Always Somethin' Charters – Key West 

4.9
(837 reviews)
 
State licensed
 1801 North Roosevelt Boulevard, Key West, FL 33040, United States–

Always Somethin' Charters – Key West 

Key West, FL, United States
–
18 ft
3
4.9
(837 reviews)

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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.

Always Somethin' Charters
Charter Operator
Always Somethin' Charters
7 years of experience
responds within an hour

Select date to see availability

Trip date:
Group Size:
November 2026
SuMoTuWeThFrSa
Group Size
2 adults • 0 children
Change
3 Hour Lobster Snorkeling
FREE Cancellation 3 days notice
3 hour trip multiple starting times (8:00 AM, 11:30 AM, 3:30 PM)
Seasonal trip
Aug 6 - Mar 31
Lobster
US $389
Entire boat: 2 people
3 Hour Trip
In high demand Last booked: 19 hours ago
FREE Cancellation 3 days notice
3 hour trip multiple starting times (8:00 AM, 11:30 AM, 3:30 PM)
Barracuda (Great)
Bonefish
Jack Crevalle
Permit
+3
US $389
Entire boat: 2 people
4 Hour Lobster Snorkeling
FREE Cancellation 3 days notice
4 hour trip multiple starting times (8:00 AM, 11:30 AM, 2:30 PM)
Seasonal trip
Aug 6 - Mar 31
Lobster
US $549
Entire boat: 2 people
4 Hour Trip
In high demand Last booked: 3 days ago
FREE Cancellation 3 days notice
4 hour trip multiple starting times (8:00 AM, 11:30 AM, 2:30 PM)
Barracuda (Great)
Bonefish
Jack Crevalle
Permit
+3
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
Snapper (Mangrove)
US $549
Entire boat: 2 people
6 Hour Trip
FREE Cancellation 3 days notice
6 hour trip multiple starting times (8:00 AM, 12:30 PM)
Barracuda (Great)
Bonefish
Jack Crevalle
Permit
+3
US $849
Entire boat: 2 people

Customer reviews

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Rating

4.9
837 reviews
4.8
Boat & equipment
4.9
Captain & crew
4.9
Fishing Experience

Anglers' gallery (937)

What anglers say

95%
Great experience
93%
Family friendly
100%
Friendly captain
98%
Good boat
97%
Recommended
93%
Caught fish

Reviews (837)

  • Christopher Schissler
    Christopher Schissler
    Repeat angler
    us
    Maryland, US
    Member since 2025
    2 trips
    5.0
    Verified

    Great guide and teacher

    3 Hour Trip - 4:45 PM on August 24, 2026 • 2 adults

    My buddy n I took this 3 hr trip to gain whatever knowledge we could to help us catch multiple species at Fort Jefferson, kayak fishing. Capn Chandler gave us a wealth of info on tackle selection, where and how to fish it on the flats relative to what structure we would encounter at the fort based on his 1st hand experience there. His patient instruction and pleasant demeanor helped us to land several nice baracuda and several mangrove snapper in a short peiod of time. He was an amicable and entertaining host with a passion and enthusiastic attitude toward puting us on to fish. Hope to fish with him again.

  • Ian Wood
    Ian Wood
    Repeat angler
    us
    Pennsylvania, US
    Member since 2023
    2 trips
    5.0
    Verified

    Captain Chandler ⭐️⭐️⭐️⭐️⭐️

    6 Hour Trip on August 8, 2026 • 2 adults

    What an incredible day fishing with Captain Chandler in Key West! From the moment we left the dock, you could tell he truly loves what he does, and his passion made the entire trip even better. We caught a ton of big fish, especially barracuda and snapper, and the action never slowed down. The real game changer was fishing the Tube Bait, it was absolutely incredible and had the fish fired up all day. Captain Chandler knew exactly where to go, shared great tips, and made sure everyone had an unforgettable experience. If you’re looking for an amazing fishing charter in Key West, book with Captain Chandler. We’ll definitely be back!

  • Steven Goetz
    Steven Goetz
    Repeat angler
    us
    New York, US
    Member since 2026
    4 trips
    5.0
    Verified

    Great Day on the Water

    3 Hour Trip on June 28, 2026 • 2 adults

    Went for a 3 hour trip with Captain Chandler. He did a great job explaining the equipment and how to use the fishing pole and bait, for the fish we were trying to catch. We kept 3 fish that we caught and a total of about 15. Captain Chandler filleted the fish and told us which restaurant to go to, so that could prepare the fish. At the restaurant, they made us blackened mangrove fish, which is what we caught and we had fish tacos which were amazing. Highly recommend this trip.

  • Nicholas Mcgee
    Nicholas Mcgee
    us
    Texas, US
    Member since 2026
    5.0
    Verified

    My Son’s First Time Fishing In Key West!!

