Double Header Sportfishing – 37' 

4.9/5 (140 reviews)
 6720 Smith Bay Road, Red Hook, 00802, U.S. Virgin Islands

Double Header Sportfishing – 37' 

4.9/5 (140 reviews)
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6720 Smith Bay Road
Red Hook, U.S. Virgin Islands

There’s a fish with your name on it and Double Header Sportfishing will help you catch it! With their captains at the helm, you’ll benefit from years of knowledge and experience.

The charter offers both inshore and offshore trips (weather and seas permitting). Inshore species include Kingfish Mackerel, Rainbow Runner, Shark, Barracuda, Yellowtail Snapper, Tarpon, etc. Offshore species include Dolphin fish (Mahi), Wahoo, Tuna, Marlin, and Sailfish (in season). On these trips, it’s common to live bait, troll, or bottom fish using light or heavy tackle.

Families who love fishing together will be glad to know that kids are welcome aboard five years and older! Snacks are never a bad idea so that nobody gets grumpy on an empty belly!

You’ll be casting lines from a 37’ Calypso center console T-top that holds up to 6 passengers. It has outriggers, downriggers, and all the essentials. There’s a head, on board for your convenience. Double Header has rods and reels for you, along with lures. Live bait is included.

Make sure to bring a camera, sunglasses, and sunblock (non-spray). There will be water, beer, and soda on board, if brand specific you are welcome to bring your own but we try to avoid glass on the boat.

Now and then the fish might get away, but a day on the water never should. Time to make it happen, with Double Header Sportfishing!

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Customer reviews

Rating summary

4.9/5
out of 5 stars from 140 reviews
Boat
4.9/5
Crew
5.0/5
Experience
5.0/5

Photos & videos by reviewers (189)

Great half day on the Doubleheader!!
Great half day on the Doubleheader!!
Great half day on the Doubleheader!!
+186

Angler rating

135
4
0
0
0

Anglers claimed

Good experience

100%

Appropriate for children

88%

Friendly captain

99%

Satisfied with the boat

99%

Recommend this charter

99%

Caught fish

100%

Showing 1 - 5 of 140 reviews
Showing: 5 of 140 reviews
Pete Damiano
Pete Damiano
5.0
Verified
New
fun trip
Half Day Trip on January 10, 20265 adults
Our group of 5 adults had a great time fishing with Tyler this morning for a half day trip. Boat was nice and appropriate. Tyler was very nice and very experienced. We caught a wide variety of fish (8 different types) including 2 big bite offs by a shark and barracuda as we were reeling them in. This day did not produce any to eat, but those who fish will understand. thanks Tyler!
0
Tiffany Davis
Tiffany Davis
5.0
Verified
Excellent fishing with Captain Tyler
Half Day Trip on December 6, 20252 adults
The Captain was very knowledgeable. We caught over 30 fish. Unfortunately, we were unable to tear into the tuna and it was too late in the season for Mahi, Mahi. But we caught plenty of yummy fish. We got 3 large meals. We caught 2 sharks but forgot to take pics with all the excitement. We caught some huge African Populus and a Amberjack 50 inches and 35 lbs. About every time we put our line out, we got a bite. The price is right and the time had was exhilarating!!!
0
Derek Conway
Derek Conway
5.0
Verified
Great trip for some first timers!
Half Day Trip - 2:00 PM on June 17, 20254 adults
Captain Tyler was very patient and very knowledgeable about the local reefs and best places to catch fish. He was so good that on his “demonstration cast” he hooked up immediately and my son reeled in his first ever shark! We had three other sharks to follow that and an over four foot barracuda! It was truly the trip of a lifetime! We had several yellow tail and some snapper immediately after that. Trying to find some calmer waters for us Ohioans we ended up hooking up to another barracuda and several needle fish which were very cool to see! Capt. Tyler worked very hard for us and kept us on the fish. I would definitely recommend going with him and we’ll try to go again sometime
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Reported catch:
Yellowtail Snapper
Caribbean Queen Snapper
Response from Captain
June 18, 2025
Thank you for fishing with us. We look forward to your next adventure!
1
Chris Seear
Chris Seear
5.0
Verified
Mahi Mahi
3/4 Day Trip - 1:00 PM on May 15, 20252 adults
We booked a 6 hour fishing charter with them. Our captain Nathan was one of a kind. He gave us a rundown before we started the trip. I am very experienced with deep sea fishing having maybe 15 charters under my belt, whereas it was my newly wed wife's first trip out on the water. We first went near a marina and he tossed a net catching a ton of chum fish. Then we headed out on the water. Overall caught 17 Mahi that we kept, countless others thrown back. Also a few jacks and barracuda. He was a perfect captain for both experienced and inexperienced fishmen/women. There were plenty of drinks/water/soda/beer. He helped us get plenty of photos and even was able to help mounting one of the Mahi. He was excellent filleting the fish as well. 10/10, one of the best charters I've ever been on.
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Reported catch:
Dolphin (Mahi Mahi)
0
Randy Hojem
Randy Hojem
5.0
Verified
New
Exceptional Day
Half Day Trip on December 17, 20254 adults
We had a few squalls to deal with and the water was a bit lumpy, but the fishing was fantastic. Tyler did a great job of putting us on fish and we caught king mackerel, bonito, blue runners, yellowtail, grouper plus others. All in all, a great day on the water.
0

