31 days in United States & Caribbean Itinerary

31 days in United States & Caribbean Itinerary

Created using Inspirock trip planner

Make it your trip
Fly
1
Seattle, United States
— 2 nights
Fly
2
Chicago, United States
— 1 night
Fly
3
New York City, United States
— 3 nights
Fly
4
Richmond, United States
— 2 nights
Fly
5
Orlando, United States
— 2 nights
Fly
6
Nassau, Bahamas
— 2 nights
Ferry
7
Harbour Island, Bahamas
— 2 nights
Unknown
8
Cayo Largo, Cuba
— 2 nights
Bus
9
Havana, Cuba
— 2 nights
Drive
10
Cayo Guillermo, Cuba
— 1 night
Unknown
11
Ocho Rios, Jamaica
— 1 night
Drive
12
Montego Bay, Jamaica
— 2 nights
Drive
13
Negril, Jamaica
— 1 night
Fly
14
Dallas, United States
— 4 nights
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Seattle, United States

— 2 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.
Kick off your visit on the 6th (Sun): take a stroll through Pike Place Market, stroll around Kerry Park, admire the masterpieces at Chihuly Garden and Glass, then don't miss a visit to Space Needle, and finally admire the striking features of Seattle Public Library. Get ready for a full day of sightseeing on the 7th (Mon): indulge your taste buds at Food & Drink, admire the local landmark of Seattle Center, then take in the waterfront at Hiram M. Chittenden Locks, then walk around Green Lake Park, and finally take in nature's colorful creations at Seattle Japanese Garden.

To find reviews, ratings, where to stay, and tourist information, you can read our Seattle itinerary planner.

Armidale, Australia to Seattle is an approximately 27-hour flight. The time zone changes from Australian Eastern Standard Time (AEST) to Pacific Standard Time (PST), which is usually a -18 hour difference. Expect a daytime high around 27°C in June, and nighttime lows around 16°C. On the 8th (Tue), wrap the sightseeing up by early afternoon so you can travel to Chicago.

Things to do in Seattle

Parks · Nature · Museums · Shopping

Side Trip

Chicago, United States

— 1 night

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kick off your visit on the 9th (Wed): snap pictures at Michigan Avenue Bridge, appreciate the extensive heritage of Chicago Riverwalk, explore the activities along Chicago River, then grab your bike and head to Lakefront Trail, then ponder the design of Buckingham Fountain, and finally try out the rides at Fox in a Box Chicago.

For other places to visit, traveler tips, photos, and more tourist information, read our Chicago holiday planning website.

Getting from Seattle to Chicago by flight takes about 7 hours. Other options: drive; or take a train. Traveling from Seattle to Chicago, you'll lose 2 hours due to the time zone difference. Expect a bit warmer temperatures when traveling from Seattle in June; daily highs in Chicago reach 32°C and lows reach 20°C. Finish your sightseeing early on the 9th (Wed) to allow enough time to travel to New York City.

Things to do in Chicago

Parks · Outdoors · Trails · Theme Parks

New York City, United States

— 3 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.
Discover out-of-the-way places like Food Tours and Speed Boats Tours. There's lots more to do: stroll through Central Park, examine the collection at New York Public Library, walk around Brooklyn Bridge Park, and take in panoramic vistas at Empire State Building.

To see reviews, maps, traveler tips, and more tourist information, refer to the New York City visit planner.

You can fly from Chicago to New York City in 5 hours. Alternatively, you can fly; or drive; or take a bus. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. In June, daytime highs in New York City are 31°C, while nighttime lows are 21°C. Cap off your sightseeing on the 12th (Sat) early enough to travel to Richmond.

Things to do in New York City

Parks · Tours · Museums · Neighborhoods

Side Trip

Richmond, United States

— 2 nights

The River City

The capital city of Virginia, Richmond has diverse architecture, a large collection of monuments, and world-class museums that reveal the city's important role in American history.
On the 13th (Sun), relax and float downstream with a rafting and tubing tour, stroll around Belle Isle, pause for some photo ops at Virginia War Memorial, then get engrossed in the history at Agecroft Hall & Gardens, and finally admire the natural beauty at Maymont. Keep things going the next day: appreciate the extensive heritage of Fan District, admire the majestic nature at Pocahontas State Park, stroll around Pony Pasture Park (James River Park System), then explore the world behind art at Virginia Museum of Fine Arts, and finally explore the landscape on two wheels at Virginia Capital Trail.

