Private Charter · Adults Only · 21+
Key West Clothing-Optional Boat Charter — private, adults-only, captained.
A discreet private charter for your invited adult group—not a public event, shared cruise or sightseeing experience.
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.
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 photography or video, period. No photography or video is permitted while onboard, or whenever the Six Fins boat appears anywhere in the frame. Crew do not record guests, and guests may not record other guests or crew. The charter is non-explicit — no sexual activity.
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.
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
Discreet questions, answered plainly.
Is this a private clothing-optional charter?
Yes. This is a private, adults-only boat charter for your group only. There are no strangers on board, no public deck, and no shared cruise atmosphere.
Six Fins handles the trip discreetly and professionally. The focus is privacy, comfort, calm water, and a captain who runs the boat without making the day awkward.
Does everyone have to remove clothing?
No. Clothing optional means optional. Guests are not required to remove clothing at any point.
Some guests stay clothed on the boat and save the clothing-optional part of the day for swimming, floating, or a secluded/discreet stop where appropriate. Others are comfortable sooner. The point is that your group controls its own comfort level within the charter rules.
Can we request a captain or crew member comfortable with the clothing-optional lifestyle?
Yes. Guests may request a captain or crew member who is familiar with or comfortable around the clothing-optional / naturist lifestyle, subject to availability.
Crew remain professional, respectful, and safety-focused at all times. The goal is not participation or spectacle; it is a comfortable private charter with a captain who understands discretion, privacy, and the tone of the trip.
Who usually books this charter?
Most guests are couples, close friends, adults-only vacation groups, experienced naturist travelers, or small private groups that want privacy instead of a crowded public cruise.
This charter is not about spectacle. It is for adults who want a private boat, a discreet anchorage, and a professional captain who understands the tone of the trip.
Is this a sexual activity charter?
No. Clothing optional means private, discreet, adults-only comfort on the water. Swinging or sexual acts are not permitted on the boat.
Six Fins keeps this charter professional, respectful, and hospitality-focused. The captain's role is to operate the vessel safely, choose a discreet location, protect guest privacy, and make the charter comfortable without turning it into an explicit environment.
What kind of boat is used?
Six Fins uses the 30-foot Jeanneau NC 895 Weekender for many clothing-optional charters. It has a walk-around deck, wide swim platform, shaded cabin, private head, changing space, Bluetooth sound system, cooler, ice, towels, and USCG-approved safety gear.
The boat works well because guests can move easily, swim comfortably, get shade when needed, and use a real private bathroom.
How many guests can come?
Up to 6 guests is the standard setup, with captain and fuel included. A 7th guest adds $150 and an 8th adds $300 under a bareboat structure, where the Charterer (21+) hires the captain separately at $65/charter-hour and fuel runs $35/charter-hour.
Six Fins would rather keep the day comfortable and discreet than overload the boat. If your group is larger, ask before booking.
Where does the boat go?
The captain chooses the anchorage, swim area, or route on the day of the charter based on wind, sun angle, tide, privacy, other boat traffic, and safety.
Local Six Fins captains know the best discreet spots. Guests may request maximum privacy and exclusivity, or they may be comfortable with other clothing-optional charters in the broader area. The captain will choose the best legal, safe, and privacy-conscious option for the day.
Are photos allowed on a clothing-optional charter?
No. Photography and video are not permitted while onboard, or whenever the Six Fins boat appears anywhere in the frame. Crew do not record guests, and guests may not record other guests or crew. Six Fins does not post about clothing-optional trips on social media.
This policy protects guest privacy, crew professionalism, and the discreet tone of the charter. The experience is private, adults-only, non-explicit, and clothing optional — not public, promotional, or photo-driven.
Can we bring food and drinks?
Yes. Bring your own food, drinks, snacks, and playlist. Six Fins provides the cooler, ice, water, towels, and onboard amenities listed for the charter.
Alcohol is allowed for guests, but the captain remains responsible for vessel safety. Keep the day relaxed, respectful, and safe.
How is this different from a public clothing-optional cruise?
A public cruise usually means strangers, a fixed schedule, public deck space, phones out, and a shared route. Six Fins is private: your group, your timing, your privacy preference, your food and drinks, and no photography.
For guests who value privacy more than crowds, private is the whole point.
What happens if weather is unsafe?
If Six Fins or the captain determines conditions are unsafe, guests may be rescheduled or refunded according to the applicable booking policy. If the trip can run safely but one anchorage is not private or protected enough, the captain may choose another location.
Privacy and safety both depend on the day's water.
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.
This experience uses standard private-charter pricing. The boat is reserved exclusively for your group.
Book the Private Charter ☎ (305) 906-2880Prefer to write first? info@sixfinscharter.com · Or text (305) 906-2880. Discreet replies, always.