Windward Fishing Charters

Windward Fishing Charters is located in Sarasota and offers to show you a memorable time out of Siesta Key and the surrounding areas. Whether you are an experienced fisherman or a first-timer, Capt. Timothy will ensure that everyone has a great time. Also, kids are more than welcome to come aboard, just make sure to let the captain know ahead of time to make sure he has child life jackets on board.

Capt. Timothy will do his best to make sure you have a fun day full of fishing. This involves 4 to 6-hour trips, mainly fishing for Snook, Snapper, Cobia, Redfish, King Mackerel, and Spotted Seatrout, depending on the season and conditions on the day. On these trips, you can expect to use techniques such as light tackle, heavy tackle, bottom fishing, and trolling.

Your fishing adventure starts on a 22’ Pathfinder boat fully restored in 2021. It’s equipped with a power pole, GPS/sonar, coolers for drinks and fish, and a wireless trolling motor. It that can safely take up to 5 anglers and also comes with an ice-box.

All rods, reels, terminal tackle, live bait, lures, bottled water, and ice are included in the price so you can focus on what really matters, fishing. Your trip will include all the necessary fishing licenses for the day. At the end of the trip, Capt. Tim will clean and bag the keepers that you want to take home.

Book your trip now and hit the water with Windward Fishing Charters.



Select date to see available trips and rates:

  • Private trip
    4 Hour Trip (AM)
    In demand! Last booked: 19 hours ago
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 8:00 AM
    $500
    This trip is a great way to spend the morning. The boat will depart at 8:00 a.m. and will go for a variety of species, also depending on what bite has been hot lately. Just bring some snacks and any drinks and the rest is taken care of!
  • Private trip
    6 Hour Trip
    FREE Cancellation 7 days notice
    6 Hour Trip, starts at 8:00 AM
    $750
    If 4 hours are not enough, this 6-hour charter will give more time to fish longer and run farther. It's recommended to bring a lunch for this trip, or you can stop at a local restaurant on the water per request. You'll target many species and also have time to do different techniques.
There are 14 people looking at this charter.

About the Captain

Timothy Crowley
Sarasota, Florida, United States
ID & License verified
36 Customer Reviews
Response time within an hour
Member since March 2022
Captain Timothy welcomes you to an enjoyable fishing adventure out of Sarasota. Explore inshore and nearshore grounds as well as flats and make some lovely memories on the beautiful waters of Florida.

About this listing

Targeted Species

Black Drum Black Drum
Cobia Cobia
King Mackerel (Kingfish) King Mackerel (Kingfish)
Pompano Pompano

Redfish Redfish
Sheepshead Sheepshead
Snapper (Mangrove) Mangrove Snapper
Snook Snook

Spotted Seatrout Spotted Seatrout
Tripletail Tripletail

Boat Specs

Pathfinder (Center console) originally built in 2000. Powered by a 175HP Yamaha engine, with a maximum cruising speed of 43 knots.

Length
22 ft
Capacity
5 persons

Types of Fishing

Inshore Fishing
Nearshore Fishing
Flats Fishing

Fishing Techniques

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Jigging
Kite Fishing

Amenities

GPS
Fishfinder
Live Bait Well
Ice Box
GPS
Fishfinder
Live Bait Well
Ice Box

Trip Includes

Rods, reels & tackle
Live Bait
Lures
Catch cleaning & filleting
Drinks
Fishing License

Cancellation Policy

Free cancellation up to 7 days prior to trip

Customers can cancel or modify their booking up to 7 days before the trip date free of charge. If the trip is canceled or modified later, or in the event of a no-show, 100% of the deposit will be charged.

Listing Policies

Pickup included in price
Transfer from hotels or jetties in Sarasota to departure site is available and included in trip rates.
Child Friendly
You Keep Catch

Payment

Book with 10% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 10% deposit to guarantee your reservation.

The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:

Cash
Visa
Mastercard
American Express

Sarasota Fishing Calendar

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Customer Reviews

Rating Summary
Excellent
4.9 / 5
out of 5 stars from 36 reviews
Boat
Excellent
4.9 / 5
Crew
Excellent
5.0 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (47)
Half day trip was perfect!
Half day trip was perfect!
Half day trip was perfect!
+44
Angler Rating
33
2
0
0
0
Anglers Claimed
Good experience
96%
Friendly captain
100%
Recommend this charter
97%
Appropriate for children
100%
Satisfied with the boat
96%
Catch intended fish
90%
Sort By:
Featured  
Showing:
5 of 36 reviews
Michael E.
Swormville, NY
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Half day morning charter with Captain Tim

VERIFIED   4 Hour Trip (AM) on April 15, 2022
Our family enjoyed a morning half day fishing charter with captain Tim. He arrived early prepared with bait and we went to...
Michael E. recommends Windward Fishing Charters
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1 person finds this review helpful
You and 1 other person found this review helpful
Michael E. recommends Windward Fishing Charters
Mark review as helpful
1 person finds this review helpful
You and 1 other person found this review helpful

Jesse S.
Denver, CO
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fishing with Timothy

VERIFIED   4 Hour Trip (AM) on March 30, 2022
Caption Tim is the real deal and he is very knowledgeable. He is very personable, super nice, easy to talk to and a great...
Jesse S. recommends Windward Fishing Charters
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Jesse S. recommends Windward Fishing Charters
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You found this review helpful

Taylor B.
Maitland, FL
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

4 hour trip AM

VERIFIED   4 Hour Trip (AM) on March 19, 2022
Tim was fantastic.  He took us on an action packed 4 trip this morning.  He was prepared, his boat was clean and well equipped. ...
Taylor B. recommends Windward Fishing Charters
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Taylor B. recommends Windward Fishing Charters
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You found this review helpful

Osvaldo V.
New York, NY
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

4 hour trip with Captain Tim

VERIFIED   NEW  4 Hour Trip (PM) on June 18, 2022
Great experience and Tim really went out of his way to find the best fishing spots. His boat was clean and perfect for the...
Osvaldo V. recommends Windward Fishing Charters
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Osvaldo V. recommends Windward Fishing Charters
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Kellie P.
Sarasota, Florida
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Half day trip with Tim

VERIFIED   NEW  4 Hour Trip (AM) on June 14, 2022
Tim as great! We went out with our 3 boys ages 13, 12 and 8. He was so patient with the boys who would get tangled. But the...
Kellie P. recommends Windward Fishing Charters
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Kellie P. recommends Windward Fishing Charters
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You found this review helpful

FAQs about Windward Fishing Charters

Windward Fishing Charters offers the following trips to customers:
  • $500 per group - 4 Hour Trip (AM) (4 hours)
  • $750 per group - 6 Hour Trip (6 hours)

When you book a trip with Windward Fishing Charters, you can expect the following amenities onboard:
  • GPS
  • Fishfinder
  • Live Bait Well
  • Ice Box

Trips booked with Windward Fishing Charters include:
  • Rods, reels & tackle
  • Live Bait
  • Lures
  • Catch cleaning & filleting
  • Drinks
  • Fishing License

Windward Fishing Charters offers the following types of fishing:
  • Inshore Fishing
  • Nearshore Fishing
  • Flats Fishing

Windward Fishing Charters offers the following fishing techniques:
  • Light Tackle
  • Heavy Tackle
  • Bottom Fishing
  • Trolling
  • Jigging
  • Kite Fishing

Top targeted fish species with Windward Fishing Charters include:
  • Black Drum
  • Cobia
  • King Mackerel (Kingfish)
  • Pompano
  • Redfish
  • Sheepshead
  • Snapper (Mangrove)
  • Snook
  • Spotted Seatrout
  • Tripletail