32 days in Anchorage, Florida & New York City Itinerary

32 days in Anchorage, Florida & New York City Itinerary

Created using Inspirock United States vacation planner

Make it your trip
Fly
1
Anchorage
— 4 nights
Fly
2
Key West
— 4 nights
Drive
3
Marathon
— 2 nights
Drive
4
Islamorada
— 1 night
Drive
5
Key Largo
— 2 nights
Drive
6
Marco Island
— 1 night
Drive
7
Naples
— 2 nights
Drive
8
Sarasota
— 2 nights
Drive
9
Orlando
— 4 nights
Drive
10
St. Augustine
— 3 nights
Fly
11
New York City
— 6 nights
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Anchorage

— 4 nights

The City of Lights and Flowers

Home to nearly half of Alaska's population, the port city of Anchorage covers a staggering area of over 4,900 sq km (1,900 sq mi) surrounded by mountains.
Explore hidden gems such as Portage Glacier and Hillside Park. And it doesn't end there: trek along Kincaid Park, examine the collection at The Roundhouse at Alyeska, walk around University Lake Dog Park, and make a trip to Fresh Spring Water at Mile 109.

For more things to do, maps, ratings, and tourist information, read our Anchorage trip planning site.

Amsterdam, The Netherlands to Anchorage is an approximately 17-hour flight. The time zone difference moving from Central European Standard Time (CET) to Alaska Standard Time (AKST) is minus 10 hours. In April, Anchorage is little chillier than Amsterdam - with highs of 10°C and lows of 0°C. Finish up your sightseeing early on the 4th (Tue) so you can travel to Key West.

Things to do in Anchorage

Parks · Outdoors · Trails · Winter Sports
Find places to stay Apr 30 — May 4:

Key West

— 4 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.
You'll discover tucked-away gems like Dry Tortugas National Park and The Overseas Highway. And it doesn't end there: stroll through Fort Zachary Taylor, relax and rejuvenate at some of the best spas, see the interesting displays at Mel Fisher Maritime Heritage Museum, and brush up on your military savvy at U.S. Coast Guard Cutter Ingham Maritime Museum.

For other places to visit, maps, reviews, and more tourist information, refer to the Key West tour itinerary maker website.

Traveling by flight from Anchorage to Key West takes 13.5 hours. Alternatively, you can drive. The time zone difference moving from Alaska Standard Time to Eastern Standard Time is 4 hours. Expect warmer temperatures when traveling from Anchorage in May; daily highs in Key West reach 34°C and lows reach 29°C. Finish your sightseeing early on the 8th (Sat) so you can drive to Marathon.

Things to do in Key West

Parks · Outdoors · Nature · Historic Sites
Find places to stay May 4 — 8:

Marathon

— 2 nights

Heart of the Florida Keys

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Start off your visit on the 9th (Sun): identify plant and animal life at The Turtle Hospital, then snap pictures at Seven Mile Bridge, and then enjoy the sand and surf at Bahia Honda State Park. Get ready for a full day of sightseeing on the next day: look for all kinds of wild species at Dolphin Research Center, then enjoy the sand and surf at Sombrero Beach, and then take a memorable tour with Tours.

Before you visit Marathon, use our trip planner to discover what you can do and see there.

You can drive from Key West to Marathon in 1.5 hours. Alternatively, you can take a bus. In May, daily temperatures in Marathon can reach 36°C, while at night they dip to 29°C. Finish your sightseeing early on the 10th (Mon) to allow enough time to drive to Islamorada.

Things to do in Marathon

Parks · Outdoors · Wildlife · Beaches

Side Trip

Find places to stay May 8 — 10:

Islamorada

— 1 night

The Village of Islands

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
On the 11th (Tue), explore the gorgeous colors at Alligator Reef Light House, then indulge your thirst for a good beer at Islamorada Brewery & Distillery, then cast your line with a fishing tour, and finally sample the tasty concoctions at Florida Keys Brewing Company.

To find traveler tips, photos, other places to visit, and tourist information, refer to the Islamorada road trip app.

You can drive from Marathon to Islamorada in an hour. Alternatively, you can take a bus. In May, daytime highs in Islamorada are 36°C, while nighttime lows are 29°C. Wrap up your sightseeing on the 11th (Tue) to allow time to drive to Key Largo.

Things to do in Islamorada

Wildlife · Breweries & Distilleries · Tours · Outdoors
Find places to stay May 10 — 11:

Key Largo

— 2 nights

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.
Start off your visit on the 12th (Wed): get up close and personal with brilliant marine life at Island Dolphin Care, then admire the majestic nature at John Pennekamp Coral Reef State Park, and then take a tour by water with Boat Tours & Water Sports. On the 13th (Thu), you'll have a packed day of sightseeing: look for all kinds of wild species at Anhinga Trail, then take a tour of African Queen Canal Cruise, and then look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center.

To find more things to do, where to stay, ratings, and other tourist information, you can read our Key Largo trip itinerary tool.

Key Largo is just a short distance from Islamorada. Traveling from Islamorada in May, Key Largo is little chillier at night with lows of 26°C. Finish your sightseeing early on the 13th (Thu) so you can drive to Marco Island.

