24 days in Florida & New York City Itinerary

24 days in Florida & New York City Itinerary

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Route & dates

24 days in Florida & New York City Itinerary

Start: Kuwait City
Fly:  20​h 15​min
1
Orlando
— 3 nights
Drive:  2​h
2
St. Augustine
— 2 nights
Drive:  6​h 45​min
3
Pensacola Beach
— 1 night
taxi + Fly:  6​h 30​min
4
Key West
— 3 nights
bus:  45​min
5
Big Pine Key
— 2 nights
Drive:  1​h 45​min
6
Key Largo
— 3 nights
Drive:  1​h 30​min
7
Miami Beach
— 2 nights
Fly:  5​h 30​min
8
New York City
— 2 nights
Fly:  15​h 15​min
End: Kuwait City

3
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.
Pack the 3rd (Sat) with family-friendly diversions at Discovery Cove. Pack the 6th (Tue) with family-friendly diversions at Universal's Islands of Adventure. It doesn't end there: discover the magic at Walt Disney World Resort and get in on the family fun at Universal Orlando Resort.

For other places to visit, maps, photos, and tourist information, you can read our Orlando trip planner .

Kuwait City, Kuwait to Orlando is an approximately 20.5-hour flight. You can also do a combination of flight and bus. The time zone difference moving from Arabia Standard Time (AST) to Eastern Standard Time (EST) is minus 8 hours. Traveling from Kuwait City in August, expect nights in Orlando to be little chillier, around 28°C, while days are cooler, around 39°C. Cap off your sightseeing on the 6th (Tue) early enough to go by car to St. Augustine.

Things to do in Orlando

Theme Parks Beaches Outdoors
Find places to stay Aug 3 — 6:
Highlights from your plan
Discovery Cove ©
Discovery Cove
Universal's Islands of Adventure ©
Universal's Islands of Adventure
Walt Disney World Resort ©
Walt Disney World Resort

2
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. On the 7th (Wed), kick back and relax at Crescent Beach Public Beach, enjoy the sand and surf at Frank Butler County Park West, and then choose your vessel at Red Boat Water Tours, LLC. On the 8th (Thu), you'll have a packed day of sightseeing: sample the fine beverages at St. Augustine Distillery, stroll through St. Augustine Beach, and then enjoy the sand and surf at Vilano Beach.

For traveler tips, other places to visit, maps, and other tourist information, use the St. Augustine trip planner .

Traveling by car from Orlando to St. Augustine takes 2 hours. Alternatively, you can take a bus. In August, plan for daily highs up to 37°C, and evening lows to 28°C. Finish up your sightseeing early on the 8th (Thu) so you can go by car to Pensacola Beach.

Things to do in St. Augustine

Outdoors Beaches Parks

Side Trip

Crescent Beach Public Beach
Find places to stay Aug 6 — 8:
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
St. Augustine Distillery ©
St. Augustine Distillery
Vilano Beach ©
Vilano Beach

1
night
Pensacola Beach

Pensacola Beach ©
Pensacola Beach is an unincorporated community located on Santa Rosa Island, a barrier island, in Escambia County, Florida, United States. Start off your visit on the 9th (Fri): tour the water at your own pace with Dolphin Express and then choose your vessel at Hot Spots Fishing Charters. On your second day here, enjoy the sand and surf at Gulf Islands National Seashore and then kick back and relax at Navarre Beach.

To see more things to do, other places to visit, maps, and other tourist information, go to the Pensacola Beach attractions app .

You can drive from St. Augustine to Pensacola Beach in 7 hours. Alternatively, you can do a combination of bus, flight, and car; or do a combination of bus, flight, and taxi. The time zone difference when traveling from St. Augustine to Pensacola Beach is minus 1 hour. Expect a daytime high around 38°C in August, and nighttime lows around 28°C. Wrap up your sightseeing on the 10th (Sat) to allow time to travel to Key West.

Things to do in Pensacola Beach

Outdoors Beaches Parks

Side Trip

Navarre Beach
Find places to stay Aug 8 — 10:
Highlights from your plan
Navarre Beach ©
Navarre Beach
Hot Spots Fishing Charters ©
Hot Spots Fishing Charters

3
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.
Visiting Key West Butterfly & Nature Conservatory and Fort Zachary Taylor will get you outdoors. There's still lots to do: examine the collection at The Ernest Hemingway Home and Museum, choose your vessel at Fun In The Sun Key West, get a new perspective on things with Boat Tours & Water Sports, and make a trip to Duval Street.

To find ratings, more things to do, reviews, and tourist information, read Key West road trip planner .

