Always Somethin' Charters – Key West 

4.9
(818 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
(818 reviews)

Booked with us before? You may qualify for a Loyalty Discount. Sign in to check.

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
ID & credentials verified
responds within an hour

Select date to see availability

Trip availability and prices

Trip date:
Group Size:
September 2026
SuMoTuWeThFrSa
Loading...
Group Size
2 adults • 0 children
Change
Almost there...
3 Hour Trip
In high demand Last booked: 1 day ago
FREE Cancellation 3 days notice
3 hour trip multiple starting times (7:00 AM, 10:30 AM, 1:30 PM, 4:45 PM)
Barracuda (Great)
Bonefish
Jack Crevalle
Permit
+5
US $389
Entire boat: 2 people
4 Hour Trip
In high demand Last booked: 6 days ago
FREE Cancellation 3 days notice
4 hour trip multiple starting times (7:00 AM, 11:30 AM, 4:00 PM)
Barracuda (Great)
Bonefish
Jack Crevalle
Permit
+5
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 (AM)
FREE Cancellation 3 days notice
6 hour trip starts at 6:30 AM
Barracuda (Great)
Bonefish
Jack Crevalle
Permit
+5
US $849
Entire boat: 2 people
There are 35 people looking at this charter.

Customer reviews

Loading...

Rating

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

Anglers' gallery (925)

What anglers say

96%
Great experience
93%
Family friendly
100%
Friendly captain
99%
Good boat
97%
Recommended
93%
Caught fish

All reviews (818)

Frequently mentioned
Showing 15 of 818 reviews
Christopher Schissler
Christopher Schissler
Repeat angler
us
Maryland, US
Member since 2025
2 trips
5.0
Verified
New
Great guide and teacher
3 Hour Trip - 4:45 PM on August 24, 20262 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.

Reported catch:
Great Barracuda
Mangrove Snapper
Always Somethin' Charters
Response from Charter operator

Thanks so much! It was great having you aboard and we are thankful you enjoyed your time on the water! Tight lines and we will catch you on the next one 🤙🏼

Ian Wood
Ian Wood
Repeat angler
us
Pennsylvania, US
Member since 2023
2 trips
5.0
Verified
Captain Chandler ⭐️⭐️⭐️⭐️⭐️
6 Hour Trip (AM) on August 8, 20262 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!

Reported catch:
Great Barracuda
Mangrove Snapper
Tarpon
Always Somethin' Charters
Response from Charter operator

Awesome! Thanks so much! It was great having you aboard and we are thankful you enjoyed your time on the water! It will never make sense to me why the fish love that tube bait so much, but it is super effective and im not going to argue with them 😂 Tight lines and we will catch you on the next one 🤙🏼

John Hagen
John Hagen
us
Ohio, US
Member since 2026
5.0
Verified
New
Great Trip!
3 Hour Trip - 10:30 AM on September 1, 20261 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!

Reported catch:
Great Barracuda
Jack Crevalle
Mangrove Snapper
Always Somethin' Charters
Response from Charter operator

So Awesome!! Thanks so much! It was great having you aboard and we are thankful you enjoyed your time on the water! Tight lines and we will catch you on the next one 🤙🏼

Mark Flynn
Mark Flynn
Repeat angler
us
Georgia, US
Member since 2026
2 trips
5.0
Verified
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.

Always Somethin' Charters
Response from Charter operator

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 🤙🏼

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, 20262 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.

Reported catch:
Mangrove Snapper
Always Somethin' Charters
Response from Charter operator

Thanks so much! It was Great having you aboard and i’m so thankful you enjoyed your time on the water! Tight lines and we will catch you on the next one 🤙🏼

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 Trip (3 hours)
  • US $389 per group, additional US $49 per person after 2 guests - 3 Hour Trip - 1:30 PM (3 hours)
  • US $389 per group, additional US $49 per person after 2 guests - 3 Hour Trip - 10:30 AM (3 hours)
  • US $389 per group, additional US $49 per person after 2 guests - 3 Hour Trip - 4:45 PM (3 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 - 4:00 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 (AM) (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

ID & license verified
843 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
Fully verified
Angler's Choice
843
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

  • Awesome Trip
    Jackson B.
    Jackson B.
  • great experience
    Anthony A.
    Anthony A.
  • Captain Chandler ⭐️⭐️⭐️⭐️⭐️
    Ian W.
    Ian W.
  • Daughter landed her first fish!
    Whelan L.
    Whelan L.
  • great trip
    Gary N.
    Gary N.
  • favorite fishing trip of all time
    John M.
    John M.
  • Great morning with a great Captain
    Garfield G.
    Garfield G.
  • amazing!
    Christopher H.
    Christopher H.

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

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
(818)
18 ft
Group size 1 - 3
1 - 3
Fish 1
Fish 2
+6
4 hour trip • 2 persons
US $549