Windward Fishing Charters 

4.9/5 (189 reviews)
 
State licensed
 946 Siesta Drive, Sarasota, FL 34242, United States

Windward Fishing Charters 

Up to 9 miles
Sarasota, FL, United States
22 ft
5
4.9/5 (189 reviews)

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 many different trip options. 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 2022. It's equipped with a tower for shade and sighting fish, power pole, GPS/sonar, coolers for drinks and fish, and a wireless trolling motor. She can safely take up to 5 anglers and also comes with an ice box to put the keeper fish in.

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!

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 many different trip options. 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 2022. It's equipped with a tower for shade and sighting fish, power pole, GPS/sonar, coolers for drinks and fish, and a wireless trolling motor. She can safely take up to 5 anglers and also comes with an ice box to put the keeper fish in.

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!

Timothy Crowley
Captain
Timothy Crowley
ID & credentials verified
responds within an hour

Trip availability and prices

Trip Date:
Group Size:
Select date to see availability
August 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
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4 Hour Trip (AM)
FREE Cancellation 3 days notice
4 hour trip starts at 8:00 AM
US $650
Entire boat: up to 3 people
4 Hour Trip (PM)
FREE Cancellation 3 days notice
4 hour trip starts at 1:00 PM
Seasonal trip
Oct 1 - Jul 1
US $650
Entire boat: up to 3 people
6 Hour Trip
FREE Cancellation 3 days notice
6 hour trip starts at 8:00 AM
US $900
Entire boat: up to 3 people
6 Hour Trip – Tarpon
FREE Cancellation 3 days notice
6 hour trip starts at 8:00 AM
Seasonal trip
May 1 - Jul 24
Tarpon
US $1,000
Entire boat: up to 3 people
There is 1 person looking at this charter.

Customer reviews

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Rating

4.9
189 reviews
4.9
Boat & equipment
4.9
Captain & crew
4.9
Fishing Experience

Anglers' gallery (216)

What anglers say

98%
Great experience
98%
Family friendly
98%
Friendly captain
98%
Good boat
97%
Recommended
96%
Caught fish

All reviews (189)

Frequently mentioned
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Showing 15 of 189 reviews
Barbara Ekker
Barbara Ekker
us
Wisconsin, US
Member since 2026
5.0
Verified
Absolute amazing time
4 Hour Trip (PM) on March 11, 20263 adults

We had an absolutely fantastic time fishing! Our captain was a blast to be around and worked hard the entire trip to make sure we had the best experience possible. We caught a ton of fish and had so much fun doing it. You can really tell he puts in the effort to make sure everyone has a great time. Highly recommend!

Reported catch:
Redfish
Sheepshead
Mangrove Snapper
King Mackerel (Kingfish)
Stephen McVey
Stephen McVey
gb
United Kingdom
Member since 2026
5.0
Verified
New
Amazing family fishing experience!!
4 Hour Trip (AM) on July 3, 20262 adults2 children

Capt Tim was great with the kids and knew all the best spots to catch a wide variety of fish. 100% would definitely go again when we are back in Sarasota.

David Crist
David Crist
Repeat angler
us
Illinois, US
Member since 2023
4 trips
5.0
Verified
Captain Tim works for you!
4 Hour Trip (PM) on March 18, 20262 adults2 children

we had a cold front come through so I knew tge fishing would be marginal at beet. Capt. Tim made multiple stops trying to grt us onto fish. we caught several Snook but the hits were tough to get. i woukd definitely recommend this boat and captain if you want someone to work hard to get on the fish!!

Reported catch:
Snook
Jimmey Rome
Jimmey Rome
Repeat angler
us
Louisiana, US
Member since 2023
3 trips
5.0
Verified
straight up good time!
4 Hour Trip (AM) on June 17, 20263 adults

Conditions weren’t the best. We targeted snook and Captain Timmy delivered. Not just snook. we caught grouper, snapper, and speckle trout. Even one hardhead. Truly, I enjoyed fishing and sharing information with Captain Timmy. 👍

Reported catch:
Snook
Speckled Trout
Mangrove Snapper
Matthew Cann
Matthew Cann
us
Massachusetts, US
Member since 2026
5.0
Verified
Captain Tim is the best!
4 Hour Trip (AM) on April 20, 20261 adult1 child

My son & I have chartered Captain Tim for multiple trips for multiple years now. And we always catch fish! He is very knowledgeable of the area, kind & friendly. We will return and recommend others to book his charter.

