Six live crawls in three formats — on foot in Old Town, by van up through the Lower Keys, or by private boat. Here's what each costs, who it's for, and the age rules that actually get enforced.
Book the Original Key West Pub Crawl at $39.95. It is the only one of the six that includes a drink at every stop — five bars, five drinks, a guide setting the pace, and a souvenir T-shirt — which makes it the best value once you would have bought two rounds anyway. It runs Tuesday, Friday and Saturday at 8:00pm from 424 Greene Street.
Going on a night it doesn't run, or watching the budget? The Bone Island Haunted crawl is $29.95 and runs six nights a week. Want the whole thing private for a bachelorette or a birthday? Skip to the bar crawls by boat.
Check Availability → $39.95 per person · Ages 21+ · Free cancellation · Instant confirmationA walking or van crawl is priced per seat, so two people pay for two tickets. A bar crawl by boat is one flat rate for the whole boat however many of you there are. Cost per head only tips toward the boats once your group is big.
| Crawl | Price & basis | Format | Schedule | Meeting point | Age |
|---|---|---|---|---|---|
| Bone Island Haunted Pub Crawl | Per person $29.95 |
Walking 2 hours |
Mon–Sat, 8:30pm | 424 Greene St, Old Town | 21+ |
| Key West Competitive Bar Crawl | Per person $37.50 |
Walking 2.5 hours |
Daily, 2:00pm & 5:00pm | Conch Republic Seafood Co, 631 Greene St | 21+ |
| Original Key West Pub Crawl | Per person $39.95 |
Walking 2.5 hours |
Tue, Fri & Sat, 8:00pm | 424 Greene St, Old Town | 21+ |
| Florida Keys Tiki Bar Crawl | Per person $83 |
By van 4 hours |
Mon, Wed & Fri, 2:00–6:00pm | Key West – Lower Keys – Marathon | 21+ |
| Bar Crawl By Boat | Whole boat, up to 6 $495 flat · ~$83/head at 6 |
By boat 3 hours |
Daily, multiple start times | Key West | Not age-gated |
| Tiki Bar Crawl by Water | Whole boat, up to 8 $1,295 flat · ~$162/head at 8 |
By boat 4 hours |
Daily, flexible start times | 7001 Shrimp Rd, Stock Island | 16–100 |
All three are guided walks around Old Town, sold by the seat, and all three are strictly 21 and over: everyone in the party needs a ticket and there is no reduced observer rate for a non-drinking guest. All three currently show free cancellation and instant confirmation.
The cheapest guided crawl on this page, and the one that doubles as a ghost tour — a storytelling-led walk between historic bars rather than a straight drinking route. Runs six nights a week, which is why it's the fallback when the Original isn't running.
Check AvailabilityA scavenger-hunt format layered on the crawl, sponsored by Dulce Vida Tequila — teams work through challenges between bars. The only daytime option here, with 2:00pm and 5:00pm departures, so it suits groups who don't want a late night.
Check AvailabilityFive bars in two and a half hours with a domestic beer or house cocktail included at each stop, plus a souvenir T-shirt. The only crawl here where the drinks are in the ticket price. Maximum 30 guests; meets next door to Captain Tony's Saloon.
Check AvailabilityThis one is not a Key West walking crawl and shouldn't be booked as a substitute for one. It is a van tour that leaves the island and works up through the Lower Keys to Marathon, so most of the four hours is driving between bars you could not otherwise reach on foot.
A custom van island-hops to three tiki bars across the Lower Keys and Marathon, with happy-hour pricing at each stop and luau party favours along the way. Cancellation is by phone with 48 hours notice — this one does not offer instant free cancellation online.
Check AvailabilityBoth are private charters priced for the whole boat, not per seat, and both reach waterfront bars you cannot walk to. Neither is a 21+ product in the way the walking crawls are, because you are chartering a vessel rather than buying bar entry — but you still need to be of age to drink aboard.
A captained three-hour bar crawl by water for up to six — they drive, you don't worry about getting back. At a full boat of six that works out around $83 a head, the same as the van crawl, but private to your group.
Check AvailabilityA four-hour dock-to-dock waterfront crawl for up to eight, departing Stock Island rather than Key West — about ten minutes further out, so build that into your timing. Listed for ages 16–100. Non-refundable inside 7 days of departure.
Check AvailabilityGuided walking pub crawls run $29.95 to $39.95 per person. The Bone Island Haunted Pub Crawl is $29.95, the Key West Competitive Bar Crawl is $37.50, and the Original Key West Pub Crawl is $39.95 with a drink included at each of five bars. A tiki bar crawl by van through the Lower Keys is $83 per person. Private bar crawls by boat are priced for the whole boat rather than per seat: $495 for up to 6 people, or $1,295 for up to 8.
Yes for every walking crawl and for the van crawl — all four are 21 and over. Everyone in the party needs their own ticket, and the operators do not sell a reduced observer rate for a non-drinking guest. The private bar crawls by boat are the exception: the Six Fins Tiki Bar Crawl by Water is listed for ages 16 to 100, because it is a private charter rather than a bar-entry product.
On the Original Key West Pub Crawl, yes — a domestic beer or house-brand cocktail is included at each of the five bars, plus a souvenir T-shirt. The Bone Island Haunted crawl and the Competitive Bar Crawl include the guided route and the entertainment rather than the drinks themselves. On the Lower Keys van crawl you get happy-hour pricing at each of the three tiki bars. Private boat crawls do not include bar tabs.
Walking crawls run 2 to 2.5 hours: the Bone Island Haunted crawl is 2 hours, and both the Original and the Competitive crawl are 2.5 hours. The Lower Keys tiki bar crawl by van is 4 hours, because most of the extra time is driving between islands. Private boat crawls are 3 hours (Fun in the Sun) or 4 hours (Six Fins).
The Original Key West Pub Crawl and the Bone Island Haunted Pub Crawl both meet at 424 Greene Street in Old Town, next door to Captain Tony's Saloon. The Competitive Bar Crawl meets a block away at Conch Republic Seafood Company, 631 Greene Street. The van crawl picks up in Key West and runs up through the Lower Keys to Marathon. The Six Fins boat crawl departs from Stock Island, at 7001 Shrimp Road.
A walking crawl is sold by the seat, so two people pay for two tickets and join a guided group of strangers. A bar crawl by boat is sold as a whole-boat private charter, so you pay one flat rate no matter how many of you there are, and no one outside your group is aboard. The boats reach waterfront tiki bars you cannot walk to. On cost per head the boats only make sense once your group is large: $495 across 6 people is about $83 each, and $1,295 across 8 is about $162 each.
Yes, but the private options are the boat crawls rather than the walking ones. Fun in the Sun runs a captained Bar Crawl By Boat for up to 6 passengers at $495 for the boat, and Six Fins runs a 4-hour Tiki Bar Crawl by Water for up to 8 at $1,295, departing Stock Island. Both are private to your group, which makes them the usual pick for a bachelorette or a birthday.
The three walking crawls do — all three show free cancellation and instant confirmation on the live booking calendar. The van crawl does not: it takes cancellations by phone with 48 hours notice for a full refund or credit. The Six Fins boat crawl is non-refundable inside 7 days of departure. Always confirm the terms on the operator's calendar before you pay.
Walk it, van it, or take the boat — live availability, booked direct with the operator.
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