Private · Up to 6 Guests · 3 Hours
A private Key West sunset cruise on a 30-foot yacht.
Anniversary, proposal, honeymoon, or just the right kind of Tuesday — the boat is yours, the captain is licensed, and the light over the Gulf does the rest.
What a Private Sunset Cruise Looks Like
Three hours, beginning to end.
You don't have to plan it. We've thought about the timing so you don't have to — you just show up, step on, and exhale.
Meet at the dock
Perry Hotel & Marina on Stock Island, about 15 minutes south of Old Town. We meet at the slip, load your cooler and any wine or champagne you've brought, and walk through the boat. No safety briefing in front of a clipboard — a quick conversation, like a friend with a captain's license.
Push off into the harbor
Slow ride out through the marina, past the shrimp boats and pelicans. The Jeanneau is quiet — you can actually talk to the person next to you. The captain points out what's worth looking at and otherwise stays out of the conversation.
Out past the cruise ships
We track west, past the harbor mouth, and find water with room. Depending on wind, that's somewhere off the Atlantic side, around Sunset Key, or out past Mallory where you can actually see the show without being in it. The boat anchors or drifts — whatever the day asks for.
The hour before the sun goes
This is the part you came for. Bow seats, glass of whatever you brought, music low. The light starts to do the thing it does in the Keys — gold to amber to pink — and you don't have to fight 400 strangers for the view. The captain hangs back. You'll have photos that don't look like everyone else's.
The minute it actually drops
Most people are surprised by how fast it happens once it starts. We've timed the boat to be where you want to be for it. Quiet. Long exhale. Sometimes applause. Sometimes a question we won't repeat here.
Cruise back under first stars
Slow ride home. The water gets glassy. The skyline lights up. You're back at the dock by 3:00, full of whatever you brought, somewhere between relaxed and lightly emotional. We tie up. You walk off. That's the cruise.
Private vs. Mallory Square
Two different ideas of a sunset cruise.
The big shared cruise boats out of Mallory Square work for some people. If you want a date night, an anniversary, or a proposal — they're not the right call. Here's the honest comparison.
Just your people, the whole boat.
- Up to 6 guests — nobody you didn't invite
- Bring your own bottle, charcuterie, playlist
- Private head (real bathroom) below deck
- USCG-licensed captain who reads the day's wind, not a script
- Flat $995 covers the boat, not a per-person ticket
- Pictures of the sunset, not the back of someone's head
You and 80 strangers, fighting for the rail.
- 60–120 guests on a single boat
- Buy-it-on-board drink prices and a souvenir cup
- Shared restrooms, sometimes a line
- Fixed route, fixed playlist, fixed seating
- Per-person pricing — cheaper headline, less of the actual thing
- Hard to hear the person you came with
The Boat
The Jeanneau NC 895
We picked this boat for sunset trips on purpose. Stable, quiet, with seating that actually faces forward — not gunwale benches you spend three hours sliding off.
30 feet of comfortable, not 30 feet of party.
A French-built day yacht that runs quiet, sits flat in chop, and has a real cabin with a real head.
Every cruise is run by a USCG-licensed Merchant Mariner captain — not a deckhand with a half-day briefing. The boat carries USCG-approved life jackets in every size, two-way radio, and full safety gear. We don't take chances with weather, with traffic, or with the sun (the captain watches all three for you).
Pricing
One flat price for the whole boat.
No per-person tickets. No tiered seating. You're booking the boat — bring two people, or six, the price is the same.
Private Sunset Cruise
3 hours · Jeanneau NC 895
$995
What's included
- 3 hours dock-to-dock, timed to sunset
- USCG-licensed captain
- Cooler, ice, bottled water, cups
- Bluetooth speaker — bring your playlist
- Bring your own bottles, charcuterie, anything else
- Fuel, dockage, all safety gear
Gratuity for the captain not included. Catering and floral arrangements available on request — just ask when you book.
You only need one good Key West sunset photo. Most people come home with a thousand of the wrong one.
That's the difference between buying a ticket and chartering the boat — the difference between watching the sunset and being inside it.
Frequently Asked
Real answers.
What time does the sunset cruise leave?
We push off about 90 minutes before sunset so you're already out on the water when the light starts to turn. Exact departure shifts with the calendar — in late spring and summer that's usually around 6:30 p.m., in winter closer to 4:30 p.m.
We'll confirm the time with you when you book and again the day before, so you don't have to do the math.
How many guests can come?
Up to six total. The Jeanneau NC 895 is comfortable for two on a date night and just as comfortable for a small group. Six is a relaxed number on this boat, not a crammed one — everyone gets a real seat and a view.
Can we bring our own food and drinks?
Yes — please do. A bottle of champagne or wine, a charcuterie board from Eaton Street Seafood, your favorite playlist on Bluetooth. The boat has a cooler, ice, bottled water, and cups stocked.
Want us to handle it? Mention catering or a specific bottle when you book and we'll arrange it. We work with a couple of local providers we trust.
Is this private — or are we sharing the boat with strangers?
Fully private. Just your group, the captain, and the boat. We don't run shared sunset cruises — this isn't the Mallory Square party-boat scene. The flat $995 covers the whole boat, not a per-person ticket.
What happens if the weather is bad?
Florida weather is honest about itself most days. If we can't safely run, the captain will know hours in advance and we'll reach out to reschedule or refund. Light rain doesn't cancel a sunset cruise; lightning or small-craft warnings do.
The captain makes the call, and the call is always made for safety, never for the booking fee.
How long is the cruise?
Three hours from dock to dock. Long enough to get out past the harbor, set up somewhere quiet for sunset, linger with a glass of something, and motor back under the first stars. Long enough to feel like the trip you were picturing.
Is there a bathroom on board?
Yes — the Jeanneau NC 895 has a private enclosed head (marine toilet) below deck. Real door, real walls. One of the reasons we picked this boat for sunset trips — three hours is a long time without one.
Can you handle a proposal or anniversary?
Yes — quietly. Tell us when you book. We can coordinate timing, flowers, a chilled bottle waiting, or whatever you need to set the moment. The captain is good at being where he needs to be and not where he doesn't.
We've also worked on small bachelor and bachelorette events — six-person sunset versions of those days too.
Book the night.
Pick a date, we'll handle the rest. Sunsets in Key West book up fast in season — especially around Valentine's, anniversaries, and full moons.
Questions first? Email info@sixfinscharter.com or text (305) 906-2880.