Rum, revolutionaries and retro cars – Cuba has a back-in-time appeal. Though a trip to Cuba seems undoubtedly romantic and exciting, you’ll need to understand how the island works to get the best out of your visit.

Cue our friends at Coast to Costa who we’ve partnered up with on an Adventure Handbook Cuba trip happening in April 2017. Think 8 days of kite surfing, driving convertibles through the city, riding horseback through the heart of Trinidad, dance halls, cigars, wine, food and all that good stuff – we’re also sending out our mate Reuben Wu to shoot the trip. To find out more about what’s in store head over to Coast to Costa:

Who are Coast to Costa?

Coast to Costa might just be perfect travel companion – they speak the local language and have all the experience and knowledge about the region to create a personalised trip to suit your needs. Founder Andrew Tyree lived in Spain for four years and has travelled extensively throughout Central and South America getting to know the locals, scoping the perfect spots. He’s now taken over 200 people out on trips which are somehow able to blend ‘adventure’ and ‘guided tour’ into a surprisingly beautiful, localised experience.

We sat down with Andrew to find out a bit more about what to expect for our upcoming colab trip in Cuba where there are 16 open spots to be flown out to Cuba for the week of a lifetime.

*The images you see in this article are from the last two trips Coast to Costa has taken.

Hey Andrew, tell us how the idea of Coast to Costa came about?

Coast to Costa came about after I lived in Spain for four years. After returning to California, I would travel back there with friends, rent a house and plan what to do while over there. At the same time, I was working in a restaurant in San Francisco called Contigo and would talk with different Spanish wine, cheese and ham producers and they would offer me tours of their properties. I basically combined the idea of group travel with friends with food and wine and Coast to Costa was born.

Highlights from some of the trips to date?

Our first two trips were to Barcelona, Spain in 2012 and 2013. Then I began taking people down to a sleepy surf town called San Pancho in Mexico. From there we started doing Day of the Dead trips to Oaxaca yearly, a snorkeling and chilling on the beach trip to Tulum, food and wine weekend trips to Baja, a group trip back to Spain, a research trip to Mexico City to begin trips down there and then….Cuba opened up to American tourism. I was already providing curated trips to Spanish speaking countries, so I was really in the right place at the right time!

What kind of people/experiences could I expect?

The people that typically come along on our trips are open minded and excited to travel. They are people who are willing to jump in a van in a foreign country with people they don’t know and expect to make friends, and they always do. They come from all walks of life but everyone has the common goal to explore and discover new places. During the trips, people make some lifelong friends.

Guided tours are something I might find either my parents or a bunch of horny gap-year students on. What would you say to someone like me who hates the idea of a tour guide?

I’m with you, man! Normally, I am not the type to go on group tours. So two things, one is that we only have one group activity per day lasting for a few hours and then the rest of the day is free time. This allows people to go and explore on their own, while still having the comfort of going with someone who knows the place. Second, I like to think of myself as a friend who has been to our destination many times, knows that language and knows of all of the cool stuff to do. We are not a typical, follow the yellow flag, kind of group tour!

How much guiding actually happens on the trips, can I take a day off to explore on my own?

As far as guiding, we employ local guides to do any and all of the actual tour guiding parts. We like to involve the local community in all aspects of our trips and who better to lead a tour than someone who is FROM there. Also, in Cuba, we have to do some activities that are educational and cultural to comply with the regulations for tourism. We just pick the things that are the most fun for us! Hemingway bars, horse rides in tobacco fields, cigar rolling, salsa concerts…

Are Coast to Costa trips fun for individuals as well as groups?

Absolutely! We very much encourage solo travelers to come and join the group. In every group, we have a good mix of some couples, some friends and some single travelers. We always stay in shared houses on ALL of the trips, so everyone shares the house. We pair single travelers in rooms together, making them roommates for the week. I really love the concept of coming “home” after a day of exploration and digesting all that has happened during the day over some beer, wine or rum. We end up creating a group culture within a culture, while exploring new things together. The discussions in the living rooms are some of my absolute favorites!

How do you go about curating the trips with so many different interests?

We curate trips for all types. We offer private groups and send individuals, families or groups of friends to our destinations, as well. That way works just fine but I truly believe that in order to understand more of what is happening in any particular place, it is helpful to have myself or members of our staff, like Brandon Rus, to help translate and answer any questions. Our trip itineraries are sent out before hand and offer a bit of art, music, outdoors, food, local drinks, walking tour, free time, etc. Basically we touch on a little bit of everything that would entice someone to travel. Again, after the one group activity a day, folks are free to wander and explore or I can help them get to see what they want to see.

What’s the feedback been like?

The feedback has been incredible! Best friends have been made, a couple got engaged, we’ve had tons of repeat guests and get TONS of referrals from friends who have been. I am on a text chain with members of a group in April that hasn’t stopped since we got back 8 months ago. I am planning on releasing a “Cuba Advanced” trip in the future for past guests that want to explore the less touristed side of the island. The experiences speak for themselves. Everyone who goes has an eye opening experience. Some expect the countries to be like America and are upset that countries don’t work how it works at home…those folks don’t come back.

What’s in store for the guys heading to the next Cuba trip?

We are doing another of our small group “Cuban Road Trip” coming up in November. It’s going to be great, I’m sure. We have a good group of excited people coming. I’m particularly excited for the trip that we’ll be doing with you guys! We will be heading up to the north side of the island, for some snorkeling or scuba diving, surfing, kayaking, going out to the Cuban keys, drinking rum from coconuts…I cannot wait to get to planning that one!