Always Somethin' Charters – Key West 

4.9/5 (764 reviews)
 
State licensed
 1801 North Roosevelt Boulevard, Key West, FL 33040, United States

Always Somethin' Charters – Key West 

 
State licensed
4.9/5 (764)
 Angler's Choice
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1801 North Roosevelt Boulevard
Key West, FL, United States
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Spend the day with Always Somethin' Charters and find out what the fishing in Key West is all about! With our captains at the helm, you're in knowledgeable and experienced hands.

Tarpon, Shark, Mangrove Snapper, Bonefish, Permit, Barracuda, Pompano, Jack Crevalle, and more could be biting, depending on the time of year. You'll target these fish by light tackle fishing, trolling, bottom fishing, or maybe something more specialized in this area.

Our captains are happy to have kids aboard, so the whole family can come and unplug for the day! The charter boat covers your fishing license, just show up ready for some fishing! You can't go wrong when you bring a hat,
sunglasses, and sunblock . Drinks like water and Gatorade will be available for you.

Your day begins aboard a 18' saltwater fishing vessel with a capacity for 3 passengers. It has all the essentials no fishing machine can run without. Your captain will provide rods and reels, along with specialized lures. Some fish have special regulations, including when you can keep them. If you don't know what to expect, ask the captain.

Go ahead and treat yourself to a day on the water with Always Somethin' Charters.

Spend the day with Always Somethin' Charters and find out what the fishing in Key West is all about! With our captains at the helm, you're in knowledgeable and experienced hands.

Tarpon, Shark, Mangrove Snapper, Bonefish, Permit, Barracuda, Pompano, Jack Crevalle, and more could be biting, depending on the time of year. You'll target these fish by light tackle fishing, trolling, bottom fishing, or maybe something more specialized in this area.

Our captains are happy to have kids aboard, so the whole family can come and unplug for the day! The charter boat covers your fishing license, just show up ready for some fishing! You can't go wrong when you bring a hat,
sunglasses, and sunblock . Drinks like water and Gatorade will be available for you.

Your day begins aboard a 18' saltwater fishing vessel with a capacity for 3 passengers. It has all the essentials no fishing machine can run without. Your captain will provide rods and reels, along with specialized lures. Some fish have special regulations, including when you can keep them. If you don't know what to expect, ask the captain.

Go ahead and treat yourself to a day on the water with Always Somethin' Charters.

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Rating

4.9
764 reviews
4.8
Boat & equipment
5.0
Captain & crew
4.9
Fishing Experience

Anglers' gallery (876)

What anglers say

96%
Great experience
93%
Family friendly
100%
Friendly captain
99%
Good boat
98%
Recommended
93%
Caught fish

All reviews (764)

