38 days in Caribbean, Central America, United States & Mexico Itinerary
Created using Klarna Trips trip planner
Start: Kingston, Jamaica
Drive
1
Ocho Rios, Jamaica
— 1 night
Drive
2
Montego Bay, Jamaica
— 4 nights
Fly
3
Puerto Plata, Dominican Republic
— 2 nights
Fly
4
Charlotte Amalie, U.S. Virgin Islands
— 3 nights
Fly
5
Isla de Vieques, Puerto Rico
— 3 nights
Fly
6
Culebra, Puerto Rico
— 3 nights
Fly
7
San Juan, Puerto Rico
— 2 nights
Fly
8
Santo Domingo, Dominican Republic
— 2 nights
Fly
9
La Fortuna de San Carlos, Costa Rica
— 5 nights
Fly
10
Honolulu, United States
— 5 nights
Fly
11
Cancun, Mexico
— 4 nights
Fly
12
Nassau, Bahamas
— 3 nights
Fly
End: Kingston, Jamaica
Thu, Feb 1 - Sat, Mar 9
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Ocho Rios, Jamaica — 1 night

Start off your visit on the 1st (Thu): stop by Jewels & Time Duty Free Jewelers, take in the dramatic scenery at Dunn's River Falls and Park, and then admire the sheer force of Blue Hole. On the 2nd (Fri), you'll have a packed day of sightseeing: hike along Fern Gully and then Head underground at Green Grotto Caves.
To find traveler tips, more things to do, ratings, and more tourist information, you can read our Ocho Rios trip planner.
Kingston to Ocho Rios is an approximately 1.5-hour car ride. You can also drive; or take a bus. In February, daily temperatures in Ocho Rios can reach 36°C, while at night they dip to 26°C. Wrap up your sightseeing on the 2nd (Fri) early enough to drive to Montego Bay.
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To find traveler tips, more things to do, ratings, and more tourist information, you can read our Ocho Rios trip planner.
Kingston to Ocho Rios is an approximately 1.5-hour car ride. You can also drive; or take a bus. In February, daily temperatures in Ocho Rios can reach 36°C, while at night they dip to 26°C. Wrap up your sightseeing on the 2nd (Fri) early enough to drive to Montego Bay.
Side Trip
Find places to stay Feb 1 — 2:
Highlights from your trip
Montego Bay, Jamaica — 4 nights

Get out of town with these interesting Montego Bay side-trips: Tryall Golf Course (in Sandy Bay) and Negril (Mary, Gate of Heaven Catholic Church & Seven Mile Beach). There's still lots to do: play a few rounds at White Witch Golf Course, glide through the air with a parasailing or paragliding tour, enjoy the sand and surf at Doctor's Cave Beach, and steep yourself in history at Rose Hall Great House.
To see where to stay, maps, other places to visit, and more tourist information, go to the Montego Bay journey website.
You can drive from Ocho Rios to Montego Bay in 2 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 35°C in February, and nighttime lows around 26°C. Wrap up your sightseeing by early afternoon on the 6th (Tue) to allow enough time to fly to Puerto Plata.
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To see where to stay, maps, other places to visit, and more tourist information, go to the Montego Bay journey website.
You can drive from Ocho Rios to Montego Bay in 2 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 35°C in February, and nighttime lows around 26°C. Wrap up your sightseeing by early afternoon on the 6th (Tue) to allow enough time to fly to Puerto Plata.
Side Trips
Find places to stay Feb 2 — 6:
Highlights from your trip
Puerto Plata, Dominican Republic — 2 nights
On the 7th (Wed), observe the fascinating underwater world at Ocean World Adventure Park, Puerto Plata. Get ready for a full day of sightseeing on the next day: steep yourself in history at Fortaleza San Felipe and then admire the sheer force of 27 Waterfalls of Damajagua.
For reviews, other places to visit, photos, and other tourist information, you can read our Puerto Plata tour itinerary maker.
You can fly from Montego Bay to Puerto Plata in 8.5 hours. The time zone difference when traveling from Montego Bay to Puerto Plata is 1 hour. Plan for little chillier nights when traveling from Montego Bay in February since evenings lows in Puerto Plata dip to 22°C. Wrap up your sightseeing on the 8th (Thu) early enough to fly to Charlotte Amalie.
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For reviews, other places to visit, photos, and other tourist information, you can read our Puerto Plata tour itinerary maker.
You can fly from Montego Bay to Puerto Plata in 8.5 hours. The time zone difference when traveling from Montego Bay to Puerto Plata is 1 hour. Plan for little chillier nights when traveling from Montego Bay in February since evenings lows in Puerto Plata dip to 22°C. Wrap up your sightseeing on the 8th (Thu) early enough to fly to Charlotte Amalie.
Find places to stay Feb 6 — 8:
Highlights from your trip
Charlotte Amalie, U.S. Virgin Islands — 3 nights

