So you want a boat to yourselves. Smart move. A private catamaran charter turns a day on the water into your day: your group, your music, your pace, and a captain and crew who work only for you. The trick is picking the right boat before you book, because the difference between a tight-budget half-day and a 60-guest celebration comes down to which cat you step aboard.
We run five private charter boats out of Philipsburg, and each one suits a different kind of group. Here is how to think it through, boat by boat, so you can self-select the right one before you ever reach out.
A shared tour is a fine way to see the island. But a private charter is a different animal. You are not sharing the deck with strangers, waiting on someone else's schedule, or jockeying for a spot on the rail with 30 people you just met. You get your own captain and crew, your own itinerary, and the freedom to linger at the beach you love and skip the one you do not.
That flexibility is the whole point. If your crew wants a lazy anchor in a calm bay, we drop anchor. If everyone would rather chase planes at Maho and toast the sunset, we do that instead. You can browse our full private charter fleet anytime, but first, let's figure out what fits.
The most common mistake is falling for a boat before counting heads. Flip it around. Answer a few honest questions first and the right boat almost picks itself:
Hold those answers in your head as we walk the docks.
Here are all five, smallest budget to biggest bash, with who each one is really for.
Magic Time is our power catamaran, and it is the easiest way to get a private boat without stretching the budget. It can be chartered for 3 or 6 hours and the rate starts at $800. It carries up to 26 passengers and keeps roughly 60% of the deck shaded (a real gift under the Caribbean sun).
One thing to know: the shorter 3-hour option is the only charter in our fleet that does not include lunch. If you want the food, go for the longer sail or one of the boats below. But for a half-day of swimming and snorkeling with a smaller group, Magic Time is hard to beat on price.
These two are our 39-foot sailing catamarans, and they are the family favorites. Both start at $1,200 and are built for comfortable, steady sailing, which matters a lot when you have kids or anyone who gets a little green on choppy water.
Tropical Time runs half-day or full-day charters and is a lovely, easygoing platform for a family day out. Too Rhum Punch is the same length but stretches to hold up to 35 people on its 4-plus-hour charters, so it is the pick when your mid-size group is a touch too big for a smaller deck. Same warm sailing experience, a little more room to spread out.
Step up to the Seaduction L47, a 47-foot sailing catamaran that starts at $1,200 for 4-plus hours. The extra length buys you a roomier layout and a livelier sail without jumping to our top price tier. If your group wants more boat and a bit more speed under sail, but you are not trying to host a small wedding, this is the sweet spot.
When the guest list gets serious, Quality Time is our biggest boat, holding up to 60 guests and starting at $2,200 for 4-plus hours. This is the one for weddings, corporate outings, milestone birthdays, and family reunions where everyone insists on coming. Room to move, room to celebrate, and a crew used to handling a crowd.
You may have noticed a theme: every boat we charter is a catamaran. That is on purpose.
A catamaran rides on two parallel hulls of equal size instead of one. That wide stance between the hulls is what makes the boat so stable, because the design resists rolling and overturning without needing heavy ballast down in the keel. In plain terms, you get a steadier, more spacious ride than you would on a comparable monohull.
For a day of Caribbean sailing, that steadiness is everything. It means more deck space to lounge, an easier walk to the bar, and far fewer queasy stomachs, which your kids (and anyone prone to seasickness) will quietly thank you for.
Whichever boat you choose, the essentials come standard. Every charter checks in at Bobby's Marina in Philipsburg, an easy 15-minute walk from the cruise ship terminal, so cruisers can step off the ship and be on the water in no time.
Every charter also includes:
Lunch is included on all of them with one exception: Magic Time's shorter 3-hour charter, as noted above. Everything else feeds you.
Here is the fun part. Our charter itineraries are flexible by design, so you help shape the day. A quick bit of geography to set the scene: this single 87-square-kilometer island has been split between France and the Netherlands since the 1648 Treaty of Concordia, which is why you can sail from the Dutch side to the French side in an afternoon. The border even runs straight across the middle of Simpson Bay Lagoon, one of the largest inland lagoons in the Caribbean. Locals just call the whole place SXM, after the airport code.
Point the bow toward the French side and you can anchor off Pinel Island, a protected nature reserve whose bay-side beach is barely a meter deep near shore. That shallow, glassy water makes it a top pick for families with little kids, and there is a trail across the island to a wilder beach on the Atlantic side. Nearby Tintamarre is the largest uninhabited island you can reach by boat, with the ruins of an old airstrip and farm still visible behind the sandy west-side beach where we usually drop anchor.
Prefer the Leeward coast? We can cruise past Long Bay and Mullet Bay and slow down at Maho Beach to watch the jets roar in low over the sand, one of the island's signature sights.
Got a full day? The bigger boats open up real island hopping. Anguilla sits just 9 miles off the North Side, close enough to see from shore. Prickly Pear is about 16 miles out, roughly an hour and a half of easy motor-sailing, which is why we save it for the full-day boats. And St. Barth's, about 19 miles to the southeast, makes a proper weather-dependent full-day run on our larger charters. Half-day trips stay closer to home; full days let you roam.
A little timing wisdom. We run charters year-round, and the Caribbean's weather here is famously steady, so booking a private trip on pretty much any visit you take is usually no problem. One tip from the crew: book toward the beginning of your stay. That way, if a spot of bad weather rolls through and Mother Nature decides to take the front seat, you will still have some wiggle room to reschedule before you head home.
It really comes down to two questions: how big is your group, and how long do you want to be out? Small group or a short, budget-friendly trip, look hard at Magic Time. Families and mid-size crews, the 39-foot sailing cats. Bigger group or a special occasion, the Seaduction L47 or Quality Time.
Once you have your boat in mind, book your private charter and we will handle the rest. See you at Bobby's Marina.