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
January 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
Half Day Trip
FREE Cancellation 3 days notice
4 Hour Trip
starts at 7:30 AM
US $850
Entire boat: up to 6 people
Half Day Trip - 2:00 PM
FREE Cancellation 3 days notice
4 Hour Trip
starts at 2:00 PM
US $850
Entire boat: up to 6 people
3/4 Day Trip
FREE Cancellation 3 days notice
6 Hour Trip
starts at 7:00 AM
US $1,200
Entire boat: up to 6 people
3/4 Day Trip - 1:00 PM
FREE Cancellation 3 days notice
6 Hour Trip
starts at 1:00 PM
US $1,200
Entire boat: up to 6 people
Full Day Trip
FREE Cancellation 3 days notice
8 Hour Trip
starts at 8:00 AM
US $1,450
Entire boat: up to 6 people
Extended Day Trip – Marlin
FREE Cancellation 3 days notice
10 Hour Trip
starts at 8:00 AM
US $1,700
Entire boat: up to 6 people
There are 29 people looking at this charter.

Customer reviews

Rating summary

4.9/5
out of 5 stars from 140 reviews
Boat
4.9/5
Crew
5.0/5
Experience
5.0/5

Photos & videos by reviewers (189)

Great half day on the Doubleheader!!
Great half day on the Doubleheader!!
Great half day on the Doubleheader!!
+186

Angler rating

135
4
0
0
0

Anglers claimed

Good experience

100%

Appropriate for children

88%

Friendly captain

99%

Satisfied with the boat

99%

Recommend this charter

99%

Caught fish

100%

Showing 1 - 5 of 140 reviews
Showing: 5 of 140 reviews
Pete Damiano
Pete Damiano
5.0
Verified
New
fun trip
Half Day Trip on January 10, 20265 adults
Our group of 5 adults had a great time fishing with Tyler this morning for a half day trip. Boat was nice and appropriate. Tyler was very nice and very experienced. We caught a wide variety of fish (8 different types) including 2 big bite offs by a shark and barracuda as we were reeling them in. This day did not produce any to eat, but those who fish will understand. thanks Tyler!
0
Tiffany Davis
Tiffany Davis
5.0
Verified
Excellent fishing with Captain Tyler
Half Day Trip on December 6, 20252 adults
The Captain was very knowledgeable. We caught over 30 fish. Unfortunately, we were unable to tear into the tuna and it was too late in the season for Mahi, Mahi. But we caught plenty of yummy fish. We got 3 large meals. We caught 2 sharks but forgot to take pics with all the excitement. We caught some huge African Populus and a Amberjack 50 inches and 35 lbs. About every time we put our line out, we got a bite. The price is right and the time had was exhilarating!!!
0
Derek Conway
Derek Conway
5.0
Verified
Great trip for some first timers!
Half Day Trip - 2:00 PM on June 17, 20254 adults
Captain Tyler was very patient and very knowledgeable about the local reefs and best places to catch fish. He was so good that on his “demonstration cast” he hooked up immediately and my son reeled in his first ever shark! We had three other sharks to follow that and an over four foot barracuda! It was truly the trip of a lifetime! We had several yellow tail and some snapper immediately after that. Trying to find some calmer waters for us Ohioans we ended up hooking up to another barracuda and several needle fish which were very cool to see! Capt. Tyler worked very hard for us and kept us on the fish. I would definitely recommend going with him and we’ll try to go again sometime
Review media 0
Review media 1
Review media 2
Reported catch:
Yellowtail Snapper
Caribbean Queen Snapper
Response from Captain
June 18, 2025
Thank you for fishing with us. We look forward to your next adventure!
1
Chris Seear
Chris Seear
5.0
Verified
Mahi Mahi
3/4 Day Trip - 1:00 PM on May 15, 20252 adults
We booked a 6 hour fishing charter with them. Our captain Nathan was one of a kind. He gave us a rundown before we started the trip. I am very experienced with deep sea fishing having maybe 15 charters under my belt, whereas it was my newly wed wife's first trip out on the water. We first went near a marina and he tossed a net catching a ton of chum fish. Then we headed out on the water. Overall caught 17 Mahi that we kept, countless others thrown back. Also a few jacks and barracuda. He was a perfect captain for both experienced and inexperienced fishmen/women. There were plenty of drinks/water/soda/beer. He helped us get plenty of photos and even was able to help mounting one of the Mahi. He was excellent filleting the fish as well. 10/10, one of the best charters I've ever been on.
Review media 0
Review media 1
Review media 2
Review media 3
Review media 4
Review media 5
Review media 6
Review media 7
Review media 8
Reported catch:
Dolphin (Mahi Mahi)
0
Randy Hojem
Randy Hojem
5.0
Verified
New
Exceptional Day
Half Day Trip on December 17, 20254 adults
We had a few squalls to deal with and the water was a bit lumpy, but the fishing was fantastic. Tyler did a great job of putting us on fish and we caught king mackerel, bonito, blue runners, yellowtail, grouper plus others. All in all, a great day on the water.
0

FAQs about Double Header Sportfishing – 37'

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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
6 persons
Boat length
37 ft
Year built
2018
Boat manufacturer
Calypso
Boat type
Center console

Engine model
Cummins
Powered by
1 x 485HP
Max cruising speed
19 knots
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