29 days in United States Itinerary

29 days in United States Itinerary

Created using Inspirock United States trip planner

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Route & dates

29 days in United States Itinerary

Start: Winston Salem
Drive:  6​h
1
Savannah
— 3 nights
Drive:  3​h 15​min
2
St. Augustine
— 2 nights
Drive:  4​h
3
St. Pete Beach
— 3 nights
Drive:  4​h 30​min
4
Miami Beach
— 2 nights
Drive:  3​h 45​min
5
Key West
— 2 nights
Drive:  7​h 30​min
6
Orlando
— 13 nights
Drive:  1​h
7
Cape Canaveral
— 2 nights
Drive:  10​h 30​min
End: Winston Salem

3
nights
Savannah

Georgia's oldest city, Savannah displays its colonial history proudly on every corner.
You'll visit kid-friendly attractions like Dolphin & Whale Watching and Fishing Charters & Tours. Change things up with a short trip to Speed Boats Tours in Hilton Head (about 50 minutes away). Next up on the itinerary: appreciate the extensive heritage of Savannah Historic District, make a trip to River Street Savannah, stroll around Forsyth Park, and take in the spiritual surroundings of Mickve Israel Temple.

Quickly create a custom-made itinerary for Savannah using our trip planner.

Winston Salem to Savannah is an approximately 6-hour car ride. You can also do a combination of bus and flight; or take a bus. In June in Savannah, expect temperatures between 89°F during the day and 72°F at night. Finish up your sightseeing early on the 14th (Sun) so you can go by car to St. Augustine.

Things to do in Savannah

Tours Wildlife Outdoors

Side Trip

Hilton Head
Highlights from your plan
Dolphin & Whale Watching
Fishing Charters & Tours
Speed Boats Tours

2
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Kick off your visit on the 15th (Tue): sample the fine beverages at St. Augustine Distillery, then enjoy the sand and surf at St. Augustine Beach, then enjoy the sea views from St. Augustine Lighthouse & Maritime Museum, Inc., and finally get thoroughly spooked out with a ghost and vampire tour. On the next day, identify plant and animal life at St. Augustine Wild Reserve and then identify plant and animal life at St. Augustine Alligator Farm Zoological Park.

Make your St. Augustine itinerary with Inspirock to find out what to see and where to go.

Traveling by car from Savannah to St. Augustine takes 3.5 hours. Alternatively, you can take a bus; or take a train. Traveling from Savannah in December, plan for somewhat warmer nights in St. Augustine, with lows around 55°F. Wrap up your sightseeing on the 16th (Wed) to allow time to drive to St. Pete Beach.

Things to do in St. Augustine

Parks Wildlife Beaches
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach

3
nights
St. Pete Beach

St. Kids will appreciate attractions like Parasailing & Paragliding and Siesta Beach. There's lots more to do: tour the pleasant surroundings at Saint Pete Beach, admire nature's wide array of creatures at Swim with the Fishes, look for gifts at Two Friend's Closet, and get up close to creatures of the deep with a dolphin and whale watching tour.

To see maps, ratings, more things to do, and tourist information, read St. Pete Beach online sightseeing planner .

Traveling by car from St. Augustine to St. Pete Beach takes 4 hours. Alternatively, you can take a bus; or do a combination of bus and flight. Traveling from St. Augustine in December, plan for somewhat warmer nights in St. Pete Beach, with lows around 63°F. Finish your sightseeing early on the 19th (Sat) to allow enough time to drive to Miami Beach.

Things to do in St. Pete Beach

Outdoors Tours Parks

Side Trips

Parasailing & Paragliding, Siesta Beach
Highlights from your plan
Parasailing & Paragliding
Siesta Beach ©
Siesta Beach
Saint Pete Beach ©
Saint Pete Beach

2
nights
Miami Beach

Miami Beach ©
Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
Start off your visit on the 20th (Sun): shop like a local with Collins Avenue, then admire all the interesting features of Lincoln Road, then tour the pleasant surroundings at South Beach, and finally get to know the fascinating history of Art Deco Historic District. On your second day here, look for gifts at The Official Art Deco Gift Shop and then take a stroll through Ocean Drive.

