36 days in Caribbean Itinerary

36 days in Caribbean Itinerary

Created using Inspirock Caribbean journey planner
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Fly
1
Montego Bay, Jamaica
— 2 nights
Fly
2
Nassau, Bahamas
— 4 nights
Fly
3
Providenciales, Turks and Caicos
— 6 nights
Fly
4
Bayahibe, Dominican Republic
— 3 nights
Drive
5
Sosua, Dominican Republic
— 1 night
Drive
6
Las Terrenas, Dominican Republic
— 3 nights
Drive
7
Punta Cana, Dominican Republic
— 3 nights
Fly
8
Willemstad, Curacao
— 4 nights
Fly
9
Oranjestad, Aruba
— 6 nights
Fly

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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.
Explore hidden gems such as Nature & Wildlife Tours and Tropicana Jewelers. There's lots more to do: kick back and relax at Doctor's Cave Beach, contemplate the long history of Rose Hall Great House, and stroll through Rocklands Bird Sanctuary.

To find other places to visit, more things to do, traveler tips, and more tourist information, read Montego Bay visit planner.

Washington DC, USA to Montego Bay is an approximately 6.5-hour flight. Traveling from Washington DC in December, expect Montego Bay to be much warmer, temps between 87°F and 74°F. Finish up your sightseeing early on the 18th (Tue) so you can catch the flight to Nassau.
Outdoors · Wildlife · Tours · Parks
Side Trip

Nassau, Bahamas — 4 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.
Explore hidden gems such as Pink Sands Beach and Blue Lagoon Island. Step out of Nassau to go to Spanish Wells and see Ponderosa Shell & Gift Shop, which is approximately 3h 45 min away. There's lots more to do: kick back and relax at Cable Beach, get your game on at Jetline Simulation Bahamas, stop by Diamonds International Nassau, and admire nature's wide array of creatures at Marine Habitat at Atlantis.

For where to stay, maps, traveler tips, and other tourist information, read our Nassau trip builder website.

You can fly from Montego Bay to Nassau in 8 hours. In December, Nassau is little chillier than Montego Bay - with highs of 82°F and lows of 69°F. Wrap up your sightseeing on the 23rd (Sun) early enough to fly to Providenciales.
Parks · Beaches · Outdoors · Zoos & Aquariums
Side Trips

Providenciales, Turks and Caicos — 6 nights

The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
Step off the beaten path and head to Mudjin Harbor and Fishing Charters & Tours. Your itinerary includes some good beach time at Long Bay Beach and Pelican Beach. There's still lots to do: see the vivid underwater world at Coral Gardens Reef, relax and rejuvenate at some of the top local wellness centers, look for gifts at Flowers by EA, and tour the pleasant surroundings at Caicos Conch Farm.

For ratings, traveler tips, where to stay, and other tourist information, use the Providenciales sightseeing planner.

You can fly from Nassau to Providenciales in 5.5 hours. Expect a bit warmer evenings in Providenciales when traveling from Nassau in December, with lows around 75°F. Finish up your sightseeing early on the 29th (Sat) so you can catch the flight to Bayahibe.
Outdoors · Parks · Beaches · Wildlife
Side Trips

Bayahibe, Dominican Republic — 3 nights

Located on the shore of the Caribbean Sea, the town of Bayahibe has grown from a fishing village into a bona fide tourist destination, with visitors mainly drawn to the many dive sites just off the coast.
Eschew the tourist crowds and head to Nature & Wildlife Tours and Scuba & Snorkeling. Next up on the itinerary: head outdoors with Outdoor Activities, explore the fascinating underground world of Cueva Padre Nuestro, and don't miss a visit to Altos de Chavon.

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

You can fly from Providenciales to Bayahibe in 5 hours. The time zone changes from Eastern Standard Time (EST) to Atlantic Standard Time (AST), which is usually a 1 hour difference. Plan for slightly colder nights when traveling from Providenciales in December since evenings lows in Bayahibe dip to 69°F. Finish your sightseeing early on the 1st (Tue) to allow enough time to drive to Sosua.
Tours · Outdoors · Wildlife · Nature
Side Trip

Sosua, Dominican Republic — 1 night

A hub for scuba-diving in the area and adventures along the north coast, Sosua itineraries tend to make good use of the scenic coastline.
Start off your visit on the 2nd (Wed): relax and rejuvenate at some of the top local wellness centers and then enjoy the sand and surf at Kite Beach. Here are some ideas for day two: enjoy the sand and surf at Beach Alicia and then tour the pleasant surroundings at Sosua Beach.