Traveling by combination of taxi and flight from Pensacola Beach to Key West takes 6.5 hours. Alternatively, you can do a combination of car and flight; or drive. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. Traveling from Pensacola Beach in August, you can expect nighttime temperatures to be a bit warmer in Key West, with lows of 32°C. Wrap up your sightseeing on the 14th (Wed) to allow time to take a bus to Big Pine Key.

Things to do in Key West

Outdoors Tours Wildlife
Find places to stay Aug 10 — 14:
Highlights from your plan
Stand-Up Paddleboarding
The Ernest Hemingway Home and Museum ©

2
nights
Big Pine Key

Big Pine Key ©
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. Kick off your visit on the 15th (Thu): shop like a local with Artists in Paradise Gallery, take a memorable tour with Tours, and then immerse yourself in nature at Bahia Honda State Park. Here are some ideas for day two: tour the pleasant surroundings at Long Beach, enjoy the sand and surf at Calusa Beach, and then look for all kinds of wild species at National Key Deer Refuge.

For reviews, maps, traveler tips, and more tourist information, refer to the Big Pine Key online day trip planner .

Getting from Key West to Big Pine Key by bus takes about an hour. Other options: drive. August in Big Pine Key sees daily highs of 39°C and lows of 31°C at night. Finish your sightseeing early on the 16th (Fri) so you can drive to Key Largo.

Things to do in Big Pine Key

Outdoors Parks Beaches
Find places to stay Aug 14 — 16:
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Stand-Up Paddleboarding
Artists in Paradise Gallery ©
Artists in Paradise Gallery

3
nights
Key Largo

Key Largo ©
The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
Visiting Key Largo Fishing Adventures and Anhinga Trail will get you outdoors. When in Key Largo, make a side trip to see Parasailing & Paragliding in Islamorada, approximately 38 minutes away. The adventure continues: look for all kinds of wild species at Wildlife Areas, zoom along the surf with a waterskiing or jet-skiing adventure, and admire all the interesting features of Spiegel Grove.

For traveler tips, maps, and tourist information, use the Key Largo trip planner .

Traveling by car from Big Pine Key to Key Largo takes 2 hours. Alternatively, you can do a combination of bus and taxi. In August, plan for daily highs up to 38°C, and evening lows to 29°C. Finish your sightseeing early on the 19th (Mon) to allow enough time to drive to Miami Beach.

Things to do in Key Largo

Outdoors Wildlife Tours

Side Trips

Parasailing & Paragliding, Anhinga Trail
Find places to stay Aug 16 — 19:
Highlights from your plan
Key Largo Fishing Adventures ©
Key Largo Fishing Adventures
Anhinga Trail ©
Anhinga Trail

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 (Tue): stroll through Fort Lauderdale Beach, browse the different shops at Bayside Marketplace, and then kick back and relax at South Beach. Here are some ideas for day two: make a trip to Ocean Drive, wander the streets of Art Deco Historic District, and then take a stroll through Lincoln Road.

To see maps, photos, reviews, and more tourist information, read Miami Beach trip itinerary maker site .

Traveling by car from Key Largo to Miami Beach takes 1.5 hours. Alternatively, you can take a bus; or do a combination of taxi and bus. In August, daytime highs in Miami Beach are 38°C, while nighttime lows are 30°C. Finish your sightseeing early on the 21st (Wed) to allow enough time to travel to New York City.

Things to do in Miami Beach

Neighborhoods Parks Shopping

Side Trips

Fort Lauderdale Beach, Bayside Marketplace
Find places to stay Aug 19 — 21:
Highlights from your plan
Lincoln Road ©
Lincoln Road
South Beach ©
South Beach
Art Deco Historic District ©
Art Deco Historic District

2
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Kick off your visit on the 22nd (Thu): go for a walk through Times Square and then take in the pleasant sights at Central Park. Keep things going the next day: enjoy the sand and surf at Point Lookout Beach, then examine the collection at 9/11 Memorial, and then choose your vessel at Tribeca Sailing.

For maps, traveler tips, and more tourist information, go to the New York City trip planner .

You can do a combination of bus, tram, and flight from Miami Beach to New York City in 5.5 hours. Other options are to do a combination of bus, tram, and flight; or drive. In August, New York City is little chillier than Miami Beach - with highs of 34°C and lows of 25°C. Wrap up your sightseeing by early afternoon on the 24th (Sat) to allow enough time to travel back home.

Things to do in New York City

Parks Outdoors Beaches

Side Trip

Point Lookout Beach
Find places to stay Aug 21 — 24:
Highlights from your plan
Central Park ©
Central Park
Times Square ©
Times Square
Tribeca Sailing ©
Tribeca Sailing

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