36 days in Caribbean Itinerary

36 days in Caribbean Itinerary

Created using Inspirock Caribbean journey planner

This plan was created by another user. Make it your plan

Route & dates

Start: Washington DC, United States
Bus + Fly:  4 h 45 min
1
Montego Bay, Jamaica
— 2 nights
Bus + Fly:  6 h 15 min
2
Nassau, Bahamas
— 4 nights
Fly:  4 h 45 min
3
Providenciales, Turks and Caicos
— 6 nights
Fly + Shuttle:  3 h 45 min
4
Bayahibe, Dominican Republic
— 3 nights
Drive:  5 h 45 min
5
Sosua, Dominican Republic
— 1 night
Shuttle:  2 h 30 min
6
Las Terrenas, Dominican Republic
— 3 nights
Drive + Fly:  3 h 45 min
7
Punta Cana, Dominican Republic
— 3 nights
+2
Drive + Shuttle + Fly:  6 h 15 min
8
Willemstad, Curacao
— 4 nights
Bus + Fly:  1 h 45 min
9
Oranjestad, Aruba
— 6 nights
Fly + Bus:  5 h 45 min
End: Washington DC, United States

2
nights
Montego Bay, Jamaica

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 Rose Hall Great House and Rocklands Bird Sanctuary. Spend the 17th (Mon) wandering through the wild on a nature and wildlife tour. There's more to do: look for gifts at Tropicana Jewelers and kick back and relax at Doctor's Cave Beach.

To see other places to visit, more things to do, traveler tips, and more tourist information, read our Montego Bay trip itinerary maker app.

Washington DC, USA to Montego Bay is an approximately 6.5- hour combination of bus and flight. You can also do a combination of train and flight; or fly. 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.

Things to do in Montego Bay

Outdoors Wildlife Tours

Side Trip

Rocklands Bird Sanctuary
Highlights from your plan
Nature & Wildlife Tours
Rocklands Bird Sanctuary ©
Rocklands Bird Sanctuary
Doctor's Cave Beach ©
Doctor's Cave Beach

4
nights
Nassau, Bahamas

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 Cable Beach. 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: head off the coast to Blue Lagoon Island, stop by Craft Cottage Bahamas, indulge your taste buds at Food & Drink, and get up close and personal with brilliant marine life at Marine Habitat at Atlantis.

To find reviews, other places to visit, photos, and other tourist information, read our Nassau trip builder website.

You can do a combination of bus and flight from Montego Bay to Nassau in 5.5 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.

Things to do in Nassau

Parks Beaches Outdoors

Side Trips

Paradise Island, Ponderosa Shell & Gift Shop, Pink Sands Beach
Highlights from your plan
Pink Sands Beach ©
Pink Sands Beach
Cable Beach ©
Cable Beach
Atlantis Casino ©
Atlantis Casino

6
nights
Providenciales, Turks and Caicos

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 Long Bay Beach and Pelican Beach. Go for a jaunt from Providenciales to Middle Caicos to see Mudjin Harbor about 3h 30 min away. There's much more to do: make a trip to The Bight Park, find your balance on the water with categoryPhrases.alias.some_of_the_best_stand_up_paddleboarding_in_the_area, look for gifts at Flavors Of The Turks And Caicos, and see what you can catch with a fishing tour.

For other places to visit, maps, photos, and more tourist information, use the Providenciales trip builder site.

You can fly from Nassau to Providenciales in 2.5 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.

Things to do in Providenciales

Outdoors Parks Beaches

Side Trips

Mudjin Harbor, Pelican Beach
Highlights from your plan
Mudjin Harbor ©
Mudjin Harbor
Long Bay Beach ©
Long Bay Beach
Fishing Charters & Tours

3
nights
Bayahibe, Dominican Republic

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 Altos de Chavon and Cueva Padre Nuestro. Next up on the itinerary: get a new perspective on things with Boat Tours & Water Sports, take a memorable tour with Tours, and get some thrills on the water with a speed boat tour.

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

You can do a combination of flight and shuttle from Providenciales to Bayahibe in 3.5 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

Outdoors Tours Wildlife

Side Trip

Altos de Chavon
Highlights from your plan
Scuba & Snorkeling
Nature & Wildlife Tours
Altos de Chavon ©
Altos de Chavon

1
night
Sosua, Dominican Republic

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 find traveler tips, 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 taxi, 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.

Things to do in Sosua

Outdoors Parks Beaches

Side Trip

Cabarete
Highlights from your plan
Sosua Beach ©
Sosua Beach
Cabarete Beach ©
Cabarete Beach
Beach Alicia ©
Beach Alicia

3
nights
Las Terrenas, Dominican Republic

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 Playa Moron. Visit Cayo Levantado 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 Coson Beach.

To find reviews, photos, ratings, 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 travel to Punta Cana.

Things to do in Las Terrenas

Outdoors Parks Beaches

Side Trips

Cayo Levantado, Samana's Picasso: Eusebio dominican paintings
Highlights from your plan
Playa Bonita ©
Playa Bonita
Playa Moron ©
Playa Moron
Playa Coson Beach ©
Playa Coson Beach

3
nights
Punta Cana, Dominican Republic

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 Juanillo Beach and Hard Rock Casino Punta Cana. There's lots more to do: tour the pleasant surroundings at Reserva Ecologica Ojos Indigenas, 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 more things to do, where to stay, and other tourist information, you can read our Punta Cana trip planning site.

Getting from Las Terrenas to Punta Cana by combination of car and flight takes about 3 hours. Other options: drive; 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.

Things to do in Punta Cana

Parks Outdoors Beaches
Highlights from your plan
Juanillo Beach ©
Juanillo Beach
Hoyo Azul ©
Hoyo Azul
Jesus Maestro Parish ©
Jesus Maestro Parish

4
nights
Willemstad, Curacao

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 Lagun. Relax by the water at Playa Kenepa Chiki 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, visit Riffort Village, and explore the world behind art at Kura Hulanda Museum.

For other places to visit, traveler tips, maps, and tourist information, read our Willemstad tour itinerary planning site.

You can do a combination of car, shuttle, and flight from Punta Cana to Willemstad in 6.5 hours. Other options are to do a combination of shuttle and flight; or fly. 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 travel to Oranjestad.

Things to do in Willemstad

Parks Outdoors Beaches

Side Trip

Curacao
Highlights from your plan
Kleine Knip ©
Kleine Knip
Playa Kenepa Chiki ©
Playa Kenepa Chiki
Playa Lagun ©
Playa Lagun

6
nights
Oranjestad, Aruba

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 The Butterfly Farm 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: tour the pleasant surroundings at Malmok Beach, explore the striking landscape at Natural Pool, stop by The Arubian Taste, and discover the deep blue sea with a scuba or snorkeling tour.

For ratings, maps, photos, and more tourist information, read our Oranjestad trip planner.

You can do a combination of bus and flight from Willemstad to Oranjestad in 2 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.

Things to do in Oranjestad

Parks Outdoors Beaches

Side Trips

Noord, Palm - Eagle Beach, Mangel Halto Beach, Donkey Sanctuary Aruba, Arashi Beach
Highlights from your plan
The Butterfly Farm ©
The Butterfly Farm
Arashi Beach ©
Arashi Beach
Malmok Beach ©
Malmok Beach

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