Trip Duration

7 Days, 6 Nights

Trip Type


Skill Level


Fitness Level


Check out the sites of Cuba, mixed in with some light adventure as we try everything from bicycles, horses, hiking, and even snorkel or scuba diving.

Trip Highlights

  • Experience the vibrant, classical city of Havana
  • Go hiking, biking, and horseback riding
  • Swim, Snorkel, or Dive at the famous yet pristine waters of the Bay of Pigs
  • Savor the tastes and sounds of Cuban dining and nightlife
  • All our trips are US govt compliant
  • Visit the beautiful seaside town of Cienfuegos
  • Explore the UNESCO World Heritage colonial city of Trinidad
  • Spend an afternoon cruising Havana in an old American convertible car

Cuba, the largest island in the Carribean and only 90 miles south of Key West Florida, is known for the vibrancy of her people and the local culture, salsa dancing, unspoiled beaches, and a strong art and music scene.

Cuba is now experiencing a warming of relations with the United States, including the recently re-opened US Embassy in Havana, symbolizing the ever-closer return of normalized relations and trade between these once-friendly nations. Although it has been open to tourism from around the world for many years, such as the Canadians and Europeans who visit Cuba, the country is still underdeveloped by most standards. For many travelers, that is part of the appeal and Cuba remains a beautiful place in transition.

$2,495 $1,995)

Trips begin on any Sunday as Day 1, for the following dates: Nov 24-30, 2019; Dec 22-28, 2019; Dec 29,2019 - Jan4, 2020; Jan 5-11, 2020 Jan 12-18, 2020; Jan 19-25, 2020; Feb 9-15, 2020; Feb 16-22, 2020; Mar 1-7, 2020 All dates guaranteed departure, no minimum necessary. Custom dates available year round, contact us for details.

$2,495 $1,995)

The Itinerary

  • Day 1 - Arrival to Havana

    Arrive to Jose Marti International Airport in Havana, where our guide will be waiting for you and transfer in a private taxi to our private home in Havana, where you will check in and relax a bit or explore briefly on your own. In the early afternoon the guide will be available for an informal walk around town to get orientated, help you change money, use internet to check in with work or family, get water/snacks/lunch, etc. Early evening there is a group dinner and a short briefing, then back to our home for the night.

  • Day 2 - Explore Havana

    After breakfast, we will take a local, privately owned 1950’s classic convertible automobile to pay a visit to a place completely off the tourist path, and into the ‘real’ Havana. After our classic convertible ride there, we’ll make a quick visit to a community center for elderly Cubans who would otherwise be home alone. These folks actually lived through the history we all hear so much about, and it’s a tremendous opportunity to hear their stories first hand, and ask them questions. Or play a game of classic Cuba dominoes. This visit has proven to be much more fun and rewarding than people have anticipated. Then, we will take bicycles on a one hour ride through the back streets of Havana to a local, privately-owned food market, to learn a little about how their food system works, and then bicycle another half hour back to the community center to drop off some fresh fruit, bread, and treats. That will conclude our visit, and then it will be time for our own lunch. After lunch, we will take a nice long (one to three hour) walk through historic old towne Havana to drop off some school supplies to a local school. Return to our casa, as always dinner out with the guide is optional but recommended, or you can strike out on your own, as long as you eat only at privately owned (paladares) restaurants. Ask your guide for details.

  • Day 3 - Bay of Pigs/Cienfuegos

    We will drive first to a local farm off the beaten path, for an hour hike around the jungle and a look at how the locals are now allowed to have their own private farm business. Then we will drive to the historic Bay of Pigs, bypassing the touristy part and to an isolated beach and a snorkeling excursion into the Carribean Sea with one of our new, local private entrepreneur partners. Small, sustainable snorkeling and diving with an emphasis on protecting the environment. Finally, after lunch we continue on to the bayside town of Cienfuegos and its classic French colonial architecture. After checking into our beautiful local home we’ll have time for a long walk around this fascinating city.

  • Day 4 - Trinidad

    First, we’ll make a short drive to El Nicho park to check in on two of our ongoing social projects. We’ll hike the famous waterfall trail with a local, private botanist who is working on cataloging all the unique flora to this region including newly discovered ones. We’ll then drive to our last destination, the UNESCO colonial jewel of Trinidad. We’ll have an amazing lunch at a private, local restaurant. Trinidad is an incredible place to walk around in with many small, private vendors and optional activities like cooking classes, salsa dance, cigar vendors, and music. We’ll do a long hiking tour throughout town with lots of authentic and organic interactions with the local people, and there is even the option of renting a bike for a ten mile bike ride out to the coast and sunset over the Caribbean
  • Day 5 -Escambray Mountains

    After breakfast we’ll drive up a very steep road into the heart of the mountains at Topes De Collantes, and hike a rugged jungle path one hour down to a dramatic waterfall and swimming hole, with one of our local partners as we help them develop their small hut business near the trailhead that sells fresh, yummy coffee from the nearby mountains. In complying with the new US regulations, we focus on helping the local, small entrepreneurs. It’s where we feel we can make the most impact, and also where you the traveler, can help the most. After the hike, return to Trinidad for lunch. Then, a three hour afternoon horseback or hiking outing into the countryside with a small, private Cuban horseman. Included is a cool stop at a local sugar cane farm, where both rum and sugar are produced.
  • Day 6 -Snorkel or Scuba our newest marine project

    Checking out of our Trinidad casa, we will drive along the coast for an hour to one of our favorite places in Cuba. We’re excited about our latest project documenting the marine life, and water temperatures, over time at our small, unspoiled dive spot in the Caribbean. Your local, private guide will take you snorkeling to see some of the best preserved coral reefs in the world, or there is the option to upgrade to scuba instead. There is also the option here of a nice hike through the jungle. We’ll have lunch here (tremendous fresh seafood the specialty) before a late afternoon return to Havana.
  • Day 7 - Departure Day

    After breakfast this morning if you have time to walk a bit around the local neighborhoods outside of the tourist circuit and maybe catch a game of pickup streetball or soccer, before bringing you to the airport for your departing flight.