Northern Chesapeake Bay Tours and Activities

A large suspension bridge over a calm body of water with a sunset in the background.
A sunset over a body of water with a bridge in the distance.
A sunset over a body of water with waves and a distant shoreline.
A suspension bridge with the sun setting behind it, reflecting on the water.
Fishing rods against a blue sky with clouds.

Things to do

Annapolis: Annapolis Harbor and U.S. Naval Academy Cruise

Annapolis: Annapolis Harbor and U.S. Naval Academy Cruise

CA $48
per adult
90% of travellers recommend
Annapolis: Annapolis Harbor and U.S. Naval Academy Cruise
Annapolis Harbor and US Naval Academy Cruise

Annapolis Harbor and U.S. Naval Academy Cruise

CA $48
per adult
Annapolis Harbor and U.S. Naval Academy Cruise
Scenic Spa Creek Cruise of Annapolis

Scenic Spa Creek Cruise of Annapolis

CA $42
per adult
Scenic Spa Creek Cruise of Annapolis
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

CA $13
per traveller
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Two Flight Indoor Skydiving Experience

Two Flight Indoor Skydiving Experience

CA $143
per traveller
94% of travellers recommend
Two Flight Indoor Skydiving Experience
Historic Annapolis Food Tour

Historic Annapolis Food Tour

CA $112
per adult
Historic Annapolis Food Tour
See all activities in Maryland

Plan a trip to see Northern Chesapeake Bay

Price found within the past 48 hours. Click for updated prices.
Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Save 100% on your flight
Price was CA $1,587, price is now CA $1,153 per person
CA $1,153
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
9.6/10 Exceptional! (128 reviews)
tiny tiny room with no closet- not sure what the “resort fee” was for- but it was in town and by a trail so that was nice. Was definitely not worth what we paid- but they get you with convenience i guess… very clean room.

Reviewed on Oct 16, 2026

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Price was CA $1,692, price is now CA $1,318 per person
CA $1,318
per person
Jan 10 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Baltimore (BWI)
9.4/10 Exceptional! (1,226 reviews)

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Price was CA $1,933, price is now CA $1,520 per person
CA $1,520
per person
Dec 25 - Jan 1
found 8 hours ago
Roundtrip flight included
Halifax (YHZ) to Baltimore (BWI)
8.4/10 Very good! (1,004 reviews)
No Breakfast for members Staff rude Very very noisy at this hotel up to 2 am Walls very thin Hear everything

Reviewed on Oct 15, 2026

Tours & day trips

See all 34 activities
Annapolis: Annapolis Harbour and US Naval Academy Cruise

Annapolis: Annapolis Harbour and US Naval Academy Cruise

Activity duration is 40 minutes
9.2 out of 10 with 37 reviews
Free cancellation available
Price is CA $48 per adult
Annapolis: Annapolis Harbour and US Naval Academy CruiseOpens in new tab

Private & custom tours

See all 6 activities
City centre Baltimore Helicopter Tour

City centre Baltimore Helicopter Tour

Activity duration is 10 minutes
10.0 out of 10 with 2 reviews
Free cancellation available
Price is CA $216 per adult
City centre Baltimore Helicopter TourOpens in new tab

Classes & workshops

See all 5 activities
Chesapeake Beach: Sunset Sailing Cruise with Snacks

Chesapeake Beach: Sunset Sailing Cruise with Snacks

Activity duration is 2 hours and 30 minutes
Free cancellation available
Price is CA $161 per adult
Chesapeake Beach: Sunset Sailing Cruise with SnacksOpens in new tab

Best Lodging Options Near Northern Chesapeake Bay

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4 out of 5
180 Pier One Road Stevensville MD
The Inn at Chesapeake Bay Beach Club
Circa 1700 Chesapeake Colonial home on the National Register.

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville MD
Circa 1700 Chesapeake Colonial home on the National Register.
Kent Island Resort

Kent Island Resort

3.5 out of 5
500 Kent Manor Dr Stevensville MD
Kent Island Resort
Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville MD
Charming Coastal/Country Home w/3 Acres & Sauna!
Island Life! Kent Island Waterfront with Pool-Bring your boat!

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville MD
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Stevensville MD
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Graduate by Hilton Annapolis
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Stevensville MD
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Historic Inns of Annapolis
See all 2,769 properties in Northern Chesapeake Bay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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