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.

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

For traveler tips, other places to visit, maps, and more tourist information, read our Montego Bay trip itinerary maker app.

Washington DC, USA to Montego Bay is an approximately 7-hour flight. Traveling from Washington DC in December, expect Montego Bay to be much warmer, temps between 87°F and 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.

Explore hidden gems such as Pink Sands Beach and Atlantis Casino. Step out of Nassau to go to Spanish Wells and see Ponderosa Shell & Gift Shop, which is approximately 3h 45 min away. And it doesn't end there: kick back and relax at Cable Beach, have some family-friendly fun at Jetline Simulation Bahamas, let your taste buds guide you at a local gastronomic tour, and steep yourself in history at Queen's Staircase.

To find traveler tips, maps, ratings, and other tourist information, use the Nassau trip planning website.

You can fly from Montego Bay to Nassau in 8 hours. Plan for a bit cooler temperatures traveling from Montego Bay in December, with highs in Nassau at 82°F and lows at 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.

Step off the beaten path and head to Mudjin Harbor and Long Bay Beach. Go for a jaunt from Providenciales to Whitby to see Pelican Beach about 3h 15 min away. And it doesn't end there: cast your line with a fishing tour, relax and rejuvenate at some of the top local wellness centers, stop by Mama's Gift Shop, and experience rural life at Caicos Conch Farm.

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 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 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.

Eschew the tourist crowds and head to Scuba & Snorkeling and Altos de Chavon. Next up on the itinerary: get interesting insight from Tours, explore the fascinating underground world of Cueva Padre Nuestro, and get a new perspective on things with Boat Tours & Water Sports.

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

You can fly from Providenciales to Bayahibe in 6 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.

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. 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 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. You'll explore the less-touristy side of things at Playa Bonita and Cayo Levantado. Visit Playa Coson 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 shuttle from Sosua to Las Terrenas takes 2.5 hours. Alternatively, you can drive; or 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.

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, don't miss a visit to Jesus Maestro Parish, trot along with a tour on horseback, 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 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. Step off the beaten path and head to Punda and Playa Kenepa Chiki. Relax by the water at Playa Lagun and Kleine Knip. Spend the 12th (Sat) exploring nature at Shete Boka Park. There's lots more to do: snap pictures at Queen Juliana Bridge, wander the streets of Riffort Village, enjoy the sand and surf at Jan Thiel Beach, and tour the pleasant surroundings at Mambo Beach.

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 7 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 travel to Oranjestad.

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 Donkey Sanctuary Aruba. 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 4.5 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 travel back home.