Stride climate

Trip Type : Group Tour
Beach summer-Cuba-652119-P

Cuba Uncovered

Headwater Holidays
5.0 . Excellent
Travel Style: You will have solid amounts of both free time and structured time with some activities and meals included. Mixed
Physical Level: Full day hiking or trekking over medium to long distances. Moderate expectation of physical fitness. Strenuous
Lodging Level: 3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards. Premium - 4 star
10 days
From: $ 2,740 $ 274 / day
Checking price



  • A fascinating insight into Cuba's unique history, politics and culture
  • Explore five UNESCO heritage sites: Old Havana, coffee plantations, Vinales Valley, Cienfuegos and Trinidad
  • White sandy beaches, clear Caribbean seas, waterfalls, rock pools and panoramic ocean views
  • Perfectly preserved colonial mansions, fabulous palaces and hugely atmospheric towns
  • Colourful street entertainers, salsa in the squares, live music everywhere
  • Jungle trails, forest paths, orchids galore and incredible bird life

Short Description

Nothing prepares you for the sheer vibrancy, colour and contrasts of Cuba! The combination of colonial palaces, tropical colours and back street salsa beats alongside sparkling Cadillacs, bareback cowboys and wild west steam trains is utterly compelling. If this is Communism, it is definitely Caribbean style!

Groups are between 25-60 people, typically ~30-40. Usually there will be many opportunities to split off and enjoy meals and excursions in smaller groups. This is the most economical way to travel, saving up to 40% versus booking the same itinerary yourself.
Trip Type Group Tour
Spend most of the time outdoors. Common trip themes and activities include cycling, hiking, kayaking, whitewater rafting.
Itinerary Focus Active
3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards.
Lodging Level Premium - 4 star
Flights & Transport Only ground transport
Start City Havana
End City Havana

Trip Includes

  • 9 nights, hotel-to-hotel
  • All breakfasts, 8 lunches and 7 evening meals
  • Managed by Headwater appointed agent
  • Internal transfers

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Day 1 - Arrive in Havana

We meet you at the airport and take you (30 mins) to your hotel in central Havana where you'll spend the next two nights. There is a lovely rooftop pool for you to enjoy a cool dip on arrival, before dinner at El Templete restaurant.

Day 2 - Havana City Tour

After admiring the exhibits (and bullet holes!) in the marble halls of the 'Museo de la Revolucion', we sidestep the tourist traps to explore the lively backstreets of Old Havana, packed with traditional shops, houses and markets. After lunch, we walk along the port to the old steam railway to browse Havana's answer to Camden Market, packed with vivid artwork. Relax back at the hotel with a panoramic city view before dinner overlooking the Cathedral.

Day 3 - Havana to Las Terrazas Casa Campesino walk 6km/4mi/2hr

We leave Havana and head south west to the Sierra del Rosario in Soroa where our walk begins in the Biosphere Reserve. Emerald hummingbirds are among 115 species here! It's an easy 6km forest trail to picnic in a ruined coffee plantation, before a visit to Soroa's world famous orchid gardens, home to 20,000 flowers! This evening, enjoy the sunset on the lake in the waterside village of Las Terrazas before dinner in the hotel.

Day 4 - Che Guevara Walk 8km/5mi/3hr

A track through red ginger, mango and apple rose leads from the hotel to the Che Guevara memorial viewpoint, a high point in the reserve, where we'll picnic with panoramic views of the ocean. Look out for the tocororo, (Cuba's national bird), on the descent amid shady terraces of mastic and pine. We head for the San Juan River nearby for a swim in the rock pools before returning to Las Terrazas. Enjoy a stroll through the village before dinner.

Day 5 - Vinales Valley Walk 12km/7.5mi/4hr

A drive south west this morning leads to the limestone rock formations, pineapple plantations and vivid red soil of the Vinales Valley. We pass palm-thatched tobacco sheds filled with scented, drying leaves and after a country picnic at a farmhouse, we walk up through an echoing limestone cave, before heading down through arrowroot and papaya to colourful Vinales. Time for a cold drink on the pastel coloured main street before driving back to Las Terrazas.

Day 6 - Las Terrazas to Trinidad

We head east today past the Bay of Pigs and Zapata Peninsula to Cienfuegos, famed for its stunning UNESCO Spanish architecture. After exploring the town, lunch is taken in the 1920's Yacht Club on the marina. In the afternoon we stroll through the extensive Botanic Gardens filled with scarlet bottlebrush, ironwood, banyan and mahogany trees, before continuing on to Trinidad in time for dinner at our hotel.

Day 7 - At Trinidad

Explore Trinidad's maze of cobbled streets this morning, or head for the nearby white sand beach for a paddle in the azure waters of the Caribbean before returning for lunch at the hotel. We tour the ancient centre this afternoon, admiring heirlooms of wealthy Spanish sugar plantation owners in the Romantic Museum, before enjoying some typical live music by the central church.

Day 8 - Trinidad Mountain walk 10km/6mi/4hr

High in the Escambray mountains behind Trinidad, forest trails lead through teak trees and coffee bushes. A steady descent into the Guayanara River Valley brings us to a series of natural pools and waterfalls - a perfect jungle shower! We drive back past thatched farms and cowboys in reedwoven Stetson hats. Perhaps try a cold guarapo juice, squeezed straight from the sugar cane, and relax in the square, or browse one of the many art galleries.

Day 9 - Trinidad to Havana

We visit the Valle de los Ingenios and an C18 sugarcane plantation before driving to Santa Clara, where the ruins of an armoured train destroyed in the 1959 revolution has been turned into a museum. The Che Guevara mausoleum and memorial are national monuments here, and after visiting, we drive back to Havana for dinner in one of Old Havana's grandest restaurants.

Day 10 - Leave Havana

We pick you up in the evening and drive you back to the airport.


Checking price
Price From $ 2,740
Price Per Day: $ 274 per day
Check Availability
  • Deposit Price: $ 217

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Flights & Transport

Only ground transport

Group Size:

Intimate Group - 12 max

A minimum of 4 people (in total) are required for each departure

Cancellation Policy:

You, or any member of your party, may cancel your tour at any time providing that the cancellation is made by the lead name in writing. Notice of cancellation will be effective upon receipt of your written communication. As we start to incur costs from the time the contract is confirmed we will retain your deposit and in addition will apply other cancellation charges as shown below. These charges are based on how many days before your booked departure we received your cancellation notice. These charges are a percentage of the total cost of your booking, not including your insurance premium. If you want to cancel one or more passengers on the booking you will have to pay a proportion of the applicable cancellation charge based on the number of passengers you wish to cancel from the booking:

Period before a departure when notice of cancellation is received  is More than 56 days before departure then Percentage of total booking price payable on cancellation is Loss of deposit

Period before a departure when notice of cancellation is received is Between 56 and 31 days before departure (inclusive) then Percentage of total booking price payable on cancellation is 50% of holiday cost

Period before a departure when notice of cancellation is received  is 30 days or less before departure (or failure to join the holiday or failure to pay any local payment due) then Percentage of total booking price payable on cancellation is 100% of holiday cost

Trip ID#:


Trip Excludes

  • Airfares
  • Passport and visa charges
  • Personal Expenses

Meals Included:

All breakfasts, 8 lunches and 7 evening meals

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