11 days in New York City & Florida Itinerary

11 days in New York City & Florida Itinerary

Created using Inspirock United States sightseeing planner

Make it your trip
1
New York City
— 2 nights
Fly
2
Key West
— 3 nights
Drive
3
Big Pine Key
— 1 night
Drive
4
Key Largo
— 1 night
Drive
5
Marco Island
— 1 night
Drive
6
Orlando
— 1 night
Fly
7
Pensacola Beach
— 1 night
Fly

S M T W T F S
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New York City

— 2 nights

Big Apple

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Museum-lovers will get to explore The Metropolitan Museum of Art and New York Public Library. Next up on the itinerary: take in the pleasant sights at Central Park, take a stroll through Times Square, enjoy breathtaking views from Empire State Building, and appreciate the history behind Statue of Liberty National Monument.

To find reviews, ratings, traveler tips, and tourist information, read New York City trip tool.

Use the Route module to find travel options from your starting location to New York City. In September, plan for daily highs up to 80°F, and evening lows to 66°F. Wrap up your sightseeing on the 25th (Fri) early enough to travel to Key West.

Things to do in New York City

Museums · Parks · Outdoors · Historic Sites

Side Trip

Key West

— 3 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.
Get outdoors at Dry Tortugas National Park and Scuba & Snorkeling. Appreciate the collections at The Ernest Hemingway Home and Museum and Alan S. Maltz Gallery. Next up on the itinerary: look for all kinds of wild species at Key West Butterfly & Nature Conservatory, view the masterpieces at 7 Artists & Friends Gallery, admire all the interesting features of Fort Zachary Taylor, and explore the gorgeous colors at Vandenberg Wreck.

To see other places to visit, more things to do, ratings, and tourist information, read our Key West trip planner.

Traveling by flight from New York City to Key West takes 7 hours. Alternatively, you can drive; or take a bus. Traveling from New York City in September, things will get somewhat warmer in Key West: highs are around 88°F and lows about 80°F. Finish your sightseeing early on the 28th (Mon) so you can drive to Big Pine Key.

Things to do in Key West

Parks · Nature · Wildlife · Outdoors

Big Pine Key

— 1 night
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 29th (Tue): take the plunge with Skydive Key West, then add some adventure to your tour with Florida Keys Kayaks and Eco Tours, and then kick back and relax at Bahia Honda State Park.

To find out how to plan a trip to Big Pine Key, use our trip itinerary maker.

Traveling by car from Key West to Big Pine Key takes an hour. Alternatively, you can take a shuttle; or take a bus. In September in Big Pine Key, expect temperatures between 90°F during the day and 79°F at night. Cap off your sightseeing on the 29th (Tue) early enough to go by car to Key Largo.

Things to do in Big Pine Key

Outdoors · Parks · Beaches · Adventure

Side Trips

Key Largo

— 1 night

Diving Capital of the World

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.
Kick off your visit on the 30th (Wed): get the adrenaline pumping with Jetpack Water Flights, then see the vivid underwater world at Spiegel Grove, then see some colorful creatures with Conch Republic Divers, and finally identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center.

For ratings, photos, other places to visit, and tourist information, use the Key Largo trip itinerary maker app.

Traveling by car from Big Pine Key to Key Largo takes 2 hours. Alternatively, you can take a bus. In September, daily temperatures in Key Largo can reach 88°F, while at night they dip to 76°F. Finish up your sightseeing early on the 30th (Wed) so you can go by car to Marco Island.

Things to do in Key Largo

Wildlife · Parks · Outdoors · Tours

Marco Island

— 1 night
Marco Island is a city in Collier County, Florida, United States, located on an island by the same name in the Gulf of Mexico off the coast of Southwest Florida. Kick off your visit on the 1st (Thu): look for all kinds of wild species at Capri Paddlecraft Park and then see majestic marine mammals with Reel Kind Fishing and Tours.

To see more things to do, reviews, traveler tips, and more tourist information, use the Marco Island online trip planner.

You can drive from Key Largo to Marco Island in 3 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of bus and ferry. In September in Marco Island, expect temperatures between 89°F during the day and 74°F at night. Wrap up your sightseeing on the 1st (Thu) to allow time to drive to Orlando.

Things to do in Marco Island

Wildlife · Outdoors · Tours · Parks

Orlando

— 1 night

Theme Park Capital of the World

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.
On the 2nd (Fri), get in on the family fun at Discovery Cove.

To see more things to do, reviews, maps, and more tourist information, read Orlando travel route planner.

You can drive from Marco Island to Orlando in 4.5 hours. Alternatively, you can do a combination of taxi, bus, and flight; or do a combination of taxi and bus. In October, daytime highs in Orlando are 85°F, while nighttime lows are 69°F. Finish up your sightseeing early on the 2nd (Fri) so you can travel to Pensacola Beach.

Things to do in Orlando

Theme Parks
Highlights from your trip

Pensacola Beach

— 1 night
Pensacola Beach is an unincorporated community located on Santa Rosa Island, a barrier island, in Escambia County, Florida, United States. On the 3rd (Sat), kick back and relax at Pensacola Beach and then see some colorful creatures with Jolly Sailing and Dolphin Cruises.

For other places to visit, reviews, maps, and more tourist information, read Pensacola Beach attractions planner.

Traveling by flight from Orlando to Pensacola Beach takes 6 hours. Alternatively, you can drive; or do a combination of bus and taxi. The time zone difference when traveling from Orlando to Pensacola Beach is minus 1 hour. Traveling from Orlando in October, expect little chillier with lows of 63°F in Pensacola Beach. Cap off your sightseeing on the 3rd (Sat) early enough to travel back home.

Things to do in Pensacola Beach

Outdoors · Tours · Wildlife · Parks

Florida travel guide

4.4
Disney Parks & Activities · Beaches · Theme Parks
The Sunshine State
The “Sunshine State,” Florida became a favorite winter destination for the affluent crowd over a century ago. Today, the state attracts visitors from around the world with its golden beaches and modern theme parks. You can spend your entire vacation enjoying the state's highly developed seaside areas, but remember that some of Florida's best-kept secrets are in secluded locations. Visit the big cities and their comfortable resorts offering top-notch dining and nightlife, but leave some time to see the peninsula's swampy landscape, filled with wild creatures and native plants. Farther away from the tourist-packed urban areas, the untamed wetlands of Florida offer a selection of things to do, such as kayaking, boat rides, and numerous other outdoor activities.