St Maarten Sunset Sailing Trimaran Tour: A Skipper's Guide
I'm Dwayne Richardson, and I've been working these waters under sail since 2014. The St Maarten sunset sailing trimaran tour is the one I send people on when they want the golden-hour magic without the rocking deck — two easy hours along the calm west coast with a drink in hand. Below is everything I'd tell you dockside, and you can size it up against the rest of our boat trips around the island.
The Sunset Trimaran Sail at a Glance
Change your plans up to 24 hours ahead and pay nothing
Lock in your seats today and settle the bill nearer the sail
Timed so you're out on the water as the light turns gold
Sporty under sail yet remarkably steady underfoot
We aim to have you mid-water as the sun meets the horizon
A glass in hand as the hills behind us catch the last light
Check Live Availability & Prices
Pick your evening below to see real-time dates and pricing for the St Maarten sunset sailing trimaran tour out of Simpson Bay.
Why Book the Sunset Trimaran Sail
After a decade of taking guests out for sunsets, I can tell you the single biggest worry I hear is the rocking. People love the idea of being on the water at golden hour, then picture themselves green by the second wave. A trimaran answers that beautifully. With three hulls spread wide instead of one keel underneath, the boat sits flat and sure across the swell — it slices forward fast but barely leans, so you can hold a glass, line up a photo or just lie back without bracing yourself the whole time.
That steadiness is what makes this two-hour west-coast sail my go-to recommendation for couples, nervous first-timers and anyone who's been put off by a wobbly boat before. The west coast of St. Maarten is the sheltered side, so the water tends to lie down in the evening, and the run from Simpson Bay keeps the island between us and the open Atlantic. With a perfect five-star record behind it, it's an easy one to vouch for. If you're weighing it against a longer day at sea, have a look through the full line-up of sailings we run.
What You'll See and Do
Two unhurried hours with the coastline on one side and the sunset dead ahead. Here's how the time tends to fill itself:
- Glide out along the calm west coast of St. Maarten under sail
- Stretch out on the netted trampoline deck strung between the hulls
- Watch the sun slide behind the hills and melt into the Caribbean
- Sip the drinks served on board as the light goes from gold to pink
- Pick out the beaches, headlands and resorts lining the shore
- Come home with the kind of sunset photos that make the trip
What's Included (and What Isn't)
What's Included
- A two-hour evening sail aboard a fast, stable trimaran
- The cruise along the sheltered west coast of St. Maarten
- Drinks served on board as the sun goes down
- Use of the netted trampoline deck to lie out on
- A relaxed, small-group crew who know the coast
Not Included
- Your own way to and from the Simpson Bay marina
- Dinner or a full meal — this is a drinks-and-views sail
- Crew gratuities, which are always welcome but never expected
How the Evening Flows
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Late afternoon
Step aboard at Simpson Bay
Meet the crew at the dock, find a spot on the trampoline deck and feel how flat the trimaran sits before we even slip the lines.
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Cast off
Sail the west coast
We ease out into the sheltered water and turn along the coast while the afternoon heat starts to soften into evening.
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Golden hour
Sunset and a glass in hand
We position for the best view as the sun drops, drinks come out, and the hills behind us light up in the last of the gold.
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After the colours fade
Glide back to the dock
Once the sky has done its work we sail home in the cool dark and bring you back to Simpson Bay.
Important Things to Know Before You Go
Nothing here is demanding — the boat does the work and you do the relaxing — but a few things are worth knowing in advance:
- If seasickness has burned you before, this is the sail to choose; the three hulls keep it about as level as a boat gets
- Turn up at the marina with time to spare, since we leave on the tide and the light, not on stragglers
- It cools quickly out on the water once the sun is down, so a light layer goes a long way
- Ask the crew which drinks come included and which you can buy, so there are no surprises
What to bring
- A light jacket or wrap for the evening breeze offshore
- A phone or camera, ideally with the lens wiped clean for the glare
- Flat, non-marking shoes that grip a wet deck
- A little cash for tips or an extra round
Where It Departs — Simpson Bay, Sint Maarten
Who This Sail Is For
I'd happily put almost anyone on this boat, but it shines brightest for a particular crowd:
- Couples chasing a calm, unfussy romantic evening on the water
- Anyone who loves the idea of a sunset sail but dreads a pitching deck
- Photographers who want a steady platform for the golden-hour light
- Cruise-ship and short-stay visitors with one free evening to spend well
Not ideal for
- Travellers set on snorkeling or a swim stop — this one stays under sail
- Families wanting a full day's adventure rather than a short cruise
- Anyone after a loud, drink-fuelled party-boat scene
Sunset Trimaran Sail — Your Questions Answered
What exactly is a trimaran, and how is it different from a catamaran?
A trimaran has three hulls — a main one in the centre with a smaller float either side — while a catamaran has two. That extra hull spreads the boat even wider, so it's sporty under sail yet sits flatter and steadier than most catamarans. If you'd rather compare a relaxed catamaran evening instead, the Lambada sunset cruise from Simpson Bay is the easy two-hulled alternative.
Is the trimaran sunset sail good for couples or a romantic evening?
It's one of the most romantic things I run. The deck is calm, the small-group feel keeps it intimate, and there's a glass in your hand while the sun goes down behind the hills. The perfect five-star record is mostly couples saying exactly that.
Will the water be rough out there?
Rarely, on this route. We sail the sheltered west coast in the evening, which is the calmest side of the island, and the trimaran's three hulls flatten out what little swell there is. It's about the gentlest sunset sail I'd point a queasy guest toward.
Are drinks really included, and can I buy more?
Yes — drinks are part of the trip and they come out as the sun sets. If you'd like something specific or an extra round, the crew can sort that on board, so bring a little cash. Not sure what's stocked on your date? Drop us a message and we'll check ahead of time.
How long is it and how much does it cost?
It's a two-hour evening sail starting from $66 per person, drinks included. If two hours feels short and you'd like a longer day with a meal, the five-hour trimaran sailing cruise with lunch is the bigger version of this same steady boat.
What Guests Say About the Sunset Trimaran
I always skip boat trips because I get sick within ten minutes. Not this time. The trimaran was flat as a table, the sunset was ridiculous, and I actually relaxed with a drink. Dwayne and the crew were lovely.
We booked it for our anniversary and it could not have gone better. Lying on the net deck between the hulls with the sky turning pink is something we'll remember for a long time. Two hours flew by.
Stepped off a cruise ship with one free evening and picked this on a whim. Best decision of the trip. Calm sail, friendly crew, drinks flowing and the most beautiful light off the west coast. Easy five stars.