Duty-free Capital of the World
Charlotte Amalie is known for wildlife, shopping, and nightlife. Your trip includes some of its best attractions: tour the pleasant surroundings at Magens Bay, enjoy the sand and surf at Coki Point Beach, take in the waterfront activity at American Yacht Harbor, and discover the deep blue sea with JJ Divers St Thomas.
To see reviews, maps, other places to visit, and other tourist information, you can read our Charlotte Amalie road trip website.
Traveling by flight from Puerto Plata to Charlotte Amalie takes 6.5 hours. Expect a bit warmer evenings in Charlotte Amalie when traveling from Puerto Plata in February, with lows around 26°C. Wrap up your sightseeing on the 11th (Sun) early enough to fly to Isla de Vieques.
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To see reviews, maps, other places to visit, and other tourist information, you can read our Charlotte Amalie road trip website.
Traveling by flight from Puerto Plata to Charlotte Amalie takes 6.5 hours. Expect a bit warmer evenings in Charlotte Amalie when traveling from Puerto Plata in February, with lows around 26°C. Wrap up your sightseeing on the 11th (Sun) early enough to fly to Isla de Vieques.
Side Trips
Find places to stay Feb 8 — 11:
Highlights from your trip
Isla de Vieques, Puerto Rico — 3 nights

Isla Nena
Isla de Vieques is known for beaches, nature, and adventure. Your trip includes some of its best attractions: kick back and relax at Balneario Sun Bay, take a leisurely stroll along Malecon, glide peacefully along the water with some of the best stand-up paddleboarding in the area, and stroll through Vieques National Wildlife Refuge.
For ratings, more things to do, traveler tips, and more tourist information, go to the Isla de Vieques trip planner.
You can fly from Charlotte Amalie to Isla de Vieques in 5 hours. In February in Isla de Vieques, expect temperatures between 33°C during the day and 26°C at night. Finish up your sightseeing early on the 14th (Wed) so you can catch the flight to Culebra.
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For ratings, more things to do, traveler tips, and more tourist information, go to the Isla de Vieques trip planner.
You can fly from Charlotte Amalie to Isla de Vieques in 5 hours. In February in Isla de Vieques, expect temperatures between 33°C during the day and 26°C at night. Finish up your sightseeing early on the 14th (Wed) so you can catch the flight to Culebra.
Find places to stay Feb 11 — 14:
Highlights from your trip
Culebra, Puerto Rico — 3 nights

Little Island
Culebra is known for beaches, wildlife, and outdoors. Your trip includes some of its best attractions: kick back and relax at Flamenco Beach, step off the mainland to explore Culebrita, stroll through Playa Tamarindo, and take a tour by water with Boat Tours & Water Sports.
For reviews, other places to visit, ratings, and tourist information, go to the Culebra day trip tool.
Fly from Isla de Vieques to Culebra in 3.5 hours. Alternatively, you can ride a ferry. In February in Culebra, expect temperatures between 34°C during the day and 26°C at night. Finish up your sightseeing early on the 17th (Sat) so you can catch the flight to San Juan.
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For reviews, other places to visit, ratings, and tourist information, go to the Culebra day trip tool.
Fly from Isla de Vieques to Culebra in 3.5 hours. Alternatively, you can ride a ferry. In February in Culebra, expect temperatures between 34°C during the day and 26°C at night. Finish up your sightseeing early on the 17th (Sat) so you can catch the flight to San Juan.
Find places to stay Feb 14 — 17:
Highlights from your trip
San Juan, Puerto Rico — 2 nights

Walled City
Start off your visit on the 18th (Sun): pause for some serene contemplation at Catedral Basilica Menor de San Juan Bautista, then take a stroll through Old San Juan, and then kick back and relax at Condado Beach. On the 19th (Mon), you'll have a packed day of sightseeing: look for gifts at Marisel Herbal Bath & Body, kick back and relax at Playa Luquillo, and then stroll through Pine Grove Beach.
For photos, maps, more things to do, and more tourist information, use the San Juan road trip planning site.
Traveling by flight from Culebra to San Juan takes 2 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry, taxi, and shuttle. In February, daily temperatures in San Juan can reach 34°C, while at night they dip to 26°C. Cap off your sightseeing on the 19th (Mon) early enough to catch the flight to Santo Domingo.
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For photos, maps, more things to do, and more tourist information, use the San Juan road trip planning site.
Traveling by flight from Culebra to San Juan takes 2 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry, taxi, and shuttle. In February, daily temperatures in San Juan can reach 34°C, while at night they dip to 26°C. Cap off your sightseeing on the 19th (Mon) early enough to catch the flight to Santo Domingo.
Side Trips
Find places to stay Feb 17 — 19:
Highlights from your trip
Santo Domingo, Dominican Republic — 2 nights

