New York Made Me Do It

Journal Entry #1 Brooklyn

Well here we are, one week out from the big day. I figured this would be the perfect time to begin my journal series here on The Kook’s Compass. While I could have begun to write entries over the past few weeks, no one needs to hear about my sad life sitting on the couch waiting to leave. During that time however, a lot has happened. Preparation has been done including trip planning, contacting people in various locations around the world, and coordinating with friends that plan to meet me somewhere on the road. All I can say is, the future is looking bright and I’m excited to share with you what my next few months on the road will look like.

I’m kicking things off in Miami, Florida. I’ve never been to Florida but I’ve heard many good…and not so good things. I’ve booked myself a little hostel in a prime location by the beach and plan on relaxing for a few days soaking up the sun. This is just a layover for me as I found the cheapest flights to Cuba leaving from Miami, however I gave myself a few days in Florida because you might as well see it if you’re already there.

This leads me to the next destination: Havana, Cuba! Beyond excited for this stop as you can imagine. I decided to go to Cuba on a whim sometime in March and while it’s a bit out of the way from where I will be backpacking, if I don’t go now, I fear I will never get the opportunity to see Cuba in its purity. Seeing as I have no choice but to travel with my surfboard for the future destinations, I started digging for opportunities to catch a few waves. Little did I know this would completely change my trip in its entirety. My research put me in contact with Eduardo Valdes, a Cuban local running a charity called Royal70, aimed at bettering Cuba’s youth through the incorporation of action sports. Their mission is a good one and while they have the opportunity to change the lives of hundreds of children, they struggle every day with obtaining proper equipment to help turn their efforts into a reality. After sending a few emails, both with Eduardo’s organization and my local surf shop here in New York, I am happy to say Royal70 will soon be getting some new boards and quality surf supplies. Putting this together was so damn easy AND a lot of fun. Do your part next time you take a trip! I also have to include, my first few nights accommodation in Havana were setup for me by a local who reached out through More info on some websites I hope to incorporate on my trip later on. After a little conversation, he booked my friend (who will be meeting me in Cuba) and I a bed at a local hostel, asking nothing more in return than a cultural exchange. What a saint.

After Cuba the fun really starts to begin. If you didn’t know, my goal was to begin my backpacking trip in Asia and it really did not matter where I started. Due to the direction of flights, I took the opportunity to make a stop at home in California to see my parents. This turned out to be a blessing in disguise as I later got in contact with another Surf Charity (Returning Wave), this one based in the Philippines with initiatives on the west coast. Their aim is to refurbish old, worn out surfboards in order to send them to locations throughout the Philippines where they will be put to use in surf programs for children who strive for academic excellence. RAD! Obviously I wanted to lend a hand as I have room for another board in my bag; I’m paying the bag fees anyways, so might as well make it worth something. After a few emails back and forth, (the internet is such a powerful tool) a few friends and I will take a road trip up to San Francisco to meet Lynn of Returning Wave to pick up a board and return to Los Angeles where I will then fly to my first Asian destination: Cebu, Philippines.

My Chapter in Asia will mark the official start to my backpacking journey and possibly the start of a new life! I have made it a point to keep my eyes and ears open to all the potential opportunities this world has to offer. If someone offers me a job working on a farm near a pumping surf break, don’t think I won’t take it because what more would you need in life? After landing in Cebu, I have a little over a month to surf my butt off. While the country is not on the map for surfers looking for the best waves, it consistently churns out great surf without the weight of intense surf tourism. My only goal at this point is to make it to Siargao, the surf capital and go with the flow from there. Friends have planned to meet me in Thailand early August, a place I have visited many times since a child and feel a responsibility to show anyone looking to see the country a good time.

Thailand caps my list of plans for the next few months of my life. While I am nervous about the long road ahead, I am confident in the path I’ve chosen and the places it will take me. When leaving on an extended trip, it is not necessary to have every step planned out. Leave some wiggle room because that’s where the magic happens. I wanted to take a quick moment and share a few tools I plan to incorporate on my trip to ensure I put myself in the right places. I’m slowly learning that the Internet is a traveler’s best friend. I have taken advantage of a few sites that will hopefully give me the opportunity to see new people and places the standard traveler will not get to experience. To start, HostelWorld is a great option for finding good deals on a bed for a few nights. I love hostels because everyone you meet is generally all on the same page. It’s also a great tool if you are in a jam or in a new country as rooms around town are generally easy to find and book. Another great site I have begun to utilize is Take some time to fill out a thoughtful biography of yourself and watch as locals around the world open up their doors for you. Couch Surfing is a great way to get in touch with good people, the number one key to a successful journey. Be smart and use your best judgment; obviously don’t take shit from anyone and only stay if you feel comfortable with your host. While this option takes some advanced planning and communication, if all goes well, you’re in for a treat. When looking for extended stay situations, such as working in exchange for meals and a room, World Packers and WWOOF are incredible tools I plan on incorporating into my trip. World Packers offers backpackers the option to apply for work opportunities as they go. List your best qualities and skills and let the site find opportunities that fit your abilities. WWOOFing is another network I am extremely excited for. As an avid gardener, WWOOFing is perfect for me as it links backpackers to opportunities on organic farms worldwide. Last but not least, most American travellers all have one quality much of the world seeks and that is the ability to speak the English language. If you have a brain and would like to use it, do some research into obtaining some teaching credentials. The TEFL course is a worldwide certification for teaching English and is a great card to have in your hand. Work on this before hand, or do it on the road like me. While it may cost me a few bucks, I have a feeling it will pay for itself when I run out of money and need to settle down and recharge.

Well that’s it. You’ve been briefed. Thanks for your time and interest in my trip! I am equally excited and amazed that I will be able to share my journey with like-minded individuals through this page and hope to bring you quality information about the world and the people within it. If any of my plans are of interest to you and you would like to see how they develop, please subscribe to the blog by entering your email below. If you would like to collaborate on a future trip, leave a comment and lets get in contact! Until the next one my friends.


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