Last September, Escape Brooklyn hosted our first group travel event in years in Livingston Manor, NY. (Did you know we’ve hosted group camping trips in the past, too?) That weekend, ten complete strangers came together for a weekend of fishing, exploring the woods, swimming, bonfire hanging and dining under the stars. Even better, the ten strangers left as new friends. It gave Escape Brooklyn the warm fuzzies, so much so that we’re doing it again. But this time, we’re forgoing New York altogether, and escaping winter. To Cuba.
Co-hosted with our Brooklyn-based friends from Bridges Cuba, during our six day guided excursion, we’ll be making the absolute most of the trip and packing in as much Cuban goodness as possible. If you’ve followed Escape Brooklyn for some time, you already know we go above and beyond to ensure that our travelers don’t get stuck in tourist traps. Instead, we’ve worked closely Bridges Cuba and their team of incredible guides to create memorable experiences that are authentic, immersive, informative, and best of all: hella fun.
First, let us address the elephant in the room: yes, travel restrictions to Cuba are once again very tight for Americans. Current restrictions prevent all Americans from traveling to Cuba except as part of an educational group tour. But that’s where Bridges Cuba comes in! For years, Bridges Cuba has been sending American travelers to Cuba, ensuring that all their travelers are 100% legally compliant with travel restrictions. Let us deal with the red tape!
Escape Brooklyn and Bridges Cuba are offering two different but equally amazing trips. Both begin with a few days in Havana before departing to explore different ends of the island, with educational focused itineraries for each. (More details on that below.) Traveling with us not only means you can go legally/confidentlybut also, you won’t have to waste time figuring out where to go, what to see, and where to eat. Not to mention, an incredible bonding experience with your ten strangers that are sure to be your ten new best friends.
Grab a mojito, click through the galleries below to get a feel for each trip, and let us know if you have any questions! For questions pertaining to the trip, or for bookings, email Bridges Cuba founder Brian Rogers at brian@bridgescuba.com. For anything Escape Brooklyn related, email howdy@escapebrooklyn.com.


Saturday, February 24 through Friday, March 2

Cuba for Art & Culture Lovers: Havana and the Historic Towns of Cienfuegos, Trindidad, and Santa Clara

The second Escape Brooklyn/Bridges Cuba trip will have an itinerary that’s focused on the art & culture of Cuba. We’ll be putting our travelers face-to-face with the innovators taking Cuba into the future, as well as delving deep into its rich cultural past. The group will spend a few days exploring the busy streets of Havana with a local guide, hitting all the must-see museums and art galleries, before packing up for our roadtrip to the eastern side of the island. Our first stop will be Santa Clara, where we’ll explore revolutionary landmarks and then continue on to the Valley of Sugar Mills. Next, we’ll explore the cobble stone streets of Trinidad and the coastal city of Cienfuegos, known for it’s incredible Spanish colonial architecture. On our last full day, we’ll take a daytrip into the mountains for a hike ending in a waterfall plunge. Here’s what’s included:
• Lodging: Private* rooms in a beautifully restored mansion in Havana, and private* rooms in a casa particulares in Cienfuegos and Trinidad. (*see below for price breakdown of private vs. shared rooms.)

• Meals: We’ll be sharing breakfast, plus at least one additional meal each day as a group. We’ve purposely left some meals open so our travelers can explore on their own. Just ask us if you need a recommendation!
• Transportation: For the duration of the trip, we will have at least one, and at times, two vans for group transportation. Around Havana, we’ll squeeze into one van to get around. On longer rides (not exceeding 2.5 hours), we’ll have a second van so everyone can travel comfortably. We’ll also arrange transportation to and from the airport.
• Guides: English speaking Cuban guide and historical expert; American Cuba expert and founder of Bridges Cuba; photographer from Escape Brooklyn.
• Activity Highlights: Local Cuban guided art/design tour of Old Havana; classic car tour of Old Havana and Vedado; guided tour of Cuba’s National Art Museum; multiple Cuban artist studio visits; salsa dancing lesson; waterfall hike in Trinidad; visit to Che Guevara Mausoleum in Santa Clara.