Kick off your visit on the 20th (Tue): contemplate the long history of Casa del Cordon, explore the historical opulence of Alcazar de Colon, pause for some serene contemplation at Basilica Cathedral of Santa Maria la Menor, then appreciate the history behind Columbus Lighthouse (Faro A Colon), and finally delve into the distant past at Monasterio de San Francisco. Get ready for a full day of sightseeing on the 21st (Wed): don't miss a visit to Zona Colonial and then take some stellar pictures from Santo Domingo Skyline.
For other places to visit, maps, where to stay, and other tourist information, you can read our Santo Domingo trip maker tool.
Traveling by flight from San Juan to Santo Domingo takes 3 hours. Alternatively, you can ride a ferry. Finish up your sightseeing early on the 21st (Wed) so you can catch the flight to La Fortuna de San Carlos.
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For other places to visit, maps, where to stay, and other tourist information, you can read our Santo Domingo trip maker tool.
Traveling by flight from San Juan to Santo Domingo takes 3 hours. Alternatively, you can ride a ferry. Finish up your sightseeing early on the 21st (Wed) so you can catch the flight to La Fortuna de San Carlos.
Find places to stay Feb 19 — 21:
Highlights from your trip
La Fortuna de San Carlos, Costa Rica — 5 nights

La Fortuna de San Carlos is known for nature, adventure, and parks. Your trip includes some of its best attractions: take in the natural beauty of Tabacon Hot Springs, view the masterpieces at Onirica Art Gallery, explore the striking landscape of Arenal Volcano, and skim along the rocks with a canyoning and rapelling tour.
To see reviews, more things to do, where to stay, and tourist information, you can read our La Fortuna de San Carlos day trip app.
Getting from Santo Domingo to La Fortuna de San Carlos by flight takes about 6.5 hours. Traveling from Santo Domingo to La Fortuna de San Carlos, you'll gain 2 hours due to the time zone difference. Finish up your sightseeing early on the 26th (Mon) so you can catch the flight to Honolulu.
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To see reviews, more things to do, where to stay, and tourist information, you can read our La Fortuna de San Carlos day trip app.
Getting from Santo Domingo to La Fortuna de San Carlos by flight takes about 6.5 hours. Traveling from Santo Domingo to La Fortuna de San Carlos, you'll gain 2 hours due to the time zone difference. Finish up your sightseeing early on the 26th (Mon) so you can catch the flight to Honolulu.
Side Trip
Find places to stay Feb 21 — 26:
Highlights from your trip
Honolulu, United States — 5 nights

Big Pineapple
Venture out of the city with trips to Haleiwa (Sunset Beach Park & Waimea Bay) and Pu’u O Mahuka Heiau State Monument (in Pupukea). And it doesn't end there: explore the different monuments and memorials at USS Arizona Memorial, examine the collection at Bishop Museum, discover the deep blue sea with a scuba or snorkeling tour, and stroll through Waikiki Beach.
To find maps, where to stay, ratings, and other tourist information, read our Honolulu trip itinerary planning site.
Getting from La Fortuna de San Carlos to Honolulu by flight takes about 17.5 hours. The time zone changes from Central Standard Time (CST) to Hawaii-Aleutian Standard Time (HST), which is usually a -4 hour difference. In February, plan for daily highs up to 32°C, and evening lows to 24°C. Finish up your sightseeing early on the 2nd (Sat) so you can catch the flight to Cancun.
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To find maps, where to stay, ratings, and other tourist information, read our Honolulu trip itinerary planning site.
Getting from La Fortuna de San Carlos to Honolulu by flight takes about 17.5 hours. The time zone changes from Central Standard Time (CST) to Hawaii-Aleutian Standard Time (HST), which is usually a -4 hour difference. In February, plan for daily highs up to 32°C, and evening lows to 24°C. Finish up your sightseeing early on the 2nd (Sat) so you can catch the flight to Cancun.
Side Trips
Find places to stay Feb 26 — Mar 2:
Highlights from your trip
Cancun, Mexico — 4 nights
©
Venture out of the city with trips to Playa del Carmen (Xcaret & Zipline). There's lots more to do: indulge in some personalized pampering at some of the best spas, don't miss a visit to El Parque de las Palapas, meet the residents at Interactive Aquarium, and buy something for everyone on your list at La Isla.
To see reviews, where to stay, other places to visit, and more tourist information, go to the Cancun trip tool.
Getting from Honolulu to Cancun by flight takes about 16.5 hours. Due to the time zone difference, you'll lose 5 hours traveling from Honolulu to Cancun. In March, plan for daily highs up to 32°C, and evening lows to 24°C. Wrap up your sightseeing on the 6th (Wed) to allow time to fly to Nassau.
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To see reviews, where to stay, other places to visit, and more tourist information, go to the Cancun trip tool.
Getting from Honolulu to Cancun by flight takes about 16.5 hours. Due to the time zone difference, you'll lose 5 hours traveling from Honolulu to Cancun. In March, plan for daily highs up to 32°C, and evening lows to 24°C. Wrap up your sightseeing on the 6th (Wed) to allow time to fly to Nassau.
Side Trip
Find places to stay Mar 2 — 6:
Highlights from your trip
Nassau, Bahamas — 3 nights

