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 Rose Hall Great House. There's lots more to do: kick back and relax at Doctor's Cave Beach, stroll through Rocklands Bird Sanctuary, 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 7-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 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 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, let your taste buds guide you at a local gastronomic tour, and try your luck at Atlantis Casino.

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 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 The Bight Park. Your itinerary includes some good beach time at Long Bay Beach and Pelican Beach. There's much more to do: see what you can catch with a fishing tour, find your balance on the water with some of the best stand-up paddleboarding in the area, stroll through Caicos Conch Farm, and browse the exhibits of Anna's Art Gallery.

For photos, reviews, maps, and more tourist information, use the Providenciales trip builder site.

You can fly from Nassau to Providenciales in 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 up 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.

Eschew the tourist crowds and head to Scuba & Snorkeling and Nature & Wildlife Tours. Next up on the itinerary: get interesting insight from Tours, 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 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 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 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 Hoyo Azul. The adventure continues: try your luck at Hard Rock Casino Punta Cana, don't miss a visit to Jesus Maestro Parish, trot along with a tour on horseback, 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 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 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, enjoy the sand and surf at Jan Thiel Beach, 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 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 Mangel Halto Beach. Explore hidden gems such as Malmok Beach and Boca Cataavlina. Go for a jaunt from Oranjestad to San Nicolas to see Baby Beach about 32 minutes away. There's lots more to do: experience rural life at The Butterfly Farm, 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 traveler tips, where to stay, reviews, and more tourist information, read our Oranjestad trip planner.

You can fly from Willemstad to Oranjestad in 4.5 hours. In January, daytime highs in Oranjestad are 86°F, while nighttime lows are 76°F. Cap off your sightseeing on the 20th (Sun) early enough to travel back home.