34 days in Caribbean Itinerary

34 days in Caribbean Itinerary

Created using Inspirock Caribbean journey planner

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

Route & dates

34 days in Caribbean Itinerary

Start: Melbourne, Australia
Fly:  25​h
1
Havana, Cuba
— 5 nights
Fly:  5​h 30​min
2
Montego Bay, Jamaica
— 3 nights
bus:  1​h 30​min
3
Ocho Rios, Jamaica
— 3 nights
bus + Fly:  10​h 30​min
4
San Juan, Puerto Rico
— 8 nights
Fly:  4​h 30​min
5
Punta Cana, Dominican Republic
— 7 nights
shuttle + Fly:  4​h
6
Oranjestad, Aruba
— 4 nights
Fly:  28​h
End: Melbourne, Australia


Learn more about your trip

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.
Bring the kids along to Playa Paraiso and Santa Maria del Mar. Your itinerary includes some good beach time at Sirena Beach and Playa Mal Tiempo. Step out of Havana with an excursion to Playa Blanca Beach in Cayo Largo--about 2 hours away. There's much more to do: don't miss a visit to El Malecon, appreciate the extensive heritage of Old Havana, and contemplate the long history of Castillo de la Real Fuerza.

For photos, more things to do, traveler tips, and other tourist information, read Havana trip builder website .

Melbourne, Australia to Havana is an approximately 25-hour flight. You can also do a combination of flight and train. The time zone changes from Australian Eastern Standard Time (Victoria) (AEST) to Cuba Standard Time (CST), which is usually a -15 hour difference. In September, Havana is much hotter than Melbourne - with highs of 36°C and lows of 26°C. Wrap up your sightseeing on the 13th (Fri) early enough to travel to Montego Bay.

Things to do in Havana

Parks Outdoors Beaches

Side Trip

Cayo Largo
Highlights from your plan
Playa Paraiso ©
Playa Paraiso
Sirena Beach ©
Sirena Beach
Playa Blanca Beach ©
Playa Blanca Beach

3
nights
Montego Bay, Jamaica

Montego Bay ©
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 get in some beach time at Seven Mile Beach and Doctor's Cave Beach. Explore the numerous day-trip ideas around Montego Bay: Original Mayfield Falls Jamaica (in Pennycooke) and Tryall Golf Course (in Sandy Bay). The adventure continues: stop by White Witch Golf Course, get engrossed in the history at Greenwood Great House, and steep yourself in history at Rose Hall Great House.

To find other places to visit, photos, and tourist information, go to the Montego Bay trip itinerary planner.

Traveling by flight from Havana to Montego Bay takes 5.5 hours. In September, daytime highs in Montego Bay are 38°C, while nighttime lows are 29°C. Cap off your sightseeing on the 16th (Mon) early enough to catcht the bus to Ocho Rios.

Things to do in Montego Bay

Outdoors Parks Golf

Side Trips

Seven Mile Beach, Tryall Golf Course, Original Mayfield Falls Jamaica
Highlights from your plan
Seven Mile Beach ©
Seven Mile Beach
Doctor's Cave Beach ©
Doctor's Cave Beach
White Witch Golf Course ©
White Witch Golf Course

3
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.
Relax by the water at Bamboo Beach Club and Ocho Rios Bay Beach. You'll find plenty of places to visit near Ocho Rios: Bob Marley Museum (in St. Ann's Bay) and Green Grotto Caves (in Runaway Bay). And it doesn't end there: admire the sheer force of Dunn's River Falls and Park, delve into the lush surroundings at Cranbrook Flower Forest, and make a trip to Marcus Garvey Birthplace.

To see where to stay and other tourist information, refer to the Ocho Rios road trip planner.

Getting from Montego Bay to Ocho Rios by bus takes about 1.5 hours. Other options: drive. Expect a daytime high around 38°C in September, and nighttime lows around 30°C. Wrap up your sightseeing on the 19th (Thu) early enough to travel to San Juan.

Things to do in Ocho Rios

Parks Nature Outdoors

Side Trips

St. Ann's Bay, Cranbrook Flower Forest, Green Grotto Caves
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Ocho Rios Bay Beach ©
Ocho Rios Bay Beach
Green Grotto Caves ©
Green Grotto Caves

8
nights
San Juan, Puerto Rico

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Relax by the water at Condado Beach and Luquillo Beach. Kids will appreciate attractions like Pine Grove Beach and Ocean Park Beach. Explore San Juan's surroundings by going to Playa Vega Baja (in Vega Baja), Museo del Tabaco Caguas (in Caguas) and Playa La Pared (in Luquillo). There's lots more to do: take a stroll through Old San Juan, skim along the rocks with a canyoning and rapelling tour, kick back and relax at Playa Mar Chiquita, and brush up on your knowledge of spirits at Casa Bacardi.

For more things to do, traveler tips, where to stay, and tourist information, refer to the San Juan online trip maker .

Do a combination of bus and flight from Ocho Rios to San Juan in 10.5 hours. Due to the time zone difference, you'll lose 1 hour traveling from Ocho Rios to San Juan. In September, plan for daily highs up to 38°C, and evening lows to 30°C. Wrap up your sightseeing on the 28th (Sat) to allow time to travel to Punta Cana.

