The
havanA
trip
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
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
Feb 5 - 9, 2025
2 spots left​
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Mar 19 - 23, 2025
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Apr 9 - 13, 2025
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May 7 - 11, 2025
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May 22 - 26, 2025
Memorial Day Trip - likely to sell out
Oct 10 - 14, 2025
Nov 26 - 30, 2025
Thanksgiving Trip
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5 days/4 nights
starting at $2,199 USD
​Limited single 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
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4 night accommodations in shared rooms (single room upgrade available on request)
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Meals: 4 breakfasts, 2 lunches, 4 dinners
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Welcome drinks
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Walking tour of old Havana
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Private visit and salsa dance lesson with Havana Queens
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Evening dinner and dance show with the Havana Queens
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Vintage car ride down the coast
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Cuban cigar and rum tasting experience
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Private ecological farm visit and farm to table experience
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Visit to a local artist's studio
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Beach access with lounge chairs
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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
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Flights to and from Cuba
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Tourist visa (more information in the Trip Notes section)
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Mandatory trip insurance
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Meals not mentioned (budget around $200)
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Incidental expenses
Day by day
Trip itineraries are subject to change. For more information, check out our FAQs HERE.
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. Here, you’ll be surrounded by stunning colonial architecture, reflecting the lasting influence of Spanish, French, British, and American cultures. You can even spot remnants of the fortified walls that once protected this historic city. 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!
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 whopping 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.
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. Under the guidance of skilled torcedores (Spanish for cigarmaker), you’ll roll your own cigar and experience firsthand the craftsmanship behind each puff. 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.
dance
Day 4 - Havana
FUN IN THE SUN
It’s our last full day in Havana, and we’re diving headfirst into the city’s vibrant art scene. We’ll visit a locally curated gallery, where the artist himself will welcome us with mojitos and give us a personal tour of his work. The gallery is tucked away in his private home, so you can kick back on the balcony, sip your drinks, and take in both the stunning art and the views.
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Afterward, we’ll head to one of Cuba’s beautiful beaches to spend the afternoon relaxing on lounge chairs. With endless sunshine and crystal-clear waters, it’s the perfect spot to unwind and swim as we soak up the last bit of this magical place.
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Before sunset, we’ll head back to shower before gathering for our final farewell dinner. And of course, we’ll toast to the adventure with one last mojito or daiquiri—perhaps followed by one last dance to cap off this unforgettable experience together!
ENJOY
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!
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.
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The official Cuban currency is the Cuban peso.
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Cuba’s main island is the largest in the Caribbean and Latin America.
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Tipping is encouraged in Cuba. Consider giving 10% at bars and restaurants.
TRIP NOTES
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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.
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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!
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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​​.
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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!
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Cuba is usually hot and sunny, so make sure you pack a hat and sunblock.
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More information regarding visa requirements and Covid restrictions can be found here.
flight information
Fly into Havana (HAV)
Arrive by 1pm 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.
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.
HAVE QUESTIONS?
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.