Visiting Annapolis in the Summer

Aleena Mehmood2024-05-10

Table of Contents


Annapolis, Maryland's charming capital city, transforms into a vibrant haven during the summer months. Sunshine bathes the historic streets, the Chesapeake Bay beckons with cool breezes, and a calendar brimming with events keeps the energy high. Whether you're a history buff seeking a walk through time, a nature enthusiast craving aquatic adventures, or a gourmand yearning for fresh seafood delights, Annapolis in summer offers an unforgettable experience.

Annapolis View

(Photo credit@TerryGranger/Unsplash)

Annapolis's Rich History

A trip to Annapolis is a journey back in time. Start your exploration at the Maryland State House, the oldest state capitol building in continuous legislative use in the United States. Guided tours unveil the fascinating stories of the signers of the Declaration of Independence who once walked these halls. Delve deeper into the city's maritime heritage with a visit to the Annapolis Harbor. Stroll along City Dock, a hubbub of activity with colorful boats bobbing on the water, or take the Watermark Harbor Cruise. Peek into the shops lining Ego Alley, once a haven for sailors and now a charming district brimming with art galleries and local boutiques.

History Comes Alive with Tripshepherd Tours

Tripshepherd offers a variety of tours designed to unveil the captivating story of Annapolis. Our "Best of Annapolis Tour with Boat Cruise" combines a guided walk through the historic district with a scenic cruise on the Chesapeake Bay, providing a well-rounded perspective of the city. For a deeper historical dive, consider our captivating walking tours, led by knowledgeable guides who bring the past to life.

Setting Sail on Summer Adventures

Annapolis and the Chesapeake Bay are synonymous with water, and summer offers the perfect opportunity to explore this aquatic playground. Set sail on a relaxing harbor cruise and soak in stunning views of the city skyline and the iconic Chesapeake Bay Bridge. Feeling more adventurous? Charter a boat for a day of fishing, kayaking, or paddleboarding. For a unique perspective, visit Thomas Point Shoal Lighthouse, accessible by boat or kayak, and learn about its vital role in maritime navigation.

Hurry up and book your Best of Annapolis Tour for the ultimate Annapolis Summer experience!

Foodie Delights and Summertime Feasts

Annapolis is a haven for food lovers, and summer brings an abundance of fresh, local seafood. Indulge in a traditional Maryland crab feast, a messy yet delightful social experience. Stroll down Spa Creek and savor the vibrant atmosphere, dotted with waterfront restaurants offering delectable dishes with breathtaking views. For a casual treat, grab a scoop of ice cream from a local shop and enjoy it while people-watching on the harbor. A visit to the Annapolis City Market is a must for foodies, with vendors offering everything from fresh produce to artisan cheeses and locally baked treats.

Summer Nights Come Alive with Entertainment

As the sun sets, Annapolis transforms into a stage for live music. Catch a performance at the Rams Head on Stage, a legendary venue that has seen countless musical icons grace its stage. Enjoy open-air concerts in the historic district or head to the Annapolis Harbor for a lively evening cruise with live music and dancing.

Exploring Maryland

Annapolis is an excellent base for exploring the surrounding areas. Take a day trip to explore the rich African American history of Historic Savage Mills. Immerse yourself in the natural beauty of Maryland by visiting Sandy Point State Park, offering pristine beaches, hiking trails, and stunning views of the Chesapeake Bay.


With its rich history, vibrant culture, and stunning natural beauty, Annapolis offers a summer getaway unlike any other. Whether you're seeking historical immersion, aquatic adventures, or a taste of Maryland's culinary scene, Annapolis has something for everyone. Let Tripshepherd be your guide to unlocking the magic of Annapolis this summer with our Annapolis tours.