The Havana Trip
Cultural • Historical • Party
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
Cultural
Adventurous
Free Time
what you’ll Love about this trip
What's 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.
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 for $559. 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!
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 spots.
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.
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.
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.
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!
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!
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.
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.
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.
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.
Let's Get Social
#ftlohavana in the wild
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 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.
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.
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.
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.
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.
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.
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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