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Showing 15 of 764 reviews
Mark Flynn
Mark Flynn
us
Georgia, US
Member since 2026
2
5.0
Verified
New
Amazing fun, zero issues!!
4 Hour Trip - 11:30 AM on May 9, 20262 adults
Did a trip with Chandler today! told us what to expect, and where to go to get the fish. He did not dissapoint at all, got us all over the Mangrove Snapper, we tore them up. Then moved a little deeper, out further, then starting ripping on the Barracudas’ it was super awesome!! He was always on point, very instructive and generous tip giving(not the money type)on how to bag the fish with changing techniques. Super cool experience, my wife and I will absolutely use them in the future. Solid five stars.
Response from Captain
May 12, 2026
Thank you so much! Im so glad you guys enjoyed it. It was great having you aboard. Tight lines and we will catch you on the next one 🤙🏼
Brad Kunz
Brad Kunz
us
Florida, US
Member since 2026
1
5.0
Verified
Great Time w/Cap’t Chandler!
3 Hour Trip on March 16, 20262 adults
We had an amazing morning of fishing with Captain Chandler! My son said it was one of the best times he’s EVER had. We caught some nice fish, decent barracuda, and had a huge 5’ barracuda on the line that may have become a shark’s breakfast…not sure if the shark caught him or not. Then, my 13-yr old hooked onto an 80 lb tarpon and had the time of his life fighting it for 5-10 mins before the smart fish wrapped our line around a crab trap and got away. It was an awesome experience. All in a few short hours… Thanks again Captain Chandler! I think you turned a teenager into a lifetime fishaholic. 😂
Reported catch:
Great Barracuda
Response from Captain
March 16, 2026
Awesome! such a fun time 🤙🏼Thank you so much! I’m so glad you guys enjoyed your time on the water. It was great having you aboard! Tight lines my friends 🤙🏼
Eric Howard
Eric Howard
us
New York, US
Member since 2026
0
5.0
Verified
Capt Chandler
3 Hour Trip (11:30 AM) on March 4, 20262 adults
I've never done a charter trip before, not knowing what to expect we did the three hour trip. Water was super choppy that day, and the fish weren't cooperating, but we still had a great time being out on the water with Capt Chandler. He definitely tried to get fish on the line for us. Despite conditions, I still caught a small barracooda and decent size mangrove snapper. Both are a first for me, so that's a win. Maybe not the best catch of my lifetime, but a bad day fishing is still better than any good day at work!!! We will definitely reach out to Chandler on our next trip. thanks Capt Chandler didn't pay me to say that, or maybe he did😉🤣..........
Reported catch:
Great Barracuda
Mangrove Snapper
Response from Captain
March 6, 2026
Awesome! so glad you enjoyed your time on the water, it was a pleasure having you aboard! the conditions have been tough the last couple days with this wind, but I am greatful we made it out and caught some fish. Tight lines , and we will see you on the next one 🤙🏼
Celeste Cole
Celeste Cole
us
Oregon, US
Member since 2024
2
5.0
Verified
Very Fishy!
4 Hour Trip (9:30 AM) on January 11, 20263 adults
Tyler was fantastic!! He had us onto fish the minute he stopped the boat. The gear was ready and after a quick and explicit demonstration on technique, it was only minutes before the first barracuda hit and they just kept coming. Tyler was very careful removing the hooks and releasing. He had a tough crowd of fish biologists on board. We then moved on to look for bone fish and mangrove snappers along with a host of others. Those two are the ones I remember. LOL Tyler took us into the mangroves where we caught snappers! The day was spectacular, sunny and warm. The water clear. We saw sharks, skip jacks and a leather back turtle. The mangroves were awesome. All we can say besides what a wonderful time is, it went by way to quick. The directions to the boat ramp where we were picked up by Tyler were perfect. However, if you have never gone fishing from this area before, it appears that all boats have a dock and name, but that is not the case. So just stay at the boat ramp and they will pick you up at the designated time. The boat was quality and very clean. The fishing gear was in good condition and stored very well. Tyler was knowledgeable with a good sense of humor and very pleasant. We took the backcountry private charter. Thank you Always Something Charters and Tyler, we'll be back next year!!!!
Reported catch:
Great Barracuda
Mangrove Snapper
Response from Captain
January 19, 2026
That is so wonderful! Thank you so much for the review, weare thankfull you guys enjoyed a beautiful day on the water, it was a pleasure having you aboard! We are looking forward to the next one my friends, tight lines🤙🏼
Daniel Diaz
Daniel Diaz
us
Illinois, US
Member since 2026
0
5.0
Verified
New
Always something (literally)
3 Hour Trip - 4:45 PM on May 10, 20262 adults
Had an awesome time on the 3-hour charter with Captain Chandler. He was super knowledgeable, easy to talk to, and really knew where to find the fish. His eye for spotting them was impressive, and thanks to him we had fish hitting the line all trip. You can tell he genuinely enjoys what he does and wants everyone to have a great experience. Definitely recommend booking a trip with him if you’re looking for a fun day on the water!
Reported catch:
Great Barracuda
Response from Captain
May 13, 2026
Thank you! I’m so glad you enjoyed it! It was great having you aboard, Tight lines and we will catch you on the next one 🤙🏼

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
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Almost there...
3 Hour Trip
FREE Cancellation 3 days notice
3 hour trip multiple starting times (7:00 AM, 10:30 AM, 1:30 PM, 4:45 PM)
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US $389
Entire boat: 2 people
4 Hour Trip
FREE Cancellation 3 days notice
4 hour trip multiple starting times (7:00 AM, 11:30 AM, 4:00 PM)
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US $549
Entire boat: 2 people
Shallow Water Spearfishing
FREE Cancellation 3 days notice
4 hour trip starts at 11:00 AM
Seasonal trip
Oct 1 - Jun 30
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US $549
Entire boat: 2 people
6 Hour Trip (AM)
FREE Cancellation 3 days notice
6 hour trip starts at 6:30 AM
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US $849
Entire boat: 2 people
There are 76 people looking at this charter.

Rating

4.9
764 reviews
4.8
Boat & equipment
5.0
Captain & crew
4.9
Fishing Experience

Anglers' gallery (876)

What anglers say

96%
Great experience
93%
Family friendly
100%
Friendly captain
99%
Good boat
98%
Recommended
93%
Caught fish

All reviews (764)

