60 days in North America & Caribbean Itinerary

60 days in North America & Caribbean Itinerary

Created using Inspirock tour planner

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Boston, United States
— 5 nights
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New York City, United States
— 6 nights
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Washington DC, United States
— 6 nights
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Culebra, Puerto Rico
— 2 nights
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5
Punta Cana, Dominican Republic
— 3 nights
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6
Providenciales, Turks and Caicos
— 2 nights
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Key West, United States
— 2 nights
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Orlando, United States
— 5 nights
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Chicago, United States
— 4 nights
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Las Vegas, United States
— 4 nights
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San Diego, United States
— 5 nights
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Los Angeles, United States
— 5 nights
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San Francisco, United States
— 5 nights
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Seattle, United States
— 5 nights
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Boston, United States

— 5 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.
Venture out of the city with trips to Hyannis Whale Watcher Cruises (in Barnstable), Atwood Museum (in Chatham) and Sandwich (Sandwich Glass Museum & Heritage Museums & Gardens). There's still lots to do: immerse yourself in nature at Nickerson State Park, contemplate the long history of Highfield Hall & Gardens, grab your bike and head to Shining Sea Bikeway, and get curious at Museum of Science.

To find reviews, photos, more things to do, and tourist information, read Boston tour planning tool.

London, UK to Boston is an approximately 10.5-hour flight. Traveling from London to Boston, you'll gain 5 hours due to the time zone difference. In August, Boston is somewhat warmer than London - with highs of 32°C and lows of 21°C. Wrap up your sightseeing on the 28th (Sun) to allow time to fly to New York City.

Things to do in Boston

Museums · Parks · Outdoors · Childrens Museums

Side Trips

Find places to stay Aug 23 — 28:

New York City, United States

— 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.
New York City is known for museums, nightlife, and shopping. Your trip includes some of its best attractions: go for a walk through Central Park, stroll around The High Line, make a trip to Empire State Building, and appreciate the history behind Statue of Liberty National Monument.

To see ratings, photos, where to stay, and other tourist information, you can read our New York City online holiday builder.

Getting from Boston to New York City by flight takes about 2.5 hours. Other options: drive; or take a train. Traveling from Boston in August, expect a bit warmer with lows of 25°C in New York City. Finish your sightseeing early on the 3rd (Sat) so you can fly to Washington DC.

Things to do in New York City

Parks · Museums · Outdoors · Tours
Find places to stay Aug 28 — Sep 3:

Washington DC, United States

— 6 nights
The capital of the United States, the District of Columbia contains the lion's share of the country's most treasured monuments, memorials, and public museums.
Washington DC is known for museums, historic sites, and nightlife. Your trip includes some of its best attractions: examine the collection at National Air and Space Museum, learn about wildlife with up-close encounters at National Zoological Park, explore the world behind art at National Gallery of Art, and get a new perspective on nature at Smithsonian National Museum of Natural History.

To see reviews, ratings, and other tourist information, read our Washington DC trip itinerary planning site.

Fly from New York City to Washington DC in 3 hours. Alternatively, you can take a train; or drive. In September, plan for daily highs up to 32°C, and evening lows to 21°C. On the 9th (Fri), wrap the sightseeing up by early afternoon so you can fly to Culebra.

Things to do in Washington DC

Museums · Parks · Zoos & Aquariums · Nature
Find places to stay Sep 3 — 9:

Culebra, Puerto Rico

— 2 nights

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Start off your visit on the 10th (Sat): enjoy the sand and surf at Flamenco Beach. On the 11th (Sun), you'll have a packed day of sightseeing: kick back and relax at Playa Zoni.

To see more things to do, where to stay, photos, and more tourist information, read our Culebra trip itinerary planning app.

Traveling by flight from Washington DC to Culebra takes 9 hours. The time zone difference when traveling from Washington DC to Culebra is 1 hour. Traveling from Washington DC in September, expect Culebra to be a bit warmer, temps between 37°C and 30°C. Wrap up your sightseeing by early afternoon on the 11th (Sun) to allow time for the flight to Punta Cana.

Things to do in Culebra

Beaches · Outdoors · Parks
Find places to stay Sep 9 — 11:
Highlights from your trip

Punta Cana, Dominican Republic

— 3 nights
In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.
Take a break from Punta Cana with a short trip to Altos de Chavon in La Romana, about 1h 20 min away. Spend a day of island exploring on the 13th (Tue) at Saona Island. There's more to do: discover the deep blue sea with Aqua Track Private Day Trips and indulge in some personalized pampering at Flavio Acuna Spa Natural Center.