    3 Hour Trip - 10:30 AM on July 1, 2026 • 2 adults • 1 child

    It was the first time in Key West for my 9 year-old son. His biggest request was that we go fishing. So, I booked this private charter with just us two and the captain, and Captain Chandler was phenomenal! He put us on fish immediately, and when it went cold, he moved to different spots where the fish were biting again. He was knowledgeable and very patient with my son. He has the heart of a teacher. I would definitely book with this company again!

  • Eric Howard
    Eric Howard
    us
    New York, US
    Member since 2026
    5.0
    Verified

    Capt Chandler

    3 Hour Trip (11:30 AM) on March 4, 2026 • 2 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😉🤣..........

  • Celeste Cole
    Celeste Cole
    us
    Oregon, US
    Member since 2024
    5.0
    Verified

    Very Fishy!

    4 Hour Trip (9:30 AM) on January 11, 2026 • 3 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!!!!

  • John Hagen
    John Hagen
    us
    Ohio, US
    Member since 2026
    5.0
    Verified

    Great Trip!

    3 Hour Trip - 10:30 AM on September 1, 2026 • 1 adult

    Captain Chandler was great. We pretty much had zero fishing experience but wanted to try it out. My wife actually decided to come last minute and she loved it too. He showed us the techniques and my wife caught two mangrove snapper right away. We ended up keeping a few to cook at the local restaurant. We also caught some grouper, yellowtail, mutton, and one giant Barracuda. It was a great time. Thank You!

  • John Mccray
    John Mccray
    us
    Colorado, US
    Member since 2026
    5.0
    Verified

    favorite fishing trip of all time

    3 Hour Trip - 4:45 PM on July 28, 2026 • 3 adults

    Captain Chandler was awesome. I was afraid we wouldn’t be able to catch fish in the late afternoon in the hot waters of the Key West flats, but we caught almost 2 dozen snapper, throwing most of them back (because we only wanted enough for two meals), and it was really fun catching barracuda. Chandler, you seem to know exactly where to go. Every time we move we caught fish. Highly, highly recommend this trip!

  • Jeremy Sylvester
    Jeremy Sylvester
    Repeat angler
    us
    Wisconsin, US
    Member since 2024
    3 trips
    5.0
    Verified

    100% recommend

    3 Hour Trip (11:30 AM) on November 21, 2025 • 2 adults

    Our experience with Always Something Charters was truly beyond our expectations. Captain Srb was incredibly friendly, accommodating, and genuinely went out of his way to make sure we had an amazing time on the water. Not only did we catch an abundance of fish, but I even had the unforgettable opportunity to catch a shark—something I never expected! The added touches, like having ice-cold water and Gatorade available, made the trip even better and showed how much they care about their guests’ comfort. Highly recommend—an outstanding experience from start to finish.

  • Daniel Stickler
    Daniel Stickler
    Repeat angler
    us
    Michigan, US
    Member since 2026
    2 trips
    5.0
    Verified
    New

    My favorite fishing trip ever

    3 Hour Trip - 10:30 AM on November 10, 2026 • 2 adults

    Fishing with Captain Chandler was awesome. 5 different species all new to us! My wife was nervous about fishing in the ocean before going out but because of Chandlers professionalism and knowledge we both can’t wait to get out again! 

