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 Rocklands Bird Sanctuary. 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 look for gifts at Tropicana Jewelers.

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 Queen's Staircase. 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 Fishing Charters & Tours. Your itinerary includes some good beach time at Long Bay Beach and Pelican Beach. The adventure continues: don't miss a visit to Thursday Fish Fry, shop like a local with Mama's Gift Shop, soothe aching muscles at some of the top local wellness centers, and take in the exciting artwork at Anna's Art Gallery.

To see ratings, photos, maps, and more tourist information, use the Providenciales itinerary planning site.

Traveling by flight from Nassau to Providenciales takes 5.5 hours. Traveling from Nassau in December, expect somewhat warmer with lows of 75°F in Providenciales. Wrap up your sightseeing on the 29th (Sat) early enough to fly 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 Cueva Padre Nuestro. The adventure continues: get outside with Outdoor Activities, don't miss a visit to Altos de Chavon, and race across the water with a speed boat tour.

To see reviews, more things to do, where to stay, and other tourist information, read Bayahibe trip itinerary builder app.

You can fly from Providenciales to Bayahibe in 5 hours. The time zone difference when traveling from Providenciales to Bayahibe is 1 hour. Plan for little chillier nights when traveling from Providenciales in December since evenings lows in Bayahibe dip to 69°F. Cap off your sightseeing on the 1st (Tue) early enough to go by car 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 · Outdoors · Beaches · 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 Punta Bonita. Visit Cayo Levantado and Playa Coson 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.

Things to do in Las Terrenas

Parks · Outdoors · Beaches · 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 Juanillo Beach. There's lots more to do: try to win big at Hard Rock Casino Punta Cana, trot along with a tour on horseback, don't miss a visit to Jesus Maestro Parish, and explore the activities along Hoyo Azul.

To find traveler tips, photos, other places to visit, and other tourist information, you can read our Punta Cana trip planning site.

Getting from Las Terrenas to Punta Cana by car takes about 4 hours. Other options: do a combination of car and flight; or take a bus. January in Punta Cana sees daily highs of 83°F and lows of 71°F at night. Finish your sightseeing early on the 9th (Wed) so you can fly 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 Playa Lagun. Relax by the water at Playa Kenepa Chiki and Mambo Beach. Spend the 12th (Sat) exploring nature at Shete Boka Park. There's lots more to do: snap pictures at Queen Juliana Bridge, contemplate the waterfront views at Kleine Knip, kick back and relax at Jan Thiel Beach, and visit Riffort Village.

For photos, where to stay, reviews, and other tourist information, you can read our Willemstad trip site.

You can fly from Punta Cana to Willemstad in 4.5 hours. In January, plan for daily highs up to 85°F, and evening lows to 75°F. Finish your sightseeing early on the 14th (Mon) so you can fly to Oranjestad.

Things to do in Willemstad

Parks · Outdoors · Beaches · 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 Boca Cataavlina. 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 Malmok 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

4.1
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.