To find photos, traveler tips, other places to visit, and other tourist information, refer to the Punta Cana day trip website.

Getting from Culebra to Punta Cana by flight takes about 7.5 hours. Other options: do a combination of ferry, taxi, and bus; or do a combination of ferry, taxi, shuttle, and bus. In September, daily temperatures in Punta Cana can reach 36°C, while at night they dip to 28°C. Finish your sightseeing early on the 14th (Wed) to allow enough time to fly to Providenciales.

Things to do in Punta Cana

Nature · Parks · Outdoors · Wildlife

Side Trips

Find places to stay Sep 11 — 14:

Providenciales, Turks and Caicos

— 2 nights
The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
Kick off your visit on the 15th (Thu): head off the coast to Little Water Cay and then kick back and relax at Grace Bay Beach. Keep things going the next day: see some colorful creatures with a scuba or snorkeling tour.

For traveler tips, photos, reviews, and other tourist information, go to the Providenciales trip builder tool.

Traveling by flight from Punta Cana to Providenciales takes 5 hours. You'll gain 1 hour traveling from Punta Cana to Providenciales due to the time zone difference. In September, daytime highs in Providenciales are 38°C, while nighttime lows are 31°C. On the 16th (Fri), wrap the sightseeing up by early afternoon so you can fly to Key West.

Things to do in Providenciales

Outdoors · Wildlife · Parks · Tours
Find places to stay Sep 14 — 16:

Key West, United States

— 2 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.
Kick off your visit on the 17th (Sat): kick back and relax at Bahia Honda State Park and then discover the deep blue sea with a scuba or snorkeling tour. Here are some ideas for day two: take a leisurely stroll along Mallory Square, then examine the collection at The Ernest Hemingway Home and Museum, and then tour the pleasant surroundings at Key West Butterfly & Nature Conservatory.

For maps, more things to do, traveler tips, and more tourist information, read Key West trip planner.

Fly from Providenciales to Key West in 8 hours. In September in Key West, expect temperatures between 36°C during the day and 31°C at night. Wrap up your sightseeing on the 18th (Sun) early enough to fly to Orlando.

Things to do in Key West

Parks · Outdoors · Wildlife · Beaches

Side Trip

Find places to stay Sep 16 — 18:

Orlando, United States

— 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.
Pack the 19th (Mon) with family-friendly diversions at Universal's Islands of Adventure. Plan for a day of cool, family-friendly fun on the 21st (Wed) at Discovery Cove. It doesn't end there: get in on the family fun at Universal Orlando Resort and make an unforgettable trip to Walt Disney World Resort.

Find out how to plan Orlando trip without stress by asking Inspirock to help create an itinerary.

Getting from Key West to Orlando by flight takes about 3 hours. Other options: drive; or take a bus. Traveling from Key West in September, you can expect nighttime temperatures to be a bit cooler in Orlando, with lows of 27°C. Cap off your sightseeing on the 23rd (Fri) early enough to catch the flight to Chicago.

Things to do in Orlando

Find places to stay Sep 18 — 23:

Chicago, United States

— 4 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, nightlife, and parks. Your trip includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, take a leisurely stroll along Navy Pier, get curious at Museum of Science and Industry, and admire the landmark architecture of 360 Chicago Observation Deck.

For where to stay, photos, maps, and other tourist information, read Chicago trip itinerary planner.

Fly from Orlando to Chicago in 4.5 hours. Alternatively, you can drive; or take a bus. Due to the time zone difference, you'll gain 1 hour traveling from Orlando to Chicago. Expect a bit cooler temperatures when traveling from Orlando in September; daily highs in Chicago reach 30°C and lows reach 19°C. Wrap up your sightseeing on the 27th (Tue) early enough to fly to Las Vegas.

Things to do in Chicago

Museums · Parks · Childrens Museums · Zoos & Aquariums
Find places to stay Sep 23 — 27:

Las Vegas, United States

— 4 nights

Sin City

Nicknamed the "Entertainment Capital of the World," Las Vegas sits in the middle of a desert in the southern section of Nevada.
Take a break from Las Vegas with a short trip to Hoover Dam in Boulder City, about 50 minutes away. There's much more to do: ponder the design of Fountains of Bellagio, try to win big at Bellagio Hotel and Casino, browse the different shops at The Grand Canal Shoppes at The Venetian Resort, and get to know the fascinating history of The Strip.

For ratings, other places to visit, photos, and tourist information, you can read our Las Vegas day trip planner.

