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 for 1–6 guests. No per-person math.
One private cruise, one price, the whole boat. Fuel, captain, cooler, water, and snacks all in for 1–6 guests. A 7th guest adds $150 and an 8th adds $300 as a bareboat add-on, with the captain hired separately at $65/charter-hour and fuel at $35/charter-hour.
- 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. A 7th guest adds $150 and an 8th adds $300 as a bareboat add-on, with fuel at $35/charter-hour and the captain hired separately at $65/charter-hour. Full refund if you cancel at least 7 days before departure; inside 7 days, non-refundable except when Six Fins or the captain cancels for unsafe weather, which is a full refund.
Frequently Asked
The questions visitors ask first.
What is the Key West Historic Harbor Cruise?
The Historic Harbor Cruise is a private, 3-hour narrated boat charter along the Key West waterfront. Your group has the boat, and the USCG-licensed captain tells the story of the island from the water instead of playing a canned audio loop.
The route may include Mallory Square, Sunset Pier, the Historic Seaport, schooners, sponge docks, shrimp boats, Coast Guard cutters, Truman Annex, the Little White House area, and skyline views, depending on wind, tide, traffic, and captain judgment.
Is this a private cruise or a shared tour?
It is fully private. The boat is reserved for your group only, so there are no strangers, no shared rail, no 49-passenger tour-boat crowd, and no fixed microphone script.
A private harbor cruise is a better fit for couples, families, small groups, photographers, history lovers, and guests who want a quieter Key West experience.
Does the captain narrate the cruise?
Yes. The captain narrates the cruise, but not from a recorded script. Expect local stories, waterfront history, working-harbor context, and answers to your questions as the route unfolds.
The best part of a private narrated cruise is that you can ask about what you are actually seeing: shrimp boats, schooners, Coast Guard activity, harbor traffic, old Navy history, or Key West landmarks.
How long is the harbor cruise and how much does it cost?
The private Historic Harbor Cruise is 3 hours and $995 for the whole boat for up to 6 guests. Pricing is per boat, not per person. A 7th guest adds $150 and an 8th adds $300 as a bareboat add-on, with the captain hired separately at $65/charter-hour and fuel at $35/charter-hour.
The base charter includes the USCG-licensed captain, fuel, safety gear, cooler with ice, bottled water, snacks, and onboard amenities. Gratuity is not included.
What landmarks will we see?
Routes vary, but common highlights include Mallory Square, Sunset Pier, Truman Annex, the Little White House area, the shrimp fleet, the Historic Seaport, schooners, sponge docks, Coast Guard cutters, and the Key West skyline.
The captain chooses the best route based on wind, tide, traffic, cruise ship activity, and light. You see Key West from the angle most visitors miss: the water.
What is the best time of day for the harbor cruise?
Late afternoon into sunset is the most photogenic window, with softer light, schooners moving through the harbor, and the Mallory Square crowd gathering as you pass by from the water.
Morning can be calmer and cooler, and midday can work well for guests who want a history-first cruise without building the day around sunset.
Is the harbor cruise good for kids?
Yes. The harbor cruise works well for kids because the pace is gentle, the boat is stable and shaded, and there is always something to look at: pelicans, working boats, Coast Guard cutters, schooners, shrimp boats, and the harbor skyline.
If your family wants swimming or more water time, mention it when booking. For a multi-activity day, the Custom Combo Charter may be a better fit.
Can we add a swim, sandbar, snorkel, or dolphin stop?
Sometimes, but the 3-hour harbor cruise is designed first as a private narrated waterfront cruise. If you want to combine harbor cruising with sandbars, snorkeling, dolphin watching, eco touring, or multiple stops, the better fit is usually the Custom Combo Charter.
The Custom Combo Charter is Six Fins' most popular private charter because the 6- or 8-hour format gives your group enough time to build the day around more than one activity without rushing the harbor story.
Is the boat comfortable?
Yes. The Jeanneau NC 895 is a 30-foot cabin cruiser with shaded seating, a private enclosed head, wide decks, cooler with ice, bottled water, and Bluetooth music.
It feels more like a private yacht than a tour boat, which is exactly the point. Three hours should feel relaxed, not cramped.
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. Wind, lightning, marine traffic, and route safety all matter.
If the charter can run safely but one waterfront section is not ideal, the captain may adjust the route and still give your group a strong private harbor experience.
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