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Key West CompassIndependent trip guidance

Fishing decision guide

What to Ask a Key West Fishing Captain Before You Book

Updated

Every disappointing charter story we've heard traces back to a question nobody asked: the deposit that vanished into a windy day, the six-year-old on a boat with no head, the vegetarian surprised that lunch was the fish. Captains answer all of it happily — before booking.

Send these by message or ask them on the phone. You'll learn as much from how a captain answers as from what they say.

The short answer

Five questions cover most of the risk: What's realistic for our dates? What's included and what's extra? What's the weather policy, exactly? What does the boat have (head, shade, seating)? How do you run trips with a group like ours? Get the weather policy in writing — it's the one that ends up mattering.

The trip itself

  1. What water will we fish for our dates, and what's biting then — honestly?
  2. How long is the block, dock to dock, and how much is running time?
  3. How many anglers fit comfortably, and can non-fishing riders come along?
  4. What happens if conditions push us off the plan — inshore fallback or reschedule?

Money and policy

  1. What's the total rate, and is fuel included at today's prices?
  2. Deposit amount — and its exact fate for weather cancellation vs. our cancellation?
  3. How far ahead do you call weather, and who makes the call?
  4. How does gratuity typically work aboard?

The boat and comfort

  1. Is there a restroom aboard? Shade? Seating out of the sun?
  2. Can we bring a cooler with our own food and drinks?
  3. Do you carry life jackets sized for our kids?
  4. Where exactly do we meet, and where do we park?

Licenses and the catch

  1. Are we covered under the boat's fishing license?
  2. What can we realistically keep in season, and will you clean it?
  3. Any nearby restaurants that cook a guest's catch?
  4. If it's all catch-and-release for our target, tell us now — some of us are here for dinner

Reading the answers

Specificity is the tell. A pro answers with details that reference your dates, your kids' ages and their own boat's quirks. Vague reassurance — 'no worries, we'll figure it out' — on questions about money or weather is your cue to keep shopping. And a captain who tells you what won't be good during your dates is showing you exactly the honesty you'll want at sea.

Frequently asked questions

Is it rude to ask captains all this?

The opposite — detailed questions signal a booking worth having, and working captains would rather settle expectations by message than manage disappointment on the water. Anyone bothered by the weather-policy question has told you something important.

Should we book direct or through a platform?

Ask these questions either way. Booking platforms standardize deposits and cancellation windows; direct booking often gives more flexibility and a relationship with the captain. What matters is that the policy you're relying on is the one in writing for your booking.

Not sure yet? That's the point of the Finder.

Not sure which trip type fits? Tell us about your group and we'll show you the kind of charter to be calling about.

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