Pricing/Payment: Escape Brooklyn/Bridges Cuba team will host ten travelers for this trip. We’re offering both shared and private rooms in order to accommodate couples, friends, and solo travelers.

  • $2,500 per person for a shared room — this means couples and solo travelers who share a room with two beds (and another solo traveler of the same gender).
  • $2,800 per person for a single room — for those who prefer to have their own room all to themselves.

To reserve a spot, guest are required to make an initial non-refundable payment of $500, with the final payment due at least 1 month prior to departure dates. The trip price will cover all lodging, guides, group transportation, breakfasts, tipping, the two group lunches and dinners, and all activity costs/entrance fees — essentially everything except for a few meals. We will be helping travelers budget appropriately for the minimal additional costs of a few meals, drinks out, and other purchases like art/rum/tobacco/souvenirs.
For questions or booking inquiries, email Bridges Cuba founder Brian Rogers at brian@bridgescuba.com.


Saturday, February 3 through Friday, February 9

Cuba for Nature Lovers: Havana and the Rural Towns of Las Terrazas, Soroa, and Viñales (FULL TRIP)


The first Escape Brooklyn/Bridges Cuba trip will have an itinerary that’s outdoor-centric. (And average daily temperatures in the 80s, you’ll be a happy camper.) The group will spend a few days in Havana with a local guide before heading out to the mountains for total immersion into rural Cuba. We’ll be exploring the eco-village Las Terrazas, go for a waterfall hike (swimming included), have a pig roast atop a mountain in a restored mansion, and horseback ride through the tobacco fields of Viñales. The spectacular landscapes of western Cuba are the perfect backdrop to this adventure-heavy tour. Here’s what’s included:
• Lodging: Private* rooms in a beautifully restored mansion in Havana, eco-hotel Moka in the mountainside town of Las Terrazas, and private* rooms in a casa particular in Viñales. (*see below for price breakdown of private vs. shared rooms.)

• Meals: We’ll be sharing breakfast, plus at least one additional meal each day as a group. We’ve purposely left some meals open so our travelers can explore on their own. Just ask us if you need a recommendation!
• Transportation: For the duration of the trip, we will have at least one, and at times, two vans for group transportation. Around Havana, we’ll squeeze into one van to get around. On longer rides (not exceeding 2.5 hours), we’ll have a second van so everyone can travel comfortably. We’ll also arrange transportation to and from the airport.
• Guides: English speaking Cuban guide and historical expert; American Cuba expert and founder of Bridges Cuba; photographer from Escape Brooklyn.
• Activity Highlights: Local Cuban guided history & architecture tour of Havana; classic car tour of Havana including a visit to a secret mini-rainforest; waterfall hike in the mountains of Soroa followed by a pig roast at a mountaintop mansion with a pool; horseback riding through the tobacco fields of Viñales; cigar rolling demonstration from local farmers; cave exploration at Cuevas de Santo Tomas, the largest cave system in Cuba.

Pricing/Payment: Escape Brooklyn/Bridges Cuba team will host ten travelers for this trip. We’re offering both shared and private rooms in order to accommodate couples, friends, and solo travelers.

  • $2,500 per person for a shared room — this means couples and solo travelers who share a room with two beds (and another solo traveler of the same gender).
  • $2,800 per person for a single room — for those who prefer to have their own room all to themselves.

To reserve a spot, guest are required to make an initial non-refundable payment of $500, with the final payment due at least 1 month prior to departure dates. The trip price will cover all lodging, guides, group transportation, breakfasts, tipping, the two group lunches and dinners, and all activity costs/entrance fees — essentially everything except for a few meals. We will be helping travelers budget appropriately for the minimal additional costs of a few meals, drinks out, and other purchases like art/rum/tobacco/souvenirs.
For questions or booking inquiries, email Bridges Cuba founder Brian Rogers at brian@bridgescuba.com.