Charter Boat Windy 

5.0/5 (8 reviews)
 59 Star Island Road, Montauk, NY 11954, United States
5.0/5 (8 reviews)
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59 Star Island Road
Montauk, NY, United States

Montauk has a fish with your name on it, so let Charter Boat Windy help you catch it! Captain John will be your guide, which allows you to benefit from years of angling experience.

Striped Bass, Yellowfin Tuna, Flounder, Bluefin Tuna, Bluefish, Blue Shark, Thresher Shark, Black Seabass, Cod, and more inhabit these waters, depending on the time of year.

On these trips, you can expect to troll and bottom fish using light or heavy tackle.

Thinking of bringing the whole family? Kids are absolutely welcome! Be sure to ask if child-sized life vests are available, otherwise you should bring your own. Also remember to bring snacks so that nobody gets cranky on an empty belly!

You’ll find yourself aboard a 40’ Downeast with room for 6 passengers. It has outriggers, downriggers, a fighting chair, and all the essentials no fishing machine can run without. There’s a toilet on board for your convenience. What’s more, this vessel is wheelchair accessible.

Your captain will provide rods and reels, along with lures. Live bait is available, but be sure to ask about it so you know if you’ll be catching it yourself.

You’ll have the help of a First Mate to put you on fish. A 10–20% tip is customary to show your appreciation for their hard work.

The charter boat covers your fishing license, just show up ready for a good time! Some fish have special regulations, including when you can keep them. If you don’t know what to expect, ask the captain.

A few items to bring include sunscreen (non-spray), a hat, bottled water, and sunglasses. If you’d like to bring other drinks, just ask. Alcohol is allowed in moderation, so long as you avoid hard liquor as well as glass bottles.

Get in touch with Capt. John below and start planning your trip today!

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Customer reviews

Rating summary

5.0/5
out of 5 stars from 8 reviews
Boat
5.0/5
Crew
5.0/5
Experience
5.0/5

Photos & videos by reviewers (19)

Did 1/2 day Sea Bass and 1 day Tuna/Sea bass
Did 1/2 day Sea Bass and 1 day Tuna/Sea bass
Did 1/2 day Sea Bass and 1 day Tuna/Sea bass
+16

Angler rating

8
0
0
0
0

Anglers claimed

Good experience

100%

Appropriate for children

100%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

73%

Caught fish

100%

Showing 1 - 5 of 11 reviews
Showing: 5 of 11 reviews
Darrell S.
Darrell S.

Alma, Ontario

5.0/5

Jun 8, 2024

Extended Day Trip – Tuna

Did 1/2 day Sea Bass and 1 day Tuna/Sea bass

We booked Windy Charters as they were recommended to us by Friends. And they DID NOT DISAPPOINT!!! John our captain was Excellent and was very focused on getting us fish, which he did well. And Mike his Mate is the hardest working Mate I have ever met. We caught lots of sea Bass and Blue fish and then went for Tuna. When we hooked up to a Monster Tuna and fought it for over 5 hrs Mike never left our side and John (Captain) kept the boat squared up to the fish all the time, These two are hard core fishermen and were absolutely awesome! I HIGHLY reccommend them... You will not be disappointed. I have done many Charters and these two guys where by far the best! Will see you again.

We booked Windy Charters as they were recommended to us by Friends. And they DID NOT DISAPPOINT!!! John our captain was Excellent...  

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Captain replied
 Darrell S. recommends Charter Boat Windy
 Darrell S. recommends Charter Boat Windy
undefined (The Captain)
Replied on June 14, 2024
Can’t wait Darrell! Best complement we can get is you had a great time and we are recommended.

Mike P.
Mike P.

Colchester, Vermont

5.0/5

Jun 19, 2024

Extended Day Trip – Tuna

June fishing trip

John and Mike are hands down the best in the business. Never in the last decade have I left without a cooler full and an experience of a lifetime. Recently brought my son who is visually impaired they accommodated accordingly and made it such a wonderful time for all that were on board. John knows the waters unlike anyone I’ve ever met and is a true Captain always ready always courteous all around a great time every time. I will be on the Windy for the rest of my life without a doubt.

John and Mike are hands down the best in the business. Never in the last decade have I left without a cooler full and an experience...  

