36 days in Caribbean Itinerary

36 days in Caribbean Itinerary

Created using Inspirock Caribbean journey planner

Make it your trip
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.

Things to do in Montego Bay

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.

Things to do in Nassau

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 Pelican Beach. And it doesn't end there: kick back and relax at Long Bay Beach, get a taste of the local shopping with Flavors Of The Turks And Caicos, explore and take pictures at Caicos Conch Farm, and take a tour by water with Boat Tours & Water Sports.

For where to stay, traveler tips, maps, and tourist information, refer to the Providenciales online tour builder.

You can fly from Nassau to Providenciales in 5.5 hours. Plan for a bit warmer nights when traveling from Nassau in December since evenings lows in Providenciales dip to 75°F. Cap off your sightseeing on the 29th (Sat) early enough to catch the flight to Bayahibe.

Things to do in Providenciales

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 Scuba & Snorkeling and Nature & Wildlife Tours. 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.

Things to do in Bayahibe

Tours · Outdoors · Wildlife · Parks

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.

Things to do in Sosua

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 Cayo Levantado. Visit Playa Coson and Playa Moron 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 Punta Bonita.

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.

Things to do in Las Terrenas

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.

Things to do in Punta Cana

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 Queen Juliana Bridge. Relax by the water at Playa Lagun and Mambo Beach. Spend the 12th (Sat) exploring nature at Shete Boka Park. And it doesn't end there: tour the pleasant surroundings at Jan Thiel Beach, look for gifts at Island Treasures Gifts and Souvenirs Curacao, explore and take pictures at Riffort Village, and explore the world behind art at Kura Hulanda Museum.

For reviews, traveler tips, more things to do, and tourist information, read our Willemstad tour itinerary planning site.

You can fly from Punta Cana to Willemstad in 4.5 hours. Expect a daytime high around 85°F in January, and nighttime lows around 75°F. Wrap up your sightseeing on the 14th (Mon) to allow time to fly to Oranjestad.

Things to do in Willemstad

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 Kay's Fine Jewelry. 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.

Things to do in Oranjestad

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.