29 days in Caribbean Itinerary

29 days in Caribbean Itinerary

Created using Inspirock Caribbean tour planner

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Route & dates

29 days in Caribbean Itinerary

Start: Melbourne, Australia
Fly:  25​h
1
Havana, Cuba
— 5 nights
Fly:  1​h 30​min
2
George Town, Cayman Islands
— 3 nights
Fly:  7​h 15​min
3
Culebra, Puerto Rico
— 4 nights
Fly:  3​h 45​min
4
Punta Cana, Dominican Republic
— 6 nights
shuttle:  2​h
5
Santo Domingo, Dominican Republic
— 3 nights
Fly:  2​h 15​min
6
Palm - Eagle Beach, Aruba
— 4 nights
Fly:  28​h
End: Melbourne, Australia

5
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, museums, nightlife, beaches, and classes. Your plan includes some of its best attractions: appreciate the extensive heritage of El Malecon, make a trip to El Capitolio, steep yourself in history at El Morro, and get engrossed in the history at Museum of the Revolution (Museo de la Revolucion).

For more things to do, traveler tips, where to stay, and more tourist information, refer to the Havana trip planning app .

Melbourne, Australia to Havana is an approximately 25-hour flight. You can also do a combination of flight and train. Due to the time zone difference, you'll gain 15 hours traveling from Melbourne to Havana. In November, Havana is somewhat warmer than Melbourne - with highs of 33°C and lows of 21°C. Finish up your sightseeing early on the 6th (Wed) so you can travel to George Town.

Things to do in Havana

Historic Sites Museums Neighborhoods
Highlights from your plan
Old Havana ©
Old Havana
El Malecon ©
El Malecon
Plaza de la Catedral ©
Plaza de la Catedral

3
nights
George Town, Cayman Islands

George Town is a city situated on Grand Cayman island of the Cayman Islands. George Town is known for wildlife, adventure, breweries & distilleries, shopping, and fun & games. Your plan includes some of its best attractions: identify plant and animal life at Stingray City Grand Cayman, look for gifts at Guy Harvey Gallery and Shoppe, contemplate the waterfront views at Devil's Grotto, and brush up on your knowledge of spirits at Cayman Spirits Co. Distillery.

For maps, ratings, more things to do, and more tourist information, use the George Town online route builder .

Traveling by flight from Havana to George Town takes 1.5 hours. Expect somewhat warmer evenings in George Town when traveling from Havana in November, with lows around 29°C. Finish up your sightseeing early on the 9th (Sat) so you can catch the flight to Culebra.

Things to do in George Town

Parks Wildlife Outdoors

Side Trips

Grand Cayman, Seven Mile Beach, Cayman Turtle Centre: Island Wildlife Encounter
Highlights from your plan
Scuba & Snorkeling
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Seven Mile Beach ©
Seven Mile Beach

4
nights
Culebra, Puerto Rico

Culebra ©
With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Culebra is known for beaches, wildlife, nature, outdoors, and adventure. Your plan includes some of its best attractions: kick back and relax at Flamenco Beach, tour the pleasant surroundings at Zoni Beach, enjoy the sea views from Culebrita Lighthouse, and get lost in a book at Culebra Public Library.

Planning Culebra trip won't be overwheling when you use's Insprock itinerary maker.

You can fly from George Town to Culebra in 7.5 hours. Alternatively, you can do a combination of flight, shuttle, and ferry. The time zone difference when traveling from George Town to Culebra is 1 hour. November in Culebra sees daily highs of 35°C and lows of 28°C at night. Finish your sightseeing early on the 14th (Thu) so you can travel to Punta Cana.

Things to do in Culebra

Parks Outdoors Beaches
Highlights from your plan
Culebrita Island ©
Culebrita Island
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach

6
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.
Change things up with these side-trips from Punta Cana: La Romana (Altos de Chavon & Teeth Of The Dog) and Bayahibe (Conquista Park & Scuba & Snorkeling). The adventure continues: get close to the beloved marine mammals with a swim-with-the-dolphins experience, play a few rounds at Punta Espada Golf Course, enjoy the sand and surf at Bavaro Beach, and take an exotic tour of a safari tour.

To see more things to do, maps, other places to visit, and tourist information, read Punta Cana route builder website .

Traveling by flight from Culebra to Punta Cana takes 4 hours. Alternatively, you can do a combination of flight and shuttle; or do a combination of ferry, shuttle, and flight. November in Punta Cana sees daily highs of 34°C and lows of 27°C at night. Wrap up your sightseeing on the 20th (Wed) early enough to take a shuttle to Santo Domingo.

Things to do in Punta Cana

Outdoors Wildlife Tours

Side Trips

Bayahibe, La Romana
Highlights from your plan
Bavaro Beach ©
Bavaro Beach
Swim with Dolphins
Saona Island ©
Saona Island

3
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.
Santo Domingo is known for historic sites, nature, shopping, museums, and beaches. Your plan includes some of its best attractions: make a trip to Zona Colonial, pause for some serene contemplation at Basilica Cathedral of Santa Maria la Menor, contemplate the long history of Fortaleza Ozama, and step into the grandiose world of Alcazar de Colon.

For where to stay, maps, photos, and tourist information, use the Santo Domingo trip maker website .

Traveling by shuttle from Punta Cana to Santo Domingo takes 2 hours. Alternatively, you can drive; or take a bus. Wrap up your sightseeing on the 23rd (Sat) early enough to travel to Palm - Eagle Beach.

Things to do in Santo Domingo

Historic Sites Parks Museums
Highlights from your plan
Alcazar de Colon ©
Alcazar de Colon
Zona Colonial ©
Zona Colonial
Catedral Primada de America
Catedral Primada de America

4
nights
Palm - Eagle Beach, Aruba

Palm - Eagle Beach ©
A long stretch of powdery white sand and aquamarine waters, Palm - Eagle Beach remains one of Aruba's most visited vacation spots.
Go for a jaunt from Palm - Eagle Beach to San Nicolas to see Baby Beach about 48 minutes away. Next up on the itinerary: enjoy the sand and surf at Eagle Beach, stroll through Hadicurari Beach, explore the wealth of natural beauty at Arikok National Park, and enjoy the sea views from California Lighthouse.

To see more things to do, other places to visit, reviews, and more tourist information, refer to the Palm - Eagle Beach trip itinerary builder site .

Traveling by flight from Santo Domingo to Palm - Eagle Beach takes 2.5 hours. In November, daytime highs in Palm - Eagle Beach are 37°C, while nighttime lows are 30°C. Cap off your sightseeing on the 27th (Wed) early enough to travel back home.

Things to do in Palm - Eagle Beach

Parks Outdoors Beaches

Side Trips

Noord, Oranjestad, Arikok National Park, Baby Beach, Arashi Beach
Highlights from your plan
Eagle Beach ©
Eagle Beach
Palm Beach ©
Palm Beach
Baby Beach ©
Baby Beach

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