28 days in New York City, Florida & Las Vegas Itinerary

28 days in New York City, Florida & Las Vegas Itinerary

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Route & dates

28 days in New York City, Florida & Las Vegas Itinerary

Start: Sydney
Fly + bus:  26​h
1
New York City
— 4 nights
bus + Fly:  6​h
2
Key West
— 3 nights
bus:  45​min
3
Big Pine Key
— 1 night
Drive:  30​min
4
Marathon
— 1 night
Drive:  2​h 45​min
5
Miami Beach
— 3 nights
Fly:  4​h
6
Orlando
— 4 nights
Drive:  2​h
7
St. Augustine
— 2 nights
Drive:  6​h
8
Santa Rosa Beach
— 2 nights
taxi + Fly:  8​h 15​min
9
Las Vegas
— 2 nights
Fly:  20​h
End: Sydney

4
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.
Deepen your sense of the past at sights like 9/11 Memorial and Ellis Island. Relax by the water at Cupsogue Beach County Park and Point Lookout Beach. You'll find plenty of places to visit near New York City: Lido Beach (in Lido Beach) and Joel L. Lefkowitz Park at West Meadow Beach (in Stony Brook). The adventure continues: take a stroll through Times Square, pause for some serene contemplation at St. Patrick's Cathedral, explore and take pictures at Central Park, and get a sense of history and politics at New York City Hall.

To see reviews, more things to do, photos, and other tourist information, read our New York City day trip site .

Sydney, Australia to New York City is an approximately 26-hour combination of flight and bus. You can also do a combination of train, flight, and bus. The time zone changes from Australian Eastern Standard Time (New South Wales) (AEST) to Eastern Standard Time (EST), which is usually a -15 hour difference. Traveling from Sydney in September, things will get a bit warmer in New York City: highs are around 31°C and lows about 22°C. Finish up your sightseeing early on the 4th (Fri) so you can travel to Key West.

Things to do in New York City

Parks Outdoors Beaches

Side Trips

Lido Beach, Joel L. Lefkowitz Park at West Meadow Beach, Point Lookout Beach, Cupsogue Beach County Park
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial
Times Square ©
Times Square

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.
Popular historic sites such as Fort Zachary Taylor and Curry Mansion are in your itinerary. Get some cultural insight at The Ernest Hemingway Home and Museum and Key West Lighthouse and Keeper's Quarters Museum. There's lots more to do: steep yourself in history at Truman Little White House, take in the waterfront at Mallory Square, see what you can catch with a fishing tour, and look for all kinds of wild species at Key West Butterfly & Nature Conservatory.

To find more things to do, traveler tips, reviews, and tourist information, read our Key West trip itinerary planner .

Getting from New York City to Key West by combination of bus and flight takes about 6 hours. Other options: fly; or drive. Traveling from New York City in October, expect Key West to be somewhat warmer, temps between 35°C and 29°C. Finish your sightseeing early on the 8th (Tue) to allow enough time to take a bus to Big Pine Key.

Things to do in Key West

Historic Sites Outdoors Parks
Highlights from your plan
Fort Zachary Taylor ©
Fort Zachary Taylor
The Ernest Hemingway Home and Museum ©
Truman Little White House ©
Truman Little White House

1
night
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. Start off your visit on the 9th (Wed): get a taste of the local shopping with Artists in Paradise Gallery, then identify plant and animal life at National Key Deer Refuge, and then admire the majestic nature at Bahia Honda State Park.

To find other places to visit, where to stay, and tourist information, read Big Pine Key trip builder .

You can take a bus from Key West to Big Pine Key in an hour. Another option is to drive. In October, daytime highs in Big Pine Key are 36°C, while nighttime lows are 29°C. Finish your sightseeing early on the 9th (Wed) so you can take a bus to Marathon.

Things to do in Big Pine Key

Parks Nature Outdoors
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Artists in Paradise Gallery ©
Artists in Paradise Gallery

1
night
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
On the 10th (Thu), kick back and relax at Sunset Park Beach, take in the architecture and atmosphere at San Pablo Catholic Church, then look for all kinds of wild species at The Turtle Hospital, and finally tour the pleasant surroundings at Sombrero Beach.

To see where to stay, reviews, other places to visit, and tourist information, read our Marathon trip planner .

Marathon is just a short distance from Big Pine Key. October in Marathon sees daily highs of 36°C and lows of 29°C at night. Cap off your sightseeing on the 10th (Thu) early enough to go by car to Miami Beach.

Things to do in Marathon

Parks Outdoors Beaches

Side Trip

Sunset Park Beach
Highlights from your plan
Sombrero Beach ©
Sombrero Beach
Sunset Park Beach ©
Sunset Park Beach
San Pablo Catholic Church ©
San Pablo Catholic Church

3
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.
You'll get in some beach time at South Beach and 12th Street Beach. Get some cultural insight at Art Deco Historic District and Vizcaya Museum and Gardens. Go for a jaunt from Miami Beach to Fort Lauderdale to see Fort Lauderdale Beach about 52 minutes away. Next up on the itinerary: take a stroll through Lincoln Road, get a taste of the local shopping with Bayside Marketplace, and make a trip to Collins Avenue.

To see reviews, more things to do, where to stay, and more tourist information, read our Miami Beach online vacation maker .

Traveling by car from Marathon to Miami Beach takes 3 hours. Alternatively, you can take a bus; or do a combination of bus and flight. Expect a daytime high around 36°C in October, and nighttime lows around 27°C. Wrap up your sightseeing on the 13th (Sun) early enough to drive to Orlando.

