Private Charter · Adults Only · 21+
Key West Clothing-Optional Boat Charter — private, adults-only, captained.
A private captained boat charter for adult travelers who already know the Key West clothing-optional world. Your group on a 30′ Jeanneau, anchored offshore in open water, with a USCG-licensed local captain who runs the trip discreetly — no other guests, no public dock, no audience.
Start here
Why a private charter is the only way to do this in Key West
Key West has had a serious, mainstream clothing-optional scene for decades. The Garden of Eden rooftop sits over Duval. The Island House and a handful of long-running clothing-optional B&Bs anchor an entire wing of the local hospitality industry. Travelers who plan their year around these places aren't looking for novelty — they're looking for the parts of Key West that are already comfortable for them.
The water is the gap. There are public clothing-optional cruises, but a public cruise is a public cruise: a fixed schedule, strangers on the boat, and someone else's idea of the right anchorage. What this audience actually wants is a private boat. The whole product is privacy — your group, the captain, the boat, and water with nobody else on it.
That's the trip. Six Fins runs it as a normal private charter on the same 30' Jeanneau NC 895 that runs our family sandbar days and our anniversary sunset cruises. The boat doesn't change. The captain doesn't change. What changes is that it's only your group, and the captain picks an anchorage where the boat isn't visible from any beach, residence, or moored vessel.
The product is privacy
Three things public cruises can't offer
Every group we book this charter for has come to it for the same three reasons. They tend to matter more than any specific itinerary.
Your group only
No other guests on the boat, ever. No shared deck, no shared swim ladder, no introductions you didn't choose to make. Couples come as couples. Bachelor and bachelorette groups come as themselves.
Out of public sight
Captain Dustin anchors far enough offshore that the boat isn't visible from any beach, dock, or moored vessel. He moves the spot day to day based on wind, sun angle, and what other boat traffic he sees on the radar.
A captain who's unfazed
This is not the first time. Six Fins has been running private clothing-optional charters for years. The crew is USCG-licensed, professional, and treats the trip exactly the way they'd treat any other private charter — no commentary, no awkwardness.
How the day actually runs — the captain's routine.
There are three modes on this charter, and the captain manages all of them. Inside the marina basin and on the dock, the boat operates like any other charter — standard dress, normal etiquette. Underway through inland and near-shore waters, the same. Once anchored offshore in state or federal waters, with no other boats nearby and no public viewing, the boat is yours and the captain steps back into a strictly nautical role. On the return, he gives a tactful heads-up roughly fifteen minutes before re-entering near-shore waters so everyone has time to re-dress without any rush.
No one ever has to ask. He explains the routine at the safety brief, runs it the same way every trip, and doesn't make a production of it.
Marina & dock
Standard dress while boarding, unloading, and anywhere in the marina basin. Same etiquette as any private charter.
Underway & near-shore
Standard dress while transiting inland channels and near-shore waters. Captain runs the boat normally, no different from any other trip.
Anchored offshore
Clothing-optional once anchored offshore in state or federal waters, out of sight of any public viewing. Captain’s focus is the boat and the radar.
Fifteen-minute call
Captain gives a tactful heads-up about fifteen minutes before re-entering near-shore waters so everyone has time to re-dress without any rush.
The bookings we see
Who books this charter
The crowd is older, more relaxed, and usually a return traveler to Key West's clothing-optional scene. A handful of patterns repeat.
Couples & anniversaries
By far the most common booking. Couples in town for an anniversary, a milestone birthday, or a no-kids week. They want the sunset cruise on their own terms, with a captain who'll quietly disappear into running the boat once the anchor's down.
Naturist-resort guests
Guests staying at one of the long-running clothing-optional resorts in Old Town — the Island House, the Garden of Eden crowd, the Lighthouse Court regulars — who want a private day on the water without leaving the comfort of the world they're already in.
Small bachelor / bachelorette
Adults-only bachelor and bachelorette groups who don't want a Duval bar crawl on a boat. Small groups, usually six or fewer, who'd rather have a relaxed sunset cruise with privacy than a public party charter with strangers.
Long-time naturist travelers
Seasoned naturist travelers who already know the etiquette, already know what they want, and just want a captain who runs the trip without commentary. This is the easiest group to take out — they know exactly how the day should feel.
The boat
Why the Jeanneau works for adult groups
The 30' Jeanneau NC 895 Weekender was built for exactly this kind of trip. A walk-around deck so nobody is climbing over anyone. A wide swim platform off the back for easy in-and-out. An enclosed cabin with a private head, a place to change, and shade when anyone wants it. Up to six guests as standard, up to eight for adults-only groups by request.