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

Fly from New York City to Richmond in 5 hours. Alternatively, you can fly; or drive; or take a train. When traveling from New York City in June, plan for somewhat warmer days and about the same nights in Richmond: temperatures range from 35°C by day to 22°C at night. Finish your sightseeing early on the 14th (Mon) so you can travel to Orlando.

Things to do in Richmond

Parks · Outdoors · Nature · Tours

Side Trip

Orlando, United States

— 2 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.
Kick off your visit on the 15th (Tue): get in on the family fun at Universal Orlando Resort and then see the world from above with a helicopter tour. Keep things going the next day: get in on the family fun at Universal's Islands of Adventure.

For traveler tips, reviews, maps, and other tourist information, read Orlando road trip planning tool.

Traveling by flight from Richmond to Orlando takes 5 hours. Alternatively, you can drive; or take a train. Traveling from Richmond in June, expect a bit warmer with lows of 26°C in Orlando. Cap off your sightseeing on the 16th (Wed) early enough to travel to Nassau.

Things to do in Orlando

Theme Parks · Tours

Nassau, Bahamas

— 2 nights
On a trip to Nassau you can immerse yourself in a dynamic city atmosphere or spend your days lazing on the soft golden sands.
Kick off your visit on the 17th (Thu): enjoy the sand and surf at Love Beaches, contemplate in the serene atmosphere at Christ Church Cathedral, then don't miss a visit to The Cloister, then observe the fascinating underwater world at Marine Habitat at Atlantis, and finally get interesting insight from Tours. On the next day, kick back and relax at Cable Beach, then stroll through Ardastra Gardens, Zoo and Conservation Center, then admire the masterpieces at Junkanoo World Museum & Arts Centre, and finally learn the secrets of beer at Islandz Tours - Cultural Walking Tours of Downtown Nassau.

To see photos, traveler tips, reviews, and more tourist information, go to the Nassau trip builder app.

Traveling by flight from Orlando to Nassau takes 5 hours. Alternatively, you can do a combination of train, bus, and ferry; or do a combination of train and ferry. In June, daytime highs in Nassau are 37°C, while nighttime lows are 28°C. Finish your sightseeing early on the 18th (Fri) so you can ride a ferry to Harbour Island.

Things to do in Nassau

Parks · Outdoors · Beaches · Zoos & Aquariums

Side Trips

Harbour Island, Bahamas

— 2 nights
The casual Bahamian vibee of Harbour Island comes through in its atmospheric seaside eateries, the colonial English architecture of its main urban zones, and its wealth of attractive coastal areas.
Start off your visit on the 19th (Sat): discover the deep blue sea with ​Eleuthera Sailing Adventures, then stop by A and A Hidden Treasures, then relax and rejuvenate at Fitness with Tamara, and finally enjoy the sand and surf at Pink Sands Beach.

To find more things to do, ratings, and more tourist information, refer to the Harbour Island trip itinerary maker tool.

Ride a ferry from Nassau to Harbour Island in 3.5 hours. On the 20th (Sun), you'll have the morning to explore before heading off to Cayo Largo.

Things to do in Harbour Island

Outdoors · Wildlife · Tours · Beaches

Cayo Largo, Cuba

— 2 nights
The stress of modern life feels a million miles away when you holiday on Cayo Largo, a small and unspoiled resort island off the coast of Cuba.
Start off your visit on the 21st (Mon): tour the pleasant surroundings at Playa Paraiso. On your second day here, enjoy the sand and surf at Sirena Beach, identify plant and animal life at Sea Turtle Hatchery, and then step off the mainland to explore Cayo Rico.

To see maps, traveler tips, ratings, and more tourist information, you can read our Cayo Largo online itinerary planner.

The Route module can help you plan travel from Harbour Island to Cayo Largo. In June, daily temperatures in Cayo Largo can reach 36°C, while at night they dip to 28°C. Finish your sightseeing early on the 22nd (Tue) so you can take a bus to Havana.

