Postcards from Puerto Rico: North Street Retreat ’22

By Dahlia Lilleslatten, Communications

North Street’s team retreat kicked off the way all great trips do: with joyous reunions in the lobby, fish tacos and sliders at the hotel’s poolside grill, and jokes and laughter deep into the night. Planning a team retreat during Covid was no easy task (spoiler alert: we learned that the hard way), but the weekend was one for the books. As a fully distributed team, it was more than just a chance to build rapport while exploring the beautiful island of Puerto Rico. It was an opportunity to do something we rarely do – kick back as friends and colleagues IRL.

Thursday, March 31st

8:00 PM, The Banyan Tree Grill After a series of airport arrivals throughout the day, we kicked night no. 1 into gear with dinner at the Banyan Tree Grill. A Resort Clubhouse-style restaurant & bar that embraces the 300 year-old Banyan Tree beside the pool, it was the perfect outdoor hangout for catching up and decompressing from a day of travel.

Friday, April 1st

11:00 AM, The Sinatra Boardroom We dedicated our first morning in Puerto Rico to a facilitated team-building session with Jaime Yordán-Frau of IntegroSuccess. Lunch was a delicious buffet stocked with comfort-food favs: cream of tomato soup, chicken and beef empanadas, roasted Atlantic salmon filet, and cheese tortellini in a mushroom cream sauce.

4:00 PM, The Scryer Distillery The team reconvened at Scryer Distillery for a guided rum tasting tour and mixology class. Because of its impressive sugar cane output, Puerto Rico holds a special place in the rum world. More than 80 percent of the world’s rum sources originate in Puerto Rico, making it the rum capital of the world!

6:30 PM, Old San Juan The team explored Old San Juan, walking down Calle de la Fortaleza to check out historic buildings before landing at the Castillo San Felipe del Morro. Constructed by the Spanish in the 16th century, this important site was designed to create devastating artillery fire over enemy ships (successfully defending San Juan from incoming sea attacks for hundreds of years!). The impressive citadel is perched on an expansive hill overlooking the Atlantic Ocean.

Saturday, April 2nd

8:00 AM, El Yunque Guided Rainforest Hike On day no. 3, our team ventured into the heart of Puerto Rico’s lush El Yunque rainforest on a half-day excursion (a special shoutout to our amazing guide, Nathan!). We soon learned why helmets, life vests, and swimsuits were non-negotiable. After spending the morning exploring the rain forest’s beautiful flora, we stopped to swim, cliff jump, and rope swing into a crystalline watering hole with a natural rock slide. Not for the faint of heart!

1:30 PM, The Fairmont El San Juan Hotel We returned to the hotel for some well-deserved downtime at the pool.

7:00 PM, Dinner at Santaella What better way to celebrate good people than with good food? Our final team meal was held at Santaella, an upscale restaurant serving tapas, mains, and creative cocktails in an industrial-style space.


Sunday, April 3rd

Departures Our last day in Puerto Rico was dedicated to relaxing and enjoying the beauty of San Juan before the team caught flights back home. With a few hiccups along the way (see: Airlines cancel hundreds of weekend flights as thunderstorms sweep through Florida), the team made it back safely and in one piece. The takeaway? Flight insurance is, in fact, worth it.


Would you like to be part of our team? Join us!

North Street is currently looking for an amazing Marketing guru with a demonstrated ability to build brand awareness and a pipeline of inbound leads. Click here for details and to apply.

About north street

We engineer the thoughtful transformation of great organizations. Our proven process helps us understand what your competitors are doing right — and wrong. Want to learn more? Let’s chat.

More Notes

A bowler hat with radio waves behind it

From Layoff to Leadership: Tom Conlon’s Journey to a Prosperous Business

Welcome to Your 2024 Branding Pep Talk

A bowler hat with radio waves behind it

CEO Tom Conlon talks shop on Podcast Marketing Secrets