Private · 3 Hours · Up to 8 Guests
A private Key West historic harbor cruise — captained, narrated, ad-libbed by a local.
Three hours along the Key West waterfront on a 30-foot Jeanneau yacht. Your group only. No fixed-departure 49-passenger boat, no canned audio loop, no rushed turnaround. Just your captain, the harbor, and the stories that built the island.
What You'll See From the Water
The Key West skyline, told the right way.
Half of Key West's history is on the waterfront, and the half that isn't is best understood looking back at the island from a hundred yards out. Routes vary with wind and tide, but most cruises take in some combination of these:
Old Town
Mallory Square & Sunset Pier
The square where the schooners moor and the sunset celebration kicks off each evening. From the water you see the working pier, the cruise ship dock, and the crowd gathering — without standing in it.
Truman Annex
The Little White House
Harry Truman's winter retreat sits a few hundred feet behind the old Navy seawall. We slow down for the view and the captain fills in the Cold War history most tour books skip.
Working Waterfront
The Shrimp Fleet
The pink-shrimp boats on Stock Island and Safe Harbor are a working fleet, not a tourist set — out at dusk, in at dawn, and they built Key West long before Duval did.
Coast Guard
The Mole Pier Cutters
Coast Guard Sector Key West keeps cutters on the Mole Pier — the big white ships you can't see by land. We cruise past at a respectful distance with a clear view.
Historic Seaport
The Schooners & Sponge Docks
The Historic Seaport, the tall ships at their berths, and the old conch sponge docks — the wreckers' warehouses that turned Key West into the richest city per capita in 1850s America.
From the Atlantic Side
The Key West Skyline
Wind permitting, we round the lower harbor for the postcard view: the lighthouse, the Casa Marina, and the long low silhouette of the island most visitors only see by car.
Why Private
A private cruise vs. the big tour boats.
The Key West sunset cruise market is full of 49-passenger catamarans with a microphone, a cash bar, and a fixed loop. Our cruise is the opposite of all three. Here's what changes when the boat is yours:
The big tour boats
- 49 to 100+ strangers sharing the deck
- Canned narration played over the PA on a loop
- Fixed route — same circle every night
- Set departure time, set return time, fixed pace
- Captain is on the bridge, not on your trip
- Bar lines, photo lines, bathroom lines
Your private Six Fins cruise
- Up to 8 guests — your group only
- Live narration, ad-libbed, your questions answered
- Route flexes with conditions and what you want to see
- Departure time you pick — sunrise, midday, or sunset
- USCG-licensed local captain talking with you the whole way
- Cooler with ice, snacks, your own playlist if you want
What a 3-Hour Harbor Cruise Covers
How the afternoon usually goes.
Times are flexible — the cruise is private, so it leaves when you do. A typical sunset cruise looks something like this, but morning and mid-day departures follow the same arc.
Cast off from Perry Hotel & Marina
Meet your captain on Dock A, Slip #32. Drinks in the cooler, lines off, and out through the harbor channel past the shrimp fleet at Safe Harbor.
The working waterfront
Up the channel past the Coast Guard cutters at the Mole Pier and the conch sponge docks. Slow pass at the Historic Seaport — the schooners and the wreckers' warehouses.
Truman Annex & Mallory Square
Around the lower harbor for the Little White House and the Navy seawall. Past Mallory as the sunset crowd gathers. If wind allows, a swing toward the Atlantic side for the open-water skyline shot.
Golden hour and home
The most-photographed window of the day — soft light, fishing fleet coming home, pelicans working the channel. Idle back to Perry.
The Jeanneau experience.
A 30-foot Jeanneau NC 895 is a yacht, not a tour boat. Shaded cabin, clean head, wide decks, quiet smooth ride at narration pace — comfortable enough that three hours feels like one.
- 30-foot Jeanneau NC 895 luxury cruiser
- Shaded enclosed cabin · head on board · bean bag seating
- Bluetooth speaker for your playlist
- Cooler with ice, bottled water, snacks included
- USCG-licensed captain on every charter
- Snorkel gear, paddleboard, lily pad on board if you want a swim stop
- Use of the Perry Hotel pool before and after — on us
Pricing
Flat rate. Up to 8 guests. No per-person math.
One private cruise, one price, the whole boat. Fuel, captain, cooler, water, and snacks all in.
- 30-foot Jeanneau NC 895 yacht — just your group
- USCG-licensed local captain narrating the cruise
- Fuel, coolers with ice, bottled water, and snacks
- Snorkel gear, paddleboard, lily pad, bean bag chairs on board
- Perry Hotel pool access for guests before and after
- Flexible start time — sunrise, midday, or sunset
Gratuity not included — 20% is customary if you're happy with the captain. Trips with more than six guests add fuel at $35/hour. Cancellations made seven days out are fully refunded; weather cancellations by your captain refund 90%.
Frequently Asked
The questions visitors ask first.
What landmarks will we see?
Mallory Square and the Sunset Pier, the Truman Annex and Truman's Little White House, the shrimp fleet on Safe Harbor, the Coast Guard cutters at the Mole Pier, the conch sponge docks, the Historic Seaport schooners and the wreckers' warehouses, and the Key West skyline from a perspective most visitors never see. Route varies with wind and tide.
Does the captain narrate the cruise?
Yes — and not from a script. Our captains are USCG-licensed locals. You'll hear about the wreckers' era (the 1850s, when Key West was the richest city per capita in America), the Spanish-American War navy years, the Hemingway and Buffett decades, and the shrimp and sponge fleets that still go out every morning. Ask questions; the answers are ad-libbed, not recorded audio.
How long is the cruise?
Three hours, dock to dock. Start times are flexible — pick sunrise, mid-day, or a sunset departure that times golden hour for the harbor.
Is the cruise private, or do we share the boat?
Fully private. The 30-foot Jeanneau is yours and your group's only — no strangers, no shared seating, no 49-passenger tour boat. Up to 8 guests at one flat rate of $995.
What's the best time of day?
Late afternoon into sunset is the most photographed window — soft light, schooners under sail, Mallory crowd gathering as you cruise past. Morning departures are calmer and cooler, with the shrimp fleet coming back from the night's catch.
Is the harbor cruise good for kids?
Very. The Jeanneau is roomy, stable, and shaded; the pace is gentle; there's plenty for kids to look at — pelicans, working boats, Coast Guard cutters, schooners. Snorkel gear and a paddleboard are on board if you want to add a swim stop.
Is the Jeanneau wheelchair accessible?
Yes — with help. Boarding requires stepping down from a fixed dock with assistance from the captain, but the Jeanneau NC 895 has wide level deck space and shaded cabin seating once aboard. Tell us about specific mobility needs when you book.
Where does the cruise leave from?
Perry Hotel & Marina, 7001 Shrimp Rd, Stock Island — Dock A, Slip #32. About 10 minutes from Old Town. Free parking. Arrive 15 minutes early. Perry pool is open to you before and after as our guest.
Ready to see Key West from the water?
Book online and pick your time, or call us and tell us what you want to see. Three hours, your group, your captain, the harbor.
Questions first? Email info@sixfinscharter.com — or browse our other charters: Sunset Cruise · Private Snorkel · All Boats