19 days in Caribbean, United States, Mexico & South America Itinerary

Make it your trip
Drive
1
Montego Bay, Jamaica
— 1 night
Fly
2
Nassau, Bahamas
— 1 night
Fly
3
Miami, United States
— 2 nights
Fly
4
Tampa, United States
— 1 night
Fly to Tallahassee Regional Airport, Drive to Havana
5
Havana, United States
— 1 night
Drive to Tallahassee Regional Airport, Fly to Honolulu
6
Honolulu, United States
— 3 nights
Fly
7
Lahaina, United States
— 3 nights
Fly
8
Cancun, Mexico
— 2 nights
Fly to Paranavaí Airport, Drive to Porto Rico
9
Porto Rico, Brazil
— 1 night
Drive to Paranavaí Airport, Fly to Punta Cana
10
Punta Cana, Dominican Republic
— 1 night
Fly

S M T W T F S
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28

Montego Bay, Jamaica — 1 night

On the 9th (Mon), get engrossed in the history at Greenwood Great House, then admire the landmark architecture of Rose Hall Great House, and then tee off at White Witch Golf Course. Keep things going the next day: play a few rounds at Tryall Golf Course.

For other places to visit, photos, maps, and tourist information, use the Montego Bay trip planner.

Kingston to Montego Bay is an approximately 3-hour car ride. You can also take a bus. October in Montego Bay sees daily highs of 38°C and lows of 28°C at night. Wrap up your sightseeing by early afternoon on the 10th (Tue) to allow time for the flight to Nassau.
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Outdoors · Golf · Museums · Historic Sites
Side Trip
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Nassau, Bahamas — 1 night

Start off your visit on the 11th (Wed): take in nature's colorful creations at Ardastra Gardens & Wildlife Conservation Centre, then admire the natural beauty at The Cloister, and then tour the pleasant surroundings at Cable Beach.

For photos, reviews, ratings, and other tourist information, you can read our Nassau itinerary builder tool.

You can fly from Montego Bay to Nassau in 8 hours. October in Nassau sees daily highs of 36°C and lows of 28°C at night. Cap off your sightseeing on the 11th (Wed) early enough to catch the flight to Miami.
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Parks · Outdoors · Beaches · Wildlife
Side Trip
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Miami, United States — 2 nights

Magic City

Start off your visit on the 12th (Thu): admire the masterpieces at Lowe Art Museum, then identify plant and animal life at Shark Valley Visitor Center, and then get the lay of the land with Walking tours. On your second day here, examine the collection at Vizcaya Museum and Gardens, get engrossed in the history at Black Police Precinct and Courthouse Museum, then appreciate the extensive heritage of Art Deco Historic District, and finally stroll through Lincoln Road.

Take the guesswork out of planning a Miami vacation by using our trip itinerary maker.

Traveling by flight from Nassau to Miami takes 3 hours. Alternatively, you can do a combination of ferry and train; or do a combination of ferry and train. In October, plan for daily highs up to 36°C, and evening lows to 27°C. Cap off your sightseeing on the 13th (Fri) early enough to catch the flight to Tampa.
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Side Trips
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Tampa, United States — 1 night

Big Guava

Kick off your visit on the 14th (Sat): get to know the resident critters at Horse Power for Kids & Animal Sanctuary, test your problem-solving skills at popular escape rooms, then pause for some photo ops at 9/11 Fallen Heroes Memorial, and finally cast your line with a fishing tour.

To see more things to do, traveler tips, ratings, and tourist information, use the Tampa itinerary planning tool.

You can fly from Miami to Tampa in 3 hours. Other options are to drive; or take a bus. Traveling from Miami in October, you can expect nighttime temperatures to be little chillier in Tampa, with lows of 24°C. Wrap up your sightseeing on the 14th (Sat) early enough to travel to Havana.
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Outdoors · Parks · Zoos & Aquariums · Wildlife
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Havana, United States — 1 night

Start off your visit on the 15th (Sun): don't miss a visit to The Planters Exchange.

To see other places to visit, where to stay, and tourist information, use the Havana day trip website.

Explore your travel options from Tampa to Havana with the Route module. Wrap up your sightseeing by early afternoon on the 15th (Sun) to allow time for travel to Honolulu.
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Honolulu, United States — 3 nights

Big Pineapple

Honolulu is known for historic sites, wildlife, and sightseeing. Your trip includes some of its best attractions: explore the galleries of USS Arizona Memorial, kick back and relax at Waikiki Beach, go for a walk through Diamond Head State Monument, and let your taste buds guide you at a local gastronomic tour.

