Printable planning kit
Weather Planning Checklist
For the week before your trip and the morning of each water day.
Wind cancels Key West boat trips; rain mostly doesn't. This checklist is built around that inversion, because it's the single most useful thing to understand about weather here.
Print it before you travel. The decisions that protect a trip get made before the disrupted morning, not during it.
A week out
- Identified which of your bookings are weather-dependent
- Confirmed those are scheduled early in your trip, not on the last day
- Read each operator's written weather policy
- Noted who makes the cancellation call and how far ahead
- Confirmed the operator has a phone number that reaches you
- Chose one low-exposure backup per outdoor day
Two days out
This is when marine conditions start to firm up.
- Checked official National Weather Service marine forecasts
- Looked at wind rather than rain percentage
- Noted whether a front or storm pattern is moving through
- Identified which day of your remaining trip looks calmest
- Contacted the operator if you want to move to a better day
The night before
- Confirmed the trip is still running
- Confirmed check-in time and meeting point
- Charged your phone and saved the operator's number offline
- Packed a light rain shell if it's storm season
- Set an alarm early enough not to rush
The morning of
- Called or messaged rather than judging by the sky from your window
- Asked whether they're running, rerouting to calmer water, or cancelling
- If rerouted: understood how the trip changes
- If cancelled: asked about the next slot inside your dates
- Resisted cancelling on your own — that usually triggers your cancellation terms
Seasonal reminders
- Summer: storms build in the afternoon — book mornings
- Winter: cold fronts bring multi-day wind, forecast well in advance
- Winter evenings on the water are genuinely cool — bring a real layer
- Hurricane season overlaps summer and early autumn — favor refundable bookings
Confirm directly with your provider
These depend on the operator and the day. We don't publish them because we can't know them for your booking.
- What wind speed or sea state makes them cancel this specific trip
- How far ahead they make the call and how they'll contact you
- Whether a sheltered alternative site exists, or it's a straight cancellation
- Refund, credit and reschedule terms in writing
Fill this in
- Weather-dependent bookings and their dates
- Operator phone numbers
- Cancellation policy summary
- My chosen backup plan per day
Key West Compass is an independent publisher, not an activity operator. We publish no prices, availability, forecasts or travel times, and we don't rank or recommend individual operators. Providers control pricing, scheduling, safety and service — verify material details with them directly.