A sunset in Key West does not always call for a tall ship or a 65-foot catamaran. Some evenings the right vessel is a floating tiki bar with your own cooler lashed on deck. Two charters fill that role here. Hula Hank's runs the Tipsy Tiki, a BYOB boat where the drink menu is whatever you carry aboard, and Sunset Watersports pours unlimited draft beer and wine on a two-hour booze cruise.
Between them these two charters hold ratings of 5 across 6 reviews (checked September 2026) and 4 across 16 reviews, and both can be cancelled free.
Short answer
Hula Hank's runs the Tipsy Tiki Sunset Cruise, a BYOB tiki boat rated 5 across 6 reviews (checked September 2026), on a run that lasts an hour and a half. Sunset Watersports handles the other listing, a two-hour sunset booze cruise with unlimited draft beer and wine, rated 4 across 16 reviews. Both charters carry free cancellation. Prices sit on the live listings rather than fixed figures here, since party-boat rates often depend on date and group size; the booking page shows the current price before you commit.
Some honest context before you scroll. These are the only two party-boat listings in this category, and both are newer to the review scene than the big catamaran and schooner operators, so the review counts run small. That cuts both ways. Fewer reviews means less crowd wisdom to lean on, but it also means these boats are not drawing the packed decks the flagship sails pull every evening. If your group wants a loose, bring-your-own evening rather than an open bar with a live band, these listings are built for exactly that.
What these boats offer that the rest of the fleet does not: a party you control. The Tipsy Tiki is BYOB, so the drinks are yours to choose and the vibe leans floating backyard hangout rather than ticketed tour. The booze cruise trades that freedom for convenience, unlimited draft beer and wine with no cooler logistics to manage. Either way you get the same Gulf sunset the tall ships sell, with less time and planning committed to it.
The two tiki charters, side by side
Rates live on the booking page and move with your date, so check there before committing.
Two hours on the water with unlimited draft beer and wine, run by Sunset Watersports out of Key West. The drinks flow from the start, which makes this listing the closest thing on this site to a classic Key West booze cruise: less sailing formality, more floating bar. It is the only roster tour built entirely around an open pour of beer and wine rather than cocktails or a full bar. Free cancellation applies, and the live booking page carries the current price and departure details.
Hula Hank's runs a tipsy tiki sunset cruise built around one simple idea: you bring the drinks. It is a BYOB trip, which sets it apart from the open-bar catamarans and the licensed party boats elsewhere on this site. The sail runs an hour and a half, shorter than the standard two-hour sunset trips, and it sits in the private, party and tiki charter category rather than the big-boat sails. Guests rated it 5 out of 5 across a small set of reviews, and the listing carries free cancellation. The live booking page has the current price and departure details.
Full control over what's in the cooler, and a shorter run
No cooler logistics, and a full two hours out
What to know before booking
Check-in
Hula Hank's boards at 205 Elizabeth St, in the Historic Seaport / Harbor Walk area. The Sunset Booze Cruise boards at 201 William St. Check your confirmation for the exact dock.
Timing
Departures track sunset, which runs from about 5:38pm in November to about 8:20pm in June. Check-in opens about 45 minutes before departure.
Cancellation
Both charters offer free cancellation, so holding a date early costs nothing if plans change.
Why this category holds only two boats
Common questions
Are drinks covered on the tiki boats?
Depends on the boat. The Sunset Booze Cruise pours unlimited draft beer and wine for the full 2 hours. Hula Hank's tiki charter runs BYOB, so you pack the cooler and the boat supplies the floating spot to drink it on. Free cancellation applies to both, so shifting plans costs nothing.
Can you bring your own drinks aboard a sunset cruise?
On Hula Hank's tiki boat, yes, that is the whole setup: BYOB, you carry aboard whatever you want to drink, and the boat provides the floating bar to drink it on. The booze cruise does the opposite, folding unlimited draft beer and wine into the fare. Catamaran and schooner sails elsewhere on this site run open bars instead, so read each listing for what is covered.
Which of the two boats is better?
Hula Hank's if you want the BYOB route: a 5 rating (checked September 2026) across 6 reviews and a shorter, looser run. The Sunset Booze Cruise if you would rather not haul a cooler, with unlimited draft beer and wine over 2 hours and a 4 rating across 16 reviews. Both cancel free, so the safer move is booking early and adjusting if the plan shifts.
Can you bring your own drinks on a Key West tiki cruise?
On Hula Hank's, yes, that is the whole model. The tiki charter is BYOB, so you load your own cooler and the crew handles the rest of the setup. The Sunset Booze Cruise goes the other way: unlimited draft beer and wine are poured on board, and outside drinks are not the point. Choose control of the bar or zero effort, whichever suits the group.
Does any tiki cruise serve food?
Not on either tiki. Both are built around drinks, one BYOB and one pouring unlimited draft beer and wine, and neither puts food on the table. If eating matters, the sushi sunset cruise from Barefoot Billy's and the open-bar dinner cruise from Sunset Watersports Key West each run 2 hours and cover the meal properly.
This category is small: two boats, two formats, and nothing else in Key West quite like them. Free cancellation on both means you can lock a date now and adjust later without losing anything.
