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The
 
havanA
 
trip

Colorful old buildings and vintage cars on the street in Havana.

For the love of

VINTAGE CARS

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DAQUIRIS & MOJITOS

 

SALSA DANCING

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 CARIBBEAN VIBES​

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​SMOKING CIGARS

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LIVE MUSIC

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​COLORFUL STREETS​

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RUM-FILLED NIGHTS​​

 

OCEAN BREEZES​

 

CUBA

People in Havana, Cuba dance in the park during a group tour.

WHAT TO EXPECT

Our small group trip to Havana is perfect for travelers in their 20s and 30s eager to explore the Cuban capital in a few days. Though only 90 miles from the U.S., Cuba feels like a world apart. It’s the best of both worlds—close enough for a quick getaway, yet transporting you to a place that feels like a time capsule of the 1950s.

 

You'll cruise through the city in vintage convertibles, sip mojitos and daiquiris where they were first crafted, and enjoy live music around every corner. For those with Havana on their bucket list but unsure about navigating the ever-changing rules and regulations, don’t worry—we’ve got you covered!

2025 dates

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Apr 9 - 13, 2025

Last Call​​​

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May 22 - 26, 2025

1 Gal spot + 3 Guy spots left

Runs over Memorial Day 

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jun 25 - 29, 2025


Oct 10 - 14, 2025

Phone-Free Trip


Nov 26 - 30, 2025

Runs over Thanksgiving

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Dec 31 - Jan 4, 2026

New Year's Eve Trip 🎉 - likely to sell out​​

5 days/4 nights

starting at $2,299 USD

 â€‹Limited private room upgrades starting from $559 are available and can be added during booking, subject to availability.

 

Payment can be broken down into a $500 deposit + 3 additional installments.

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INcluded

  • 4 night accommodations in shared rooms (private room upgrade available on request)

  • Meals: 4 breakfasts, 3 lunches, 4 dinners

  • Welcome drinks

  • Walking tour of old Havana

  • Private visit and salsa dance lesson with Havana Queens

  • Evening dinner and dance show with the Havana Queens

  • Vintage car ride down the coast

  • Cuban cigar and rum tasting experience

  • Private ecological farm visit and farm to table experience

  • Visit to a local artist's studio

  • Community beach day 

  • FTLO Trip Leader

*All activities are weather dependent; in the unlikely event that we are unable to run an activity, we will have a suitable alternative in place.

not included

  • Flights to and from Cuba

  • Tourist visa (more information in the Trip Notes section)

  • Mandatory trip insurance

  • Meals not mentioned (budget around $50)

  • Incidental expenses

A flag hangs in a colorful building in Havana,

Day by day

Trip itineraries are subject to change. For more information, check out our FAQs HERE. 

Day by day
Day 1 - Havana
HOLA HAVANA!

Welcome to one of the most intriguingly beautiful cities in the Caribbean! With five incredible days ahead, we’re wasting no time kicking off day 1 with welcome drinks (we suggest a mojito or daiquiri, both of which originate here in Cuba) to meet your new crew before we dive into our walking tour, led by a local guide.

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First stop: the vibrant, cobblestone streets of Old Havana, a UNESCO World Heritage Site. Our guide will share captivating stories about Havana’s past—from its foundation by the Spanish Crown and the pirate attacks that almost destroyed it, to the economic boom driven by the sugar and tobacco trades in the 19th century.

 

We’ll finish up at a rooftop paladar—a privately owned Cuban restaurant where you can savor authentic local dishes while enjoying sweeping views of the city at sunset. A perfect introduction to Havana!

Two men play music in front of a store in Havana.

DISCOVER

Day 2 - Havana
CUBAN CLASSICS

There’s no better way to experience Havana than from the backseat of a classic convertible. These iconic cars are a symbol of the city (rumor has it there are a 10,000 on the streets), so naturally, we’ll take you and the crew out for a spin before diving into your first salsa lesson with the renowned Havana Queens, one of Cuba’s top dance troupes.

 

Salsa was born right here in Cuba, so whether you're a seasoned dancer or stepping onto the floor for the first time, it doesn’t matter! You’ll have a team of expert dancers to get you moving to the rhythm of Havana’s heart-pounding beats.

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We’ll head back to freshen up because the night is just getting started. With your new moves in tow, we’ll enjoy a live salsa performance along with dinner, setting the stage for us to show the streets of Havana what we’ve got! Afterward, it’s time to hit the dance floor and salsa the night away at a local bar.

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cruise

Day 3 - Havana
SIP & SMOKE

We’ll kick off day 3 in the lush countryside of Havana, where you’ll get an up-close look at traditional sustainable agriculture practices. After exploring the farm, we’ll sit down for a delicious Creole lunch made from fresh, locally grown ingredients, all while soaking in breathtaking views and enjoying live music that captures the soul of Cuba.

