8 days in Virginia Beach & Key West Itinerary

8 days in Virginia Beach & Key West Itinerary

Created using Inspirock United States visit planner

Make it your trip
Train
1
Virginia Beach
— 2 nights
Fly
2
Key West
— 5 nights
Fly

S M T W T F S
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Virginia Beach

— 2 nights

The Resort City

Holding a record for the longest pleasure beach in the world, Virginia Beach showcases 35 miles of coastline and maintains a longstanding reputation as a family-friendly vacation destination.
You'll find plenty of places to visit near Virginia Beach: Williamsburg (Colonial Williamsburg & George Wythe House), The Noland Trail (in Newport News) and St. Luke's Historic Church & Museum (in Smithfield). There's much more to do: brush up on your military savvy at Military Aviation Museum, take a leisurely stroll along Virginia Beach Boardwalk, and sample the fine beverages at Tarnished Truth Distilling Company.

Take the guesswork out of planning a Virginia Beach vacation by using our trip itinerary maker.

Norfolk to Virginia Beach is an approximately half hour train ride. You can also drive; or take a bus. October in Virginia Beach sees daily highs of 74°F and lows of 56°F at night. Finish your sightseeing early on the 16th (Sat) to allow enough time to fly to Key West.

Things to do in Virginia Beach

Historic Sites · Museums · Outdoors · Trails

Side Trips

Key West

— 5 nights

Conch Republic

Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Key West is known for museums, adventure, and wildlife. Your trip includes some of its best attractions: examine the collection at The Ernest Hemingway Home and Museum, glide through the air with a parasailing or paragliding tour, look for gifts at Peppers of Key West, and take in the waterfront at Mallory Square.

To find more things to do, where to stay, traveler tips, and other tourist information, read our Key West planner.

You can fly from Virginia Beach to Key West in 6 hours. Other options are to drive; or do a combination of train and bus. Expect somewhat warmer weather when traveling from Virginia Beach in October: highs in Key West hover around 86°F, while lows dip to 77°F. Cap off your sightseeing on the 21st (Thu) early enough to catch the flight back home.

Things to do in Key West

Historic Sites · Outdoors · Museums · Parks