Always Somethin' Charters – Key West 

4.9/5 (557 reviews)
 
State licensed
 1801 North Roosevelt Boulevard, Key West, FL 33040, United States
You may qualify for a Loyalty Program discount with Always Somethin' Charters – Key West. To check if you can use a Loyalty Program discount for your selected dates, please sign in.

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 an 18' Sterling 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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Trip availability and prices

Trip Date:
Days:
Group Size:
Almost there...
3 Hour Trip (AM)
FREE Cancellation 3 days notice
3 Hour Trip, starts at 7:00 AM
Price for 2 people
US $389 
3 Hour Trip (Late AM)
FREE Cancellation 3 days notice
3 Hour Trip, starts at 11:00 AM
Price for 2 people
US $389 
3 Hour Trip (PM)
FREE Cancellation 3 days notice
3 Hour Trip, starts at 4:00 PM
Price for 2 people
US $389 
4 Hour Trip (AM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 7:00 AM
Price for 2 people
US $549 
4 Hour Trip (Mid AM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 9:30 AM
Price for 2 people
US $549 
6 Hour Trip (AM)
FREE Cancellation 3 days notice
6 Hour Trip, starts at 7:00 AM
Price for 2 people
US $849 
There are 65 people looking at this charter.

Customer reviews

Rating summary

4.9/5
out of 5 stars from 557 reviews
Boat
4.9/5
Crew
5.0/5
Experience
4.9/5

Photos & videos by reviewers (693)

Amazing
We had a great experience!
We had a great experience!
+690

Angler rating

527
21
8
1
0

Anglers claimed

Good experience

97%

Appropriate for children

95%

Friendly captain

100%

Satisfied with the boat

99%

Recommend this charter

98%

Caught fish

94%

Showing 1 - 5 of 557 reviews
Mark K.
Mark K.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Best Trip Ever

VERIFIED
NEW

6 Hour Trip (AM) on June 12, 2025

For my Son’s graduation present, he wanted to come to Key West to do what we love…catch fish! We decided to spend a day on the water inshore, trying our luck at catching the elusive Tarpon. After scrolling through countless Guides in Key West, we decided to book our trip with Srbo, and we couldn’t have been happier with our decision. We started the morning 30 minutes later than planned. Some people may view this as a negative, but the Captain’s knowledge of the tide schedule allowed him to call this audible in order to maximize our time on the water…and boy, did it pay off! After about a 30 minute boat ride to the islands off of Key West, we were instantly on fish and stayed on them til we left. We caught Barracuda and Snapper at will with artificials while we searched the waters around the island for Tarpon. With heavy winds all day, the Captain worked his butt off to consistently put the boat in the best position for us to catch fish. On two separate occasions, we even hooked up on large sharks with our light tackle. The sharks ended up getting the best of us, but all of us enjoyed the battle! After hours of catching fish, Srbo spotted a school of Tarpon chasing bait fish. After a consistent battle of chasing fish and fighting the wind, Srbo did what we set out to do…give us the opportunity to catch Tarpon! My Son, his grandfather, and myself all caught our first Tarpon, WHAT A DAY! With our trip coming to a close, Srbo wanted to give us a shot at catching a Bone Fish, so we went over to another island with only about 15 minutes left in the day. We did not find any Bone Fish, but we did find our third shark of the day, and this one didn’t get away! My Son fought the fish for what seemed like forever before getting it to the boat. What a way for him to catch his first Shark at over 6’ in length!!! After the day we had, a lot of guides would have just headed back to the ramp, as one would expect, but you could tell Srbo wanted more for us and decided to make that last trip to the nearby island. This is what you get when you fish with Srbo…someone who is genuine, patient, knowledgeable, and professional. Thank you Srbo for the amazing day, I continue to smile even as I write this review!!! Also, Sandy’s Sandito sandwich was THE REAL DEAL!!!!

For my Son’s graduation present, he wanted to come to Key West to do what we love…catch fish! We decided to spend a day on the water inshore, trying our luck at catching the elusive Tarpon. After scrolling through countless Guides in Key West, we decided to book our trip with Srbo, and we couldn’t have been happier with our decision. We started the morning 30 minutes later than planned. Some people may view this as a negative, but the Captain’s knowledge of the tide schedule allowed him to...  

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 Mark K. recommends Always Somethin' Charters – Key West
2 persons find this review helpful
undefined (The Captain)
Replied on June 13, 2025
Freakin awesome job my friends! I am truly appreciative, it was an amazing time having you guys aboard and I’m so thankful you guys had such a wonderful day on the water! And yes the sandito is 🔥! I eat it all the time, it’s a problem 😂 looking forward to the next one, tight lines 🤙🏼

Caid M.
Caid M.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Srbo was awesome

VERIFIED

3 Hour Trip (PM) on June 7, 2025

My wife and I had an awesome time on the 3 hour trip with Srbo. The first thing I noticed upon arriving to the dock and meeting him was, unlike some of the other charter boat crews, he was respectful and kept a clean boat. I felt completely comfortable taking my wife out on the water with him, something I can’t say about some of the other guys we saw on the dock. Srbo was both energetic and encouraging with an obvious love for the ocean. He got us on fish (barracuda) almost immediately and after catching some small ones, we were able to use them as bait for sharks. Overall, we had a great experience fishing with Always Somethin’ Charters and hope to be back and do a float plane trip with Srbo! * He does not own a float plane at the time of this review but once you meet this guy you will understand why I have no doubt that he will fulfill his dream of owning and operating one!

