International airfare

Additional meals, excursions and activities not listed

Tips to your local guides and drivers

Alcohol or other drinks, unless specified

Required travel insurance

Arrive at Havana international airport (HAV) and be picked up by our private driver to check in at our central B&B. Rest up or explore before our Welcome Dinner of fantastic Cuban fare!

Meals: D

Wake up early to catch the sunrise then enjoy a delicious breakfast at our central Havana B&B. We’ll then take an architecture, history and art walking tour with our local expert. Enjoy lunch from a variety of local options before our van tour of outer Havana in the afternoon. The evening is yours to enjoy in Old Havana for drinks, dinner and music.

Meals: B

After breakfast & coffee, we’ll head out on the ocean route toward the center of Cuba to the Bay of Pigs and brush up some history before we throw our bags down in our beachfront casas and hit the sand for rest and a swim at a secluded beach.

We’ll have a fantastic lunch at our secret seaside spot and enjoy the day snorkeling, swimming and exploring. A sunset will top off the day before having dinner in our casas on the water.

Meals: B, L

Enjoy another sunrise during breakfast & coffee at your Bay of Pigs B&B. Take one last dip in the beautiful clear water before we hit the road to Trinidad, one of Cuba’s best-preserved colonial towns and a UNESCO world heritage site.

A short 2.5 hr drive and we check into our colonial B&B before we explore the thriving art scene of this gorgeous city. We’ll visit a 5th generation pottery studio and do a walking tour to take in the town’s brightly colored buildings and cobblestone streets.

Enjoy evening for some local dinner specialties and more music out on the town.

Meals: B

Today we’ll have a full day to enjoy the colonial city of Trinidad. Enjoy breakfast on the private patio with sweeping views of the whole town. Our expert guide will give you a walking tour and will highlight the local art of the city, which is amazing. The rest of the afternoon you'll have time to explore on your own, eat through the town, listen to live music and even catch some nightlife at a club in a cave!!

Meals: B

Wake up to our fresh breakfast in your colonial B&B. After breakfast you’ll jump back on the road to Havana (4-5) hrs. We'll make stops at roadside stands, play Cuban music and watch Cuba go by as we make our way back to bustling Havana.

Once we arrive, we'll check back into our original B&B in Old Havana then hit the streets for an art walking tour, followed by a VIP tour from the curators of Havana's hippest art gallery, music venue, bar, restaurants...the Fabrica de Arte Cubano. Eat and dance the night away!

Meals: B

After breakfast & coffee this morning we’ll head to another UNESCO world heritage site, Viñales, in the Cuban countryside in the north-central Pinar del Rio province. We’ll jump on horses to ride through tobacco fields followed by a cigar rolling demonstration. Then, we’ll head to a local finca for a huge farm-to-table Farewell Lunch - a true multi-course feast! Back in Havana you’ll have time to enjoy your last evening on the island.

Meals: B, L

After breakfast & coffee, squeeze in any last minute photo ops, museums or shopping before heading to the airport any time that works for you today.

Meals: B

You'll be paired with a roommate unless you request your own room. Limited solo spots available, first come first serve

STARTING at $4495 per person - double occupancy

2026 price $4695

+$495 'My own room' option

Trip price based on double occupancy. Single rooms will require the single supplement. Minimum 2 people to book this tour

STARTING at $4695 per person, double occupancy

2026 price $4895

+$495 single occupancy

Extra nights before or after your trip, price on request

Heck yes it is! According to the US Department of Treasury, you are still allowed to travel to Cuba with American tour operators (us) with proper licensing (also us) on group educational tours. We pepper in the required educational aspects of the tour, a walking tour of Old Havana, a horse ride through a tobacco plantation with cigar rolling lessons and meetings with local artists. We like to keep it smart AND super entertaining! We are very happy to keep providing legal, culturally immersive trips to the island!

Yes! Cuba has a great selection of seasonal, local fare. Though it can be a bit meat-heavy, there are lots of fish options and vegetarian alternatives. There are also many naturally gluten free carbohydrates, like plantains (yum!) We’ll collect dietary restrictions in advance to prepare for your arrival.

Absolutely! Some of the best travel is done by yourself. The retreat is designed to better know yourself while being in a supportive group setting. And without a doubt, you'll leave with new friends!