Things to do in San Juan

Outdoors Parks Beaches

Side Trips

Carolina, Luquillo, Manati, Museo del Tabaco Caguas, Horseback Riding Tours
Highlights from your plan
Horseback Riding Tours
Luquillo Beach ©
Luquillo Beach
Condado Beach ©
Condado Beach

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.
You'll visit kid-friendly attractions like Bavaro Beach and Playa La Vacama. You'll enjoy a bit of beach vacationing at Macao Beach and Juanillo Beach. Get out of town with these interesting Punta Cana side-trips: La Romana (Teeth Of The Dog & Altos de Chavon). There's still lots to do: head off the coast to Saona Island, get close to the beloved marine mammals with a swim-with-the-dolphins experience, have some family-friendly fun at Escape Room Punta Cana, and look for gifts at Dominicana Rai.

To see ratings, where to stay, traveler tips, and tourist information, use the Punta Cana trip itinerary builder .

Traveling by flight from San Juan to Punta Cana takes 4.5 hours. Alternatively, you can do a combination of flight and shuttle; or do a combination of ferry and bus. Expect a daytime high around 36°C in September, and nighttime lows around 28°C. Wrap up your sightseeing on the 5th (Sat) early enough to travel to Oranjestad.

Things to do in Punta Cana

Outdoors Parks Beaches

Side Trip

La Romana
Highlights from your plan
Bavaro Beach ©
Bavaro Beach
Macao Beach ©
Macao Beach
Juanillo Beach ©
Juanillo Beach

4
nights
Oranjestad, Aruba

Oranjestad ©
When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
We've included these beaches for you: Eagle Beach and Baby Beach. Attractions like Palm Beach and Hadicurari Beach make great kid-friendly stops. The adventure continues: kick back and relax at Arashi Beach, tour the pleasant surroundings at Rodgers Beach, enjoy the sea views from California Lighthouse, and explore the striking landscape of Arikok National Park.

To see photos, traveler tips, other places to visit, and more tourist information, use the Oranjestad trip planner.

You can do a combination of shuttle and flight from Punta Cana to Oranjestad in 4 hours. Alternatively, you can fly. Expect somewhat warmer evenings in Oranjestad when traveling from Punta Cana in October, with lows around 32°C. Finish your sightseeing early on the 9th (Wed) so you can travel back home.

Things to do in Oranjestad

Parks Outdoors Beaches

Side Trips

Palm - Eagle Beach, Noord, San Nicolas, Arashi Beach, Arikok National Park
Highlights from your plan
Eagle Beach ©
Eagle Beach
Palm Beach ©
Palm Beach
Baby Beach ©
Baby Beach

Similar Plans

35 days in Jamaica BY A USER FROM UNITED STATES December, outdoors, relaxing, romantic, beaches, wildlife, slow & easy, popular & hidden gems PREFERENCES: December, outdoors, relaxing, romantic, beaches, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 43 days in United States & Caribbean BY A USER FROM UNITED KINGDOM July, culture, outdoors, relaxing, romantic, beaches, shopping, wildlife, popular & hidden gems PREFERENCES: July, culture, outdoors, relaxing, romantic, beaches, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 36 days in Caribbean BY A USER FROM NORWAY June, popular sights PREFERENCES: June ATTRACTION STYLE: Popular sights PACE: Medium 37 days in Caribbean BY A USER FROM ISRAEL September, popular sights PREFERENCES: September ATTRACTION STYLE: Popular sights PACE: Medium 44 days in Mexico, Central America & Caribbean BY A USER FROM AUSTRALIA June, culture, outdoors, relaxing, beaches, historic sites, wildlife, hidden gems PREFERENCES: June, culture, outdoors, relaxing, beaches, historic sites, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium 10 days in Caribbean BY A USER FROM UNITED STATES January, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, popular & hidden gems PREFERENCES: January, culture, outdoors, relaxing, romantic, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 35 days in Caribbean BY A USER FROM AUSTRALIA September, kids, popular sights PREFERENCES: September, kids ATTRACTION STYLE: Popular sights PACE: Medium 7 days in Jamaica BY A USER FROM SOUTH AFRICA December, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: December, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 7 days in Jamaica BY A USER FROM SOUTH AFRICA December, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: December, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 47 days in Caribbean BY A USER FROM AUSTRALIA July, kids, culture, outdoors, beaches, popular sights PREFERENCES: July, kids, culture, outdoors, beaches ATTRACTION STYLE: Popular sights PACE: Medium 23 days in Jamaica BY A USER FROM PORTUGAL November, culture, outdoors, beaches, historic sites, hidden gems PREFERENCES: November, culture, outdoors, beaches, historic sites ATTRACTION STYLE: Hidden gems PACE: Medium 22 days in Caribbean BY A USER FROM UNITED KINGDOM December, culture, outdoors, relaxing, beaches, shopping, wildlife, popular & hidden gems PREFERENCES: December, culture, outdoors, relaxing, beaches, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium
View more plans