Traveling by flight from Chicago to Las Vegas takes 5 hours. Alternatively, you can drive; or do a combination of train and bus. Traveling from Chicago to Las Vegas, you'll gain 2 hours due to the time zone difference. In September, Las Vegas is somewhat warmer than Chicago - with highs of 39°C and lows of 25°C. Finish up your sightseeing early on the 1st (Sat) so you can catch the flight to San Diego.

Things to do in Las Vegas

Parks · Shopping · Nature · Neighborhoods

Side Trip

Find places to stay Sep 27 — Oct 1:

San Diego, United States

— 5 nights

America's Finest City

Divided into neighborhoods with distinct characters and cultural heritages, San Diego sits just north of the Mexican border and offers visitors a blend of tourist attractions, including a lively nightlife, diverse cuisine, and a thriving musical scene.
Change things up with a short trip to Self Realization Fellowship Hermitage & Meditation Gardens in Encinitas (about 32 minutes away). Spend the 2nd (Sun) exploring the fascinating underwater world at SeaWorld San Diego. The adventure continues: learn about wildlife with up-close encounters at San Diego Zoo, let the kids burn off some steam at Balboa Park, immerse yourself in nature at Torrey Pines State Natural Reserve, and enjoy the sand and surf at La Jolla Cove.

To see photos, traveler tips, more things to do, and more tourist information, read our San Diego trip builder website.

Getting from Las Vegas to San Diego by flight takes about 2.5 hours. Other options: drive; or take a bus. In October, daytime highs in San Diego are 30°C, while nighttime lows are 20°C. Finish up your sightseeing early on the 6th (Thu) so you can go by car to Los Angeles.

Things to do in San Diego

Parks · Zoos & Aquariums · Theme Parks · Outdoors

Side Trip

Find places to stay Oct 1 — 6:

Los Angeles, United States

— 5 nights

City of Angels

Surrounded by mountain ranges, forests, valleys, beaches, and deserts, the metropolitan area of Los Angeles is home to over 17 million people.
Change things up with these side-trips from Los Angeles: Disneyland Park (in Anaheim) and Mulholland Drive (in Beverly Hills). Pack the 8th (Sat) with family-friendly diversions at Universal Studios Hollywood. And it doesn't end there: get to know the fascinating history of Santa Monica Pier, admire all the interesting features of 26-Mile Bike Path, see the interesting displays at The Getty Center, and get curious at La Brea Tar Pits and Museum.

For other places to visit, reviews, photos, and more tourist information, read Los Angeles trip itinerary planning website.

Drive from San Diego to Los Angeles in 2 hours. Alternatively, you can fly; or take a bus. In October, plan for daily highs up to 32°C, and evening lows to 19°C. Cap off your sightseeing on the 11th (Tue) early enough to catch the flight to San Francisco.

Things to do in Los Angeles

Theme Parks · Outdoors · Parks · Museums

Side Trips

Find places to stay Oct 6 — 11:

San Francisco, United States

— 5 nights

City by the Bay

San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
San Francisco is known for nature, parks, and museums. Your trip includes some of its best attractions: steep yourself in history at Golden Gate Bridge, take a stroll through Union Square, make a trip to Coit Tower, and take some stellar pictures from Twin Peaks.

For more things to do, photos, where to stay, and more tourist information, refer to the San Francisco online road trip planner.

Traveling by flight from Los Angeles to San Francisco takes 3 hours. Alternatively, you can drive; or take a bus. Traveling from Los Angeles in October, expect San Francisco to be a bit cooler, temps between 26°C and 15°C. Wrap up your sightseeing on the 16th (Sun) to allow time to fly to Seattle.

Things to do in San Francisco

Parks · Museums · Childrens Museums · Neighborhoods
Find places to stay Oct 11 — 16:

Seattle, United States

— 5 nights

Emerald City

Nicknamed the "Emerald City" because of its abundant evergreen trees, Seattle is the cultural and business center of the Pacific Northwest, as well as a popular holiday destination.
Seattle is known for museums, parks, and wineries. Your trip includes some of its best attractions: view the masterpieces at Chihuly Garden and Glass, make a trip to Space Needle, head outdoors with Outdoor Activities, and explore the world behind art at Seattle Art Museum.

To see ratings, more things to do, maps, and tourist information, use the Seattle trip maker.

Fly from San Francisco to Seattle in 3.5 hours. Alternatively, you can drive; or take a bus. Prepare for little chillier weather when traveling from San Francisco in October: high temperatures in Seattle hover around 20°C and lows are around 11°C. Finish your sightseeing early on the 21st (Fri) so you can fly back home.

Things to do in Seattle

Parks · Museums · Shopping · Outdoors
Find places to stay Oct 16 — 21: