New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Free AI trip planner

Annapolis and Chesapeake Beach Delights

Annapolis and Chesapeake Beach Delights Itinerary

Last updated: 2024 Jun 14

Waterfront Wonders and Haunted History

Morning
Start your day with a delightful breakfast at 208 Talbot, known for its charming ambiance and delicious dishes. Afterward, take a leisurely stroll along the waterfront and enjoy the serene views.
Afternoon
For lunch, savor the fresh seafood at The Crab Claw Restaurant, a local favorite. Afterward, immerse yourself in the haunted history of Annapolis with the Annapolis Crabtown Boos and Booze Haunted Pub Crawl. Explore the city's spooky side while enjoying some drinks.
Evening
In the evening, dine at Bistro St. Michaels, a cozy spot with a great selection of dishes. Take a relaxing walk after dinner and enjoy the peaceful atmosphere of the town.
Bedtime
Find amazing hotels in Wade's Point, Maryland, USA.
Visit Annapolis Crabtown Boos and Booze Haunted Pub Crawl in Wade's Point, Maryland, USA

Annapolis Crabtown Boos and Booze Haunted Pub Crawl

Book Now
next arrow

Annapolis Exploration and Scavenger Hunt

Morning
Enjoy a delicious breakfast at Ava's Pizzeria & Wine Bar before embarking on the Annapolis Private Scavenger Hunts. It's a fun and interactive way to discover the hidden gems of Annapolis.
Afternoon
For lunch, head to Limoncello Italian Restaurant & Wine Bar for authentic Italian cuisine. Afterward, continue your exploration of Annapolis with the Best of Annapolis Walking Tour. Learn about the city's rich history and architecture.
Evening
Indulge in a fine dining experience at Miles River Yacht Club, known for its elegant setting and exquisite cuisine. After dinner, take a leisurely evening stroll along the waterfront.
Bedtime
Find amazing hotels in Annapolis, Maryland, USA.
Visit Annapolis Private Scavenger Hunts in Annapolis, Maryland, USA

Annapolis Private Scavenger Hunts

Book Now
Visit Best of Annapolis Walking Tour in Annapolis, Maryland, USA

Best of Annapolis Walking Tour

Book Now

Chesapeake Beach Relaxation and Guided Tours

Morning
Start your day with a hearty breakfast at St. Michaels Crab & Steak House, a local gem. After breakfast, take a scenic drive to Chesapeake Beach and enjoy the coastal views.
Afternoon
For lunch, try the seafood specialties at Perry Cabin by Belmond - Stars Restaurant. Afterward, join the Chesapeake Beach North Beach Scenic Guided Walking Tour to learn about the area's history and charm.
Evening
Have a casual dinner at Ava's Pizzeria & Wine Bar and unwind after a day of exploration. Enjoy a relaxing evening in Chesapeake Beach.
Bedtime
Find amazing hotels in Chesapeake Beach, Maryland, USA.
Visit Chesapeake Beach North Beach Scenic Guided Walking Tour in Chesapeake Beach, Maryland, USA

Chesapeake Beach North Beach Scenic Guided Walking Tour

Book Now
next arrow

Nature and Culinary Delights

Morning
Enjoy a peaceful morning at Wade's Point, taking in the natural beauty of the surroundings. Have a leisurely breakfast at a local cafe or prepare a picnic to enjoy outdoors.
Afternoon
Spend the afternoon exploring the nearby nature trails or engaging in water activities. For a late lunch, opt for a seafood feast at a waterfront restaurant.
Evening
For dinner, have a barbecue or seafood cookout at a scenic spot, watching the sunset over the water. Relax by a bonfire and enjoy the evening under the stars.
Bedtime
Find amazing hotels in Wade's Point, Maryland, USA.

Farewell to the Chesapeake Bay

Morning
On your last morning, savor a leisurely breakfast at a local cafe, reminiscing about your Chesapeake Bay adventures. Take a final walk along the waterfront and soak in the peaceful atmosphere.
Afternoon
If time allows, visit a nearby lighthouse or historic site for a last glimpse of the region's maritime heritage. Enjoy a light lunch at a cozy eatery before heading back.
Evening
End your trip with a memorable dinner at 208 Talbot, where you can enjoy a taste of the local flavors and bid farewell to the Chesapeake Bay in style.
Bedtime
Find amazing hotels in Wade's Point, Maryland, USA.
kayakFind the right stay during your trip.
Got a question about your trip?