36 days in Caribbean Itinerary

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.

You'll explore the less-touristy side of things at Nature & Wildlife Tours and Tropicana Jewelers. The adventure continues: look for all kinds of wild species at Rocklands Bird Sanctuary, tour the pleasant surroundings at Doctor's Cave Beach, and steep yourself in history at Rose Hall Great House.

For reviews, photos, more things to do, and other tourist information, read Montego Bay attractions planning app .

Washington DC, USA to Montego Bay is an approximately 5-hour combination of subway, bus, and flight. You can also do a combination of train and flight; or fly. Expect much warmer temperatures when traveling from Washington DC in December; daily highs in Montego Bay reach 87°F and lows reach 74°F. Wrap up your sightseeing on the 18th (Tue) early enough to travel to Nassau.

On a trip to Nassau you can immerse yourself in a dynamic city atmosphere or spend your days lazing on the soft golden sands.

Step off the beaten path and head to Pink Sands Beach and Pirates of Nassau Museum. Go for a jaunt from Nassau to Spanish Wells to see Ponderosa Shell & Gift Shop about 1h 30 min away. There's lots more to do: stop by Diamonds International, contemplate the long history of Queen's Staircase, try your luck at Atlantis Casino, and head off the coast to Blue Lagoon Island.

To find reviews, other places to visit, maps, and tourist information, read Nassau driving holiday planner .

You can fly from Montego Bay to Nassau in 6.5 hours. Traveling from Montego Bay in December, things will get slightly colder in Nassau: highs are around 82°F and lows about 69°F. Finish your sightseeing early on the 23rd (Sun) so you can travel to Providenciales.

The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.

You'll explore the less-touristy side of things at Stand-Up Paddleboarding and Bight Reef. We've included these beaches for you: Mudjin Harbor and Grace Bay Beach. Step out of Providenciales to go to Whitby and see Pelican Beach, which is approximately 1h 05 min away. And it doesn't end there: tour the pleasant surroundings at Long Bay Beach, get interesting insight from Tours, relax in the rural setting at Caicos Conch Farm, and make a trip to Thursday Fish Fry.

For maps, reviews, where to stay, and more tourist information, read Providenciales travel route builder .

Getting from Nassau to Providenciales by flight takes about 5 hours. Traveling from Nassau in December, you can expect nighttime temperatures to be a bit warmer in Providenciales, with lows of 75°F. Finish your sightseeing early on the 29th (Sat) so you can travel to Bayahibe.

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.

Discover out-of-the-way places like Nature & Wildlife Tours and Speed Boats Tours. When in Bayahibe, make a side trip to see Altos de Chavon in La Romana, approximately 36 minutes away. There's still lots to do: discover the deep blue sea with a scuba or snorkeling tour and explore the fascinating underground world of Cueva Padre Nuestro.

To find photos, maps, reviews, and more tourist information, read our Bayahibe trip maker tool .

Traveling by combination of flight and shuttle from Providenciales to Bayahibe takes 4 hours. Traveling from Providenciales to Bayahibe, you'll lose 1 hour due to the time zone difference. Expect slightly colder evenings in Bayahibe when traveling from Providenciales in December, with lows around 69°F. Cap off your sightseeing on the 1st (Tue) early enough to catch the shuttle to Sosua.

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 Cabarete Beach. On your second day here, kick back and relax at Beach Alicia and then stroll through Sosua Beach.

To see where to stay, reviews, ratings, and tourist information, use the Sosua trip planner.

You can take a shuttle from Bayahibe to Sosua in 6 hours. Alternatively, you can take a bus. Expect a daytime high around 84°F in January, and nighttime lows around 66°F. Finish up your sightseeing early on the 3rd (Thu) so you can catch the shuttle to Las Terrenas.

Las Terrenas is a town on the northeast coast of the Dominican Republic, located in the province of Samaná. Explore hidden gems such as Playa Bonita and Punta Bonita. Your itinerary includes some good beach time at Playa Moron and Cayo Levantado. Take a break from Las Terrenas 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: kick back and relax at Playa Coson Beach.

To find where to stay, traveler tips, reviews, and tourist information, read our Las Terrenas day trip planning tool .

You can take a shuttle from Sosua to Las Terrenas in 2.5 hours. Other options are to drive; or take a bus. In January in Las Terrenas, expect temperatures between 84°F during the day and 71°F at night. Finish your sightseeing early on the 6th (Sun) to allow enough time to take a shuttle to Punta Cana.

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.

Step off the beaten path and head to Indigenous Eyes Ecological Park & Reserve and Horseback Riding Tours. There's lots more to do: kick back and relax at Juanillo Beach, explore the activities along Hoyo Azul, try to win big at Hard Rock Casino Punta Cana, and don't miss a visit to Jesus Maestro Parish.

For photos, maps, where to stay, and tourist information, read our Punta Cana road trip tool .

You can take a shuttle from Las Terrenas to Punta Cana in 4 hours. Other options are to drive; or take a bus. In January, daily temperatures in Punta Cana can reach 83°F, while at night they dip to 71°F. Finish your sightseeing early on the 9th (Wed) so you can travel to Willemstad.

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. Explore hidden gems such as Playa Lagun and Mambo Beach. You'll get in some beach time at Jan Thiel Beach and Playa Kenepa Chiki. Spend the 12th (Sat) exploring nature at Shete Boka National Park. Next up on the itinerary: take a stroll through Riffort Village, take an in-depth tour of Kura Hulanda Museum, stop by Island Treasures, and snap pictures at Queen Juliana Bridge.

For more things to do, other places to visit, and other tourist information, read Willemstad planning app .

You can do a combination of shuttle and flight from Punta Cana to Willemstad in 6.5 hours. Alternatively, you can fly. In January, plan for daily highs up to 85°F, and evening lows to 75°F. Finish your sightseeing early on the 14th (Mon) to allow enough time to travel to Oranjestad.

When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.

Visit Malmok Beach and Baby Beach for some beach relaxation. You'll discover tucked-away gems like Donkey Sanctuary Aruba and Kay's Fine Jewelry. Next up on the itinerary: tour the pleasant surroundings at Boca Catalina, admire all the interesting features of The Butterfly Farm, kick back and relax at Mangel Halto Beach, and look for gifts at The Arubian Taste.

Find out how to plan Oranjestad trip without stress by asking Inspirock to help create an itinerary.

Traveling by combination of bus and flight from Willemstad to Oranjestad takes 2 hours. January in Oranjestad sees daily highs of 86°F and lows of 76°F at night. Finish up your sightseeing early on the 20th (Sun) so you can travel back home.