Things to do in Cayo Largo

Parks · Beaches · Outdoors · Wildlife

Havana, Cuba

— 2 nights

Rome of the Caribbean

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Kick off your visit on the 23rd (Wed): capture your vacation like a pro with an inspiring photography tour, steep yourself in history at Palacio De Los Capitanes Generales, don't miss a visit to Plaza de Armas, make a trip to Plaza de la Catedral, then steep yourself in history at Fortaleza de San Carlos de la Cabana, and finally contemplate the long history of El Morro. On the 24th (Thu), you'll have a packed day of sightseeing: head outdoors with Outdoor Activities, then appreciate the extensive heritage of Malecón of Havana, and then deepen your understanding at University of Havana.

To see ratings, other places to visit, where to stay, and other tourist information, read Havana vacation maker website.

Traveling by bus from Cayo Largo to Havana takes 5.5 hours. Alternatively, you can fly. Expect a daytime high around 36°C in June, and nighttime lows around 26°C. Finish your sightseeing early on the 24th (Thu) to allow enough time to drive to Cayo Guillermo.

Things to do in Havana

Tours · Historic Sites · Outdoors · Wildlife

Cayo Guillermo, Cuba

— 1 night
A kay of the Jardines del Rey archipelago, Cayo Guillermo has become a popular international tourist destination, buoyed by the construction of luxury all inclusive resorts that dot the paradisal island.
Start off your visit on the 25th (Fri): head off the coast to Cayo Media Luna and then stroll through Playa Pilar.

To see photos, traveler tips, other places to visit, and other tourist information, read our Cayo Guillermo tour builder tool.

Traveling by car from Havana to Cayo Guillermo takes 7 hours. Alternatively, you can do a combination of bus and car; or do a combination of train and taxi. In June, daily temperatures in Cayo Guillermo can reach 36°C, while at night they dip to 28°C. Wrap up your sightseeing by early afternoon on the 25th (Fri) to allow enough time to travel to Ocho Rios.

Things to do in Cayo Guillermo

Parks · Beaches · Outdoors · Nature
Highlights from your trip

Ocho Rios, Jamaica

— 1 night
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
Start off your visit on the 26th (Sat): admire the sheer force of Dunn's River Falls and Park, take in the architecture and atmosphere at Our Lady of Fatima Catholic Church, then get up close to creatures of the deep with Sip N Tour with Mark - Day Tours, and finally take an in-depth tour of Coyaba River Garden and Museum.

To see traveler tips, other places to visit, reviews, and other tourist information, refer to the Ocho Rios trip planner.

Use the Route module to find suitable travel options from Cayo Guillermo to Ocho Rios. In June, daytime highs in Ocho Rios are 38°C, while nighttime lows are 30°C. Finish your sightseeing early on the 26th (Sat) to allow enough time to drive to Montego Bay.

Things to do in Ocho Rios

Parks · Outdoors · Nature · Wildlife

Montego Bay, Jamaica

— 2 nights
The second largest city in Jamaica, Montego Bay boasts an international airport and a major cruise-line terminal, so it regularly receives a big influx of visitors to the island.
Start off your visit on the 27th (Sun): explore the activities along Martha Brae Rafting Village, tee off at Cinnamon Hill Golf Course, then contemplate the long history of Rose Hall Great House, and finally relax and rejuvenate at Half Moon Rosehall, A Rock Resort. Here are some ideas for day two: tour in harmony with nature at Rastasafari Experience, then kick back and relax at Doctor's Cave Beach, and then get some thrills on the water with a speed boat tour.

To find reviews, other places to visit, maps, and other tourist information, refer to the Montego Bay trip planner.

Traveling by car from Ocho Rios to Montego Bay takes 2 hours. Alternatively, you can take a bus. In June, daytime highs in Montego Bay are 38°C, while nighttime lows are 29°C. Finish your sightseeing early on the 28th (Mon) so you can drive to Negril.

Things to do in Montego Bay

Outdoors · Tours · Parks · Beaches

Negril, Jamaica

— 1 night
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
Kick off your visit on the 29th (Tue): take in the architecture and atmosphere at Mary, Gate of Heaven Catholic Church, then look for gifts at Irie Art, and then enjoy the sand and surf at Seven Mile Beach.

