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2023 dates

*Trip availabilities change throughout the day and may not be accurately reflected here. To see if space is available for the date you are interested in, please click through to the booking form.


Nov 8 - 12, 2023



Nov 22 - 26, 2023

SOLD OUT - Waitlist only

Nov 29 - Dec 3, 2023

Dec 13 - 17, 2023


Dec 28 - Jan 1, 2024

Gal spots SOLD OUT + 1 Guy spot + 1 single room left

5 days/4 nights

starting at $2,499 USD

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

In Cuba, arts and music are thriving and waiting to be explored.

2024 dates

$100 off with


Jan 17 - 21, 2024

Feb 7 - 11, 2024

Phone-Free Departure

Feb 15 - 19, 2024


March 13 - 17, 2024


March 20 - 24, 2024


April 3 - 7, 2024

May 1 - 5, 2024

May 23 - 27, 2024

Memorial Day trip

Nov 20 - 24, 2024

Nov 27 - Dec 1, 2024

Thanksgiving trip - likely to sell out

Dec 4 - 8, 2024

Dec 11 - 15, 2024


Dec 28 - Jan 1, 2025

NYE trip - likely to sell out

5 days/4 nights

starting at $2,299 USD

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

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Our small group trip to Havana caters to travelers in their 20s and 30s searching for rich culture, excitement in the streets, and eye-popping architecture around every colorful corner.

On this five-day Havana trip, you’ll discover the ins and outs of the Cuban capital, a city frozen in time and only recently opened back up to Americans. With ornate, baroque designs everywhere you look and a 16th-century fortress guarding the harbor, the history is impossible to ignore.

So come along and enjoy the land of salsa, cigars, and enough rum to help even the most musically challenged belt out “Havana, ooh na-na.”

For the love of














  • 4 nights of accommodations in Havana, Cuba

  • All accommodations in a shared room with one other person with the option to upgrade to a private room (limited availability)

  • Meals: 4 breakfasts, 2 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 the world renowned Fabrica de Arte

  • Local community and nonprofit experiences

*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 $200)

  • Incidental Expenses

more details
The colorful Cuban culture is full of history.

Day by day

*Itinerary is indicative and is subject to change

Day by day
Day 1 - Havana
the old town

Check into your hotel nestled in Old Havana and grab a drink with your travel crew.

In the afternoon, we’ll head out on a walking tour where you’ll get your first taste of architecture so significant it earned a spot on UNESCO’s World Heritage List. Continue on and give a mojito a go—the local favorite and Cuban national drink has been a staple on these lively shores for centuries.


That night, we’ll all head out together to grab some dinner and check out local live music in one of the neighborhood's trendiest joints.

In Havana, music is an important part of life.


Day 2 - Havana
old school cool

After an early breakfast at the hotel, we’re rolling with the top down—Cuba’s culture of preservation and ingenuity has turned this island into a haven for classic cars, and today we’re taking full advantage. 

Cruise down the shore to explore a bit of the coast on the way to a behind the scenes rehearsal and salsa lesson with one of Cuba’s most acclaimed dance troupes. After that, check out a ceramic wonderland before we stop for a waterfront lunch along the bay.

That evening, we’re off to a rum and cigar experience with a local expert, where we’ll get the low down on Cuba’s most famous exports. At that point, you’ll really be reaching peek old-school cool levels, so it makes a lot of sense that we’ll finish off our day with dinner and one incredible dance show.

Cruise Cuba in classic cars with new friends.


Day 3 - Havana
locally grown

Today, we’re heading toward Havana’s agricultural outskirts for an authentic farm-to-table experience. We’ll learn the ins and outs of organic farming, island style, before we sit down for a bite, a bit of dancing and music, and some more of those spectacular Cuban cocktails.

We’ll head back to town and make a pit stop by the harbor for some more local vibes. Get lost in one of the city’s coolest outdoor markets, pick up some souvenirs from Havana’s arts community, and grab a beer before you make your way back to the hotel. 

That night, we’re heading for rooftop cocktails and then to one of Cuba’s coolest modern arts and dance spaces, for dinner and a night of bohemian good times.

The Havana tour is a chance to soak up Cuba's lively night life.


Day 4 - Havana
state of the arts

Enjoy breakfast with friends at the hotel, before we roll out for a day of Cuban arts. We’re going to get things going by heading to a local non-profit working to revive the craft of hairdressing.


We’ll keep the theme going by moving on to Callejon de Hamel, where we’ll dive into the complex world of Afro-Cuban art. Check out some of the impressive studios and immerse yourself in the thriving Havana art scene. Feel free to find lunch nearby with friends, and then the afternoon is yours to explore the city.


We’ll all meet up that night for one final dinner together before we say our farewells.

Head to a cigar bar and learn abou one Cuba's most important exports.


Day 5 - Havana

Find breakfast with the group at the hotel before you head to the airport for your flight back home.


We recommend booking flights for later in the day, allowing you to continue to explore the city of Havana today.​

Remember, Cuba’s just a short flight away, so don’t be a stranger. The mojitos are always waiting.

“Cuba may be the only place in the world where you can be yourself and more than yourself at the same time.”
– Pedro Juan Gutierrez

The streets in Havana are full of classic cars.


Fast facts


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Cuba travel tour for young professionals and young adults

Legendary writer Ernest Hemingway made his second home just outside Havana in the small town of San Francisco de Paula.

Rumor has it, it takes more than 100 steps to produce a single Cuban cigar.

Lega cuba travel for young professionals an young adults

Cuba has one of the world’s largest collections of classic cars—it’s estimated that there are 60-70,000 vintage rides rolling these streets.


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

  • Due to relations between the United States and Cuba, 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.

about cuba

Cuba has undergone something of a modern renaissance in terms of arts and culture. While the nation’s music has long been widely renowned, today, dance and theater troupes also thrive. Performers take center stage at the Gran Teatro de La Habana, yet increasingly local troupes are traveling abroad, often to great acclaim. Within Cuba, Havana remains, by and large, the nation’s cultural mecca and plays host to a diverse group of music halls, museums, and centers of arts.


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  • Cuba’s official currency is the Cuban peso.

  • Cuba’s main island is the largest in the entire Caribbean.

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

The Cuban capital is home to incredible architecture.



Fly into Havana (HAV)

Arrive by 1pm on day 1 and grab a cab to the hotel. With the recent amount of flight delays, we recommend planning to arrive a day early just to be safe.

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.

Want to check out flights for your trip?

Feel free to also set up flight alerts to Havana so you can grab the best deal!

*FTLO is not responsible for any fees or costs related to flights. We strongly suggest that all travelers wait until they receive the official FTLO Greenlight Email to book flights. This will be sent 3-4 months prior to the start date of your trip.

Image by Jake Nackos

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. 

Alumni Reviews
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Make new friends on the Havana trip along the coast of the Carribean.


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