FAQs about Always Somethin' Charters – Key West

Always Somethin' Charters – Key West offers the following trips to customers:
  • US $389 per group, additional US $49 per person after 2 guests - 3 Hour Lobster Snorkeling (3 hours)
  • US $389 per group, additional US $49 per person after 2 guests - 3 Hour Lobster Snorkeling - 11:30 AM (3 hours)
  • US $389 per group, additional US $49 per person after 2 guests - 3 Hour Lobster Snorkeling - 3:30 PM (3 hours)
  • US $389 per group, additional US $49 per person after 2 guests - 3 Hour Trip (3 hours)
  • US $389 per group, additional US $49 per person after 2 guests - 3 Hour Trip - 11:30 AM (3 hours)
  • US $389 per group, additional US $49 per person after 2 guests - 3 Hour Trip - 3:30 PM (3 hours)
  • US $549 per group, additional US $49 per person after 2 guests - 4 Hour Lobster Snorkeling (4 hours)
  • US $549 per group, additional US $49 per person after 2 guests - 4 Hour Lobster Snorkeling - 11:30 AM (4 hours)
  • US $549 per group, additional US $49 per person after 2 guests - 4 Hour Lobster Snorkeling - 2:30 PM (4 hours)
  • US $549 per group, additional US $49 per person after 2 guests - 4 Hour Trip (4 hours)
  • US $549 per group, additional US $49 per person after 2 guests - 4 Hour Trip - 11:30 AM (4 hours)
  • US $549 per group, additional US $49 per person after 2 guests - 4 Hour Trip - 2:30 PM (4 hours)
  • US $549 per group, additional US $49 per person after 2 guests - Shallow Water Spearfishing (4 hours)
  • US $849 per group, additional US $49 per person after 2 guests - 6 Hour Trip (6 hours)
  • US $849 per group, additional US $49 per person after 2 guests - 6 Hour Trip - 12:30 PM (6 hours)
When you book a trip with Always Somethin' Charters – Key West, you can expect the following amenities onboard:
  • GPS
  • Fishfinder
  • Live bait well
  • Ice box
  • Radar
Trips booked with Always Somethin' Charters – Key West include:
  • Rods, reels & tackle (Available for both right and left handed)
  • Lures (The Captains choice based on whats working)
  • Catch cleaning & filleting (Cleaned and bagged how you want them)
  • Drinks (Gatorade , and water are aboard)
  • Fishing license (Captains got you covered under there license)
  • Fly fishing equipment (upon request only)
Always Somethin' Charters – Key West offers the following types of fishing:
  • Inshore fishing
  • Nearshore fishing
  • Flats fishing
  • Backcountry fishing
Always Somethin' Charters – Key West offers the following fishing techniques:
  • Light tackle
  • Heavy tackle
  • Bottom fishing
  • Trolling
  • Jigging
  • Popping
  • Fly fishing
Top targeted fish species with Always Somethin' Charters – Key West include:
  • Barracuda (Great)
  • Bonefish
  • Jack Crevalle
  • Permit
  • Shark (Blacktip)
  • Snapper (Mangrove)
  • Snook
  • Tarpon

Your operator

Always Somethin' Charters
Always Somethin' Charters
Key West, Florida, United States
863 Customer reviews
Typical response within an hour
Member since December 2020
Angler's Choice
The Angler's Choice Award is given to listings that consistently deliver a high-quality service and earn great reviews from customers.
Since I could walk, I've had a fishing pole in my hands. I've fished all over the United States and Canada for all kinds of fish but ultimately fell in love with the fishing here in Florida. With all the diversity of species here, it was a hard spot to pass up, and what better job than as a charter captain, where I can share what I love, with those that visit? Tight lines, and I'll see you at the dock.
Our Team
Tyler S.
Tyler S.
Captain
Chandler O.
Chandler O.
Captain
Grason S.
Grason S.
Captain
Always Somethin' Charters
Always Somethin' Charters
Angler's Choice
863
reviews
2020
member since
~1h
response
Since I could walk, I've had a fishing pole in my hands. I've fished all over the United States and Canada for all kinds of fish but ultimately fell in love with the fishing here in Florida. With all the diversity of species here, it was a hard spot to pass up, and what better job than as a charter captain, where I can share what I love, with those that visit? Tight lines, and I'll see you at the dock.
The crew
Tyler S.
Tyler S.
Captain
Chandler O.
Chandler O.
Captain
Grason S.
Grason S.
Captain

The fish you can target

Great Barracuda
Great Barracuda
Bonefish
Bonefish
Jack Crevalle
Jack Crevalle
Permit
Permit
Blacktip Shark
Blacktip Shark
Mangrove Snapper
Mangrove Snapper
Snook
Snook
Tarpon
Tarpon
Great Barracuda
Great Barracuda
Bonefish
Bonefish
Jack Crevalle
Jack Crevalle
Permit
Permit
Blacktip Shark
Blacktip Shark