Things to do in Key Largo

Parks · Wildlife · Nature · Outdoors

Side Trip

Find places to stay May 11 — 13:

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. Start off your visit on the 14th (Fri): kick back and relax at South Marco Beach, then stroll around Frank E. Mackle Park, and then take a tour by water with Boat Tours & Water Sports.

To find reviews, where to stay, ratings, and other tourist information, read our Marco Island holiday builder.

Getting from Key Largo to Marco Island by car takes about 3 hours. Other options: do a combination of bus and taxi; or do a combination of bus and ferry. In May, plan for daily highs up to 36°C, and evening lows to 24°C. Finish your sightseeing early on the 14th (Fri) so you can drive to Naples.

Things to do in Marco Island

Outdoors · Parks · Wildlife · Tours
Find places to stay May 13 — 14:

Naples

— 2 nights
Kick off your visit on the 15th (Sat): identify plant and animal life at Corkscrew Swamp, stop by Fifth Avenue South, and then take a leisurely stroll along Naples Pier. On the 16th (Sun), you'll have a packed day of sightseeing: learn about wildlife with up-close encounters at Naples Zoo at Caribbean Gardens, take in nature's colorful creations at Naples Botanical Garden, and then get some thrills on the water with a speed boat tour.

To see reviews, traveler tips, ratings, and other tourist information, read Naples road trip tool.

Naples is just a short distance from Marco Island. In May in Naples, expect temperatures between 36°C during the day and 24°C at night. Finish your sightseeing early on the 16th (Sun) so you can drive to Sarasota.

Things to do in Naples

Parks · Wildlife · Neighborhoods · Shopping

Side Trip

Find places to stay May 14 — 16:

Sarasota

— 2 nights
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. state of Florida. Start off your visit on the 17th (Mon): admire the masterpieces at The Ringling, then enjoy the sand and surf at Siesta Beach, and then glide peacefully along the water with some of the best stand-up paddleboarding in the area. Get ready for a full day of sightseeing on the 18th (Tue): admire the masterpieces at Imagine Museum, admire the masterpieces at The Dali Museum, and then tour the pleasant surroundings at Saint Pete Beach.

To see reviews, more things to do, traveler tips, and other tourist information, you can read our Sarasota route planner.

Drive from Naples to Sarasota in 2 hours. Alternatively, you can take a bus; or do a combination of bus and taxi. Expect a daytime high around 36°C in May, and nighttime lows around 23°C. Finish your sightseeing early on the 18th (Tue) to allow enough time to drive to Orlando.

Things to do in Sarasota

Museums · Outdoors · Beaches · Parks

Side Trips

Find places to stay May 16 — 18:

Orlando

— 4 nights

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.
Step off the beaten path and head to Boat Tours & Water Sports and Disney’s Blizzard Beach Water Park. Pack the 19th (Wed) with family-friendly diversions at Universal's Islands of Adventure. Have a day of magic on the 21st (Fri) at Walt Disney World Resort. There's more to do: discover the magic at Disney's Typhoon Lagoon Water Park and find something for the whole family at Universal Orlando Resort.

To find maps, ratings, other places to visit, and other tourist information, go to the Orlando road trip tool.

Drive from Sarasota to Orlando in 2.5 hours. Alternatively, you can drive; or take a bus; or do a combination of bus and train. In May, plan for daily highs up to 36°C, and evening lows to 24°C. Wrap up your sightseeing on the 22nd (Sat) early enough to drive to St. Augustine.

Things to do in Orlando

Theme Parks · Tours · Outdoors

Side Trip

Find places to stay May 18 — 22:

St. Augustine

— 3 nights
St. Explore hidden gems such as Fort Clinch State Park and St. Augustine Lighthouse & Maritime Museum, Inc.. The adventure continues: identify plant and animal life at St. Augustine Alligator Farm Zoological Park, don't miss a visit to St. George Street, take in the architecture and atmosphere at Cathedral Basilica of St. Augustine, and deepen your understanding at Flagler College.

For photos, reviews, traveler tips, and other tourist information, refer to the St. Augustine route planner.

Getting from Orlando to St. Augustine by car takes about 2 hours. Other options: drive; or take a bus. When traveling from Orlando in May, plan for a bit cooler days and about the same nights in St. Augustine: temperatures range from 33°C by day to 22°C at night. On the 25th (Tue), wrap the sightseeing up by early afternoon so you can travel to New York City.

Things to do in St. Augustine

Parks · Historic Sites · Wildlife · Nature

Side Trip

Find places to stay May 22 — 25:

New York City

— 6 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.
You'll discover tucked-away gems like New York Botanical Garden and Ground Zero Museum Workshop. There's lots more to do: take in the pleasant sights at Central Park, hit the best photo ops around with an inspiring photography tour, enjoy breathtaking views from Empire State Building, and see the interesting displays at New York Public Library.

To find more things to do, photos, traveler tips, and other tourist information, use the New York City driving holiday planner.

Getting from St. Augustine to New York City by flight takes about 8 hours. Other options: drive; or take a bus. Traveling from St. Augustine in May, expect New York City to be a bit cooler, temps between 24°C and 15°C. Wrap up your sightseeing on the 31st (Mon) to allow time to travel back home.

Things to do in New York City

Museums · Parks · Tours · Neighborhoods

Side Trip

Find places to stay May 25 — 31:

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.