The Havana Trip
Cultural • Historical • Nightlife
For the love of colorful Old Havana streets, classic-car cruises, and farm-fresh mojitos — add salsa lessons, cigar-rolling workshops, and sunset beach bliss. That’s our Havana trip.
Welcome to Havana!
5 Days / 4 Nights
Starting At $2,399
Up To 16
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!
Physical Activity
Nightlife
Foodie Trip
Cultural
Adventurous
Trip Pace
what you’ll Love about this trip
What's Included
Trip Logistics:
4 nights in a centrally accommodation in Havana’s historic district (shared twin room with one other traveler, optional private upgrade subject to availability)
4 breakfasts, 3 lunches, and 4 curated dinners throughout the trip, including a welcome dinner and farewell dinner
Private van transportation for all included activities throughout the trip
Included Experiences:
Welcome drinks and orientation to kick off the trip and meet your travel crew
Guided walking tour of Old Havana, a UNESCO World Heritage Site, led by a local expert sharing the city’s layered history and culture
Classic 1950s convertible ride through Havana’s iconic neighborhoods and along the Malecón, including stops at historic landmarks like Castillo de los Tres Reyes del Morro and Cristo de La Habana with scenic viewpoints across Havana Bay
Seaside lunch along Havana’s coastline with views of the Caribbean
Guided visit to artist José Fuster’s mosaic-covered home and studio in Fusterlandia, exploring the colorful compound that helped transform the surrounding neighborhood into an open-air art landmark
Private rehearsal space experience with the internationally acclaimed Havana Queens salsa company, featuring an intimate live performance, behind-the-scenes Q&A, and a hands-on salsa lesson led by the dancers themselves
Evening dinner show featuring the Havana Queens, showcasing high-energy choreography, live music, and the opportunity to join the performers on stage
Private countryside visit to a locally operated agroecological farm, learning about Cuba’s sustainable farming methods, seasonal crops, and small-scale livestock systems
Farm-to-table Creole lunch prepared with seasonal ingredients from the farm, accompanied by live local music
Visit to a local open-air artisan market, browsing handmade crafts and artwork from Cuban artisans and independent makers
Cuban rum and cigar tasting experience with a local expert, learning about traditional distillation methods and craftsmanship
Evening at Fábrica de Arte Cubano, Havana’s iconic former factory turned multidisciplinary art and nightlife space featuring rotating galleries and live music
Visit to Santa María del Mar, a beloved beach for Havana residents, with time to swim alongside local beachgoers and learn about the cultural and historical context of the area
Private visit to a working Cuban artist’s studio, with conversation about contemporary Cuban art and daily creative life on the island
Trip Support & Extras:
Dedicated FTLO Trip Leader throughout the trip, coordinating logistics and providing local knowledge
Access to our pre-departure hub with detailed trip information, packing guidance, cultural tips, and a space to connect with fellow travelers before departure
All entrance fees, taxes, and activity costs for listed experiences
Certain cultural venues and experiences are dependent on local availability and operating conditions. In the unlikely event that an activity cannot operate as planned, a suitable alternative will be arranged.
What's Not Included
Flights to and from Cuba (fly in and out of Havana)
Trip arrival and departure airport transfers
Mandatory trip insurance
Additional food and drinks (budget around $50, depending on consumption habits)
Incidental expenses
Tourist visa ($50-100 USD, more information in the Trip Notes section)
Where you'll be going
Trip Dates
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Limited private room upgrades are available at checkout starting from $599. If no longer available, you can inquire after booking, and we may be able to secure one.
Standard payments include a $500 deposit + 3 installments. Extended payment plans are available upon request.
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Day by Day
Read through an outline of what’s in store for our Havana trip. This itinerary may be updated as needed.
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.
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!
Trip Notes
Read through helpful flight details, trip notes and details about our Havana Trip.
Arrive
Fly into José Martí international Airport (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!
Depart
Fly out of José Martí international Airport (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.
Private Room Upgrades
Private room upgrades are available for an additional amount and can be added during booking. These are available on a first-come basis, so plan to book in advance if you are interested in your own room.
Culture
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!
Dietary Restrictions
Cuban cuisine centers on meat, rice, and beans. Bananas and plantains are common in traditional dishes; please inform us of any allergies or sensitivities so we can assist accordingly.
Accommodations
You'll stay in a centrally located boutique hotel offering a cozy, authentic Cuban experience. Expect charming decor, a welcoming atmosphere, and easy access to Havana's vibrant culture and rich history.