FAQs about Windward Fishing Charters

Windward Fishing Charters offers the following trips to customers:
  • US $650 per group, additional US $50 per person after 3 guests - 4 Hour Trip (AM) (4 hours)
  • US $650 per group, additional US $50 per person after 3 guests - 4 Hour Trip (PM) (4 hours)
  • US $900 per group, additional US $950 per person after 3 guests - 6 Hour Trip (6 hours)
  • US $1,000 per group, additional US $50 per person after 3 guests - 6 Hour Trip – Tarpon (6 hours)
When you book a trip with Windward Fishing Charters, you can expect the following amenities onboard:
  • GPS
  • Fishfinder
  • Live bait well
  • Wireless trolling motor
  • Ice box
Trips booked with Windward Fishing Charters include:
  • Rods, reels & tackle
  • Live bait (Bait is on the boat ready to go before the trip starts and is included in the price. )
  • Lures
  • Catch cleaning & filleting
  • Drinks
  • Fishing license (Fishing licenses are included and cover all guests. )
Windward Fishing Charters offers the following types of fishing:
  • Inshore fishing
  • Nearshore fishing
  • Flats fishing
  • Backcountry fishing
Windward Fishing Charters offers the following fishing techniques:
  • Light tackle
  • Heavy tackle
  • Bottom fishing
  • Trolling
  • Jigging
Top targeted fish species with Windward Fishing Charters include:
  • Black Drum
  • Cobia
  • King Mackerel (Kingfish)
  • Pompano
  • Redfish
  • Sheepshead
  • Snapper (Mangrove)
  • Snook
  • Speckled Trout
  • Tripletail

Your captain

Timothy Crowley
Timothy Crowley
Timothy Crowley

Sarasota, Florida, United States

1 Fishing Report
ID & license verified
189 Customer reviews
Typical response within an hour
Member since March 2022

Captain Tim grew up fishing these waters that he will take you fishing on. He dreamed of becoming a fishing charter captain since he was a child, and will always go the extra mile to make sure everyone on the boat has a great time. Captain Tim also loves to be able to teach his guests new fishing techniques and takes great pride in his work.

1 Fishing Report
ID & license verified
189 Customer reviews
Typical response within an hour
Member since March 2022

Captain Tim grew up fishing these waters that he will take you fishing on. He dreamed of becoming a fishing charter captain since he was a child, and will always go the extra mile to make sure everyone on the boat has a great time. Captain Tim also loves to be able to teach his guests new fishing techniques and takes great pride in his work.

The fish you can target

Black Drum
Black Drum
Cobia
Cobia
King Mackerel (Kingfish)
King Mackerel (Kingfish)
Pompano
Pompano
Redfish
Redfish
Sheepshead
Sheepshead
Mangrove Snapper
Mangrove Snapper
Snook
Snook
Speckled Trout
Speckled Trout
Tripletail
Tripletail
Black Drum
Black Drum
Cobia
Cobia
King Mackerel (Kingfish)
King Mackerel (Kingfish)
Pompano
Pompano
Redfish
Redfish

What is the boat like?

Boat image
Boat category
Center console boats
Capacity
5 persons
Boat length
22 ft
Year built
2000
Restored in
2022
Boat manufacturer
Pathfinder
Boat type
Center console
Engine model
Yamaha
Powered by
1 x 175HP
Max cruising speed
43 knots

What kind of fishing will you do?

Inshore Fishing
Nearshore Fishing
Flats Fishing
Backcountry Fishing

Which fishing techniques you can try

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Jigging

Which amenities are available onboard

GPS
Fishfinder
Live bait well
Wireless trolling motor
Ice box

What's included in the trip price

Rods, reels & tackle
Live bait
Bait is on the boat ready to go before the trip starts and is included in the price.
Lures
Catch cleaning & filleting
Drinks
Fishing license
Fishing licenses are included and cover all guests.

How cancellations work

Free cancellation up to 3 days prior to trip

You can cancel or modify your booking up to 3 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.

More details

What the listing policies are

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

How you can pay

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

When paying the remaining balance with a credit card, an additional 3% charge will apply.

What’s biting in Sarasota right now

Black DrumBlack Drum
CobiaCobia
King Mackerel (Kingfish)King Mackerel (Kingfish)
RedfishRedfish
SheepsheadSheepshead
SnookSnook
Speckled TroutSpeckled Trout
TripletailTripletail

Compare similar fishing charters

Current
Windward Fishing Charters
Windward Fishing Charters
State licensed
4.9
(189)
22 ft
Group size 1 - 5
1 - 5
Fish 1
Fish 2
+8
4 hour trip • 3 persons
US $650