14 days in Daytona Beach, Orlando & Key West Itinerary

14 days in Daytona Beach, Orlando & Key West Itinerary

Created using Inspirock Florida trip planner

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Route & dates

Start: Winston Salem
Drive:  9 h 15 min
1
Daytona Beach
— 3 nights
Drive:  1 h
2
Orlando
— 6 nights
Fly + Bus:  4 h 15 min
3
Key West
— 3 nights
+4
Fly + Bus + Foot + Train + Bus:  8 h 15 min
End: Winston Salem

3
nights
Daytona Beach

Daytona Beach ©
The iconic seaside destination of Daytona Beach once supported sugar mill plantations, but now entertains up to 8 million visitors a year.
Change things up with these side-trips from Daytona Beach: Stetson Mansion (in DeLand), Dolphin & Whale Watching (in New Smyrna Beach) and St. Augustine (The Ximenez-Fatio House, Flagler College, &more). The adventure continues: enjoy the sand and surf at Andy Romano Beachfront Park, brush up on your military savvy at Veterans Museum & Education Center, join the crowd at Daytona International Speedway, and take in the waterfront at Daytona Beach Boardwalk and Pier.

To see where to stay, traveler tips, photos, and more tourist information, go to the Daytona Beach journey maker site.

Winston Salem to Daytona Beach is an approximately 7- hour combination of bus and flight. You can also do a combination of bus, flight, and shuttle; or drive. Plan for somewhat warmer temperatures traveling from Winston Salem in May, with highs in Daytona Beach at 85°F and lows at 66°F. Finish up your sightseeing early on the 6th (Thu) so you can go by car to Orlando.

Things to do in Daytona Beach

Outdoors Historic Sites Museums

Side Trips

St. Augustine, Stetson Mansion, Dolphin & Whale Watching, Andy Romano Beachfront Park, Ponce de Leon Inlet Lighthouse & Museum
Find places to stay May 3 — 6:
Highlights from your plan
Stetson Mansion ©
Stetson Mansion
St. Augustine Distillery ©
St. Augustine Distillery
Dolphin & Whale Watching

6
nights
Orlando

Orlando ©
For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Orlando is known for theme parks, nightlife, and fun & games. Your plan includes some of its best attractions: discover the magic at Walt Disney World Resort, get in on the family fun at Universal's Islands of Adventure, try out the rides at Disney’s Hollywood Studios, and have some family-friendly fun at The Escape Game Orlando.

To find ratings, photos, reviews, and other tourist information, read Orlando road trip planning tool.

You can drive from Daytona Beach to Orlando in an hour. Another option is to take a bus. In May in Orlando, expect temperatures between 88°F during the day and 69°F at night. Wrap up your sightseeing on the 12th (Wed) to allow time to travel to Key West.

Things to do in Orlando

Theme Parks Parks Outdoors

Side Trip

Charles Hosmer Morse Museum of American Art
Find places to stay May 6 — 12:
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure
Universal Orlando Resort ©
Universal Orlando Resort

3
nights
Key West

Key West ©
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.
Get out of town with these interesting Key West side-trips: Marathon (The Turtle Hospital & Sombrero Beach). Next up on the itinerary: examine the collection at The Ernest Hemingway Home and Museum, take a tour by water with Boat Tours & Water Sports, steep yourself in history at Truman Little White House, and look for all kinds of wild species at Key West Butterfly & Nature Conservatory.

To find reviews, more things to do, traveler tips, and more tourist information, use the Key West trip planner.

Do a combination of flight and bus from Orlando to Key West in 4.5 hours. Alternatively, you can do a combination of bus and flight; or drive. Traveling from Orlando in May, Key West is somewhat warmer at night with lows of 77°F. Finish up your sightseeing early on the 15th (Sat) so you can travel back home.

Things to do in Key West

Parks Museums Outdoors

Side Trip

Marathon
Find places to stay May 12 — 15:
Highlights from your plan
7 Artists & Friends Gallery ©
7 Artists & Friends Gallery
The Ernest Hemingway Home and Museum ©
The Ernest Hemingway Home and Museum
Key West Butterfly & Nature Conservatory ©
Key West Butterfly & Nature Conservatory

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