My wife and I had an awesome time on the 3 hour trip with Srbo. The first thing I noticed upon arriving to the dock and meeting him was, unlike some of the other charter boat crews, he was respectful and kept a clean boat. I felt completely comfortable taking my wife out on the water with him, something I can’t say about some of the other guys we saw on the dock. Srbo was both energetic and encouraging with an obvious love for the ocean. He got us on fish (barracuda) almost immediately and after...  

 Caid M. recommends Always Somethin' Charters – Key West
1 person finds this review helpful
undefined (The Captain)
Replied on June 8, 2025
Thank you so much! I truly appreciate that! It was awesome having you guys out there! And I’m looking forward to it! Those trips are going to be so fun, a float plane will be such a game changer 🎣✈️ tight lines my friends 🤙🏼

Riley P.
Riley P.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

The real deal!

VERIFIED

3 Hour Trip (PM) on May 1, 2025

Capt. Srb is hands down one of the coolest guys out there, I took my mom and girlfriend out and not only did we have an amazing time the energy and vibes that the Capt. has is incredible! He was very patient with me as I had never spearfished in my life and took me to such cool spots in the mangroves. Although I didn’t shoot any fish that day it wasn’t even an issue. I had so much fun looking at all the cool things we got to see from the boat. His knowledge of the water is unmatched and I will be looking forward to my next trip with Capt. Srb. Legit a life changing experience and I’m so grateful for the opportunity to have been takin out by such an incredible captain. Thanks again Srb for everything.

Capt. Srb is hands down one of the coolest guys out there, I took my mom and girlfriend out and not only did we have an amazing time the energy and vibes that the Capt. has is incredible! He was very patient with me as I had never spearfished in my life and took me to such cool spots in the mangroves. Although I didn’t shoot any fish that day it wasn’t even an issue. I had so much fun looking at all the cool things we got to see from the boat. His knowledge of the water is unmatched and I will...  

 Riley P. recommends Always Somethin' Charters – Key West
2 persons find this review helpful
undefined (The Captain)
Replied on May 3, 2025
Thank you so much! That truly means a lot to me! I’m very thankful you had a wonderful day on the water, it was a pleasure having you guys aboard and I’m looking forward to the next one! Tight lines my friends 🤙🏼

Mia Q.
Mia Q.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Best charter experience in the Florida Keys!!! Do not skip this opportunity!

VERIFIED

3 Hour Trip (PM) on April 25, 2025

From start to finish, this fishing charter was absolutely top-notch. The captain and crew were incredibly knowledgeable, friendly, and clearly passionate about what they do. They took us to some amazing spots, and we were pulling in fish all day—mangrove snapper, barracuda, even a couple of tarpon! The boat was clean, comfortable, and well-equipped with everything we needed. They made sure we were safe, had fun, and learned a few things along the way. Whether you're a seasoned angler or a total beginner, this trip is a must-do while in Key West. Can’t wait to come back and do it again!

From start to finish, this fishing charter was absolutely top-notch. The captain and crew were incredibly knowledgeable, friendly, and clearly passionate about what they do. They took us to some amazing spots, and we were pulling in fish all day—mangrove snapper, barracuda, even a couple of tarpon! The boat was clean, comfortable, and well-equipped with everything we needed. They made sure we were safe, had fun, and learned a few things along the way. Whether you're a seasoned angler or a total...  

 Mia Q. recommends Always Somethin' Charters – Key West
1 person finds this review helpful
undefined (The Captain)
Replied on April 27, 2025
Thank you so much! I truly appreciate that! You guys were awesome out there and I’m thankful you had a wonderful day on the water. Tight lines my friends and we will see you on the next one 🤙🏼

Melinda D.
Melinda D.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Windy But Wonderful!

VERIFIED

4 Hour Trip (AM) on April 23, 2025

My husband & I really enjoyed our four hour fishing trip with Captain Grason. He was very friendly, helpful, and knowledgeable. We fished in an area of the mangroves trying to catch tarpon. We saw a couple of tarpon breaking the surface of the water but were unsuccessful in our fishing in that spot. We then moved to a couple more spots in the flats and began catching barracuda. My husband caught around 8 barracuda and one mangrove snapper. I caught a couple of barracuda and a juvenile Goliath grouper. The grouper put up a good fight but Captain Grason almost went out of boat under the mangroves to help me get it onboard. This fish is endangered and doesn’t usually bite artificial bait like we were using. This was definitely a special treat. We had a great time and are looking forward to another trip to the Keys. We’d definitely book Always Something Charters again!

My husband & I really enjoyed our four hour fishing trip with Captain Grason. He was very friendly, helpful, and knowledgeable. We fished in an area of the mangroves trying to catch tarpon. We saw a couple of tarpon breaking the surface of the water but were unsuccessful in our fishing in that spot. We then moved to a couple more spots in the flats and began catching barracuda. My husband caught around 8 barracuda and one mangrove snapper. I caught a couple of barracuda and a juvenile Goliath...  

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 Melinda D. recommends Always Somethin' Charters – Key West
undefined (The Captain)
Replied on April 24, 2025
Wonderful! I’m so thankful you had such a great time on the water! Thank you and we are looking forward to the next one. Tight lines my friends 🤙🏼

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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
2020
Boat manufacturer
Sterling
Boat type
Skiff

Engine model
Mercury
Powered by
1 x 60HP
Max cruising speed
30 knots
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What’s biting in Key West right now

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