Decisions, decisions; difficult enough at the best of times but when involving a holiday to either Cuba or Jamaica, impossible.
To take away painful decisions and provide the perfect 2-week Caribbean holiday, Mocking Bird Hill have put together an exclusive package to allow you to make the most of these Caribbean islands; located just 150 km (90 miles) apart, they nevertheless offer a wealth of cultural diversity. Explore Cuba & Jamaica to your heart’s content, luxuriously & responsibly.
Most people would love a flexible island hop that would cater to all their travelling & holiday dreams. That would mean time to dip into a warm turquoise Caribbean Sea and stroll along white sand beaches to nearby fishing villages framed by lush tropical forests; a ramble up high in the mountains for an aerial view in the company of jewel-coloured birds that sit in trees with sweet tropical fruit. Explore a fascinating historical past and understand its influence on culture, the music, literature & arts that both Cuba & Jamaica are famed for throughout the world. Last but not least there are tasty forays into fusion style Caribbean cuisine, alongside uncovering fine rums and perhaps even a pimento liqueur on the way.
During your Caribbean sojourn you’ll spend your first week discovering Havana’s cobbled streets and the nearby fishing villages that attracted the likes of Hemingway, taking exhilarating and stimulating breaks to rum & cigar tastings. Orchid parks & waterfalls combined with legendary nightlife will create a Cuban cornucopia of holiday memories.
Your second week will be spent at Jamaica’s favourite eco-boutique hotel in Port Antonio, described as an eco-foodie paradise. Here you’ll uncover Jamaica’s lush north east coast, hiking in the Blue Mountains famed for their superior coffee, and gentle rafting along the Rio Grande. You’ll visit Jamaica’s best beaches the un-crowded Frenchman’s Cove, Winifred Beach, as well a ramble and freshwater bath in the Reach Waterfalls followed by dining at the celebrated Mille Fleurs Restaurant, acclaimed by the likes of The Guardian, OK Magazine & Gremolata.
![]() |
|
| Day 1: Arrival |
You will be transferred to your charming colonial-style hotel in Havana’s historical old town. You will meet your personal guide here to discuss your holiday. |
| Day 2: Havana’s Old Town, Cigars and Rum |
After breakfast you will visit the world famous Partaga Tobacco Factory after which you will be taken to see the Capitolio.Your tour continues in a stylish horse drawn carriage across the Prado to the Cathedral Square. From Cathedral Square you will continue on foot to discover Havana’s colonial old town which has been declared a World Heritage Site by UNESCO.In the afternoon discover what makes Cuban Rum special at the Rum Museum “Fundación Havana Club”. |
| Day 3: History, Present and the famous Tropicana |
After breakfast your tour takes you through the Vedado district where you will see the Revolution Square and the legendary Colón Cemetery.Your tour then continues to San Francisco de Paula where you will visit Hemingway’s Finca.The morning ends in the beautiful gardens of the legendary Hotel Nacional.In the evening drive in an American Oldtimer across the Malecón through the villa district of Miramar to the world famous Tropicana Cabaret. |
| Day 4: The Hershey Train |
Today you will travel eastwards to Hershey on the 80 year old nostalgic locomotive train, the Hershey Train. The train is named after the town’s station which has given its name to the train and is today, restored in its original wooden construction.In the evening you are invited to a ‘Smoke Dinner” with experts and lovers of good Cuban cigars in the Hotel Villanueva. This is optional. |
| Day 5: Hemingway |
Hemingway is today’s theme. You will visit his home, the Finca Villa Vigia which is now a museum.A visit to the Fishing Village of Cojimar where Hemingway wrote his famous novel “The Old Man and The Sea” is also part of today’s programme.You will also visit the El Morro Fort on the way back to Havana. From here you can enjoy panorama views of Havana and the sea. |
| Day 6: Las Terrazas and the Orchid Park in Soroa |
Today we invite you to a day in the national reserve Las Terrazas, a place where many Habaneros go for relaxation.You will visit the Orchid Park and see the Soroa Waterfall. You also have the chance for a refreshing river swim. |
| Day 7: A day of free time for you |
The last day is yours to discover Havana on your own. If you would like to have an expert guide please make these arrangements with personal guide. |
![]() |
|
| Day 8: Departure Cuba Arrival Kingston |
After breakfast you will be taken to the airport ready for your transfer to Jamaica.Arrival at Kingston Airport, transfer to Hotel Mocking Bird Hill, with accommodation in one of the hotel’s Superior Rooms and a 3-course organic dinner at the legendary Mille Fleurs Restaurant |
| Day 9: Frenchmans Cove |
After a full Mille Fleurs breakfast, there is transfer to Frenchmans Cove to make the most of your first full day at the beach.Not only will you be able to enjoy pristine white sands & the warm Caribbean Sea but you’ll have time to gently to explore its freshwater stream & lush tropical gardens.Frenchmans Cove is regarded as Jamaica’s prettiest beach, no wonder this is the spot where Errol Flynn fell in love with Jamaica.Dinner is at the Mille Fleurs Restaurant. |
| Day 10: Reich Falls |
Transfer to Reich Fallsto enjoy a stunning series of cascades which tumble over limestone tiers from one hollowed, jade-coloured pool to another.We recommend getting to the Falls before mid-morning the enjoy the best light as the sun hits the river.The Reich Fall pools are differing depths so no matter your confidence and swimming ability you will feel secure, if you are slightly more confident with the guide you can explore the underwater caves and of course jump from the top! currents.’A half mile hike upriver leads to Mandingo Cave, which has a whirlpool and is worth the hike.
3-course dinner at Mille Fleurs Restaurant. |
| Day 11: Rafting on the Rio Grande & Exploring Port Antonio |
A wonderful scenic morning spent slowly rafting along the ‘Rio Grande’ river .This 6 mile journey takes just over 2.5 hours, from Grant’s Level or Rafter’s Village, a mile east of Berridale, to Rafter’s Rest, at St Margaret’s Bay.You will get to experience a taste of rural Jamaican life along the riverbanks, where women and children bathe and wash clothes, shore side peddlers strum guitars for a tip, and others sell sodas and coconuts, often from other rafts.After lunch you will be transferred to Port Antonio where you can explore this old colonnial own or go to the beach.
Dinner at Mille Fleurs Restaurant. |
| Day 12: Winnifred Beach |
A day spent on a secluded golden-sand crescent! The offshore coral reef at Winnifred Beach provides good snorkelling. Lunch can be eaten at the Jamaica Crest Resort opposite the beach itself.Dinner Mille Fleurs Restaurant. |
| Day 13: Blue Mountains Hike |
Enjoy a hike in the Blue Mountains, home to most famous coffee in the world led by a member of the Natural History Society of Jamaica.This means that apart from enjoying the wonderful vistas and the lush countryside you will also take a wealth of knowledge home with you. The chosen hike to either Cedar Valley or Hollywell will depend on preference & ability.Dinner at Mille Fleurs Restaurant. |
| Day 14: Free Day or Frenchmans Cove |
Your final full day. Either a transfer down to Frenchmans Cove for a last day at the beach or alternatively explore Portland independently.Dinner at Mille Fleurs Restaurant. |
| Day 15: | Return transfer to Kingston & flight home |