To see where to stay, photos, and tourist information, you can read our Sosua trip itinerary planner.

You can drive from Bayahibe to Sosua in 4.5 hours. Other options are to do a combination of flight and shuttle; or take a bus. In January, daily temperatures in Sosua can reach 84°F, while at night they dip to 66°F. Finish up your sightseeing early on the 3rd (Thu) so you can go by car to Las Terrenas.
Parks · Beaches · Outdoors · Spas
Side Trip

Las Terrenas, Dominican Republic — 3 nights

Las Terrenas is a town on the northeast coast of the Dominican Republic, located in the province of Samaná. You'll explore the less-touristy side of things at Playa Bonita and Playa Coson. Visit Cayo Levantado and Punta Bonita for some beach relaxation. Change things up with a short trip to Samana's Picasso: Eusebio dominican paintings in Santa Barbara de Samana (about 52 minutes away). There's still lots to do: stroll through Playa Moron.

For more things to do, where to stay, photos, and more tourist information, read our Las Terrenas vacation planning tool.

Traveling by car from Sosua to Las Terrenas takes 2.5 hours. Alternatively, you can take a bus. In January, daily temperatures in Las Terrenas can reach 84°F, while at night they dip to 71°F. Finish up your sightseeing early on the 6th (Sun) so you can go by car to Punta Cana.
Parks · Beaches · Outdoors · Shopping
Side Trips

Punta Cana, Dominican Republic — 3 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.
You'll discover tucked-away gems like Reserva Ecologica Ojos Indigenas and Hoyo Azul. The adventure continues: try your luck at Hard Rock Casino Punta Cana, trot along with a tour on horseback, don't miss a visit to Jesus Maestro Parish, and kick back and relax at Juanillo Beach.

For more things to do, where to stay, and tourist information, refer to the Punta Cana attractions planner.

You can drive from Las Terrenas to Punta Cana in 4 hours. Alternatively, you can do a combination of car and flight; or take a bus. In January, daily temperatures in Punta Cana can reach 83°F, while at night they dip to 71°F. Cap off your sightseeing on the 9th (Wed) early enough to catch the flight to Willemstad.
Parks · Outdoors · Beaches · Tours

Willemstad, Curacao — 4 nights

Willemstad is the capital city of Curaçao, an island in the southern Caribbean Sea that forms a constituent country of the Kingdom of the Netherlands. Step off the beaten path and head to Punda and Shete Boka Park. Relax by the water at Playa Lagun and Mambo Beach. There's lots more to do: snap pictures at Queen Juliana Bridge, visit Riffort Village, explore the world behind art at Kura Hulanda Museum, and stop by Island Treasures Gifts and Souvenirs Curacao.

For other places to visit, maps, more things to do, and more tourist information, use the Willemstad online trip itinerary builder.

Traveling by flight from Punta Cana to Willemstad takes 4.5 hours. In January, daytime highs in Willemstad are 85°F, while nighttime lows are 75°F. Cap off your sightseeing on the 14th (Mon) early enough to catch the flight to Oranjestad.
Parks · Beaches · Outdoors · Nature
Side Trip

Oranjestad, Aruba — 6 nights

When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
You'll get in some beach time at Arashi Beach and Malmok Beach. Explore hidden gems such as The Butterfly Farm and Boca Cataavlina. Go for a jaunt from Oranjestad to San Nicolas to see Baby Beach about 32 minutes away. There's much more to do: stroll through Mangel Halto Beach, discover the deep blue sea with a scuba or snorkeling tour, enjoy the sand and surf at Eagle Beach, and stop by The Arubian Taste.

For ratings, maps, where to stay, and other tourist information, read our Oranjestad driving holiday planning tool.

You can fly from Willemstad to Oranjestad in 4 hours. In January, plan for daily highs up to 86°F, and evening lows to 76°F. Finish your sightseeing early on the 20th (Sun) to allow enough time to fly back home.
Parks · Outdoors · Beaches · Wildlife
Side Trips

Dominican Republic travel guide

4.2
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.