis Opera or the Maryland Theatre, immersing yourself in the local arts scene. End your day with a dessert at a cozy café, enjoying a rich local coffee or a slice of homemade pie.

day 4
Adventure on the Water
morning
:

Start your day with a sailing lesson on the Chesapeake Bay, where you can learn the basics while surrounded by beautiful waters and stunning vistas. Enjoy a light breakfast on the dock before heading out, taking in the crisp morning air and the sounds of the water. This hands-on experience is perfect for both beginners and experienced sailors.

afternoon
:

After your sailing adventure, explore the Maryland Science Center, where you can engage in interactive exhibits and witness an impressive planetarium show. Grab lunch at the center's café and recharge for an afternoon of discovery. Consider renting a paddleboard or jet ski to continue your adventures on the water, feeling the thrill of the waves.

evening
:

As dusk falls, indulge in a seafood feast at a quaint restaurant along the waterfront, where the catch of the day is sure to impress. Seek out a local bar for some craft cocktails, soaking in the lively atmosphere and mingling with friendly locals. As the night progresses, take a night cruise to experience the enchanting sights of the city lights reflecting off the water.

day 5
Historic Landmarks and Local Flavors
morning
:

Kick off your day with a visit to the Chase-Lloyd House, an exquisite example of Georgian architecture, featuring beautiful gardens and historical significance. Afterward, savor breakfast at a nearby diner famous for their hearty portions and classic American fare. Enjoy conversations with locals who share their insights about the area's history and culture.

afternoon
:

Explore the William Paca House and Garden, where you can take a guided tour to learn about the life of one of Maryland's signers of the Declaration of Independence. Spend your lunch in the stunning gardens, relaxing among the blooms before venturing to the nearby Market House for a taste of local food vendors. Engage in casual shopping, where you'll find handmade crafts and unique treasures from local artisans.

evening
:

For dinner, try a cozy bistro that serves a farm-to-table menu featuring local ingredients. As the sun sets, stroll the charming streets of Annapolis, with twinkling lights creating a magical atmosphere. Finally, find a local bar for a nightcap, where you can unwind and reflect on the day's adventures.

day 6
Family Fun and Entertainment
morning
:

Begin your family-friendly day at the Annapolis Maritime Museum, where kids can learn about the rich maritime history through hands-on exhibits and engaging programs. Enjoy a family breakfast at a nearby café, where the menu caters to all ages with appealing selections. Let the kids explore the interactive displays as you enjoy the captivating stories of the bay.

afternoon
:

Visit the local zoo or park for an afternoon filled with outdoor fun—take a picnic lunch along and enjoy time together in nature. Allow the kids to run and explore, and maybe even try a new activity like frisbee or kite flying before heading to a nearby ice cream shop for a cool treat. Keep an eye on the schedule for any special family events or shows happening in town.

evening
:

End your day with a casual dinner at a family-friendly restaurant, where everyone can find their favorite dish on the menu. After dinner, attend a live performance or family movie night hosted in one of the local parks to engage with the community. Conclude this family-focused day with a relaxing walk along the waterfront, sharing stories and laughter about your adventures.

day 7
Gastronomic Experiences
morning
:

Start your day at a local farmer's market, where vibrant stands of fresh produce and homemade goods create a colorful morning atmosphere. Sample artisanal cheeses, fresh fruits, and baked goods while chatting with the friendly vendors. Take the ingredients from your morning stop and plan for a cooking class later in the day.

afternoon
:

Join a culinary tour where you can taste various local dishes, learning about the history and culture behind each one. Enjoy lunch at a well-reviewed restaurant known for its regional specialties and innovative twists on classic recipes. Participate in a hands-on cooking class in the afternoon, where you'll create multiple courses with guidance from a talented local chef.

evening
:

Relish the fruits of your labor with a celebratory dinner, pairing your dishes with suitable wines provided during the class. Find a cozy spot to enjoy a casual after-dinner drink, sampling local craft beers or wines. Reflect on your gastronomic journey while taking a leisurely stroll through the charming streets and waterfront.

day 8
Outdoor Adventures
morning
:

Kick off your outdoor adventure with an exhilarating bike ride along the picturesque trails of the B&A Trail, a 13.3-mile route perfect for all skill levels. Enjoy the calm of the early morning sun as you pedal past stunning landscapes filled with natural charm. Stop at a local café for a hearty breakfast to fuel your journey ahead.

afternoon
:

Take a break from biking to hike at Broadneck Park, exploring the scenic woodland trails and discovering hidden gems within nature. Pack a picnic lunch to enjoy amidst the calming backdrop or discover one of the park's designated areas for dining. As the afternoon sun rises higher, consider jet skiing or paddle boating on the nearby waters for a thrilling experience.

evening
:

After an action-packed day, enjoy a relaxed dinner at a casual outdoor eatery, giving yourself the chance to savor the fresh air. Reflect on your adventures while enjoying a local brew, taking in the sunset views over the bay. End your bustling day with a peaceful evening at a local park or beach, listening to the sounds of nature.

day 9
Art and History
morning
:

Start your day at the Art Farm, engaging in art workshops or browsing the unique galleries that promote local artists. Enjoy breakfast at a nearby café that celebrates the local arts scene, showcasing works from local creators on their walls. This immersive environment sparks creativity while fueling you for the day ahead.

afternoon
:

After breakfast, head to the local art museum, where you can explore rotating exhibits and installations that highlight both local and international artists. Enjoy a leisurely lunch at a nearby eatery where the décor often displays local artwork, continuing the inspiration of the morning. Spend the afternoon exploring historical sites like the Peabody Library, immersing yourself in the history that shapes the community.

evening
:

Conclude your art-filled day with dinner at a restaurant that offers dishes inspired by the local culinary scene, ensuring a delightful experience. After dinner, attend a local art opening or performance that showcases emerging talents, allowing you to enjoy a dynamic art scene. Wrap up with drinks at a gallery space, mingling with artists and art lovers alike.

Discover Annapolis Neck

Read more in our Annapolis Neck 2025 Travel Guide.

Annapolis Neck Travel Guide