Real catches by this captain

  • Solo adult angler fishing from the bow of a center-console boat on open coastal waters, with a cooler visible on deck.
    Alan H.
    Alan H.
    Wonderful day of fishing with Capt. Chandler. He gave great instructions and knew where the fish were. I highly recommend.
  • Close-up of a spotted grouper-style fish being held over the water beside a fishing rod.
    Fish 1
    Fish 2
    Gag Grouper
    Andrew S.
    Andrew S.
    chandler was awesome and very knowledgeable!
  • Solo angler holding a large barracuda on the bow of a boat in clear coastal waters surrounded by mangroves.
    Fish 1
    Great Barracuda
    Daniel S.
    Daniel S.
    Fishing with Captain Chandler was awesome. 5 different species all new to us! My wife was nervous about fishing in the ocean before going out but because of Chandlers professionalism and knowledge we both can’t wait to get out again! 
  • Adult angler proudly holding a large silver bonefish over clear coastal waters during an inshore fishing trip.
    Fish 1
    Great Barracuda
    Bill B.
    Bill B.
    Capt. Chandler and I fished in the Gulf on a cloudless, windy day. I caught 8 fish: 4 Great Barracudas, 2 Mangrove Snappers, a Needlefish, and a Bonefish. The biggest Barracuda was 30", the Bonefish was 24¼”, and the Needlefish was 19". The whole day was cast and retrieve with a variety of Chandler's lures. It was fun.
  • Angler proudly displaying a large Barracuda while fishing on a boat in open waters.
    Fish 1
    Great Barracuda
    Cristie H.
    Cristie H.
    Caught a huge great barracuda!
  • A young angler and adult proudly display a colorful snapper aboard a center-console fishing boat in calm coastal waters.
    Fish 1
    Fish 2
    Mutton Snapper
    Nathan M.
    Nathan M.
    I took my son for 6th birthday and we had an incredible time! The captain was good and patient with my son the whole day, he even made a stop at a sandbar so my little guy could take a break and swim. We were on the fish all day and I cannot say enough abiut how great this trip was. 10/10 - will do it again!
  • A young angler casting a fishing rod while accompanied by an adult on a calm day at sea.
    Stephanie M.
    Stephanie M.
    My family had such a fun time fishing with Captain Chandler. We appreciated his guidance and insight. We had to reschedule due to bad weather but he was able to get us the next day. Overall, I recommend this group!
  • Adult angler holding a large barracuda aboard a small fishing boat in calm tropical coastal waters.
    Fish 1
    Fish 2
    +2
    Great Barracuda
    John H.
    John H.
    Captain Chandler was great. We pretty much had zero fishing experience but wanted to try it out. My wife actually decided to come last minute and she loved it too. He showed us the techniques and my wife caught two mangrove snapper right away. We ended up keeping a few to cook at the local restaurant. We also caught some grouper, yellowtail, mutton, and one giant Barracuda. It was a great time. Thank You!
  • Adult angler holding a large silver tarpon aboard a boat at sunset on calm coastal waters.
    John C.
    John C.
    went out after hours and hooked up with numerous tarpon. hap plenty of bone fish and multiple shots at permit.
  • Adult angler holding a large barracuda over shallow coastal water surrounded by mangroves.
    Fish 1
    Great Barracuda
    Christopher S.
    Christopher S.
    My buddy n I took this 3 hr trip to gain whatever knowledge we could to help us catch multiple species at Fort Jefferson, kayak fishing. Capn Chandler gave us a wealth of info on tackle selection, where and how to fish it on the flats relative to what structure we would encounter at the fort based on his 1st hand experience there. His patient instruction and pleasant demeanor helped us to land several nice baracuda and several mangrove snapper in a short peiod of time. He was an amicable and entertaining host with a passion and enthusiastic attitude toward puting us on to fish. Hope to fish with him again.

What is the boat like?

Boat image
Boat category
Skiffs and flats boats
Capacity
3 persons
Boat length
18 ft
Year built
2008
Restored in
2024
Boat manufacturer
Sterling Tr7
Boat type
Flats boat
Engine model
Mercury
Powered by
1 x 60HP
Max cruising speed
30 knots

What kind of fishing will you do?

Inshore Fishing
Nearshore Fishing
Flats Fishing
Backcountry Fishing

Which fishing techniques you can try

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Jigging
Popping
Fly Fishing

Which amenities are available onboard

GPS
Fishfinder
Live bait well
Ice box
Radar
What's included in the trip price
Rods, reels & tackle
Available for both right and left handed
Lures
The Captains choice based on whats working
Catch cleaning & filleting
Cleaned and bagged how you want them
Drinks
Gatorade , and water are aboard
Fishing license
Captains got you covered under there license
Fly fishing equipment
upon request only

How cancellations work

Free cancellation up to 3 days prior to trip
You can cancel or modify your booking up to 3 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.
More details

What the listing policies are

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child friendly
Children of all ages are welcome aboard!
You keep catch
We will fillet your catch and bag them for you
Catch and release allowed
Let em' go, let em' grow. always allowed

How you can pay

Pay online in full
Pay online in full through FishingBooker and save on credit card fees at the dock.
No additional fees.
Book with 30% deposit, pay rest to captain
When the captain confirms your trip, FishingBooker charges your credit card a 30% deposit to guarantee your reservation.
The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:
 Cash
 Visa
 Mastercard
 American Express
 PayPal
 Checks
 Bank transfer
When paying the remaining balance with a credit card, an additional 3.5% charge will apply.

What’s biting in Key West right now

Barracuda (Great)Barracuda (Great)
BonefishBonefish
Jack CrevalleJack Crevalle
PermitPermit
Shark (Blacktip)Shark (Blacktip)
Snapper (Mangrove)Snapper (Mangrove)
SnookSnook
TarponTarpon

Compare similar fishing charters

Current
Always Somethin' Charters – Key West
Always Somethin' Charters – Key West
State licensed
4.9
(837)
18 ft
Group size 1 - 3
1 - 3
Fish 1
Fish 2
+6
4 hour trip • 3 persons
US $549