33 days in Jamaica, Dominican Republic & Puerto Rico Itinerary

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Fly
1
Montego Bay, Jamaica
— 6 nights
Drive
2
Ocho Rios, Jamaica
— 6 nights
Fly
3
Santo Domingo, Dominican Republic
— 6 nights
Shuttle
4
Punta Cana, Dominican Republic
— 6 nights
Fly
5
San Juan, Puerto Rico
— 6 nights
Fly

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Montego Bay, Jamaica — 6 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.
Take a break from the city and head to Seven Mile Beach and Doctor's Cave Beach. Get some cultural insight at Ahhh...Ras Natango Gallery and Garden and Rose Hall Great House. Get out of town with these interesting Montego Bay side-trips: Fishing Charters & Tours (in Falmouth), Original Mayfield Falls Jamaica (in Pennycooke) and Tryall Golf Course (in Sandy Bay). There's much more to do: look for gifts at Cinnamon Hill Golf Course, steep yourself in history at The Cage, see Off-Road Tours, and get a dose of the wild on a nature and wildlife tour.

To see traveler tips, photos, other places to visit, and other tourist information, read Montego Bay trip itinerary maker tool.

London, UK to Montego Bay is an approximately 13-hour flight. Traveling from London to Montego Bay, you'll gain 5 hours due to the time zone difference. Traveling from London in December, things will get warmer in Montego Bay: highs are around 36°C and lows about 27°C. Finish your sightseeing early on the 21st (Wed) so you can drive to Ocho Rios.
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Outdoors · Parks · Wildlife · Tours
Side Trips

Ocho Rios, Jamaica — 6 nights

A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
Relax by the water at James Bond Beach and Ocho Rios Bay Beach. For shopping fun, head to Island Village or Jewels & Time Duty Free Jewelers. Change things up with a short trip to Bob Marley Museum in St. Ann's Bay (about 1h 15 min away). And it doesn't end there: take in the dramatic scenery at Dunn's River Falls and Park, head outdoors with Outdoor Activities, fulfill a lifelong dream with a swim-with-the-dolphins experience, and witness a stunning natural landmark at Firewater Mineral Healing Spring.

To see photos, ratings, where to stay, and tourist information, refer to the Ocho Rios trip planner.

Traveling by car from Montego Bay to Ocho Rios takes 2 hours. Alternatively, you can take a bus. December in Ocho Rios sees daily highs of 36°C and lows of 28°C at night. On the 27th (Tue), wrap the sightseeing up by early afternoon so you can fly to Santo Domingo.
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Outdoors · Parks · Tours · Nature
Side Trip

Santo Domingo, Dominican Republic — 6 nights

Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Head to Mercado Modelo and Agora Mallfor plenty of shopping. Alcazar de Colon and Basilica Cathedral of Santa Maria la Menor will appeal to history buffs. Step out of Santo Domingo with an excursion to Scuba & Snorkeling in Boca Chica--about 44 minutes away. The adventure continues: make a trip to Zona Colonial, explore the world behind art at Amber Museum, explore the striking landscape of The 3 Eyes National Park, and examine the collection at Columbus Lighthouse (Faro A Colon).

To find traveler tips, photos, reviews, and other tourist information, read Santo Domingo holiday planner.

You can fly from Ocho Rios to Santo Domingo in 8.5 hours. The time zone changes from Eastern Standard Time (EST) to Atlantic Standard Time (AST), which is usually a 1 hour difference. Wrap up your sightseeing on the 2nd (Mon) early enough to take a shuttle to Punta Cana.
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Parks · Shopping · Historic Sites · Nature
Side Trip

Punta Cana, Dominican Republic — 6 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 Aqua Track Private Day Trips. You'll get in some beach time at Tropical Treasure and Playa La Vacama. Explore Punta Cana's surroundings by going to Nature & Wildlife Tours (in Bayahibe) and Altos de Chavon (in La Romana). Spend the 7th (Sat) spotting exotic species with a safari tour. There's much more to do: whizz through the canopy at some of the top local zipline courses and adventure parks, tee off at Punta Espada Golf Course, and enjoy the sand and surf at Macao Beach.

For reviews, maps, and other tourist information, read Punta Cana trip builder site.

Getting from Santo Domingo to Punta Cana by shuttle takes about 2 hours. Other options: drive; or fly. January in Punta Cana sees daily highs of 33°C and lows of 25°C at night. Finish your sightseeing early on the 8th (Sun) so you can fly to San Juan.
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Outdoors · Tours · Wildlife · Parks
Side Trips

San Juan, Puerto Rico — 6 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.
Escape the urban bustle at El Yunque National Forest and Playa Luquillo. We've included these beaches for you: Pine Grove Beach and Condado Beach. Step out of San Juan to go to Rio Grande and see Zipline, which is approximately 44 minutes away. There's much more to do: get to know the fascinating history of Old San Juan, steep yourself in history at Sitio Histórico de San Juan, browse the exhibits of La Casa de los Contrafuertes, and get some fabulous bargains at Coach Outlet Store.

To see maps, other places to visit, ratings, and other tourist information, read our San Juan sightseeing planner.

Traveling by flight from Punta Cana to San Juan takes 3 hours. Alternatively, you can do a combination of bus and ferry. In January, plan for daily highs up to 34°C, and evening lows to 26°C. Cap off your sightseeing on the 14th (Sat) early enough to catch the flight back home.
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Parks · Outdoors · Beaches · Shopping
Side Trips

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.
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Dominican Republic travel guide

4.1
Beaches · Islands · Zipline
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

4.5
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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