Windward Fishing Charters 

4.9/5 (186 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 (186 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!

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Customer reviews

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Rating

4.9
186 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 (186)

Frequently mentioned
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Showing 15 of 186 reviews
Jimmey Rome
Jimmey Rome
Repeat angler
us
Louisiana, US
Member since 2023
3 trips
5.0
Verified
New
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
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)
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
Derek  Wert
Derek Wert
us
Tennessee, US
Member since 2026
5.0
Verified
New
Great time
4 Hour Trip (AM) on June 3, 20262 adults

Great time. Knowledgeable and helpful. Knows the water and how to get on fish. Would recommend.

Reported catch:
Snook
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.

Trip availability and prices

Trip Date:
Group Size:
Select date to see availability
June 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
4 Hour Trip (AM)
4 hour trip starts at 8:00 AM
US $650
Entire boat: up to 3 people
4 Hour Trip (PM)
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
6 hour trip starts at 8:00 AM
US $900
Entire boat: up to 3 people
6 Hour Trip – Tarpon
6 hour trip starts at 8:00 AM
Seasonal trip
May 1 - Jul 24
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US $1,000
Entire boat: up to 3 people
There are 7 people looking at this charter.

Customer reviews

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Rating

4.9
186 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 (186)

Frequently mentioned
Loading...Loading...Loading...Loading...Loading...Loading...Loading...Loading...
Showing 15 of 186 reviews
Jimmey Rome
Jimmey Rome
Repeat angler
us
Louisiana, US
Member since 2023
3 trips
5.0
Verified
New
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
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)
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
Derek  Wert
Derek Wert
us
Tennessee, US
Member since 2026
5.0
Verified
New
Great time
4 Hour Trip (AM) on June 3, 20262 adults

Great time. Knowledgeable and helpful. Knows the water and how to get on fish. Would recommend.

Reported catch:
Snook
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

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The fish you can target

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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
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