27 days in Florida, Massachusetts & New York City Itinerary

27 days in Florida, Massachusetts & New York City Itinerary

Created using Inspirock United States trip planner

Make it your trip
Fly
1
Key West
— 5 nights
Fly
2
Orlando
— 5 nights
Fly
3
Boston
— 4 nights
Fly
4
Provincetown
— 2 nights
Drive
5
Hyannis
— 3 nights
Fly
6
New York City
— 7 nights
Fly

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Key West

— 5 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.
Visit Fort Zachary Taylor and Truman Little White House for their historical value. Bring the kids along to Alan S. Maltz Gallery and KEPart Studio-Gallery. The adventure continues: discover the deep blue sea with a scuba or snorkeling tour, take in the exciting artwork at Key West Pottery, stroll through Key West Butterfly & Nature Conservatory, and hunt for treasures at Sunset Celebration.

To see where to stay, photos, traveler tips, and tourist information, read Key West day trip tool.

Lagos, Nigeria to Key West is an approximately 23-hour flight. Traveling from Lagos to Key West, you'll gain 6 hours due to the time zone difference. Traveling from Lagos in September, plan for somewhat warmer nights in Key West, with lows around 31°C. Wrap up your sightseeing on the 12th (Sun) early enough to fly to Orlando.

Things to do in Key West

Find places to stay Sep 7 — 12:

Orlando

— 5 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.
Attractions like Universal's Islands of Adventure and Discovery Cove make great kid-friendly stops. Have a day of magic on the 16th (Thu) at Walt Disney World Resort. The adventure continues: find something for the whole family at Universal Orlando Resort, browse the different shops at The Mall at Millenia, make an unforgettable trip to Magic Kingdom Park, and get outside with Outdoor Activities.

To find maps, ratings, photos, and other tourist information, go to the Orlando trip planner.

Getting from Key West to Orlando by flight takes about 3 hours. Other options: drive; or take a bus. Plan for a bit cooler nights when traveling from Key West in September since evenings lows in Orlando dip to 27°C. Wrap up your sightseeing on the 17th (Fri) to allow time to fly to Boston.

Things to do in Orlando

Find places to stay Sep 12 — 17:

Boston

— 4 nights

Beantown

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Attractions like Old South Meeting House and Faneuil Hall Marketplace make great kid-friendly stops. You'll explore and learn at Louisa May Alcott's Orchard House and Museum of Fine Arts. Take a break from Boston with a short trip to Dolphin & Whale Watching in Gloucester, about 50 minutes away. There's much more to do: wander the streets of Newbury Street, browse the different shops at Copley Place, appreciate the extensive heritage of Louisburg Square, and take in the architecture and atmosphere at Trinity Church.

To find maps, where to stay, reviews, and other tourist information, you can read our Boston trip itinerary planning site.

Fly from Orlando to Boston in 4.5 hours. Alternatively, you can drive; or take a train. Traveling from Orlando in September, expect Boston to be little chillier, temps between 28°C and 17°C. Finish up your sightseeing early on the 21st (Tue) so you can catch the flight to Provincetown.

Things to do in Boston

Side Trips

Find places to stay Sep 17 — 21:

Provincetown

— 2 nights

Birthplace of American Liberty

A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
On the 22nd (Wed), pause for some photo ops at Pilgrim Monument & Provincetown Museum and then stroll through Cape Cod National Seashore. Here are some ideas for day two: take a leisurely stroll along MacMillan Wharf, then kick back and relax at Corn Hill Beach, then kick back and relax at Nauset Light Beach, and finally steep yourself in history at Captain Penniman House.

For maps, traveler tips, ratings, and more tourist information, read Provincetown online route planner.

Traveling by flight from Boston to Provincetown takes 2 hours. Alternatively, you can ride a ferry; or drive. September in Provincetown sees daily highs of 25°C and lows of 16°C at night. Finish your sightseeing early on the 23rd (Thu) to allow enough time to drive to Hyannis.

Things to do in Provincetown

Outdoors · Parks · Beaches · Museums

Side Trips

Find places to stay Sep 21 — 23:

Hyannis

— 3 nights

Capital of Cape Cod

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Visiting Hyannis Whale Watcher Cruises and Chatham Lighthouse Beach will get you outdoors. Kids will enjoy Atwood Museum and Chatham Marconi Maritime Center. Step out of Hyannis with an excursion to Nauset Beach in Orleans--about 40 minutes away. There's still lots to do: see the interesting displays at Heritage Museums & Gardens, contemplate the long history of Captain Bangs Hallet House Museum, explore the galleries of Edward Gorey House, and engage your brain at Sandwich Glass Museum.

To see where to stay, other places to visit, photos, and more tourist information, you can read our Hyannis trip itinerary maker tool.

You can drive from Provincetown to Hyannis in 1.5 hours. Another option is to take a bus. In September, daytime highs in Hyannis are 26°C, while nighttime lows are 16°C. Wrap up your sightseeing on the 26th (Sun) to allow time to fly to New York City.

Things to do in Hyannis

Outdoors · Museums · Historic Sites · Parks

Side Trips

Find places to stay Sep 23 — 26:

New York City

— 7 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.
Shop till you drop at Fifth Avenue and Studio Manhattan. Popular historic sites such as 9/11 Memorial and Trinity Church are in your itinerary. Go for a jaunt from New York City to New Paltz to see DM Weil Gallery about 1h 45 min away. And it doesn't end there: make a trip to The Metropolitan Museum of Art, take in the architecture and atmosphere at St. Patrick's Cathedral, take in the pleasant sights at The High Line, and take an in-depth tour of Ellis Island.

For photos, traveler tips, and more tourist information, go to the New York City holiday planning app.

Fly from Hyannis to New York City in 3 hours. Alternatively, you can drive; or do a combination of bus and train. In September, New York City is a bit warmer than Hyannis - with highs of 31°C and lows of 22°C. Cap off your sightseeing on the 3rd (Sun) early enough to catch the flight back home.

Things to do in New York City

Side Trip

Find places to stay Sep 26 — Oct 3:

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.

Massachusetts travel guide

4.3
The Bay State
Known as the "Bay State" because of the three bays dominating its coastline, Massachusetts has played a significant cultural and commercial role through most of the country's history. An increasingly popular vacation destination for foreign travelers, Massachusetts offers numerous places to visit, ranging from historical sites to modern urban centers famous for their culinary, art, and nightlife scenes. With the majority of its population living in and around the city of Boston, in the 20th century Massachusetts went from a state largely dependent on fishing and agriculture to the country's leader in higher education, healthcare, high technology, and financial services. Home to renowned universities and research centers, the state's cities attract a young crowd of students, scientists, artists, and business professionals.