March 19, 2026
Where do you actually start with a catamaran tour business in St. Maarten?
Not the boat. I know that's not the answer you expected, but the order you do this in is the whole thing.
I grew up here. My parents started Eagle Tours, which today runs more than five boats across St. Martin, Anguilla, and St. Barts. I worked my way from deckhand to captain on their operation. I've watched this industry from the inside for a long time. And I have seen a lot of people come to this island with money, a beautiful catamaran, and real enthusiasm -- and be gone in under two years. Almost every single one made the same mistake: they started with the boat.
Most new operators buy the boat first and figure out the dock, the permits, and the concierges later. That is backwards. And it is why most of them fail.
A catamaran sitting on a mooring with no dock access, no concierge relationships, and no commercial permits is not a business. It is an expensive liability with antifouling paint on it. Before you put a dollar toward a vessel, you need to know where you are going to operate from, who is going to send you guests, and whether you have the right to run commercially in those waters.
Get those three things sorted first. Then buy the boat.
I have seen a captain try to launch with a beautiful 45-foot Lagoon and no dock lined up. He thought he could sort it later. He spent his first season anchoring out of Simpson Bay lagoon and tendering guests to his boat by dinghy. His TripAdvisor reviews were full of comments about the awkward boarding process. He lost guests to operators with a proper dock setup -- not because his boat was worse, but because his logistics were a mess.
Where you dock controls which concierges call you and how fast a cruise passenger can get from the pier to your swim step. Philipsburg and Great Bay put you next to the cruise piers -- essential if you are running shared day sails targeting walk-on guests. Simpson Bay is better for Dutch-side hotel guests and private charters. Marigot and the French side give you access to Grand Case, Orient Bay, and the villa concierge market, which skews toward stay-over guests who spend more per head. IGY Yacht Club Philipsburg is premium facilities and premium dock fees -- right for a private-charter-focused operation.
Pick your dock before you do anything else.
St. Maarten is two jurisdictions on one island and they do not automatically recognize each other. On the Dutch side, register as a Besloten Vennootschap (B.V.) with the Chamber of Commerce. You need a business license, a managing director license, and an operational license for a commercial dock. Your skipper needs a Certificate of Competency from the Ports Authority Maritime Department -- an 80-question exam, minimum 80% to pass. Your boat needs an annual Certificate of Seaworthiness before any paying guests step aboard.
If you plan to operate from the French side or want that concierge network, you are dealing with a separate charter permit structure. Get local legal advice for both sides. And insurance: figure $8,000 to $15,000 per year for a proper commercial policy on a 40 to 45-foot cat. Standard yacht policies do not cover commercial charter operations. That gap has ended operators who thought they were covered and were not.
For a day-tour operation here, the sweet spot is a used 40 to 45-foot sailing catamaran -- a Lagoon 42 or Bali 4.3 in decent charter-ready condition runs $250,000 to $400,000. Go bigger and your per-trip operating costs get hard to manage. Go smaller and you have capacity problems when you want 20 guests aboard for the Pinel or Tintamarre run.
Three entry paths, each with real trade-offs:
Shared day sails to Pinel Island run around $139 per person -- a full boat at 25 passengers grosses $3,475. Tintamarre private charters go from $2,095 half-day to $2,795 and up full-day. Anguilla is the premium product -- longer, higher fuel, customs to clear, but guests who want that run pay $200 per person or more. Build everything as all-inclusive. Food, open bar, snorkel gear, paddleboards in the base rate. That is the expectation in this market.
Concierges and hotel activity desks are the real engine on the stay-over side. Two or three strong relationships with activity desks at Grand Case or Orient Bay hotels will fill your private charters more reliably than any amount of paid advertising. Those relationships take time. You show up, you are reliable, you take care of their guests, they keep calling you.
TripAdvisor reviews are your cruise passenger engine. If you have 200 reviews at 4.8 stars and your competitor has 40 at 4.2, you win. Ask every satisfied guest to leave a review. OTAs like Viator and GetYourGuide are useful for early visibility, but use them to fill gaps and build review history -- not as your primary channel. The commissions add up fast.
Whatever channels you use, your booking process needs to work on a phone, accept cards instantly, and show real-time availability. Junglebee was built specifically for Caribbean charter operators -- booking widget, payments, and agent net rates for concierge bookings. Get it running before your first season.
On costs: dock fees run $1,500 to $3,000 per month and do not stop in low season. Crew runs $300 to $500 per trip. Fuel, maintenance at roughly 10% of hull value per year, insurance -- it adds up fast. You need cash reserves for at least twelve months of operating costs. Operators who came in thinking they just needed enough for the boat are the ones who disappeared.
Nearly 1.6 million cruise visitors came through in 2025. The demand is real, the routes are beautiful, and a well-run operation with the right dock and the right concierge relationships can do very well here.
But do it in the right order. Dock, permits, concierges. Then boat. The operators who start that way are still here five years later. The ones who started with the boat -- you stop seeing their names after a while.
I learned which one works. You do not have to learn it the hard way.
