Windward Fishing Charters

Siesta Key, Florida
Book Now Meet Your Guide
4 Hour Inshore Trip

About Your Guide

Profile photo of Captain Experiences guide Tim Crowley

Tim Crowley

Independent Guide
Talkative
Laid-back
Instructional
Beginner Oriented
Adventurous
Quality
I am a local fishing guide that has been fishing these waters since I was a little kid. I am very enthusiastic and love to share my love and knowledge of these waters to others, for the best experience possible.

About Your Guide

Profile photo of Captain Experiences guide Tim Crowley

Tim Crowley

Independent Guide
I am a local fishing guide that has been fishing these waters since I was a little kid. I am very enthusiastic and love to share my love and knowledge of these waters to others, for the best experience possible.
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Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?
Swordfish
If you were cooking for all your friends what would you cook?
fish
What’s your favorite band?
Alabama
What’s your favorite movie?
The Perfect Storm

Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?
Swordfish
If you were cooking for all your friends what would you cook?
fish
What’s your favorite band?
Alabama
What’s your favorite movie?
The Perfect Storm
What’s your favorite sports team?
Tampa Bay Buccaneers
What’s your drink of choice?
Redbull
What was your last halloween costume?
Inflatable Shark
What do you want for Christmas this year?
Fishing gear
How did you get started guiding?
lifelong goal
What makes you different from other guides?
Enthusiastic and Passionate
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Windward Fishing Charters Trips

Choose a trip to get started
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Sarasota

4 Hour Inshore Trip

100% (2) Guided by Tim
22 ft 1 - 10 People From $650
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Sarasota

4 Hour Inshore Lido Key

100% (2) Guided by Tim
22 ft 1 - 5 People From $650

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Potential Target Species

Color-coded seasonality below is based on .
View Full Species Seasonality Chart » View Recent Sarasota Fishing Reports »
  • Get it while it's HOT!
  • This species is in play.
  • You might get lucky (as long as things are in-season).
  • Couldn't tell ya! (no data)

Techniques

Artificial Lure Fishing
Light Tackle Fishing
Live Bait Fishing
Sight Casting

Type of Fishing

Inshore

Windward Fishing Charters Photo Gallery

4 Hour Inshore Trip
4 Hour Inshore Trip
September 9th, 2025
Sarasota, Florida
4 Hour Inshore Trip
4 Hour Inshore Lido Key
September 8th, 2026
Sarasota, Florida
4 Hour Inshore Trip
4 Hour Inshore Lido Key
September 8th, 2026
Sarasota, Florida
4 Hour Inshore Trip
4 Hour Inshore Trip
September 9th, 2025
Sarasota, Florida
4 Hour Inshore Trip
4 Hour Inshore Trip
September 9th, 2025
Sarasota, Florida
4 Hour Inshore Trip
4 Hour Inshore Lido Key
September 8th, 2026
Sarasota, Florida
4 Hour Inshore Trip
4 Hour Inshore Trip
September 9th, 2025
Sarasota, Florida
4 Hour Inshore Trip
4 Hour Inshore Lido Key
September 8th, 2026
Sarasota, Florida
4 Hour Inshore Trip
4 Hour Inshore Trip
September 9th, 2025
Sarasota, Florida
4 Hour Inshore Trip
4 Hour Inshore Lido Key
September 8th, 2026
Sarasota, Florida
4 Hour Inshore Trip
4 Hour Inshore Lido Key
September 8th, 2026
Sarasota, Florida
4 Hour Inshore Trip
4 Hour Inshore Trip
September 9th, 2025
Sarasota, Florida
4 Hour Inshore Trip
4 Hour Inshore Lido Key
September 8th, 2026
Sarasota, Florida
4 Hour Inshore Trip
4 Hour Inshore Trip
September 9th, 2025
Sarasota, Florida
4 Hour Inshore Trip
4 Hour Inshore Lido Key
September 8th, 2026
Sarasota, Florida
4 Hour Inshore Trip
4 Hour Inshore Trip
September 9th, 2025
Sarasota, Florida
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