Out of Office Series 001: Cabarete, Dominican Republic

Out of Office Series 001: Cabarete, Dominican Republic

Surfboards lined up at Playa El Encuentro

By the numbers


Dominican Republic 


Surfing, kiting, wingfoil, chilling

Fave #rallytime

Celebratory Rally at the locals only golf tournament

Best restaurant

Shoutout to Ali's BBQ!


On New Year's Day 2022, Alan - our fearless leader + CEO, and Kayla Rocca set off for the first true "Out of Office" experience since launching the business. Read on below to check out their trip!


When looking for my first trip since the pandemic, I knew that I wanted to go somewhere new, but I also knew that I had to take along the kites & wings, so wind & waves were certainly top of mind. This was also the first trip that Kayla (if you didn't know, we're partners!) and I ever took together! This meant we had to balance the wind/wave forecast with some killer restaurants, a boutique hotel, and some cultural attractions beyond the adventure ones. 

Rugged coastline in Cabarete, Dominican Republic

In the past, I'll admit, I've been a creature of habit, so I find myself always returning to the old faithful spots! For me, I've been going to La Ventana in Baja Mexico for 10 years, and it has a special place in my heart! However, this year, with Kayla - we knew we wanted to experience somewhere new just the two of us. We searched high & low at flights as we honed in on our locale, and ultimately landed on Cabarete - a beautiful seaside town on the northern coast of Dominican Republic. Cabarete is widely known as a mecca for windsports and one of the Caribbean's best surf spots. Little did Kayla know this at the time, but we also found a very cool hotel and there were a ton of national parks around for day trips & adventures. And the best part - all of it is just a 4-hour flight from Toronto Pearson, and a fraction the cost of heading to further afield destinations. 

Alan flying his 12M kite

In the end, we loved Cabarete! We rented a scooter to get around the island, quickly met the right locals who helped us get surf lessons from one of the local pros, and Kayla was catching wave after wave almost every single morning. For me, I was able to catch a few waves in the AM, and then head over to kite beach for a kite and wing session on the outer reef in the afternoons. Nights were typically filled with scooter adventures around the nightlife and grabbing dinner at little dive bars in Cabarete!

Alan, right before wiping out

My 2 personal highlights from the trip included watching Kayla pickup surfing in record time, and being invited by the locals to play in the Cabarete golf open! Little did they know, I have a history in junior golf and I was able to win 3rd place! It was an awesome throw back to what the game of golf is really about - 3 holes cut out of the majestic landscape, motorcycles zipping around constantly, and groups of 12 sharing clubs and watching balls fly every which way...I can get behind Cabarete golf! 

Alan showing off his bronze medal from Cabarete Open

 Oh, and of course we smuggled a few Rally's to share with the locals! 


Alexander De La Cruz, professional surfer and our instructor about to enjoy a post-surf Extra Mile