To see maps, more things to do, traveler tips, and other tourist information, read Negril trip planner.

Traveling by car from Montego Bay to Negril takes 1.5 hours. Alternatively, you can take a bus. In June, plan for daily highs up to 38°C, and evening lows to 29°C. Finish your sightseeing early on the 29th (Tue) to allow enough time to travel to Dallas.

Things to do in Negril

Beaches · Parks · Outdoors · Historic Sites

Dallas, United States

— 4 nights

Big D

One of the country's most popular shopping destinations, Dallas and its sprawling suburbs include more shopping centers per capita than any other urban center in America.
Discover out-of-the-way places like Fort Worth Stockyards National Historic District and Big Rocks Park. Explore Dallas' surroundings by going to National Videogame Museum (in Frisco), Texas Civil War Museum (in White Settlement) and Spa Habitat Legacy (in Plano). There's much more to do: see the interesting displays at The Sixth Floor Museum at Dealey Plaza, get outside with Frisco RoughRiders, explore the world behind art at Sid Richardson Museum, and don't miss a visit to Pioneer Plaza.

To find where to stay, ratings, other places to visit, and more tourist information, read our Dallas online visit planner.

You can fly from Negril to Dallas in 10 hours. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. In June, daily temperatures in Dallas can reach 39°C, while at night they dip to 28°C. Finish your sightseeing early on the 4th (Sun) so you can travel back home.

Things to do in Dallas

Parks · Museums · Nature · Outdoors

Side Trips

United States travel guide

4.5
Specialty Museums · Beaches · Historic Sites
More than the country of car-packed streets seen in TV shows and movies, the United States of America is a complex and diverse home to over 300 million people living in a wide range of landscapes and climates. From its big-city skyscrapers to its sprawling natural parks, the country's ''melting pot'' combines many ethnic groups that share a strong sense of national identity despite their cultural differences. A country of road trips and big blue skies, the United States harbors orderly cities filled with restaurants, parks, museums, and innumerable sightseeing opportunities, as well as pristine natural areas perfect for a holiday in the great outdoors. To see as much as you can of this diverse land quickly, drive over some of the more than 6 million km (4 million mi) of highways leading through deserts, mountain peaks, fertile fields, and giant urban centers.

Bahamas travel guide

3.6
Beaches · Islands · Water & Amusement Parks
Part of an archipelago encompassing hundreds of islets and cays, Bahamas boast many pink beaches, which get their vibrant color from fractured seashells mixed with ordinary sand. For most pleasure seekers an ideal holiday in Bahamas consists of various sea activities, occasionally interrupted by tours of several cities, offering an eclectic music scene dominated by calypso, soca, and junkanoo genres. Romantic enough to attract newlyweds from around the globe, the islands are also a major center of eco-tourism, with visits to national parks and diving tours in colorful reefs among the most popular things to do in Bahamas.

Cuba travel guide

4.4
Beaches · Historic Walking Areas · Landmarks
The largest island in the Caribbean, Cuba lies just 140 km (90 mi) south of Florida and captivates a growing number of Western visitors with its tropical landscapes and cultural attractions. Sightseeing in Cuba inevitably begins in Havana, a city of photogenic architecture, lively nightlife, and a passion for baseball. The country's smaller colonial towns usually feature central squares, ideal places to meet the locals under wrought-iron street lamps. Savvy visitors escape the cities during their Cuba holidays, devoting plenty of time to the country's charming countryside, where you can get the feel for this diverse land by conversing with friendly tobacco farmers and small-scale fruit producers.

Jamaica travel guide

4.1
Waterfalls · Beaches · Nightlife
The third most populous English-speaking country in the Americas, Jamaica remains a member of the Commonwealth of Nations, with the British monarch its official head of state. Jamaica tourism thrives thanks to the island nation's reputation for natural beauty, outstanding cuisine, and lively music scene. The country's landscape is as diverse as its population, its tropical climate supporting varied ecosystems that include everything from savannahs to rugged mountain slopes. For most visitors, a holiday in Jamaica is a largely outdoor affair, with hiking, fishing, golfing, camping, snorkeling, horseback riding, and kite surfing among the most popular things to do.