New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Historic and Culinary Delights of Annapolis Itinerary

Last updated: 2024 Jun 14

Sailing Through History and Seafood Delights

Morning

Start your day with a delightful breakfast at Iron Rooster, known for its delicious homemade pop tarts. Afterward, immerse yourself in Annapolis' maritime history with the Annapolis Walking In App Audio Tour in Sailing Capital. Explore the charming streets at your own pace.

Afternoon

For lunch, savor the fresh seafood at Carrol's Creek Cafe with a view of the water. Afterward, take a relaxing sail on the Chesapeake Bay with the 90-minute Annapolis Private Scavenger Hunts. Enjoy the sea breeze and the beautiful views of the city.

Evening

In the evening, experience a true Annapolis tradition with dinner at Cantler's Riverside Inn, a local favorite for steamed crabs. Afterward, take a leisurely stroll along the waterfront and enjoy the maritime atmosphere.

Bedtime

Find amazing hotels in Annapolis.

Annapolis Walking In App Audio Tour in Sailing Capital
Book Now

Annapolis Private Scavenger Hunts
Book Now

Ghosts, Galleries, and Gastronomy

Morning

Enjoy a hearty breakfast at Miss Shirley's Cafe, Annapolis, known for its Southern comfort food. Then, brace yourself for a spooky adventure on the Phantoms of Annapolis Ghost Walking Tour. Explore the haunted history of the city.

Afternoon

For lunch, head to The Point Crab House & Grill for a taste of Maryland's famous crab cakes. Afterward, spend the afternoon visiting the art galleries and boutiques in the historic district.

Evening

Conclude your Annapolis experience with a fine dining experience at Lewnes' Steakhouse, a local landmark known for its aged prime beef. Raise a toast to your time in the sailing capital of the world.

Bedtime

Find amazing hotels in Annapolis.