15 days in Cuba & Jamaica Itinerary

15 days in Cuba & Jamaica Itinerary

Created using Inspirock Caribbean trip itinerary builder

Make it your trip
Fly
1
Havana, Cuba
— 4 nights
Drive
2
Vinales, Cuba
— 1 night
Drive
3
Varadero, Cuba
— 1 night
Fly
4
Montego Bay, Jamaica
— 3 nights
Drive
5
Ocho Rios, Jamaica
— 2 nights
Drive
6
Negril, Jamaica
— 1 night
Fly

S M T W T F S
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27

Havana, Cuba

— 4 nights

Rome of the Caribbean

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: make a trip to Malecón of Havana, wander the streets of Christopher Columbus Cemetery (Cemetario de Colon), appreciate the extensive heritage of Old Havana, and contemplate the long history of Castillo de la Real Fuerza.

Start your trip to Havana by creating a personalized itinerary on Inspirock.

Sydney, Australia to Havana is an approximately 27-hour flight. The time zone difference moving from Australian Eastern Standard Time to Cuba Standard Time is minus 15 hours. Traveling from Sydney in November, you will find days in Havana are a bit warmer (33°C), and nights are about the same (21°C). Finish your sightseeing early on the 14th (Sun) so you can drive to Vinales.

Things to do in Havana

Historic Sites · Museums · Neighborhoods · Wildlife

Vinales, Cuba

— 1 night
Offering a taste of authentic rural life, Vinales remains a small agricultural town, dominated by surrounding low mountain ranges.
On the 15th (Mon), take a pleasant ride with a tour on horseback, appreciate the views at Valle de Vinales, and then take in the architecture and atmosphere at Iglesia del Sagrado Corazon de Jesus.

You can plan Vinales trip in no time by asking Inspirock to help create your itinerary.

Drive from Havana to Vinales in 2.5 hours. Alternatively, you can take a shuttle; or take a bus. Expect a daytime high around 34°C in November, and nighttime lows around 24°C. Wrap up your sightseeing on the 15th (Mon) early enough to drive to Varadero.

Things to do in Vinales

Outdoors · Tours · Nature · Parks

Varadero, Cuba

— 1 night
One of the largest resort towns in the Caribbean, Varadero boasts a 20 km (12 mi) long stretch of sand, lined with hotels and all-inclusive resorts.
On the 16th (Tue), walk around Josone Park, then identify plant and animal life at Varahicacos Ecological Reserve, and then kick back and relax at Varadero Beach.

For more things to do, ratings, photos, and other tourist information, go to the Varadero trip itinerary website.

Getting from Vinales to Varadero by car takes about 4.5 hours. Other options: take a bus. November in Varadero sees daily highs of 32°C and lows of 22°C at night. Wrap up your sightseeing on the 16th (Tue) early enough to travel to Montego Bay.

Things to do in Varadero

Parks · Beaches · Outdoors · Wildlife

Montego Bay, Jamaica

— 3 nights
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.
Change things up with these side-trips from Montego Bay: Tryall Golf Course (in Sandy Bay) and Original Mayfield Falls (in Pennycooke). Spend the 18th (Thu) wandering through the wild on a nature and wildlife tour. The adventure continues: steep yourself in history at Rose Hall Great House, see exotic creatures in open habitats at Rastasafari Experience, tee off at Cinnamon Hill Golf Course, and browse the different shops at Whitter Village Shopping Mall.

For other places to visit, traveler tips, where to stay, and other tourist information, go to the Montego Bay trip planner.

Fly from Varadero to Montego Bay in 6 hours. Plan for somewhat warmer temperatures traveling from Varadero in November, with highs in Montego Bay at 36°C and lows at 28°C. Finish up your sightseeing early on the 19th (Fri) so you can go by car to Ocho Rios.

Things to do in Montego Bay

Outdoors · Wildlife · Tours · Golf

Side Trips

Ocho Rios, Jamaica

— 2 nights
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 20th (Sat): trek along Fern Gully, take in the dramatic scenery at Dunn's River Falls and Park, then stop by Jewels & Time Duty Free Jewelers, and finally pause for some serene contemplation at Our Lady of Fatima Catholic Church. On the 21st (Sun), you'll have a packed day of sightseeing: take in the dramatic scenery at Blue Hole, stroll around Konoko Falls, and then fulfill a lifelong dream with a swim-with-the-dolphins experience.

For where to stay, more things to do, photos, and more tourist information, you can read our Ocho Rios road trip app.

Traveling by car from Montego Bay to Ocho Rios takes 2 hours. Alternatively, you can take a bus. In November, plan for daily highs up to 37°C, and evening lows to 28°C. Wrap up your sightseeing on the 21st (Sun) to allow time to drive to Negril.

Things to do in Ocho Rios

Parks · Outdoors · Nature · Trails

Negril, Jamaica

— 1 night
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
Start off your visit on the 22nd (Mon): surround yourself with nature on Kingsley's Take Care Tours - Day Tours, stroll through Seven Mile Beach, and then relax and rejuvenate at some of the top local wellness centers.

For reviews, more things to do, where to stay, and tourist information, read Negril tour itinerary planner.

Traveling by car from Ocho Rios to Negril takes 3 hours. Alternatively, you can take a bus. In November in Negril, expect temperatures between 36°C during the day and 28°C at night. Finish up your sightseeing early on the 22nd (Mon) so you can travel back home.

Things to do in Negril

Outdoors · Beaches · Parks · Wildlife

Cuba travel guide

4.4
Beaches · Historic Walking Areas · Landmarks
The largest island in the Caribbean, Cuba lies just 140 km (90 mi) south of Florida and captivates a growing number of Western visitors with its tropical landscapes and cultural attractions. Sightseeing in Cuba inevitably begins in Havana, a city of photogenic architecture, lively nightlife, and a passion for baseball. The country's smaller colonial towns usually feature central squares, ideal places to meet the locals under wrought-iron street lamps. Savvy visitors escape the cities during their Cuba holidays, devoting plenty of time to the country's charming countryside, where you can get the feel for this diverse land by conversing with friendly tobacco farmers and small-scale fruit producers.

Jamaica travel guide

4.1
Waterfalls · Beaches · Nightlife
The third most populous English-speaking country in the Americas, Jamaica remains a member of the Commonwealth of Nations, with the British monarch its official head of state. Jamaica tourism thrives thanks to the island nation's reputation for natural beauty, outstanding cuisine, and lively music scene. The country's landscape is as diverse as its population, its tropical climate supporting varied ecosystems that include everything from savannahs to rugged mountain slopes. For most visitors, a holiday in Jamaica is a largely outdoor affair, with hiking, fishing, golfing, camping, snorkeling, horseback riding, and kite surfing among the most popular things to do.