Where we started

Our History

Dockside has grown with the island and alongside the ever-changing size and scope of visiting yachts over the years. Nevertheless, the road to the present day hasn’t always been easy. Founded in 1990, the company originally catered to any vessel visiting St. Maarten. Four years later, Kass Johnson joined the fray.

Dockside grew organically from that point along with the number and size of yachts visiting the island. This growth continued strongly until Hurricane Irma devastated the island in 2017. Following the passage of Irma, the future of yachting in St. Maarten – and along with it, of local companies like Dockside – seemed suddenly imperiled. With infrastructure damaged and yachts largely bypassing the islands, times were difficult for all.

It was around this time that Lila and Kass joined forces with Norina Edelman. Facing an uncertain future at the end of her career, Lila was unsure what to do. Norina stepped in to help rebuild the company with Lila & Kass. Fortunately, in the wake of the hurricane, the boats did, indeed, return, and yachting helped restore the local economy. Just a few short years later, COVID-19 caught the world by storm, nearly stopping all stayover tourism throughout the world. During the pandemic, yachting continued when no other sectors were able to, essentially keeping the island’s economy afloat. Through two serious crises, yachting was a primary economic driver for St. Maarten, demonstrating the importance of yachting for our island ecosystems.

At present, the company has continued to grow from strength to strength and is well equipped to handle the needs of vessels of any size – from a 20-meter catamaran to a 100m plus vessel – while remaining very much an independent, boutique company. In recent years, and at the request of numerous clients, Dockside has expanded into St. Barths, providing the same offering and service at the neighboring island.
A far cry from the simple agency catering for small sailing vessels and military ships back in the day, Dockside’s reputation has grown alongside its expansion. But while Dockside is now established as the superyacht captain’s go-to in the region, the management and team still hold true to their original cheerful can-do attitude, and the promise of excellence made easy.

From our Founders

A bit about Lila & Kass

Dockside’s Dynamic Duo Lila Rosen & Kass Johnson are no strangers to the sea. Both keen sailors, their seaward paths brought them to sun-kissed St.Maarten after years in their respective businesses.

Lila arrived in the Caribbean in 1975, with years of experience as professional yacht crew in her pocket. For many years, she ran a ferry service between the islands of St.Maarten and St. Barths. Lila had a clear vision of which services were necessary to support private and charter yachts visiting the region, and, in 1990, she launched Dockside Management.

Lila’s partner, Kass Johnson, joined the team soon after, in 1994. With vast knowledge of the cruise ship industry and a passion for sailing, she was instrumental in developing Dockside’s evolving relationship with the larger vessels visiting Sint Maarten, as they began to include the island in their itineraries.

Jointly, Lila and Kass were able to pool their experience to find the first real yacht agent’s office in the islands. Starting at their original office in the main port of Philipsburg before expanding into their offices in Simpson Bay as the center of yachting shifted, finally moving into their home at t the Isle de Sol Yacht Club Lila and Kass are not only the founders of Dockside, but were both integral to the development of yachting in St. Maarten – and in the Caribbean more widely.

“Kass is not only my most trusted agent in the Caribbean but I now count her as a dear friend as well.”

BRUCE, CAPTAIN 50M M/Y