New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

5 Days Exploring Annapolis Itinerary

Last updated: 2024 Jul 04

Welcome to Annapolis

Morning

Start your day with a visit to the iconic United States Naval Academy. This prestigious institution offers guided tours that provide insight into the history and traditions of the U.S. Navy. It's a great way to get acquainted with Annapolis' rich maritime heritage. Afterward, enjoy a leisurely stroll along the picturesque waterfront at City Dock, where you can watch boats sail by and take in the charming atmosphere.

Afternoon

In the afternoon, embark on Best of Annapolis Walking Tour. This tour will take you through historic downtown Annapolis, showcasing its colonial architecture and significant landmarks. You'll learn about the city's fascinating history and culture from a knowledgeable guide. After the tour, take some time to explore Main Street's boutique shops and art galleries.

Evening

For dinner, head to O'Learys Seafood Restaurant for some of the freshest seafood in town. Afterward, join Annapolis: Crabtown Boos and Booze Haunted Pub Crawl. This spooky pub crawl combines ghost stories with visits to some of Annapolis' most haunted bars and pubs. It's a fun way to experience the city's nightlife while learning about its haunted past.

Bedtime

Find amazing hotels in Annapolis, Maryland.

Best of Annapolis Walking Tour
Book Now

Annapolis: Crabtown Boos and Booze Haunted Pub Crawl
Book Now

History and Haunts

Morning

Begin your day with a visit to the Maryland State House, the oldest state capitol still in continuous legislative use. Take a self-guided tour of this historic building where George Washington resigned his commission as commander-in-chief of the Continental Army. Next, head over to St. Anne's Church for a moment of reflection in this beautiful 19th-century Episcopal church.

Afternoon

After lunch at Chick & Ruth's Delly, it's time for an adventure with Annapolis: Private Scavenger Hunts. This interactive activity is perfect for families or groups looking for a fun way to explore Annapolis while solving puzzles and uncovering hidden gems around town.

Evening

For dinner, dine at Carrol's Creek Cafe, known for its stunning waterfront views and delicious cuisine. In the evening, delve into more eerie tales with Phantoms of Annapolis Ghost Walking Tour. This ghost walking tour will take you through some of Annapolis' most haunted locations as your guide shares chilling stories from the past.

Bedtime

Find amazing hotels in Annapolis, Maryland.

Annapolis: Private Scavenger Hunts
Book Now

4.67
Phantoms of Annapolis Ghost Walking Tour
Book Now

Maritime Adventures

Morning

Kick off your day with breakfast at Eggcellence Brunchery, then make your way to the Annapolis Maritime Museum & Park. Here you can learn about Chesapeake Bay's maritime heritage through interactive exhibits and displays that highlight local history and ecology.

Afternoon

Have lunch at Boatyard Bar & Grill before heading out on a sailing excursion on Chesapeake Bay with Schooner Woodwind Sailing Cruises (book separately). Enjoy breathtaking views of the bay as you relax on this classic schooner sailboat.

Evening

Wrap up your day with dinner at The Iron Rooster, famous for its comfort food classics served all day long. Spend your evening exploring more local nightlife or simply enjoy a peaceful walk along Spa Creek.

Bedtime

Find amazing hotels in Annapolis, Maryland.

Cultural and Culinary Delights

Morning

Start your day with a visit to the Banneker-Douglass Museum, Maryland's official museum of African American heritage. Here, you can explore exhibits that highlight the contributions of African Americans to Maryland's history and culture. Afterward, take a leisurely walk through the historic district, admiring the well-preserved colonial architecture.

Afternoon

For lunch, head to Mason's Famous Lobster Rolls for a taste of New England right in Annapolis. In the afternoon, join a guided tour at the Hammond-Harwood House. This beautifully preserved colonial mansion offers insights into 18th-century life in Annapolis and features exquisite architecture and period furnishings.

Evening

Dine at Vin 909 Winecafe, known for its farm-to-table cuisine and extensive wine list. After dinner, enjoy a performance at the Annapolis Summer Garden Theatre if it's in season or catch some live music at one of the local bars like Rams Head Tavern. End your evening with a relaxing stroll along Ego Alley to see boats illuminated against the night sky.

Bedtime

Find amazing hotels in Annapolis, Maryland.

Nature and Nautical Fun

Morning

Annapolis: Crabtown Boos and Booze Haunted Pub Crawl - Start your final day with this unique tour that combines ghost stories with visits to some of Annapolis' most haunted bars and pubs. It's a fun way to experience the city's nightlife while learning about its haunted past.

Afternoon

Annapolis: Private Scavenger Hunts - Spend your afternoon on an interactive scavenger hunt around Annapolis. This activity is perfect for families or groups looking for a fun way to explore while solving puzzles and uncovering hidden gems around town.

Evening

Phantoms of Annapolis Ghost Walking Tour - Conclude your trip with this ghost walking tour that takes you through some of Annapolis' most haunted locations as your guide shares chilling stories from the past.

Bedtime

Find amazing hotels in Annapolis, Maryland.