Imagine having your own boat for the day, swimming in beautiful spots, discovering little islands, and enjoying the Caribbean at your own pace. That’s the pitch behind a private charter out of St Martin, and it’s also where most travelers get stuck. Pull up a map, and St. Martin, Anguilla, and St. Barts sit close enough together to look interchangeable.
Each one offers a different kind of day on the water, and the best charters are built around who’s coming rather than a list of places pulled from someone else’s photos. Before anyone talks about boats, I help travelers work out which experience suits them.
Private Boat Charters in St Martin / St Maarten
Spend a day on the water with an island-based team that works directly with a small network of trusted, licensed captains. They’ll help you pick the right charter for your group and the kind of day you have in mind, then stay on hand before and after you book.
Where you can go:
St Maarten charters: cruise the coast of St Maarten and St Martin
Anguilla trips: a full day exploring Anguilla by private boat
St Barts trips: sail across to St Barts for the day
Travel Dudes partners with local operators to help you book experiences mentioned in this article.
Three Very Different Days, All Within Reach of St Martin
You meet your captain at the confirmed marina or departure point, get settled on board, and head out. Once you clear the harbor, the whole island opens up in a way you can’t get from land, and that holds for a day along St Martin’s coast or a crossing to another island.
A Day Along St Martin’s Own Coastline
This is often the easiest choice for a first-timer, and it doesn’t mean settling for less. Depending on the route, you might cruise the coast, stop for a snorkel at Creole Rock, then head toward Tintamarre and Pinel for a swim.
I think it’s often when we reach somewhere like Tintamarre and guests see that turquoise water for the first time. They’ve been enjoying the ride, chatting, taking in the coastline, and then suddenly they’re leaning over the side getting their snorkel gear ready. That’s usually the moment people realize the day is going to be something they remember.
Anguilla: Beaches and Clear Water
Anguilla is a different rhythm entirely. It’s known for its beaches and its water clarity, with spots like Little Bay and Sandy Island giving you the kind of stretch of sand and color you’d want to spend hours on rather than rush past. Guests who want a proper beach day, rather than several short stops, tend to gravitate here.
St Barts: A Different Character Altogether
St Barts feels distinct again. There’s coastline and bays worth exploring by boat, and the option to spend part of your day in Gustavia if you’d like a bit of town mixed in with your time on the water. It suits guests who want variety within the day, not just swimming.
How Weather and Sea Conditions Shape the Route
Some days the water is calm enough that any of these routes works well. Other days there’s more wind and swell, and that changes what’s sensible. Your captain adjusts the route to the conditions on the day, not the plan you had in your head last week, and that’s a good thing. A route that looks perfect on paper isn’t much fun if you spend it being tossed around instead of swimming.
What to Look for in a Private Charter Quote
A charter quote should tell you more than a price. Look for who’s included, what the departure point actually is, and whether the destination is fixed or flexible depending on conditions. We help guests choose both the destination and the boat beforehand, because a boat that’s perfect for two couples who want to snorkel all day isn’t the same boat you’d want with young kids aboard for six hours.
The Question That Matters More Than the Itinerary
I wish more people asked, “What kind of day would actually suit us?” Guests often arrive with a list of places they’ve seen online, or assume they need the biggest boat they can afford. I’d rather know who’s coming: whether they love swimming and snorkeling, want a relaxed beach day, have young children, or are excited about exploring somewhere new. Once I understand that, I can help them choose between St. Martin, Anguilla, and St. Barts, and match them with a boat that actually fits the group. That’s how you end up with a good day on the water, not just a busy one.
Don’t Try to Fit In Too Many Stops
There’s a tendency, in a lot of guides, to turn a boat day into a checklist. You see St. Martin, Anguilla, and St. Barts on a map and think you should squeeze in all three. They are very different experiences, and the best day is usually the one with fewer stops and a boat sized to the group.
Some guests want to explore. Others are perfectly happy swimming, having a drink, and enjoying the sunshine without moving the boat again for two hours. Both are good days. You might spend a long while snorkeling, find a spot worth relaxing at, stop somewhere for lunch, or simply enjoy being out there. “Take your time” is the closest thing I have to a rule for this. You’ve got the whole day ahead of you, so there’s no need to rush from one stop to the next.