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Next, we’re off to experience two of Cuba’s most iconic exports—rum and cigars. We’ll sample a few different dark, aged rums alongside this robust cigar to enhance the rich, smoky flavors. As you indulge in this pairing, you’ll learn about the rum distillation process and the history of this legendary spirit—a true taste of Cuban tradition.

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As the sun sets, we’ll head to one of the hottest spots in town—an art-gallery-turned-nightclub that’s buzzing with locals.

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EXPLORE

Day 4 - Havana
FUN IN THE SUN

 If there’s one thing this trip has proven, it’s that unforgettable memories—and friendships—can be made in just a few days. Imagine everything you would have missed if you’d never booked the trip! For our final full day in Havana, we’re heading to Habaneros’ “house beach”—a vibrant gathering spot where we’ll connect with the local community, soak in its rich cultural and historical significance, lounge in the warm Caribbean breeze, and enjoy fresh guarapo (sugarcane juice) purchased from local vendors.

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On our way out, we’ll stop for lunch before making our way to a gallery, where the artist himself will welcome us with mojitos and personally guide us through his collection, tucked away inside his private home. Havana has long been a magnet for artists, writers, and creatives—even Ernest Hemingway’s old haunts are famous around here.

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As the sun sets, we’ll return to the hotel for one final dinner, raising our glasses to an adventure we’ll never forget. But the night’s far from over—it’s time to put those salsa lessons to the test! With your fellow travelers as built-in dance partners, we’ll hit the dance floor one last time, closing out our time in Cuba on the perfect note.

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ADMIRE

Day 5 - Havana
HASTA PRONTO

You've journeyed through the vibrant layers of this incredible country, all in just five days! We hope this tropical escape leaves you with memories and friendships to cherish for a lifetime.

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If you have a bit more time to spare, consider extending your Havana vacation for a few extra hours! Grab lunch with your new friends as you hunt down some delicious ropa vieja—the Cuban national dish, featuring tender shredded beef combined with veggies and aromatic spices. Or, if you're craving more Caribbean sunshine, why not venture to nearby Belize? It's one of Central America’s premier destinations for nature enthusiasts, offering stunning landscapes and rich biodiversity just waiting to be explored!

The streets in Havana are full of classic cars.

FAST FACTS

Fast facts
about cuba

Cubans are known for their warmth and hospitality, and they have also pioneered a vibrant culture rich in music, dance, and art. From the rhythmic beats of salsa to crafting cocktails like the mojito and daiquiri, they have created a lively atmosphere that draws visitors from around the world.

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Despite the confusion surrounding travel to Cuba in recent years, it remains entirely possible for Americans to explore this unique Caribbean destination, even with some new red tape.

Good to Know
  • The official Cuban currency is the Cuban peso.

  • Cuba’s main island is the largest in the Caribbean and Latin America.

  • Tipping is encouraged in Cuba. Consider giving 10% at bars and restaurants.

TRIP NOTES

  • While we can’t guarantee private rooms when you visit Havana, you should book your trip earlier if you prefer one, as they usually fill up.

  • Due to relations between the United States and the Cuban government, all trips must have a meaningful cultural aspect to them. We think this is a fantastic thing!

  • FTLO travelers who hold a US passport will need to purchase a tourist visa with “Support for the Cuban People” as the general license category. This can be done through your airline and will cost between $50 and $100, depending on the processing fee. If you are not a US passport holder, please check your embassy’s website for further information. You can always contact us if you have additional questions or need assistance. For all other nationalities, please check here​​.

  • One of our experiences is a bit smokey as it involves local cigars. If you’re sensitive to smoke or not a fan of cigars, don’t worry, you can head out and explore instead!

  • Cuba is usually hot and sunny, so make sure you pack a hat and sunblock.

  • More information regarding visa requirements and Covid restrictions can be found here.

flight information

Fly into Havana (HAV)

Arrive by 12 pm on day 1 and grab a cab to the hotel. We do recommend flying in earlier to have some time to explore the city on your own!

Fly out of Havana (HAV)

Fly out of Havana at any time on the last day. We recommend an afternoon flight so you have more time to explore the city.

A palm tree near the coast in Havana, Cuba.

alumni reviews

Alumni Reviews

We know how much you'll love the Havana trip...
but don't take our word for it! Check out some of our alumni reviews. 

Two friends in a classic car near the coast in Havana.

HAVE QUESTIONS?

Learn More

Interested in learning more about our Havana trip?

Have a question? We're here to help! Whether you're curious about accommodations, accessibility, group vibe, or dietary needs, fill out the form below, and we'll get back to you ASAP.

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