25 days in Lewes, Chesapeake Bay & Norfolk Itinerary

25 days in Lewes, Chesapeake Bay & Norfolk Itinerary

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Route & dates

25 days in Lewes, Chesapeake Bay & Norfolk Itinerary

Start: Wilmington
Fly + taxi:  5​h 30​min
1
Lewes
— 6 nights
Drive:  2​h 45​min
2
Colonial Beach
— 5 nights
Drive:  1​h 45​min
3
Gloucester
— 6 nights
Drive:  1​h 15​min
4
Norfolk
— 7 nights
Fly:  3​h 45​min
End: Wilmington

6
nights
Lewes

Lewes ©
Lewes is an incorporated city on the Delaware Bay in eastern Sussex County, Delaware. Visit Cape May Lighthouse and St. Peter's Episcopal Church for their historical value. Explore Lewes' surroundings by going to Wildwood (Original Old Time Photo & Breakfast in The Sky), Air Mobility Command Museum (in Dover) and Cape May (Emlen Physick Estate, Cape May City Beaches, & more). And it doesn't end there: immerse yourself in nature at Cape Henlopen State Park, stroll around George H. P. Smith Park, get to know the fascinating history of Fort Miles Historic Area at Cape Henlopen State Park, and examine the collection at Lightship Overfalls.

To see ratings, other places to visit, photos, and more tourist information, read our Lewes trip builder app .

Wilmington to Lewes is an approximately 5.5-hour combination of flight and taxi. You can also drive; or do a combination of bus and train. In October, Lewes is little chillier than Wilmington - with highs of 70°F and lows of 51°F. Finish your sightseeing early on the 29th (Tue) to allow enough time to travel to Colonial Beach.

Things to do in Lewes

Historic Sites Parks Museums

Side Trips

Cape May, Wildwood, Blue Earl Brewing Company, St. Edmond's Catholic Church, Air Mobility Command Museum
Highlights from your plan
Cape May Lighthouse ©
Cape May Lighthouse
Emlen Physick Estate ©
Emlen Physick Estate
St. Peter's Episcopal Church ©
St. Peter's Episcopal Church

5
nights
Colonial Beach

Colonial Beach ©
Colonial Beach is a town in Westmoreland County, Virginia, United States. Popular historic sites such as George Washington Birthplace National Monument and Menokin are in your itinerary. Change things up with these side-trips from Colonial Beach: St. Michaels (1879 Hooper Strait Lighthouse & Chesapeake Bay Maritime Museum), Calvert Marine Museum and Drum Point Lighthouse (in Solomons) and Essex County Museum and Historical Society (in Tappahannock). Next up on the itinerary: go for a stroll along the water at Bayside Marina, do a tasting at Ingleside Plantation Vineyards, relax in the rural setting at Westmoreland Berry Farm & Market, and immerse yourself in nature at Westmoreland State Park.

To see where to stay, ratings, traveler tips, and more tourist information, read Colonial Beach trip maker website .

Traveling by car from Lewes to Colonial Beach takes 3.5 hours. In October, plan for daily highs up to 67°F, and evening lows to 50°F. Finish up your sightseeing early on the 3rd (Sun) so you can go by car to Gloucester.

Things to do in Colonial Beach

Museums Historic Sites Parks

Side Trips

Oak Grove, St. Michaels, Menokin, "On Watch" Monument, Calvert Marine Museum and Drum Point Lighthouse
Highlights from your plan
Menokin ©
Menokin
1879 Hooper Strait Lighthouse ©
1879 Hooper Strait Lighthouse

6
nights
Gloucester

Gloucester ©
Gloucester Courthouse is a census-designated place (CDP) in and the county seat of Gloucester County, Virginia, United States. Get some historical perspective at Historic Jamestowne and Colonial Williamsburg. Change things up with these side-trips from Gloucester: Historic Christ Church (in Irvington), Hughlett Point Natural Area (in Reedville) and Williamsburg (George Wythe House, Bounce House & Laser Tag, & more). The adventure continues: witness the site of a historic battle at Yorktown Battlefield, kick back and relax at Gloucester Point Beach Park, take in the architecture and atmosphere at Grace Episcopal Church, and tour the pleasant surroundings at Tyndall's Point Park.

To find ratings, reviews, other places to visit, and other tourist information, use the Gloucester online trip planner .

You can drive from Colonial Beach to Gloucester in 2 hours. November in Gloucester sees daily highs of 61°F and lows of 37°F at night. Finish up your sightseeing early on the 9th (Sat) so you can go by car to Norfolk.

Things to do in Gloucester

Historic Sites Museums Parks

Side Trips

Williamsburg, Yorktown, Historic Christ Church, Hughlett Point Natural Area
Highlights from your plan
Historic Jamestowne ©
Historic Jamestowne
Colonial Williamsburg ©
Colonial Williamsburg
Jamestown Settlement ©
Jamestown Settlement

7
nights
Norfolk

Norfolk ©
Norfolk formed around a natural harbor that’s home to the world’s largest naval base, which helped cement the city as a keystone for strategic military planning and government.
Popular historic sites such as Wright Brothers National Memorial and Bodie Island Lighthouse are in your itinerary. Explore Norfolk's surroundings by going to St. Luke's Historic Church & Museum (in Smithfield), Suffolk Seaboard Station Railroad Museum (in Suffolk) and Corolla (Off-Road Tours & Currituck Beach Lighthouse and Museum). Next up on the itinerary: admire the masterpieces at Chrysler Museum of Art, take a tour of Battleship Wisconsin, enjoy the sea views from Old Point Comfort Lighthouse, and take in nature's colorful creations at Maymont.

To find reviews, where to stay, maps, and tourist information, go to the Norfolk day trip website .

Getting from Gloucester to Norfolk by car takes about 1.5 hours. Traveling from Gloucester in November, expect a bit warmer with lows of 44°F in Norfolk. Finish up your sightseeing early on the 16th (Sat) so you can travel back home.

Things to do in Norfolk

Historic Sites Museums Parks

Side Trips

Nags Head, Corolla, Richmond, Old Point Comfort Lighthouse, St. Luke's Historic Church & Museum
Highlights from your plan
Wright Brothers National Memorial ©
Wright Brothers National Memorial
St. Luke's Historic Church & Museum ©
Bodie Island Lighthouse ©
Bodie Island Lighthouse

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