22 days in Caribbean Itinerary

22 days in Caribbean Itinerary

Created using Inspirock Caribbean Trip Planner

Plan created by another user. Make it yours

Route & dates

1
Havana, Cuba
— 2 nights
2
Nassau, Bahamas
— 4 nights
3
Willemstad, Curacao
— 3 nights
4
Philipsburg, St. Maarten-St. Martin
— 2 nights
5
Ocho Rios, Jamaica
— 2 nights
6
Punta Cana, Dominican Republic
— 3 nights
7
San Juan, Puerto Rico
— 2 nights

2
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Havana is known for historic sites, nightlife, and museums. Your plan includes some of its best attractions: don't miss a visit to Malecón of Havana, steep yourself in history at Old Square (Plaza Vieja), see the interesting displays at Wifredo Lam Center, and appreciate the extensive heritage of Old Havana.

To find reviews, where to stay, other places to visit, and other tourist information, you can read our Havana trip planner.

Chennai, India to Havana is an approximately 27-hour flight. The time zone difference when traveling from Chennai to Havana is minus 10.5 hours. Expect little chillier temperatures when traveling from Chennai in August; daily highs in Havana reach 38°C and lows reach 26°C. On the 30th (Wed), wrap the sightseeing up by early afternoon so you can travel to Nassau.

Things to do in Havana

Historic Sites · Neighborhoods · Museums
Find places to stay Aug 28 — 30:
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Fortaleza de San Carlos de la Cabana ©
Fortaleza de San Carlos de la Cabana

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.
Nassau is known for theme parks, beaches, and shopping. Your plan includes some of its best attractions: kick back and relax at Cable Beach, observe the fascinating underwater world at Marine Habitat at Atlantis, look for gifts at Tag Heuer Boutique, and tour the pleasant surroundings at Cabbage Beach.

For more things to do, where to stay, ratings, and tourist information, go to the Nassau trip planning website.

Fly from Havana to Nassau in 4.5 hours. Traveling from Havana in August, expect somewhat warmer with lows of 30°C in Nassau. Finish up your sightseeing early on the 3rd (Sun) so you can travel to Willemstad.

Things to do in Nassau

Parks · Outdoors · Beaches

Side Trip

Paradise Island
Find places to stay Aug 30 — Sep 3:
Highlights from your plan
Marine Habitat at Atlantis ©
Marine Habitat at Atlantis
Cable Beach ©
Cable Beach
Blue Lagoon Island ©
Blue Lagoon Island

3
nights
Willemstad, Curacao

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. On the 3rd (Sun), take in the views from Queen Emma Pontoon Bridge. On your second day here, enjoy the sand and surf at Mambo Beach and then discover the deep blue sea with a scuba or snorkeling tour.

To find other places to visit, reviews, ratings, and tourist information, refer to the Willemstad trip itinerary website.

Traveling by flight from Nassau to Willemstad takes 11 hours. The time zone changes from Eastern Standard Time to Atlantic Standard Time, which is usually a 1 hour difference. In September, plan for daily highs up to 38°C, and evening lows to 32°C. You'll set off for Philipsburg on the 6th (Wed).

Things to do in Willemstad

Outdoors · Parks · Beaches

Side Trip

Curacao
Find places to stay Sep 3 — 6:
Highlights from your plan
Scuba & Snorkeling
Queen Emma Pontoon Bridge ©
Queen Emma Pontoon Bridge
Cas Abao Beach ©
Cas Abao Beach

2
nights
Philipsburg, St. Maarten-St. Martin

Philipsburg ©
Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Start off your visit on the 6th (Wed): look for gifts at Joe's Jewelry, don't miss a visit to Boardwalk, and then tour the pleasant surroundings at Mullet Bay Beach. Get ready for a full day of sightseeing on the 7th (Thu): stroll through Orient Bay Beach.

To see where to stay, reviews, ratings, and tourist information, you can read our Philipsburg day trip planner.

Getting from Willemstad to Philipsburg by flight takes about 5.5 hours. In September in Philipsburg, expect temperatures between 36°C during the day and 31°C at night. You'll set off for Ocho Rios on the 8th (Fri).

Things to do in Philipsburg

Outdoors · Parks · Beaches

Side Trips

Mullet Bay Beach, Orient Bay Beach
Find places to stay Sep 6 — 8:
Highlights from your plan
Joe's Jewelry ©
Joe's Jewelry
Mullet Bay Beach ©
Mullet Bay Beach

2
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.
Kick off your visit on the 8th (Fri): stop by Wassi Art.

To find other places to visit, traveler tips, photos, and more tourist information, you can read our Ocho Rios online tour itinerary planner.

You can fly from Philipsburg to Ocho Rios in 9.5 hours. Traveling from Philipsburg to Ocho Rios, you'll gain 1 hour due to the time zone difference. September in Ocho Rios sees daily highs of 38°C and lows of 30°C at night. Finish your sightseeing early on the 10th (Sun) to allow enough time to travel to Punta Cana.

Things to do in Ocho Rios

Parks · Nature · Outdoors
Find places to stay Sep 8 — 10:
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Fern Gully ©
Fern Gully
Wassi Art ©
Wassi Art

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.
Kick off your visit on the 10th (Sun): make a trip to Jesus Maestro Parish. Keep things going the next day: get close to the beloved marine mammals with a swim-with-the-dolphins experience, enjoy the sand and surf at Bavaro Beach, and then stop by Life is good.

For reviews, other places to visit, where to stay, and more tourist information, read our Punta Cana day trip site.

Getting from Ocho Rios to Punta Cana by flight takes about 10.5 hours. Traveling from Ocho Rios to Punta Cana, you'll lose 1 hour due to the time zone difference. In September, daytime highs in Punta Cana are 36°C, while nighttime lows are 28°C. Finish up your sightseeing early on the 13th (Wed) so you can travel to San Juan.

Things to do in Punta Cana

Outdoors · Wildlife · Tours
Find places to stay Sep 10 — 13:
Highlights from your plan
Bavaro Beach ©
Bavaro Beach
Swim with Dolphins
Macao Beach ©
Macao Beach

2
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Go for a jaunt from San Juan to El Yunque National Forest to see El Yunque Rain Forest about 1h 10 min away. Next up on the itinerary: get to know the fascinating history of Old San Juan, look for gifts at Puerto Rican Art & Crafts, take in the architecture and atmosphere at Catedral Metropolitana Basilica de San Juan Bautista, and enjoy the sand and surf at Condado Beach.

To see maps, where to stay, and other tourist information, read San Juan route planning site.

Traveling by flight from Punta Cana to San Juan takes 2.5 hours. Alternatively, you can do a combination of bus and ferry. In September, plan for daily highs up to 38°C, and evening lows to 30°C. Wrap up your sightseeing on the 15th (Fri) early enough to travel back home.

Things to do in San Juan

Parks · Wildlife · Nature

Side Trip

El Yunque Rain Forest
Find places to stay Sep 13 — 15:
Highlights from your plan
El Yunque Rain Forest ©
El Yunque Rain Forest
Old San Juan ©
Old San Juan
Condado Beach ©
Condado Beach