Annapolis

Day Trips

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

day 1
Historic Annapolis Exploration
morning
:

Start your day with a visit to the Maryland State House, the oldest state capitol in continuous use. Take a guided tour to learn about its rich history and architecture.

afternoon
:

Enjoy lunch at a local eatery on Main Street before visiting the U.S. Naval Academy. Take a self-guided tour to admire the stunning campus and its historic buildings.

evening
:

Dine at a waterfront restaurant with beautiful views of the Chesapeake Bay. After dinner, stroll along the docks and enjoy the vibrant atmosphere.

day 2
Sailing on the Bay
morning
:

Start with a hearty breakfast, then head to the Annapolis waterfront for a sailing lesson. Experience the thrill of being on the water while learning the basics of sailing.

afternoon
:

After your sailing adventure, grab lunch at a nearby seafood spot. Spend the afternoon exploring the nearby shops and boutiques for unique souvenirs.

evening
:

Wind down with a sunset cruise around the harbor. Enjoy the breathtaking views and sip on a refreshing drink as the sun sets over the water.

day 3
Art and Culture Day
morning
:

Visit the Maryland Hall for the Creative Arts and explore local art exhibits. Take part in a workshop if time allows to unleash your inner artist.

afternoon
:

Head to the Banneker-Douglass Museum to learn about African American history in Maryland. Break for lunch at a cafe downtown, sampling local flavors.

evening
:

Attend a performance at the Annapolis Symphony Orchestra or a theater show. End the night with dessert at a cozy local cafe.

day 4
Nature and Parks Adventure
morning
:

Begin with a visit to Sandy Point State Park for a refreshing morning hike along the scenic trails. Enjoy the fresh air and beautiful views of the Bay.

afternoon
:

Pack a picnic to enjoy at the park before exploring the nearby Broadneck Park. Engage in outdoor activities like tennis or frisbee.

evening
:

Head back to the city for dinner at a farm-to-table restaurant. Take a leisurely walk along the waterfront to soak in the evening ambiance.

day 5
Taste of Annapolis
morning
:

Start off with breakfast at a local diner famous for its crab cakes. Afterward, take a tour of a crab processing facility to learn about Maryland's crab industry.

afternoon
:

Enjoy a crab feast for lunch at a waterfront restaurant. Spend the afternoon exploring local markets and artisanal shops.

evening
:

Experience a culinary tour that features diverse cuisine throughout Annapolis. Cap off the night with a cocktail at a speakeasy-style bar.

day 6
Beach and Relaxation
morning
:

Spend your morning at Sandy Point Beach, soaking up the sun and relaxing by the water. Bring a book or enjoy some beach games.

afternoon
:

Grab a seafood lunch at a nearby beach shack and then visit the nearby maritime museum. Explore the fascinating exhibits on marine life and preservation.

evening
:

Find a beachside restaurant for a relaxed dinner with ocean views. Enjoy a bonfire on the beach to finish the day under the stars.

day 7
Wellness and Mindfulness Retreat
morning
:

Kick off your day with a yoga class at a local studio. Enjoy the calming atmosphere and refreshing start to your day.

afternoon
:

Pamper yourself with a spa treatment or massage. Grab a healthy lunch at a farm-fresh cafe afterward.

evening
:

Attend a guided meditation session or wellness workshop. Enjoy a light dinner at a health-conscious restaurant in the area.

day 8
Family Fun Day
morning
:

Start with breakfast at a family-friendly restaurant. Then head to the Annapolis Children’s Museum for engaging and interactive exhibitions.

afternoon
:

Enjoy a picnic at Quiet Waters Park, where the kids can explore the trails and playground. Make sure to pack plenty of snacks!

evening
:

End the day with an arcade or bowling trip, combining fun and competition. Choose a casual dining option for dinner where the whole family can relax.

day 9
Local History and Heritage Tour
morning
:

Start your historic day with a guided tour of the US Naval Academy Museum. Learn about naval heritage with interesting artifacts.

afternoon
:

Visit the Hammond-Harwood House to admire its stunning architecture and art collection. Break for lunch in the quaint arts district nearby.

evening
:

Take a lantern-lit historic walking tour through Annapolis. Finish with dinner at a tavern that serves traditional recipes from the colonial era.

day 10
Photography Expedition
morning
:

Begin with breakfast at a cafe known for its aesthetic. Spend the morning capturing stunning shots of the historic landmarks around Annapolis.

afternoon
:

Continue your photographic journey at the local parks and waterfront areas. Join a photography workshop focusing on composition and technique.

evening
:

Showcase your best shots at a local gallery or at a sunset meet-up with fellow photographers. Wrap up the day with dinner at a charming bistro.

Discover Annapolis

Read more in our Annapolis 2024 Travel Guide.

Annapolis Travel Guide