30 days in Caribbean & United States Itinerary

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Make it your trip
Fly
1
Montego Bay, Jamaica
— 3 nights
Drive
2
Ocho Rios, Jamaica
— 2 nights
Fly
3
Providenciales, Turks and Caicos
— 5 nights
Fly
4
Port-au-Prince, Haiti
— 1 night
Fly
5
Santo Domingo, Dominican Republic
— 3 nights
Shuttle
6
Punta Cana, Dominican Republic
— 5 nights
Fly
7
San Juan, Puerto Rico
— 4 nights
Fly to Tallahassee Regional Airport, Drive to Havana
8
Havana, United States
— 2 nights
Drive to Tallahassee Regional Airport, Fly to Nassau
9
Nassau, Bahamas
— 2 nights
Fly
10
Grand Bahama Island, Bahamas
— 2 nights
Fly

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Montego Bay, Jamaica — 3 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.
Step out of the city life by going to Nature & Wildlife Tours and Scuba & Snorkeling. We've included these beaches for you: Bloody Bay and Seven Mile Beach. And it doesn't end there: enjoy the sand and surf at Doctor's Cave Beach, admire the striking features of Rose Hall Great House, and tour the pleasant surroundings at Rocklands Bird Sanctuary ( Montego Bay).

To see more things to do, photos, reviews, and more tourist information, read Montego Bay tour itinerary maker site.

Vancouver, Canada to Montego Bay is an approximately 12-hour flight. Traveling from Vancouver to Montego Bay, you'll lose 3 hours due to the time zone difference. Traveling from Vancouver in April, things will get much warmer in Montego Bay: highs are around 37°C and lows about 28°C. Wrap up your sightseeing on the 4th (Tue) to allow time to drive to Ocho Rios.
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Outdoors · Parks · Wildlife · Beaches
Side Trip
Find places to stay Apr 1 — 4:

Ocho Rios, Jamaica — 2 nights

A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
On the 5th (Wed), get outside with Outdoor Activities, look for gifts at Jewels & Time Duty Free Jewelers, and then surround yourself with nature on a nature and wildlife tour. On the 6th (Thu), you'll have a packed day of sightseeing: take in the dramatic scenery at Dunn's River Falls and Park and then trot along with a tour on horseback.

To find traveler tips, other places to visit, maps, and other tourist information, refer to the Ocho Rios road trip tool.

Drive from Montego Bay to Ocho Rios in 2 hours. Alternatively, you can take a bus. April in Ocho Rios sees daily highs of 36°C and lows of 27°C at night. Finish your sightseeing early on the 6th (Thu) to allow enough time to fly to Providenciales.
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Tours · Outdoors · Wildlife · Nature
Find places to stay Apr 4 — 6:

Providenciales, Turks and Caicos — 5 nights

The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
Your itinerary includes some good beach time at Grace Bay Beach and Leeward Beach. You'll discover tucked-away gems like Scuba & Snorkeling and Taylor Bay Beach. Spend the 11th (Tue) exploring nature at Chalk Sound. There's still lots to do: stroll through Half Moon Bay, relax and rejuvenate at some of the top local wellness centers, explore the gorgeous colors at Little Water Cay, and trot along with a tour on horseback.

To see ratings, maps, traveler tips, and other tourist information, read our Providenciales sightseeing planning website.

Traveling by flight from Ocho Rios to Providenciales takes 5 hours. In April, daytime highs in Providenciales are 34°C, while nighttime lows are 28°C. Wrap up your sightseeing on the 11th (Tue) to allow time to fly to Port-au-Prince.
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Parks · Outdoors · Beaches · Nature
Find places to stay Apr 6 — 11:

Port-au-Prince, Haiti — 1 night

Port-au-Prince, the capital of Haiti, gives most visitors their first taste of the country, along with all of its rugged and lively charm.
On the 12th (Wed), explore the ancient world of Papillon Enterprise, then examine the collection at The Bureau of Ethnology, then see the interesting displays at Musee du Pantheon National Haitien, and finally browse the eclectic array of goods at Marche de Fer.

Planning Port-au-Prince trip won't be overwhelming when you use Klarna Trips's itinerary maker.

You can fly from Providenciales to Port-au-Prince in 5 hours. In April, daytime highs in Port-au-Prince are 37°C, while nighttime lows are 30°C. Wrap up your sightseeing on the 12th (Wed) to allow time to fly to Santo Domingo.
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Shopping · Museums · Historic Sites
Find places to stay Apr 11 — 12:

Santo Domingo, Dominican Republic — 3 nights

Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Popular historic sites such as Calle Las Damas and Alcazar de Colon are in your itinerary. Get a sense of the local culture at The 3 Eyes National Park and Basilica Cathedral of Santa Maria la Menor. And it doesn't end there: browse the different shops at Agora Mall, contemplate the long history of Fortaleza Ozama, examine the collection at Museo De Las Casas Reales, and appreciate the history behind Columbus Lighthouse (Faro A Colon).

To find reviews, traveler tips, photos, and tourist information, read Santo Domingo trip maker site.

You can fly from Port-au-Prince to Santo Domingo in 4.5 hours. Other options are to drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Port-au-Prince to Santo Domingo. Finish up your sightseeing early on the 15th (Sat) so you can catch the shuttle to Punta Cana.
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Nature · Parks · Historic Sites · Museums
Find places to stay Apr 12 — 15:

Punta Cana, Dominican Republic — 5 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 the city and head to Bavaro Beach and Nature & Wildlife Tours. You'll get in some beach time at Public Beach Playa Dominicus and Juanillo Beach. Explore the numerous day-trip ideas around Punta Cana: Altos de Chavon Regional Museum of Archaeology (in La Romana) and Bayahibe (Cueva Padre Nuestro & Speed Boats Tours). Next up on the itinerary: explore the activities along Hoyo Azul, trot along with a tour on horseback, indulge in some personalized pampering at Ocean Adventures Punta Cana, and play a few rounds at Punta Espada Golf Course.

