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Roam Around

9-Day Annapolis Adventure Itinerary

Last updated: 2024 Jun 14

Welcome to Annapolis

Morning

Start your day with a hearty breakfast at Miss Shirley's Cafe, Annapolis. Known for its Southern-inspired breakfast and brunch menu, this spot is perfect for fueling up before a day of exploration.

Afternoon

Embark on the Best of Annapolis Tour. This comprehensive tour will introduce you to the city's rich history and vibrant culture. You'll visit key landmarks and learn fascinating stories about Annapolis' past.

Evening

Dine at Carrol's Creek Cafe, offering stunning waterfront views and delicious seafood. It's the perfect place to unwind after a day of sightseeing.

Bedtime

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Best of Annapolis Tour
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History and Haunts

Morning

Enjoy a leisurely breakfast at Iron Rooster, famous for its all-day breakfast menu. Don't miss their homemade pop-tarts!

Afternoon

Take part in the Phantoms of Annapolis Ghost Walking Tour. This spooky tour will take you through some of the most haunted spots in Annapolis while sharing eerie tales from the city's past.

Evening

Head to Boatyard Bar & Grill for dinner. This casual spot is known for its fresh seafood and lively atmosphere.

Bedtime

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Phantoms of Annapolis Ghost Walking Tour
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Exploring Local Flavors

Morning

Kick off your day with breakfast at Joss Cafe & Sushi Bar. While known for sushi, they also offer delightful breakfast options.

Afternoon

Join the Annapolis Crabtown Boos and Booze Haunted Pub Crawl. This unique experience combines ghost stories with visits to some of Annapolis' best pubs.

Evening

Savor dinner at Lewnes' Steakhouse, renowned for its prime steaks and elegant setting.

Bedtime

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Annapolis Crabtown Boos and Booze Haunted Pub Crawl
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Scavenger Hunts and Scenic Views

Morning

Begin your morning with a delicious meal at Preserve, which offers farm-to-table cuisine with a focus on local ingredients.

Afternoon

Engage in an exciting adventure with the Annapolis Private Scavenger Hunts. It's a fun way to explore the city while solving puzzles and challenges.

Evening

Conclude your day with dinner at O'Learys Seafood Restaurant, where you can enjoy fresh seafood dishes in a cozy setting.

Bedtime

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Annapolis Private Scavenger Hunts
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Walking Tours and Wine

Morning

Start your day with a delightful breakfast at Rams Head Tavern Annapolis. Known for its historic charm and hearty breakfast options, it's a great way to begin your morning.

Afternoon

Take the Best of Annapolis Walking Tour. This tour will guide you through the city's picturesque streets, showcasing its beautiful architecture and historical landmarks.

Evening

Enjoy dinner at Vin 909 Winecafe, a cozy spot known for its excellent wine selection and farm-to-table dishes.

Bedtime

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Best of Annapolis Walking Tour
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Audio Tours and Sushi

Morning

Have breakfast at Iron Rooster again. Their all-day breakfast menu is worth revisiting for another delicious start to your day.

Afternoon

Experience the Annapolis Walking In App Audio Tour in Sailing Capital. This self-guided tour allows you to explore Annapolis at your own pace while learning about its rich maritime history.

Evening

Dine at Joss Cafe & Sushi Bar once more. Their sushi is highly rated and perfect for an evening meal.

Bedtime

Find amazing hotels in Annapolis, Maryland, USA.

Annapolis Walking In App Audio Tour in Sailing Capital
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Ghosts and Seafood

Morning

Begin your day with breakfast at Miss Shirley's Cafe, Annapolis, known for its Southern-inspired dishes that are sure to satisfy.

Afternoon

Revisit the spooky side of Annapolis with the Phantoms of Annapolis Ghost Walking Tour. It's a thrilling way to spend your afternoon if you missed it earlier or want to experience it again.

Evening

Head to O'Learys Seafood Restaurant for dinner. Enjoy their fresh seafood offerings in a cozy atmosphere.

Bedtime

Find amazing hotels in Annapolis, Maryland, USA.

4.67
Phantoms of Annapolis Ghost Walking Tour
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Scavenger Hunts and Fine Dining

Morning

Start your morning with breakfast at Preserve, offering farm-to-table cuisine that highlights local ingredients.

Afternoon

Engage in another round of fun with the Annapolis Private Scavenger Hunts. It's an exciting way to discover more hidden gems around the city.

Evening

Conclude your day with an elegant dinner at Lewnes' Steakhouse, renowned for its prime steaks and sophisticated ambiance.

Bedtime

Find amazing hotels in Annapolis, Maryland, USA.

Annapolis Private Scavenger Hunts
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Farewell Annapolis

Morning

Begin your final day with a hearty breakfast at Iron Rooster. Their all-day breakfast menu and homemade pop-tarts are the perfect way to start your morning.

Afternoon

Spend your afternoon on a relaxing and informative Annapolis Walking In App Audio Tour in Sailing Capital. This self-guided tour allows you to explore the city at your own pace while learning about its rich maritime history.

Evening

For your farewell dinner, head to Carrol's Creek Cafe. Enjoy stunning waterfront views and delicious seafood as you reflect on your memorable trip to Annapolis.

Bedtime

Find amazing hotels in Annapolis, Maryland, USA.