Captain replied
 Mike P. recommends Charter Boat Windy
 Mike P. recommends Charter Boat Windy
undefined (The Captain)
Replied on June 27, 2024
Thanks mike see ya soon

Nathan M.
Nathan M.

The Bronx, New York

5.0/5

Jun 10, 2023

Full Day trip – Inshore

Early Father’s Day

Captain John and his Crew were amazing! They helped the beginner fishers and provided clear instruction on how to use the rods. They were responsive and helpful when the beginners tangled up their lines. Heading out with Captain John is a guarantee catch. Crew cleans the fish however you want and all I can say is I am always content with everything that the Windy has to provide.

Captain John and his Crew were amazing! They helped the beginner fishers and provided clear instruction on how to use the rods....  

Review media 0
Captain replied
 Nathan M. recommends Charter Boat Windy
 Nathan M. recommends Charter Boat Windy
undefined (The Captain)
Replied on June 10, 2023
Thanks Nate, looking forward to next year!

Kevim D.
Kevim D.

Jacksonville, FL

5.0/5

Jul 12, 2023

Half Day Trip (AM)

Half day trip with Captain John

VERIFIED

What a great day on the water with Captain John. He knew exactly where the fish were. We caught large porgies and Sea Bass, porgies were plenty! Boat was comfortable with plenty of room and the crew were fun to fish with. Will be trying an overnighter next time!!!!!

What a great day on the water with Captain John. He knew exactly where the fish were. We caught large porgies and Sea Bass, porgies...  

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Captain replied
 Kevim D. recommends Charter Boat Windy
 Kevim D. recommends Charter Boat Windy
undefined (The Captain)
Replied on July 12, 2023
Thankyou so much for coming. Really glad you guys had a great time. Looking forward to next year

Lenita K.
Lenita K.

Sep 28, 2024

The captain canceled

VERIFIED

The charter operator canceled 1 days prior to the trip date. This is an automated posting.

 

Captain replied
1 person finds this review helpful
1 person finds this review helpful
undefined (The Captain)

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
August 2025
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
Sunset Cruise
FREE Cancellation 14 days notice
3 Hour Trip, starts at 6:00 PM
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US $500 
Entire boat: up to 6 people
Twilight
FREE Cancellation 14 days notice
4 Hour Trip, starts at 3:00 PM
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US $800 
Entire boat: up to 6 people
Half Day Trip (PM)
FREE Cancellation 14 days notice
5 Hour Trip, starts at 12:00 PM
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US $850 
Entire boat: up to 6 people
Half Day Trip (AM)
FREE Cancellation 14 days notice
5 Hour Trip, starts at 5:00 AM
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US $900 
Entire boat: up to 6 people
Full Day trip – Inshore
FREE Cancellation 14 days notice
10 Hour Trip, starts at 5:00 AM
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US $1,600 
Entire boat: up to 6 people
All Day Trip – Shark
FREE Cancellation 14 days notice
12 Hour Trip, starts at 8:00 AM
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US $2,000 
Entire boat: up to 6 people
Extended Day Trip – Tuna
FREE Cancellation 14 days notice
18 Hour Trip, starts at 2:00 AM
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US $2,800 
Entire boat: up to 6 people
There are 7 people looking at this charter.

Customer reviews

Rating summary

5.0/5
out of 5 stars from 8 reviews
Boat
5.0/5
Crew
5.0/5
Experience
5.0/5

Photos & videos by reviewers (19)

Did 1/2 day Sea Bass and 1 day Tuna/Sea bass
Did 1/2 day Sea Bass and 1 day Tuna/Sea bass
Did 1/2 day Sea Bass and 1 day Tuna/Sea bass
+16

Angler rating

8
0
0
0
0

Anglers claimed

Good experience

100%

Appropriate for children

100%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

73%

Caught fish

100%

Showing 1 - 5 of 11 reviews
Showing: 5 of 11 reviews
Darrell S.
Darrell S.

Alma, Ontario

5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Did 1/2 day Sea Bass and 1 day Tuna/Sea bass

Extended Day Trip – Tuna on June 8, 2024

We booked Windy Charters as they were recommended to us by Friends. And they DID NOT DISAPPOINT!!! John our captain was Excellent and was very focused on getting us fish, which he did well. And Mike his Mate is the hardest working Mate I have ever met. We caught lots of sea Bass and Blue fish and then went for Tuna. When we hooked up to a Monster Tuna and fought it for over 5 hrs Mike never left our side and John (Captain) kept the boat squared up to the fish all the time, These two are hard core fishermen and were absolutely awesome! I HIGHLY reccommend them... You will not be disappointed. I have done many Charters and these two guys where by far the best! Will see you again.

