30 days in Caribbean Itinerary

30 days in Caribbean Itinerary

Created using Inspirock Caribbean Trip Planner

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Route & dates

30 days in Caribbean Itinerary

Start: Baton Rouge, United States
+2
Drive + Fly + Drive:  13​h 15​min
1
Negril, Jamaica
— 3 nights
bus:  1​h 30​min
2
Montego Bay, Jamaica
— 4 nights
bus:  1​h 30​min
3
Ocho Rios, Jamaica
— 5 nights
+2
bus + Fly + shuttle:  5​h 15​min
4
Punta Cana, Dominican Republic
— 7 nights
shuttle:  1​h 30​min
5
Santo Domingo, Dominican Republic
— 6 nights
Fly:  1​h 15​min
6
Port-au-Prince, Haiti
— 2 nights
Fly:  12​h
7
Santiago de Cuba, Cuba
— 1 night
Fly + Drive:  19​h 15​min
End: Baton Rouge, United States

3
nights
Negril, Jamaica

Negril ©
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
When in Negril, make a side trip to see Reggae Style Mayfield Falls in Savanna La Mar, approximately 1h 05 min away. Next up on the itinerary: kick back and relax at Seven Mile Beach, take in the dramatic natural features at Negril Cliffs, pause for some serene contemplation at Mary, Gate of Heaven Catholic Church, and stroll through Bloody Bay.

To see more things to do, reviews, other places to visit, and other tourist information, read our Negril itinerary planner.

Baton Rouge, USA to Negril is an approximately 13.5-hour flight. Due to the time zone difference, you'll lose 1 hour traveling from Baton Rouge to Negril. In June, daytime highs in Negril are 91°F, while nighttime lows are 77°F. Finish your sightseeing early on the 4th (Mon) to allow enough time to drive to Montego Bay.

Things to do in Negril

Parks Outdoors Beaches

Side Trips

Reggae Style Mayfield Falls, Mayfield Falls Jamaica (Original)
Find places to stay Jun 1 — 4:
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Seven Mile Beach ©
Seven Mile Beach
Bloody Bay ©
Bloody Bay

4
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.
You'll find plenty of places to visit near Montego Bay: YS Falls (in Santa Cruz) and Tryall Golf Course (in Sandy Bay). The adventure continues: enjoy the sand and surf at Doctor's Cave Beach, tee off at White Witch Golf Club, steep yourself in history at Rose Hall Great House, and take some stellar pictures from Ahhh...Ras Natango Gallery and Garden.

For reviews, more things to do, ratings, and other tourist information, refer to the Montego Bay tour planner.

Traveling by car from Negril to Montego Bay takes 1.5 hours. Alternatively, you can take a bus. In June, daily temperatures in Montego Bay can reach 91°F, while at night they dip to 77°F. Finish your sightseeing early on the 8th (Fri) so you can take a bus to Ocho Rios.

Things to do in Montego Bay

Outdoors Parks Shopping

Side Trips

YS Falls, Tryall Golf Course
Find places to stay Jun 4 — 8:
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Nature & Wildlife Tours
YS Falls ©
YS Falls
Rose Hall Great House ©
Rose Hall Great House

5
nights
Ocho Rios, Jamaica

Ocho Rios ©
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
Venture out of the city with trips to Blue Mountain Peak (in Blue Mountains National Park), Blue Mountains (in Kingston) and Green Grotto Caves (in Runaway Bay). And it doesn't end there: take in the dramatic scenery at Dunn's River Falls and Park, relax and float downstream with a rafting and tubing tour, look for gifts at KDK LoFt Jamaica, and admire the natural beauty at Shaw Park Gardens & Waterfalls.

To see ratings, more things to do, and more tourist information, refer to the Ocho Rios travel itinerary creator.

Traveling by bus from Montego Bay to Ocho Rios takes 1.5 hours. Alternatively, you can drive. June in Ocho Rios sees daily highs of 89°F and lows of 78°F at night. On the 13th (Wed), wrap the sightseeing up by early afternoon so you can travel to Punta Cana.

Things to do in Ocho Rios

Parks Nature Outdoors

Side Trips

Green Grotto Caves, Blue Mountains, Blue Mountain Peak
Find places to stay Jun 8 — 13:
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Blue Mountains ©
Blue Mountains
Blue Mountain Peak ©
Blue Mountain Peak

7
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.
Venture out of the city with trips to La Romana (Altos de Chavon & Teeth of the Dog) and Isla Saona (in Parque Nacional del Este). Spend the 18th (Mon) spotting exotic species with a safari tour. And it doesn't end there: kick back and relax at Bavaro Beach, get close to the beloved marine mammals with a swim-with-the-dolphins experience, tour the water at your own pace with La Pachanga Punta Cana, and stroll through Macao Beach.