Itinerary Changes
This itinerary is subject to change based on the weather conditions and traveler feedback. In the unlikely event that we are unable to run a specific activity, we will have a suitable alternative in place.
Passport Requirements
To enter Cuba, your passport must be valid for the duration of your stay. However, some airlines may require at least six months of validity, so it's best to check with your airline before departure.
Smoking
One of our local experiences includes Cuban cigars, so the environment may be a bit smoky. If you're sensitive to smoke or simply not into cigars, no worries – you’re welcome to opt out and explore the area at your own pace instead!
Weather
Havana has a warm, tropical climate year-round, with high humidity. Our trips run during the Dry Season, when you can expect sunny skies, lower humidity, and pleasant, comfortable temperatures – perfect for exploring the city.
Let's Get Social
#ftlohavana in the wild
How much should I budget for meals and extras?
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All meals are included in this trip, which is a rare treat. Just plan to bring around $50 for extra snacks, drinks, or personal items.
ATMs are limited and cards may not work everywhere, so FTLO recommends bringing cash and budgeting carefully.
I have dietary restrictions. Will there be options for me?
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Yes, we can usually accommodate most dietary needs, especially if you let us know in advance.
Vegetarian and dairy-free travelers should do fine, though options may be more limited. Cuban cuisine is hearty and simple – think rice, beans, meats, and root vegetables – and you’ll get a taste of everything from home-cooked meals to farm-to-table experiences.
What are the accommodations like?
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You’ll stay in locally owned guesthouses or boutique-style casas, chosen for their charm and central location. These spots offer an authentic experience and a warm welcome, though rooms may be basic and vary in size.
Shared rooms are the default, and private upgrades are limited – book early if that’s important to you.
What should I pack?
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Cuba is hot and humid, so bring light, breathable clothing that keeps you cool. You’ll want comfortable walking shoes for cobblestone streets, sunscreen, a hat, and swimwear for the beach day. A small daypack comes in handy for excursions, and a light jacket is smart for breezy evenings or AC indoors.
Any recommendations if I'd like to extend my time abroad?
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If you have extra time, you can explore more of Cuba by visiting Viñales, Trinidad, or Varadero. You could also fly to nearby Mexico or Panama City for easy regional connections. For more Caribbean sunshine, Belize offers stunning landscapes and rich biodiversity waiting to be explored!
When’s the best time to go to Havana?
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Havana has a warm, tropical climate year-round, with average temps between 70°F and 85°F and high humidity.
The dry season (November to April) is the most popular time to visit, with sunny skies and comfortable weather — just expect more crowds at major spots.
The rainy season (May to October) brings heavier humidity and quick afternoon showers, but rain usually passes fast, leaving plenty of time for exploring the city’s vibrant streets and rooftops.
When should I arrive and depart, and how do I get to the hotel?
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Plan to arrive at Havana’s José Martí International Airport (HAV) by 12:00 PM on Day 1 so you can get to the hotel and settle in before group activities. Taxis from the airport are easy to find and take about 30–40 minutes into the city.
On Day 5, you’re free to depart anytime after breakfast — later flights give you more time for one last café visit or wander around Old Havana.
What’s the pace of the itinerary?
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The days are full, with group meals, city explorations, and immersive cultural activities. You’ll be on your feet often, but the pace allows for spontaneous dancing, people-watching, or grabbing a cocktail with your new travel crew. Evenings are lively, but there’s always time to recharge.
What’s the vibe of this trip?
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This trip is vibrant, full of movement, and packed with local flavor. You’ll dive into Havana’s rich history and culture through music, dance, and street life, while enjoying warm connections with your group. From salsa nights to local artist visits, the energy is welcoming and social — perfect for travelers looking to experience Havana beyond the tourist spots.
Do I need a visa?
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Yes, U.S. travelers need a Cuban Tourist Card issued under the “Support for the Cuban People” category. This usually costs $50–$100 USD, and you can often purchase it directly through your airline.
Be sure to apply at least a few weeks in advance and bring proof of travel insurance. For the most updated information, please check a reputable source.
Common Questions about this trip
Trip Reviews
Read through helpful flight details, trip notes and details about our Havana Trip.
Traveler Review Summary
5 Star Rating
The Havana trip with FTLO receives overwhelmingly positive reviews for its immersive cultural experiences, vibrant atmosphere, and thoughtfully curated local activities. Travelers frequently highlight salsa dancing, classic car rides, live music, and exploring Havana’s historic neighborhoods as standout moments throughout the itinerary. Reviews also praise the welcoming group dynamic and authentic experiences that made the trip feel both memorable and deeply connected to local culture.
Interested in learning more about our Havana trip?
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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