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 you book.
Which bars do you go to?
Depends on the day and which docks are accessible. We typically route to 3–4 of the waterfront tiki bars and casual spots. Tell us if you have a specific request — we’ll build it in where we can.
Do we pay for our own drinks?
Yes — the charter doesn’t cover bar tabs. Bring cash or card for each stop. The captain doesn’t drink on duty.
Is lunch included?
No, but we route past bars that do food. Tell us when you book if you want a lunch stop built into the route.
Good for a bachelorette party?
Yes — this is one of our most-booked options for bachelor and bachelorette groups. The combination of privacy (your own boat) with the fun of bar hopping tends to hit well.