Filter
Frequently mentioned
Loading...Loading...Loading...Loading...Loading...Loading...Loading...Loading...
Showing 15 of 764 reviews
Mark Flynn
Mark Flynn
us
Georgia, US
Member since 2026
2
5.0
Verified
New
Amazing fun, zero issues!!
4 Hour Trip - 11:30 AM on May 9, 20262 adults
Did a trip with Chandler today! told us what to expect, and where to go to get the fish. He did not dissapoint at all, got us all over the Mangrove Snapper, we tore them up. Then moved a little deeper, out further, then starting ripping on the Barracudas’ it was super awesome!! He was always on point, very instructive and generous tip giving(not the money type)on how to bag the fish with changing techniques. Super cool experience, my wife and I will absolutely use them in the future. Solid five stars.
Response from Captain
May 12, 2026
Thank you so much! Im so glad you guys enjoyed it. It was great having you aboard. Tight lines and we will catch you on the next one 🤙🏼
Brad Kunz
Brad Kunz
us
Florida, US
Member since 2026
1
5.0
Verified
Great Time w/Cap’t Chandler!
3 Hour Trip on March 16, 20262 adults
We had an amazing morning of fishing with Captain Chandler! My son said it was one of the best times he’s EVER had. We caught some nice fish, decent barracuda, and had a huge 5’ barracuda on the line that may have become a shark’s breakfast…not sure if the shark caught him or not. Then, my 13-yr old hooked onto an 80 lb tarpon and had the time of his life fighting it for 5-10 mins before the smart fish wrapped our line around a crab trap and got away. It was an awesome experience. All in a few short hours… Thanks again Captain Chandler! I think you turned a teenager into a lifetime fishaholic. 😂
Reported catch:
Great Barracuda
Response from Captain
March 16, 2026
Awesome! such a fun time 🤙🏼Thank you so much! I’m so glad you guys enjoyed your time on the water. It was great having you aboard! Tight lines my friends 🤙🏼
Eric Howard
Eric Howard
us
New York, US
Member since 2026
0
5.0
Verified
Capt Chandler
3 Hour Trip (11:30 AM) on March 4, 20262 adults
I've never done a charter trip before, not knowing what to expect we did the three hour trip. Water was super choppy that day, and the fish weren't cooperating, but we still had a great time being out on the water with Capt Chandler. He definitely tried to get fish on the line for us. Despite conditions, I still caught a small barracooda and decent size mangrove snapper. Both are a first for me, so that's a win. Maybe not the best catch of my lifetime, but a bad day fishing is still better than any good day at work!!! We will definitely reach out to Chandler on our next trip. thanks Capt Chandler didn't pay me to say that, or maybe he did😉🤣..........
Reported catch:
Great Barracuda
Mangrove Snapper
Response from Captain
March 6, 2026
Awesome! so glad you enjoyed your time on the water, it was a pleasure having you aboard! the conditions have been tough the last couple days with this wind, but I am greatful we made it out and caught some fish. Tight lines , and we will see you on the next one 🤙🏼
Celeste Cole
Celeste Cole
us
Oregon, US
Member since 2024
2
5.0
Verified
Very Fishy!
4 Hour Trip (9:30 AM) on January 11, 20263 adults
Tyler was fantastic!! He had us onto fish the minute he stopped the boat. The gear was ready and after a quick and explicit demonstration on technique, it was only minutes before the first barracuda hit and they just kept coming. Tyler was very careful removing the hooks and releasing. He had a tough crowd of fish biologists on board. We then moved on to look for bone fish and mangrove snappers along with a host of others. Those two are the ones I remember. LOL Tyler took us into the mangroves where we caught snappers! The day was spectacular, sunny and warm. The water clear. We saw sharks, skip jacks and a leather back turtle. The mangroves were awesome. All we can say besides what a wonderful time is, it went by way to quick. The directions to the boat ramp where we were picked up by Tyler were perfect. However, if you have never gone fishing from this area before, it appears that all boats have a dock and name, but that is not the case. So just stay at the boat ramp and they will pick you up at the designated time. The boat was quality and very clean. The fishing gear was in good condition and stored very well. Tyler was knowledgeable with a good sense of humor and very pleasant. We took the backcountry private charter. Thank you Always Something Charters and Tyler, we'll be back next year!!!!
Reported catch:
Great Barracuda
Mangrove Snapper
Response from Captain
January 19, 2026
That is so wonderful! Thank you so much for the review, weare thankfull you guys enjoyed a beautiful day on the water, it was a pleasure having you aboard! We are looking forward to the next one my friends, tight lines🤙🏼
Daniel Diaz
Daniel Diaz
us
Illinois, US
Member since 2026
0
5.0
Verified
New
Always something (literally)
3 Hour Trip - 4:45 PM on May 10, 20262 adults
Had an awesome time on the 3-hour charter with Captain Chandler. He was super knowledgeable, easy to talk to, and really knew where to find the fish. His eye for spotting them was impressive, and thanks to him we had fish hitting the line all trip. You can tell he genuinely enjoys what he does and wants everyone to have a great experience. Definitely recommend booking a trip with him if you’re looking for a fun day on the water!
Reported catch:
Great Barracuda
Response from Captain
May 13, 2026
Thank you! I’m so glad you enjoyed it! It was great having you aboard, Tight lines and we will catch you on the next one 🤙🏼

FAQs about Always Somethin' Charters – Key West

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The fish you can target

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What is the boat like?

Boat image
Boat category
Skiffs and flats boats
Capacity
3 persons
Boat length
18 ft
Year built
2006
Restored in
2024
Boat manufacturer
Sterling Tr7
Boat type
Flats boat
Engine model
Mercury
Powered by
1 x 60HP
Max cruising speed
30 knots
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