Parole

Day Trips

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

day 1
Exploring Historic Center
morning
:

Start your day with a visit to the historic Annapolis City Dock, where the charm of colonial architecture meets the serene waters of the harbor. Enjoy a leisurely breakfast at a local café, sampling fresh pastries and coffee while taking in the bustling atmosphere. Spend some time walking along the waterfront, admiring the boats and the vibrant energy of the morning.

afternoon
:

After lunch, dive into the rich history of Annapolis at the Maryland State House, the oldest state capitol still in continuous use. Explore the exhibits and learn about the pivotal role this city played in American history. Take a stroll through the nearby Historic District, where cobblestone streets lead you to quaint shops and galleries.

evening
:

As the sun sets, head to a waterfront restaurant for dinner, savoring local seafood dishes while enjoying stunning views of the harbor. Afterward, take a leisurely walk along the water, perhaps catching a glimpse of the Chesapeake Bay Bridge lit up against the night sky. End your evening with live music at a local venue, immersing yourself in the vibrant culture of the area.

day 2
Chesapeake Bay Adventures
morning
:

Begin your day with an exciting kayak tour in the Chesapeake Bay, paddling through serene waters surrounded by lush landscapes. The morning light glistening on the water makes for a picturesque start as you navigate through the tranquil coves. Keep an eye out for local wildlife, including herons and otters, making this a unique experience.

afternoon
:

After your kayaking adventure, enjoy a picnic lunch at Sandy Point State Park, where you can relax on the beach or take a short hike on the nature trails. Spend the afternoon basking in the sun, swimming, or simply enjoying the scenic views of the bay. Consider renting a bike to explore more of the park's extensive trails.

evening
:

Wrap up your day with a sunset cruise on the bay, where you can soak in breathtaking views as the sky transforms with vibrant colors. Enjoy light refreshments on board while listening to the soothing sounds of the water. This serene experience is the perfect way to reflect on your day amidst the beauty of nature.

day 3
Cultural Immersion at Museums
morning
:

Start your day at the Banneker-Douglass Museum, dedicated to preserving and promoting the history of African Americans in Maryland. Engage with interactive exhibits and guided tours that bring the stories of the past to life. The museum's rich narratives will captivate your interest and deepen your understanding of the local culture.

afternoon
:

Next, head to the United States Naval Academy Museum to explore the fascinating history of the naval forces. Discover artifacts, photographs, and exhibits that showcase naval traditions and innovations over the years. Afterward, enjoy lunch at a nearby eatery, sampling some local favorites.

evening
:

In the evening, attend a performance at the Maryland Hall for the Creative Arts, where local artists showcase their talents through music, dance, and visual art. This vibrant venue offers a taste of the local arts scene and an opportunity to connect with the community. Finish the night with a stroll through downtown Annapolis, appreciating the lively atmosphere and perhaps stopping for dessert at a local ice cream shop.

day 4
Nature Hiking and Exploration
morning
:

Start your adventure with a hearty breakfast before heading to Broadneck Park for a morning hike through its beautiful trails. The park features diverse landscapes, including wooded areas and open fields, making it perfect for nature lovers. Breathe in the fresh air as you enjoy the sounds of chirping birds and rustling leaves.

afternoon
:

After your hike, take a short drive to the scenic Broadneck Park Nature Center, where you can explore educational exhibits about local ecology. Participate in a guided nature walk, learning about the flora and fauna that thrive in this region. Enjoy a packed lunch in the park, surrounded by the beauty of nature.

evening
:

Conclude your day with a visit to the nearby Severn River, where you can relax by the water's edge as the sun sets. Consider bringing a book or simply take in the tranquil surroundings while enjoying a light dinner at a riverside restaurant. The evening offers a peaceful end to an adventurous day outdoors.

day 5
Culinary Delights and Wine Tasting
morning
:

Kick off your culinary adventure with a breakfast class at a local cooking school, where you can learn to make a classic Maryland crab cake. The hands-on experience allows you to immerse yourself in the local cuisine while bonding with fellow food lovers. Enjoy your creations alongside fresh fruit and locally sourced coffee.

afternoon
:

After the cooking class, visit a local farmers market to explore fresh produce and artisanal goods. Sample homemade jams, baked goods, and local cheeses while interacting with farmers and vendors. Following your market adventure, head to a nearby winery for an afternoon of wine tasting, learning about the winemaking process and savoring fine local wines.

evening
:

In the evening, indulge in a gourmet dinner at one of Annapolis' renowned restaurants, where you can savor dishes crafted from locally sourced ingredients. Pair your meal with the perfect wine chosen by the knowledgeable staff. Finish the night with a nightcap at a cozy bar, reflecting on the culinary delights you experienced throughout the day.

day 6
Historical Landmarks and Tours
morning
:

Begin your day with a visit to the William Paca House and Garden, where you can learn about the life of this Founding Father. Explore the beautifully preserved historic house and stroll through the stunning gardens, designed in the 18th-century style. The tranquil environment provides a perfect backdrop for a morning of exploration.

afternoon
:

After lunch, take a guided walking tour of the historic district, where a knowledgeable guide will share intriguing stories about Annapolis' past. Visit prominent landmarks, including St. Anne's Church and the Maryland State House, while learning about the city's colonial heritage. The tour will provide a deeper appreciation for the architecture and history surrounding you.

evening
:

As night falls, enjoy a dinner cruise on the Chesapeake Bay, where you can appreciate the stunning skyline of Annapolis illuminated at night. The gentle rocking of the boat and the soft sounds of live music create a perfect ambiance for a memorable evening. Conclude your day with a leisurely walk along the dock, reflecting on the rich history you've uncovered.

day 7
Outdoor Sports and Recreation
morning
:

Kickstart your day with a refreshing morning jog along the scenic trails of the Annapolis Greenway, surrounded by nature's beauty. The crisp morning air invigorates you as you pass by picturesque views of the water and lush greenery. This active start prepares you for an exciting day of recreation.

afternoon
:

After your run, spend the afternoon enjoying outdoor sports at the nearby Broadneck Park, where you can play a game of tennis or join a friendly match of soccer. The park's facilities cater to various sports, making it a perfect spot for both relaxation and activity. After some fun in the sun, grab lunch at a local café or pack a picnic to enjoy in the park.

evening
:

As the day winds down, unwind with a leisurely bike ride along the scenic shoreline, enjoying the cool evening breeze. Stop at a local park to watch the sunset over the water, providing the perfect backdrop for reflection and relaxation. Cap off your evening with a dinner at a local grill, where you can savor hearty American classics.

day 8
Shopping and Local Artisans
morning
:

Start your shopping adventure in downtown Annapolis, where unique boutiques and local artisans await. Stroll through the charming streets and browse through shops selling handmade crafts, jewelry, and clothing. Take your time to find that perfect souvenir or gift that captures the essence of your trip.

afternoon
:

After a morning of shopping, enjoy lunch at a nearby café, then visit the Art Gallery of Annapolis to appreciate local artwork. The gallery showcases a variety of pieces, from contemporary to traditional styles, providing insight into Maryland's art scene. Engage with local artists and perhaps purchase a piece that speaks to you.

evening
:

As the day comes to a close, attend a local craft fair or art market, where you can meet artists, enjoy live demonstrations, and shop for unique handmade items. The lively atmosphere offers a glimpse into the creative community in Parole. Finish your evening with a casual dinner at a trendy eatery, celebrating your finds from the day.

day 9
Scenic Drives and Water Views
morning
:

Begin your day with a scenic drive along the Chesapeake Bay, taking in breathtaking views of the water and coastal landscapes. Stop at various lookout points to capture stunning photographs and enjoy the serenity of the bay. This leisurely drive sets a relaxing tone for the day ahead.

afternoon
:

After your drive, visit the picturesque town of Cape May, where you can enjoy lunch at a quaint waterfront restaurant. Explore the charming streets lined with Victorian-style homes and unique shops. Consider renting a bike to explore more of the area, including the beautiful beaches.

evening
:

As the sun sets, return to Annapolis for a farewell dinner at a popular seafood restaurant, where you can indulge in the freshest catches of the day. Reflect on your journey while enjoying the lively atmosphere and perhaps some live music. Complete your trip with a night walk along the harbor, soaking in the beautiful views and memories made.

Discover Parole

Read more in our Parole 2025 Travel Guide.

Parole Travel Guide