CUBA

APRIL 6–14, 2027 · FIRST PLANNED DEPARTURE

Raw, vibrant, and impossible to forget.

Cuba is bound to be unlike anything else you have ever experienced — and the kind of place that leaves a mark on your heart. This is a small-group trip for people who want a different kind of adventure.

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9 days · 8 nightsFirst planned departure

Small groupsMore connection. Less crowd.

Locally ledCasas, guides, food, and stories

The proposed route

A week and a half of Cuba, close up.

We move through Havana, the Bay of Pigs, Trinidad, Playa Ancón, and Viñales — making room for neighborhood walks, music, local meals, the sea, and the people who give each place its character.

First planned trip09days in motion

April 6–14, 2027

The first group arrives in Havana on a Tuesday and travels home the following Wednesday. A second group may follow with a four-day rest and reset in between; final dates and availability will be shared before bookings open.

Havana

Centro Habana, Old Havana, Vedado, local food, and the first long conversations.

Playa Larga

Coastal communities, snorkeling, history, and a slower rhythm by the water.

Trinidad

Artisans, cobblestones, live music, and a night at Disco Ayala.

Playa Ancón

Sea air, fishermen, open coast, and time to let the day unfold.

Viñales

Sunrise, tobacco country, coffee, limestone mountains, and family farms.

Route and activities may shift with local conditions. That flexibility is part of traveling well in Cuba.

Who this is for

A distinct sense of adventure.

This is for travelers ready to take a different kind of trip: intimate, local, occasionally improvised, and full of the details that never make it onto a postcard.

You are curious about everyday Cuban life.
You enjoy local hosts, small groups, and real conversation.
You can stay patient when fuel, power, or transport changes the plan.

People before postcards

Built to give back as we go.

We stay in locally owned casas particulares, eat at privately run restaurants, and work with independent Cuban guides and hosts. A portion of trip costs will go toward supporting local Cuban charities.

There is no resort bubble here. The point is to meet Cuba on its own terms — with respect, curiosity, and a willingness to adapt.

Travel framework

Travel thoughtfully. Travel within the rules.

The trip is being planned around the U.S. Support for the Cuban People travel category and applicable OFAC requirements. Final guest guidance, inclusions, and documentation will be shared before bookings open. Each traveler is responsible for confirming their own eligibility and requirements.

What to expect

Come prepared for the real version.

Bring cashBringing about $1,000 USD in cash is essential. Expect to buy little or nothing once you arrive.

Pack lightApril is pleasant: shorts, lightweight khakis, going-out shirts, sunscreen, bug spray, and comfortable walking shoes.

Stay adaptablePower banks are smart. An unlocked phone that takes a physical SIM can use optional local service for a separate fee.

April 2027 · interest list only

Maybe Cuba is your next story.

Leave your details below to hear when dates, pricing, inclusions, and spaces are confirmed. No deposit. No obligation. No space reserved.

Continue to the interest form

Please wait for confirmed trip details before booking flights or making nonrefundable arrangements.