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

The Route module can help you plan travel from Havana to Honolulu. Traveling from Havana to Honolulu, you'll gain 5 hours due to the time zone difference. In October, plan for daily highs up to 36°C, and evening lows to 27°C. Finish your sightseeing early on the 18th (Wed) to allow enough time to fly to Lahaina.
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Lahaina, United States — 3 nights

Crown Jewel of Maui

Kick off your visit on the 19th (Thu): stroll through Kapalua Beach, then get outside with Outdoor Activities, and then discover the deep blue sea with a scuba or snorkeling tour. Keep things going the next day: walk around Lahaina Banyan Court, then get engrossed in the history at Baldwin Home Museum, then meet the residents at Maui Ocean Center, and finally admire the majestic nature at Iao Valley.

To find out how to plan a trip to Lahaina, use our trip itinerary maker.

Fly from Honolulu to Lahaina in 2.5 hours. October in Lahaina sees daily highs of 34°C and lows of 26°C at night. Cap off your sightseeing on the 21st (Sat) early enough to catch the flight to Cancun.
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Parks · Outdoors · Tours · Adventure
Side Trips
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Cancun, Mexico — 2 nights

Start off your visit on the 22nd (Sun): stop by Tattoo Studio Henna, then buy something for everyone on your list at La Isla, and then relax and rejuvenate at some of the best spas. Get ready for a full day of sightseeing on the next day: make a trip to El Parque de las Palapas, then let your taste buds guide you at a local gastronomic tour, and then get close to the beloved marine mammals with a swim-with-the-dolphins experience.

To find traveler tips, ratings, where to stay, and other tourist information, read our Cancun itinerary builder app.

Traveling by flight from Lahaina to Cancun takes 17 hours. The time zone changes from Hawaii-Aleutian Standard Time to Eastern Standard Time, which is usually a 5 hour difference. In October, daytime highs in Cancun are 35°C, while nighttime lows are 26°C. Finish your sightseeing early on the 23rd (Mon) so you can travel to Porto Rico.
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Side Trip
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Porto Rico, Brazil — 1 night

On the 25th (Wed), cool off at Parque das Aguas and then discover the deep blue sea with Centro de Mergulho ProDiver.

To find maps, other places to visit, where to stay, and other tourist information, go to the Porto Rico trip planner.

Use the Route module to find suitable travel options from Cancun to Porto Rico. The time zone difference when traveling from Cancun to Porto Rico is 1 hour. Finish your sightseeing early on the 25th (Wed) so you can travel to Punta Cana.
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Outdoors · Wildlife · Tours · Theme Parks
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Punta Cana, Dominican Republic — 1 night

On the 27th (Fri), see some colorful creatures with Aqua Track Private Day Trips and then indulge in some personalized pampering at Flavio Acuna Spa Natural Center.

To find ratings, reviews, other places to visit, and other tourist information, you can read our Punta Cana trip itinerary app.

The Route module can help you plan travel from Porto Rico to Punta Cana. In October in Punta Cana, expect temperatures between 36°C during the day and 28°C at night. Finish your sightseeing early on the 27th (Fri) so you can fly back home.
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Outdoors · Wildlife · Tours · Spas
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Highlights from your trip

Bahamas travel guide

3.9
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.
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United States travel guide

4.6
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.
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Hawaii travel guide

4.4
The Aloha State
An archipelago of hundreds of volcanic islands located in a geological hot spot in the middle of Pacific, Hawaii offers diverse natural scenery and a warm tropical climate. The six major islands open to tourism draw visitors with their sun-drenched public beaches and craggy natural trails. Thanks to their mid-Pacific location, the islands boast a vibrant native culture influenced by both North America and Asia. You can spend your vacation basking in the modern comforts of the big hotels, but to experience the true spirit of these islands, remember that real Hawaiians live outdoors. Encounter nature by surfing, swimming, fishing, and picnicking, or join a guided tour across the ancient lava flows to the top of Hawaii's rugged volcanic peaks.
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Mexico travel guide

4.4
Tailor-made for anyone seeking that traditional sun-and-sand experience, Mexico vacations allow visitors to explore nearly 10,000 km (6,200 mi) of picturesque coastlines. Idyllic beaches and favorable year-round weather aside, this diverse country with a rich pre-Colombian history allows tourists a chance to discover a fascinating cuisine, numerous archaeological sites, state-of-the-art museums, colonial-era haciendas, and outstanding examples of 21st-century architecture. Most visitors get to know the country by its cities, but if you want a well-rounded Mexico tour, spend some time exploring its jungles, cloud forests, Caribbean reefs, snowcapped volcanoes, vast deserts, and tranquil lagoons. Life is lived outdoors in Mexico, so wherever you go, don't forget to dine alfresco and stroll the country's colonial streets.
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