For photos, other places to visit, where to stay, and tourist information, go to the Miami Beach online trip maker .

You can drive from St. Pete Beach to Miami Beach in 4.5 hours. Other options are to take a bus; or do a combination of bus and flight. Traveling from St. Pete Beach in December, you will find days in Miami Beach are somewhat warmer (81°F), and nights are about the same (68°F). Finish your sightseeing early on the 21st (Mon) so you can travel to Key West.

Things to do in Miami Beach

Neighborhoods Shopping Historic Sites
Highlights from your plan
Collins Avenue ©
Collins Avenue
South Beach ©
South Beach
Lincoln Road ©
Lincoln Road

2
nights
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.
Start off your visit on the 22nd (Tue): take a memorable tour with Tours, look for all kinds of wild species at Key West Butterfly & Nature Conservatory, then fly like a bird with a parasailing or paragliding tour, and finally shop like a local with Alan S. Maltz Gallery. Get ready for a full day of sightseeing on the next day: admire the majestic nature at Bahia Honda State Park.

To see traveler tips, where to stay, maps, and tourist information, read our Key West trip maker app .

Getting from Miami Beach to Key West by flight takes about 3 hours. Other options: drive; or take a bus. In December, daytime highs in Key West are 79°F, while nighttime lows are 71°F. Finish your sightseeing early on the 23rd (Wed) to allow enough time to travel to Orlando.

Things to do in Key West

Outdoors Wildlife Tours

Side Trip

Bahia Honda State Park
Highlights from your plan
Dolphin & Whale Watching
Bahia Honda State Park ©
Bahia Honda State Park

13
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.
Kids will enjoy Universal's Islands of Adventure and Walt Disney World Resort. Explore Orlando's surroundings by going to Crystal River (Stand-Up Paddleboarding & Scuba & Snorkeling), The Twilight Zone Tower of Terror (in Anaheim) and Hidden Waters Preserve (in Eustis). The adventure continues: find something for the whole family at SeaWorld, have some family-friendly fun at The Escape Game Orlando, laugh and play at Disney's Hollywood Studios, and make an unforgettable trip to Magic Kingdom Park.

To find reviews, photos, where to stay, and other tourist information, read Orlando driving holiday planner .

Getting from Key West to Orlando by flight takes about 4.5 hours. Other options: drive; or take a bus. Traveling from Key West in December, you can expect nighttime temperatures to be a bit cooler in Orlando, with lows of 59°F. Wrap up your sightseeing on the 5th (Tue) early enough to drive to Cape Canaveral.

Things to do in Orlando

Theme Parks Outdoors Parks

Side Trips

Crystal River, Machine Gun America, Charles Hosmer Morse Museum of American Art, The Twilight Zone Tower of Terror, Hidden Waters Preserve
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Universal Orlando Resort ©
Universal Orlando Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure

2
nights
Cape Canaveral

Cape Canaveral ©
Cape Canaveral is a city in Brevard County, Florida. On the 6th (Wed), see the interesting displays at Parker Brothers Concepts, then enjoy the sand and surf at Jetty Park, and then try your luck at Victory Casino Cruises. Keep things going the next day: stroll around Manatee Sanctuary Park, then enjoy breathtaking views from Exploration Tower, and then have some family-friendly fun at Golf-N-Gator.

For traveler tips, maps, other places to visit, and other tourist information, refer to the Cape Canaveral trip itinerary builder tool .

Getting from Orlando to Cape Canaveral by car takes about an hour. Other options: do a combination of bus and taxi; or take a shuttle. In January in Cape Canaveral, expect temperatures between 70°F during the day and 54°F at night. Cap off your sightseeing on the 7th (Thu) early enough to travel back home.

Things to do in Cape Canaveral

Fun & Games Outdoors Parks

Side Trip

Parker Brothers Concepts
Highlights from your plan
Victory Casino Cruises ©
Victory Casino Cruises
Golf-N-Gator ©
Golf-N-Gator
Parker Brothers Concepts ©
Parker Brothers Concepts

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