To see where to stay, maps, other places to visit, and tourist information, read our Punta Cana tour planner.

Traveling by shuttle from Santo Domingo to Punta Cana takes 2 hours. Alternatively, you can drive; or fly. In April in Punta Cana, expect temperatures between 35°C during the day and 27°C at night. Finish up your sightseeing early on the 20th (Thu) so you can catch the flight to San Juan.
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Outdoors · Parks · Beaches · Tours
Side Trips
Find places to stay Apr 15 — 20:

San Juan, Puerto Rico — 4 nights

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S. jurisdiction and one of the oldest in the Americas.
Explore hidden gems such as Kayaking & Canoeing and Catedral Basilica Menor de San Juan Bautista. You'll enjoy a bit of beach vacationing at Condado Beach and Playa Luquillo. You'll find plenty of places to visit near San Juan: Trollbeads (in Canovanas) and El Yunque National Forest (in El Yunque National Forest). Next up on the itinerary: steep yourself in history at Old San Juan, stop by Pure Soul Living, and kick back and relax at Pine Grove Beach.

To find ratings, where to stay, maps, and tourist information, you can read our San Juan online route planner.

Traveling by flight from Punta Cana to San Juan takes 3 hours. Alternatively, you can do a combination of bus and ferry. In April, daytime highs in San Juan are 36°C, while nighttime lows are 28°C. Wrap up your sightseeing by early afternoon on the 24th (Mon) to allow enough time to travel to Havana.
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Parks · Outdoors · Beaches · Nature
Side Trips
Find places to stay Apr 20 — 24:

Havana, United States — 2 nights

Havana is a town in Gadsden County, Florida, United States, and a suburb of Tallahassee. Start off your visit on the 25th (Tue): immerse yourself in nature at Torreya State Park and then look for all kinds of wild species at Apalachicola Bluffs and Ravines Preserve. On the 26th (Wed), you'll have a packed day of sightseeing: admire the majestic nature at Three Rivers State Park.

To see where to stay, more things to do, ratings, and tourist information, read Havana trip maker website.

Explore your travel options from San Juan to Havana with the Route module. The time zone changes from Atlantic Standard Time to Eastern Standard Time, which is usually a -1 hour difference. Wrap up your sightseeing by early afternoon on the 26th (Wed) to allow enough time to travel to Nassau.
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Parks · Nature · Wildlife
Side Trips
Find places to stay Apr 24 — 26:

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 27th (Thu): tour the pleasant surroundings at Ardastra Gardens & Wildlife Conservation Centre, look for gifts at Diamonds International Nassau, and then steep yourself in history at Queen's Staircase. On the 28th (Fri), you'll have a packed day of sightseeing: head off the coast to Blue Lagoon Island, then explore the world behind art at The National Art Gallery of The Bahamas, and then kick back and relax at Cable Beach.

To see ratings, photos, other places to visit, and other tourist information, use the Nassau online attractions planner.

Use the Route module to find suitable travel options from Havana to Nassau. April in Nassau sees daily highs of 34°C and lows of 25°C at night. Finish up your sightseeing early on the 28th (Fri) so you can catch the flight to Grand Bahama Island.
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Parks · Shopping · Beaches · Outdoors
Find places to stay Apr 26 — 28:

Grand Bahama Island, Bahamas — 2 nights

Despite its name, Grand Bahama Island isn't the biggest island in its archipelago.
Start off your visit on the 29th (Sat): explore and take pictures at Port Lucaya Marketplace and then get up close to creatures of the deep with Unexso. Here are some ideas for day two: enjoy the sand and surf at Gold Rock Beach and then stop by Coastal Mojo.

To see where to stay, photos, traveler tips, and other tourist information, refer to the Grand Bahama Island trip itinerary planning site.

You can fly from Nassau to Grand Bahama Island in 3 hours. Alternatively, you can ride a ferry. April in Grand Bahama Island sees daily highs of 32°C and lows of 24°C at night. On the 30th (Sun), wrap the sightseeing up by early afternoon so you can fly back home.
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Outdoors · Tours · Wildlife · Shopping
Find places to stay Apr 28 — 30:

Jamaica travel guide

4.1
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.
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Turks and Caicos travel guide

4.5
Beaches · Scuba & Snorkeling · Landmarks
Known as the location of one of the longest coral reefs in the world, Turks and Caicos offer scenic white-sand beaches, calm waters, and warm, sunny weather. Apart from the upscale resorts in Providenciales, which is known for its award-winning beach, the rest of the scenery remains mostly pristine and uncrowded. On a trip to Turks and Caicos, you can spend days lazing on a deserted beach, go island hopping, and enjoy a range of fun activities, from world-class snorkeling and diving, to hiking, sailing, deep-sea fishing, and bird-watching.
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Haiti travel guide

3.7
Historic Walking Areas · Historic Sites · Zipline
The culture of Haiti has always been the reason for people to visit, and it will be the reason people visit in larger and larger numbers as the nation heals from the devastating effects of the 2010 earthquake. The interesting tale of colonialism, revolution, and political struggle has left Haiti with a wealth of historical sites and cultural influences. Sightseeing in Haiti offers perspectives on the many stages in the country's history, with colonial forts standing in ruins and monuments memorializing the revolution. The music, the art, the folklore, and the cuisine of Haiti all deserve to be explored in person.
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Dominican Republic travel guide

4.2
Beaches · Zipline · Islands
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.
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Puerto Rico travel guide

4.6
Historic Walking Areas · Beaches · Kayaking & Canoeing
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.
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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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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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