To find traveler tips, where to stay, more things to do, and other tourist information, you can read our Punta Cana trip itinerary maker.

Getting from Ocho Rios to Punta Cana by combination of bus, flight, and taxi takes about 5.5 hours. The time zone difference when traveling from Ocho Rios to Punta Cana is 1 hour. Expect a daytime high around 88°F in June, and nighttime lows around 76°F. Wrap up your sightseeing on the 20th (Wed) to allow time to travel to Santo Domingo.

Things to do in Punta Cana

Outdoors Tours Wildlife

Side Trip

La Romana
Find places to stay Jun 13 — 20:
Highlights from your plan
Saona Island ©
Saona Island
Bavaro Beach ©
Bavaro Beach
Swim with Dolphins

6
nights
Santo Domingo, Dominican Republic

Santo Domingo ©
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Spend the 23rd (Sat) exploring nature at Parque Nacional Los Haitises. Spend the 24th (Sun) exploring nature at National Botanical Garden. There's much more to do: don't miss a visit to Zona Colonial, wander the streets of Malecon, contemplate the long history of Ruinas del Hospital San Nicolás de Bari, and get a sense of history and politics at National Palace.

To see ratings, photos, traveler tips, and tourist information, use the Santo Domingo trip builder.

Getting from Punta Cana to Santo Domingo by combination of flight and taxi takes about 1.5 hours. Other options: drive; or take a bus. In June, plan for daily highs up to 89°F, and evening lows to 77°F. Finish your sightseeing early on the 26th (Tue) to allow enough time to travel to Port-au-Prince.

Things to do in Santo Domingo

Nature Parks Neighborhoods

Side Trip

Los Haitises National Park
Find places to stay Jun 20 — 26:
Highlights from your plan
Los Haitises National Park ©
Los Haitises National Park
Alcazar de Colon ©
Alcazar de Colon
Zona Colonial ©
Zona Colonial

2
nights
Port-au-Prince, Haiti

Port-au-Prince ©
Port-au-Prince, the capital of Haiti, gives most visitors their first taste of the country, along with all of its rugged and lively charm.
Start off your visit on the 27th (Wed): admire the natural beauty at Parc de Martissant, make a trip to Champ de Mars, then delve into the distant past at Papillon Enterprise, and finally hunt for treasures at Marche de Fer.

To find ratings, traveler tips, maps, and other tourist information, you can read our Port-au-Prince trip itinerary builder.

Traveling by combination of taxi and flight from Santo Domingo to Port-au-Prince takes 1.5 hours. Alternatively, you can drive; or take a bus. Traveling from Santo Domingo to Port-au-Prince, you'll gain 1 hour due to the time zone difference. Expect a daytime high around 91°F in June, and nighttime lows around 81°F. Finish your sightseeing early on the 28th (Thu) so you can travel to Santiago de Cuba.

Things to do in Port-au-Prince

Shopping Parks Historic Sites
Find places to stay Jun 26 — 28:
Highlights from your plan
Papillon Enterprise ©
Papillon Enterprise
Marche de Fer ©
Marche de Fer
Parc de Martissant ©
Parc de Martissant

1
night
Santiago de Cuba, Cuba

Santiago de Cuba ©
Santiago de Cuba has taken almost as much influence from Haiti and the Dominican Republic as it has from Havana, distilling a concoction of cultures to create a city with a distinct identity.
Kick off your visit on the 29th (Fri): get engrossed in the history at Casa de Diego Velazquez, explore the different monuments and memorials at Cementerio Santa Ifigenia, then contemplate the long history of Moncada Barracks, then make a trip to Antonio Maceo Revolution Square, and finally explore the historical opulence of San Pedro de la Roca del Morro Castle.

To find traveler tips, reviews, other places to visit, and tourist information, refer to the Santiago de Cuba sightseeing planner.

Use the Route module to find suitable travel options from Port-au-Prince to Santiago de Cuba. Expect slightly colder evenings in Santiago de Cuba when traveling from Port-au-Prince in June, with lows around 74°F. Wrap up your sightseeing on the 29th (Fri) to allow time to travel back home.

Things to do in Santiago de Cuba

Historic Sites Museums
Find places to stay Jun 28 — 29:
Highlights from your plan
Castillo de San Pedro de la Roca ©
Castillo de San Pedro de la Roca
Cementerio Santa Ifigenia ©
Cementerio Santa Ifigenia
Casa de Diego Velazquez ©
Casa de Diego Velazquez

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