Sometimes the stop nobody was particularly excited about beforehand ends up being everyone’s favorite part of the day. It happens more often than you’d think.
The Captain Sets the Tone
We work with different local captains, each with their own personality and their own knowledge of these waters. A good captain knows where to go for the day’s conditions, when to suggest one more stop, and when to simply let everyone relax. That judgment matters more than any fixed route, and it’s a big part of why the day feels easy rather than rushed.
What the Water Sounds and Feels Like
Heading out of the harbor, it’s engine noise, wind, and water, plus plenty of chatting and laughing on board. Stop for a swim and the whole soundscape changes: water slapping against the hull, waves against the shore, maybe some music playing softly in the background. It’s warm and tropical most of the year, but once you’re moving, the sea breeze does a lot of work. The sun is stronger than it feels, even on days that don’t seem that hot, which is worth remembering before you’re three hours in.
Fresh sea air, sunscreen, a cold drink after that first proper swim. Depending on the day, lunch might mean a beach restaurant, something eaten on board, or a relaxed meal over in Anguilla. It’s all part of the day, not an interruption to it.
Practical Information
Best Time to Go
Private charters operate year-round, although the weather and sea conditions change throughout the year. Some days are beautifully calm; others are windier or have more swell. We help guests plan ahead, but the captain makes the final decision about the route and whether it’s safe to go based on the conditions.
Getting There
Departure points vary depending on the boat and itinerary, with options around Simpson Bay, Cole Bay, Marigot, Nettle Bay, Philipsburg, Grand Case and Anse Marcel. We confirm the exact marina, meeting point and arrival instructions before the charter. If you’re heading to Anguilla or St Barts, we’ll also explain the passport and customs arrangements in advance.
Costs
Pricing depends on the boat, the destination, and how long you’re out for, so it’s worth treating any quote as a starting point for a conversation rather than a fixed menu. Ask what’s included and how flexible the route is if conditions change.
What to Bring
Sun protection matters more than most people expect, even on days that don’t feel especially hot once you’re moving. Bring swimwear, a change of clothes, and a way to protect your phone or camera around water. If lunch isn’t included on your route, it’s worth checking in advance whether you’ll need cash on the day.
Frequently Asked Questions
Is a private boat charter from St Martin better than a group tour or ferry?
It depends what you’re looking for. If you simply need to get from St Martin to Anguilla or St Barts, a ferry may be the more practical option. A private charter is about enjoying the journey itself, swimming, snorkelling, exploring the coastline and spending the day with your own group. It’s a different experience altogether.
How do I decide between St Martin, Anguilla, and St Barts for a day trip?
Think about your group before the destination. If you want beaches and clear water without much else, Anguilla fits well. If you want a mix of swimming, snorkeling, and small islands close by, staying around St Martin works. St Barts suits people who want some town time in Gustavia alongside the water.
Can the boat trip be adjusted if the weather changes?
Yes, within reason. Your captain may adjust the route or stops to suit the conditions, but changing from St Martin to Anguilla or St Barts isn’t something that can simply happen on the day. International trips involve passport and customs arrangements. If the weather makes the planned charter unsafe, we’ll discuss the available options with you.
Is a boat day from St Martin suitable for families with young kids?
It can be, but the right boat and pace matter more than the destination. Let the operator know ahead of time who’s coming, so they can suggest a boat size and route that fits kids rather than assuming a longer, busier day works for everyone.
Do I need snorkeling experience to enjoy stops like Creole Rock or Tintamarre?
Not necessarily. You don’t need to be an experienced snorkeller to enjoy a private boat day, and there’s plenty to enjoy without snorkelling at all. Let us know your group’s swimming abilities beforehand, and the captain can advise on suitable stops and conditions. Nobody should feel pressured to get into the water.
How many stops should we plan for in one day?
Fewer than you’d think. A day built around two or three places, with real time to enjoy each one, usually beats a day that tries to cover everything on the map.