We booked Windy Charters as they were recommended to us by Friends. And they DID NOT DISAPPOINT!!! John our captain was Excellent and was very focused on getting us fish, which he did well. And Mike his Mate is the hardest working Mate I have ever met. We caught lots of sea Bass and Blue fish and then went for Tuna. When we hooked up to a Monster Tuna and fought it for over 5 hrs Mike never left our side and John (Captain) kept the boat squared up to the fish all the time, These two are hard...  

Review media 0
Review media 1
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Review media 8
 Darrell S. recommends Charter Boat Windy
undefined (The Captain)
Replied on June 14, 2024
Can’t wait Darrell! Best complement we can get is you had a great time and we are recommended.

Mike P.
Mike P.

Colchester, Vermont

5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

June fishing trip

Extended Day Trip – Tuna on June 19, 2024

John and Mike are hands down the best in the business. Never in the last decade have I left without a cooler full and an experience of a lifetime. Recently brought my son who is visually impaired they accommodated accordingly and made it such a wonderful time for all that were on board. John knows the waters unlike anyone I’ve ever met and is a true Captain always ready always courteous all around a great time every time. I will be on the Windy for the rest of my life without a doubt.

John and Mike are hands down the best in the business. Never in the last decade have I left without a cooler full and an experience of a lifetime. Recently brought my son who is visually impaired they accommodated accordingly and made it such a wonderful time for all that were on board. John knows the waters unlike anyone I’ve ever met and is a true Captain always ready always courteous all around a great time every time. I will be on the Windy for the rest of my life without a doubt.  

 Mike P. recommends Charter Boat Windy
undefined (The Captain)
Replied on June 27, 2024
Thanks mike see ya soon

Nathan M.
Nathan M.

The Bronx, New York

5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Early Father’s Day

Full Day trip – Inshore on June 10, 2023

Captain John and his Crew were amazing! They helped the beginner fishers and provided clear instruction on how to use the rods. They were responsive and helpful when the beginners tangled up their lines. Heading out with Captain John is a guarantee catch. Crew cleans the fish however you want and all I can say is I am always content with everything that the Windy has to provide.

Captain John and his Crew were amazing! They helped the beginner fishers and provided clear instruction on how to use the rods. They were responsive and helpful when the beginners tangled up their lines. Heading out with Captain John is a guarantee catch. Crew cleans the fish however you want and all I can say is I am always content with everything that the Windy has to provide.  

Review media 0
 Nathan M. recommends Charter Boat Windy
undefined (The Captain)
Replied on June 10, 2023
Thanks Nate, looking forward to next year!

Kevim D.
Kevim D.

Jacksonville, FL

5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Half day trip with Captain John

VERIFIED

Half Day Trip (AM) on July 12, 2023

What a great day on the water with Captain John. He knew exactly where the fish were. We caught large porgies and Sea Bass, porgies were plenty! Boat was comfortable with plenty of room and the crew were fun to fish with. Will be trying an overnighter next time!!!!!

What a great day on the water with Captain John. He knew exactly where the fish were. We caught large porgies and Sea Bass, porgies were plenty! Boat was comfortable with plenty of room and the crew were fun to fish with. Will be trying an overnighter next time!!!!!  

Review media 0
Review media 1
Review media 2
Review media 3
 Kevim D. recommends Charter Boat Windy
undefined (The Captain)
Replied on July 12, 2023
Thankyou so much for coming. Really glad you guys had a great time. Looking forward to next year

Lenita K.
Lenita K.

The captain canceled

VERIFIED

Trip was supposed to happen on September 28, 2024

The charter operator canceled 1 days prior to the trip date. This is an automated posting.

 

1 person finds this review helpful
undefined (The Captain)

FAQs about Charter Boat Windy

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The fish you can target

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What is the boat like?

Boat Image
Boat category
Cabin cruisers
Capacity
6 persons
Boat length
40 ft
Year built
1990
Restored in
2023
Boat manufacturer
Young Brothers
Boat type
Downeast

Engine model
John Deere
Powered by
1 x 550HP
Max cruising speed
24 knots
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