The Havana Trip
Cultural • Historical • Party
Fallout is a creative agency
specializing in signage, video
production, social media
management, content creation,
and social media strategy.
Our mission is to help businesses
stand out and connect with
their audience through
compelling visual storytelling.
Fallout is a creative agency
specializing in signage, video
production, social media
management, content creation,
and social media strategy.
Our mission is to help businesses
stand out and connect with
their audience through
compelling visual storytelling.
Welcome to Havana!
5 Days / 4 Nights
Starting At $2,299
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!
What's Included
Accommodations: 4 nights in shared rooms (single room upgrade available on request)
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 a local artist's studio
Beach access with lounge chairs
FTLO Trip Leader
What's Not Included
Flights to and from Cuba
Tourist visa (more information in the Trip Notes section)
Mandatory trip insurance
Meals not mentioned and optional activities (budget around $200)
Incidental expenses
what you’ll Love about this trip
Where you'll be going
Trip Dates
Feb 5 - Feb 9, 2025
Gal spots SOLD OUT + 2 Guy spots left
Mar 19 - Mar 23, 2025
Apr 9 - Apr 13, 2025
May 7 - May 11, 2025
Phone-Free Departure
May 22 - May 26, 2025
Runs over Memorial Day - likely to sell out
Oct 10 - Oct 14, 2025
Phone-Free Departure
Nov 26 - Nov 30, 2025
Runs over Thanksgiving
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 $199 deposit + 3 additional installments.
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. 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!
Arrive
Private sail around Milos and S with lunch and drinks on deck. Did we mention drinks?
Depart
Private sail around Milos and S with lunch and drinks on deck. Did we mention drinks?
Let's Get Social
Common Questions about this trip
Fallout is a creative agency specializing in
Fallout is a creative agency specializing in
signage, video production, social media
signage, video production, social media
management, content creation, and social media
management, content creation, and social media
strategy. Our mission is to help businesses stand
strategy. Our mission is to help businesses stand
out and connect with their audience through
out and connect with their audience through
compelling visual storytelling.
compelling visual storytelling.
Fallout is a creative agency
specializing in signage, video
production, social media
management, content creation,
and social media strategy.
Our mission is to help businesses
stand out and connect with
their audience through
compelling visual storytelling.
Fallout is a creative agency
specializing in signage, video
production, social media
management, content creation,
and social media strategy.
Our mission is to help businesses
stand out and connect with
their audience through
compelling visual storytelling.