- Walk-around deck — everyone moves freely, nobody climbs over anyone
- Wide swim platform off the stern for easy water access
- Enclosed cabin with a private head (full bathroom) and a place to change
- Bluetooth sound system — bring your own playlist
- Cold-water cooler, ice, towels, USCG-approved gear all on board
- Up to 6 guests standard; 7–8 by request for adults-only groups
Discretion
How we handle privacy — in writing
Because the question matters and the answer should be on the page, not over the phone.
What we commit to
No crew photography of guests, ever. The captain and mate do not photograph guests at any point. Personal photos within your group are entirely your call.
No commentary, no social posting. The crew doesn't talk about specific charters, doesn't post on social media about who was on the boat, and doesn't share names or itineraries with anyone outside Six Fins.
Discreet anchorage selection. Captain Dustin picks the spot the morning of the trip based on wind, sun angle, and what other boat traffic he can see. He has a short list of working anchorages and rotates between them — we don't publish coordinates and we don't repeat the same spot on consecutive days.
Booking under any name. The booking can be under one name in the group — we don't need everyone's information, just the lead booker and a safety contact.
Pricing snapshot
Flat-rate private charters. Adults only.
Pricing is per boat, not per person — up to six guests standard, up to eight for adults-only groups by request. All trips include captain, fuel, ice, water, and on-board gear.
Prices include captain, fuel, ice, water, USCG-approved equipment, and on-board gear. Gratuity not included. Want a different angle on the same boat? See the Key West Sunset Cruise, the Sandbar Charter, or the general Private Boat Charter.
Private vs Public
Why a private clothing-optional boat charter beats joining a public cruise
Public clothing-optional cruises do exist in Key West, and they suit a certain traveler — usually first-timers comfortable on a crowded deck with strangers. Most of the guests who book Six Fins have done the public version once and decided they want the water to themselves the next time. Here's the honest comparison.
The Key West clothing-optional scene — the Island House, the Garden of Eden rooftop, Lighthouse Court, and the Old Town naturist resorts — runs on discretion and on guests' relationships with each place. A private boat charter is the water version of the same idea: small, comfortable, and arranged around you.
Honest answers
Frequently asked — before you book
Is a clothing-optional boat charter actually legal?
Yes, when handled correctly — and the captain handles it. There are three modes on this charter. Standard dress in the marina basin and on the dock. Standard dress while underway through inland and near-shore waters. Clothing-optional only once anchored offshore in state or federal waters, away from any public viewing. Captain Dustin explains the routine at the safety brief and runs it the same way every trip.
Where do we actually anchor?
Far enough offshore that the boat isn't visible from any beach, residence, or moored vessel. The captain picks the spot the day of the trip based on wind, sun angle, and what other boat traffic he sees on the radar. He has a short list of working anchorages he rotates through; we don't publish coordinates and we don't repeat the same anchorage on consecutive days.
Are kids allowed?
No. This trip is adults-only, 18 and over, no exceptions. If you're traveling with kids, we run the same boat for kid-friendly trips — have a look at the Sandbar Charter or the Private Snorkel Adventure.
Can we bring our own drinks?
Yes. Wine, beer, hard seltzer, champagne for special occasions — whatever fits the trip. Glass is fine. We provide cold water, ice, and a stocked cooler. We ask that guests drink at a pace that keeps everyone steady on the swim platform; the captain will tactfully slow service if he thinks anyone needs it.
What about photos?
The captain and mate do not photograph guests at any point during the trip. Personal photos within your own group are entirely your call. If you'd like a group photo at sunset, just ask — otherwise nothing leaves the boat unless you take it with you.
What do you bring and what should we bring?
We bring cold water, ice, a stocked cooler, towels, a fresh-water rinse on the swim platform, USCG-approved life jackets, and a Bluetooth speaker. You bring reef-safe sunscreen (and plenty of it — you'll be applying it in places you don't normally have to think about), sunglasses with a strap, a hat, your food, and your drinks. A light cover-up for the trip in and the trip out is a good idea, even if you don't think you'll want it.
Is there a private bathroom on board?
Yes. The Jeanneau NC 895 has an enclosed marine head (private bathroom) inside the cabin with a door that closes. There's also a fully enclosed cabin with seating if anyone wants shade, a place to change, or simply some privacy at any point during the trip.
Does the captain regularly run these trips?
Yes. Six Fins has been running private clothing-optional charters out of Key West for years. Captain Dustin is USCG-licensed and unfazed; he treats this trip the way he treats any other private charter — with professionalism, no commentary, and total focus on running the boat safely.
Pick a day. We'll pick the anchorage.
The same boat, the same USCG-licensed captain, the same Stock Island marina. Adults-only, your group, the most private spot we can find for that day's wind. Four hours, five hours, or a full day — whatever fits the week.
Prefer to write first? info@sixfinscharter.com · Or text (305) 906-2880. Discreet replies, always.