Key West’s best waterfront bars. No Uber required.
Key West has some of the best waterfront bars in Florida and almost all of them are accessible by water. This charter routes your group to 3–4 of them in four hours — captain navigates, group drinks, no designated driver needed.
The captain handles the docking and timing between stops. Tell us your preferences (lighter or heavier on the food side, how many stops you want, any specific bars) and we build the route. Schedule it lunch-timed or dinner-timed at booking — same charter, same captain, you pick the start time.
Best for bachelorettes, birthdays, and anyone who has watched boats pull up to the tiki docks and thought “that should be us.”
The Practicals
What’s included. What to bring.
We provide
- USCG-licensed local captain
- Fuel for the full charter
- All marine safety equipment
- Ice and soft drinks on board
- Bluetooth sound system
- Perry Hotel pool access
You bring
- Cash or card for bar tabs (not included)
- Good shoes for stepping on/off docks
- Reef-safe sunscreen
- Whatever energy the occasion calls for
How the day runs
A typical crawl.
The captain running your tiki crawl.
What people who took this trip say.
"Mac and Captain Dustin were professional, went above and beyond to make me feel comfortable, and the charter was well worth the expense. Highly recommend."
"Seamless from the prep call to the boat. Captain Dustin took us to spots we never would have found on our own. 100% will do this again."
Before the crawl.
What is a Tiki Bar Crawl by Water?
It is a private 4-hour boat charter that takes your group to waterfront tiki bars and casual dockside stops by boat instead of by car or rideshare.
The appeal is the route: private boat, captain, music, water views, dockside drinks, and a Key West bar crawl that feels like a charter instead of a crowded bar bus.
How many bars will we visit?
Most Tiki Bar Crawl charters aim for 3–4 waterfront stops, depending on dock access, timing, crowding, weather, and how long your group wants to stay at each place.
No specific dock, bar, or number of stops is guaranteed. The captain adjusts the route based on what is open, safe, and realistic that day.
How long is the charter and what does it cost?
The Tiki Bar Crawl by Water is a 4-hour private charter priced at $1,295 for the boat. Pricing is flat rate, not per person.
It includes the Jeanneau NC 895, USCG-licensed captain, fuel, safety equipment, and the private boat experience. Guests pay their own bar tabs.
Are drinks or food included?
No. Drinks and food at the tiki bars are not included. Your group pays its own tabs at each stop.
The captain can route to places that serve food when timing and dock access allow. If lunch or dinner is important, tell Six Fins before departure so the route can be planned around that.
Can we drink on the boat?
Guests may bring drinks for the boat, and guests may drink at the waterfront stops. The captain does not drink on duty and remains responsible for vessel safety.
This is meant to be fun and safe, not a reckless drinking cruise. The captain can adjust the route or end unsafe behavior if needed.
Is this good for bachelorette parties or birthdays?
Yes. The Tiki Bar Crawl by Water is a strong fit for bachelorettes, birthdays, friend groups, couples, and small private parties that want a social day without sharing a public tour boat.
You control the group, the music, and the pace, while the captain handles the boat and route.
Can we add a sandbar or swim stop?
Sometimes, but the 4-hour Tiki Bar Crawl is designed around waterfront bar stops. If you want tiki bars plus sandbar, snorkeling, dolphins, sunset, or multiple activities, the Custom Combo Charter is usually the better fit.
The Custom Combo Charter gives your group 6 or 8 hours to build a more complete day without rushing the bar stops.
Where does the charter depart?
The Tiki Bar Crawl by Water departs from Perry Hotel & Marina in Stock Island / Key West, unless your confirmation gives a different instruction.
Arrive early enough to load your group, connect the playlist, and get the captain's safety briefing before departure.
What should we bring?
Bring photo ID, payment method for bar tabs, sunscreen, sunglasses, hats, casual boat clothes, and a playlist. If you want drinks or snacks on the boat between stops, bring those too.
Avoid glass when possible. Boat decks, bare feet, and glass are a bad mix.
What happens if weather or dock access changes?
If Six Fins or the captain determines conditions are unsafe, guests may be rescheduled or refunded according to the applicable booking policy. If the charter can run safely but a dock, bar, or route is unavailable, the captain may adjust the crawl.
The goal is a safe, private waterfront bar day — not forcing a specific stop when the water or dock conditions say otherwise.