Things to do in Miami Beach

Parks Neighborhoods Shopping

Side Trips

Miami, Fort Lauderdale Beach
Highlights from your plan
Lincoln Road ©
Lincoln Road
Art Deco Historic District ©
Art Deco Historic District
South Beach ©
South Beach

4
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.
Do some cultural sightseeing at Stetson Mansion and St. Peter Catholic Church. Deepen your sense of the past at sights like St. Barnabas Episcopal Church and City Hall. Go for a jaunt from Orlando to Titusville to see NASA Kennedy Space Center Visitor Complex about 1h 10 min away. Pack the 14th (Mon) with family-friendly diversions at Discovery Cove. Have a day of magic on the 15th (Tue) at Walt Disney World Resort. Next up on the itinerary: discover the magic at Happily Ever After Fireworks and explore the world behind art at Charles Hosmer Morse Museum of American Art.

For traveler tips, photos, where to stay, and tourist information, you can read our Orlando trip maker site .

Getting from Miami Beach to Orlando by car takes about 4 hours. Other options: take a bus; or take a train. Expect little chillier evenings in Orlando when traveling from Miami Beach in October, with lows around 24°C. Cap off your sightseeing on the 17th (Thu) early enough to go by car to St. Augustine.

Things to do in Orlando

Theme Parks Outdoors Beaches

Side Trips

DeLand, Charles Hosmer Morse Museum of American Art, NASA Kennedy Space Center Visitor Complex
Highlights from your plan
Discovery Cove ©
Discovery Cove
Stetson Mansion ©
Stetson Mansion

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 18th (Fri): take in the architecture and atmosphere at Cathedral Basilica of St. Augustine, then visit a coastal fixture at St. Augustine Lighthouse & Maritime Museum, Inc., then enjoy the sand and surf at St. Augustine Beach, and finally brush up on your knowledge of spirits at St. Augustine Distillery. Get ready for a full day of sightseeing on the 19th (Sat): kick back and relax at Frank Butler County Park West, explore and take pictures at Flagler College, then look for gifts at Market to Market, and finally don't miss a visit to St. George Street.

To find where to stay, reviews, ratings, and more tourist information, read St. Augustine online trip itinerary maker .

Traveling by car from Orlando to St. Augustine takes 2 hours. Alternatively, you can take a bus. When traveling from Orlando in October, plan for little chillier days in St. Augustine, with highs around 31°C, while nights are about the same with lows around 22°C. Finish your sightseeing early on the 19th (Sat) to allow enough time to drive to Santa Rosa Beach.

Things to do in St. Augustine

Outdoors Beaches Parks
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
Cathedral Basilica of St. Augustine ©

2
nights
Santa Rosa Beach

Santa Rosa Beach ©
On the 20th (Sun), enjoy the sand and surf at Rosemary Beach Public Beach, admire the majestic nature at Eden Gardens State Park, and then stroll through Santa Rosa Beach. On the next day, enjoy the sand and surf at Crystal Sands Beach, take a leisurely stroll along Village of Baytowne Wharf, and then admire the majestic nature at Grayton Beach State Park.

For where to stay, photos, other places to visit, and other tourist information, refer to the Santa Rosa Beach trip tool .

You can drive from St. Augustine to Santa Rosa Beach in 6 hours. Another option is to take a bus. The time zone difference when traveling from St. Augustine to Santa Rosa Beach is minus 1 hour. In October, daytime highs in Santa Rosa Beach are 32°C, while nighttime lows are 22°C. Cap off your sightseeing on the 21st (Mon) early enough to travel to Las Vegas.

Things to do in Santa Rosa Beach

Parks Outdoors Beaches

Side Trips

Destin, Rosemary Beach Public Beach, Eden Gardens State Park
Highlights from your plan
Eden Gardens State Park ©
Eden Gardens State Park
Grayton Beach State Park ©
Grayton Beach State Park
Rosemary Beach Public Beach ©
Rosemary Beach Public Beach

2
nights
Las Vegas

Las Vegas ©
Nicknamed the "Entertainment Capital of the World," Las Vegas sits in the middle of a desert in the southern section of Nevada.
Get a sense of the local culture at The Strip and The Mob Museum. Step out of Las Vegas to go to Fort Mohave and see Willow Beach, which is approximately 1h 10 min away. There's lots more to do: admire the local landmark of Bellagio Fountains, enjoy breathtaking views from Eiffel Tower Viewing Deck, see the interesting displays at The Neon Museum, and take in nature's colorful creations at Bellagio Conservatory & Botanical Gardens.

For photos, ratings, and tourist information, use the Las Vegas attractions planner.

Traveling by flight from Santa Rosa Beach to Las Vegas takes 8.5 hours. Alternatively, you can do a combination of car and flight; or drive. You'll gain 2 hours traveling from Santa Rosa Beach to Las Vegas due to the time zone difference. Traveling from Santa Rosa Beach in October, you can expect nighttime temperatures to be a bit cooler in Las Vegas, with lows of 18°C. Finish up your sightseeing early on the 24th (Thu) so you can travel back home.

Things to do in Las Vegas

Parks Historic Sites Shopping

Side Trip

Willow Beach
Highlights from your plan
Fountains of Bellagio ©
Fountains of Bellagio
The Strip ©
The Strip
The Mob Museum ©
The Mob Museum

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