Nassau is known for theme parks, beaches, and shopping. Your trip includes some of its best attractions: observe the fascinating underwater world at Marine Habitat at Atlantis, admire the natural beauty at Ardastra Gardens & Wildlife Conservation Centre, look for gifts at Craft Cottage Bahamas, and kick back and relax at Cabbage Beach.
To find ratings, more things to do, where to stay, and other tourist information, read Nassau holiday maker site.
You can fly from Cancun to Nassau in 7 hours. In March, daytime highs in Nassau are 32°C, while nighttime lows are 22°C. Cap off your sightseeing on the 9th (Sat) early enough to catch the flight back home.
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To find ratings, more things to do, where to stay, and other tourist information, read Nassau holiday maker site.
You can fly from Cancun to Nassau in 7 hours. In March, daytime highs in Nassau are 32°C, while nighttime lows are 22°C. Cap off your sightseeing on the 9th (Sat) early enough to catch the flight back home.
Side Trip
Find places to stay Mar 6 — 9:
Highlights from your trip
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Dominican Republic travel guide
Sharing the island of Hispaniola with Haiti, friendly Dominican Republic offers two distinct coastlines, one bathed by the Caribbean Sea and the other by the Atlantic Ocean. Nearly 1,600 km (1,000 mi) of palm-shaded beaches figure highly on most Dominican Republic itineraries, allowing visitors to design their vacation around a range of water-based activities. The sun-kissed country benefits from pleasant temperatures throughout the year, so it's no surprise that holidays in Dominican Republic remain a popular choice for visitors from distant and colder corners of the world. A big producer of coffee, cocoa, rum, sugarcane, and tobacco, the country provides a vibrant cultural experience in multicultural cities and quaint countryside.
St. Thomas travel guide
Plan a trip to St. Thomas for a holiday full of duty-free shopping, relaxing, and sightseeing. Although the most commercialized of the U.S. Virgin Islands, St. Thomas is rich in culture and history. A popular cruise ship destination, the hilly island boasts idyllic beaches, upscale resorts, a lively nightlife, and a fine dining scene. Whether you're looking to visit churches and museums, laze on tropical beaches, or have an outdoor adventure, you won't run out of things to do on St. Thomas.
Puerto Rico travel guide
A U.S. territory encompassing one big island and several smaller ones, Puerto Rico appeals to visitors from around the globe with its rich history, pleasant climate, natural beauty, and renowned local cuisine. Most tourists take a vacation in Puerto Rico for that classic seaside experience, though the island offers much more than just sun and sand. Tours of Puerto Rico usually start in the city of San Juan, which boasts a trendy bar scene and plenty of art museums for visitors looking to add a bit of culture to their vacation. A short drive from the island's urban centers, pristine rainforests serve as peaceful retreats from the city bustle and ensure plenty of chances to spot wildlife and take exhilarating nature walks.
Costa Rica travel guide
Tiny in terms of land area, Costa Rica is astoundingly diverse when it comes to culture and natural attractions. In a country called "Rich Coast", it's no surprise most Costa Rica vacations dedicate at least a few days to picturesque Pacific and Caribbean beaches, ideal for water sports and relaxation. Few small countries offer such a range of landscapes, allowing tourists to observe towering volcanoes while soaking away their worries in a hot spring, or hike into dense rainforests in the morning and surf at a modern resort in the afternoon. A trip to Costa Rica also lets you discover pristine national parks, ensuring plenty of chances to view wildlife from the comfort of eco-friendly lodges packed with amenities even ardent nature lovers secretly desire.
United States travel guide
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.
Mexico travel guide
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Bahamas travel guide
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