Always Somethin' Charters – Vessel 2 

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

Always Somethin' Charters – Vessel 2 

Key West, FL, United States
–
18 ft
3
4.9
(25 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 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.

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.

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 date:
Group Size:
October 2026
SuMoTuWeThFrSa
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Group Size
2 adults • 0 children
Change
Almost there...
3 Hour Trip (AM)
In high demand Last booked: 5 days ago
FREE Cancellation 3 days notice
3 hour trip starts at 7:30 AM
Barracuda (Great)
Bonefish
Permit
Snook
+4
US $389
Entire boat: 2 people
3 Hour Trip (Late AM)
FREE Cancellation 3 days notice
3 hour trip starts at 11:30 AM
Seasonal trip
Oct 1 - Jun 30
Barracuda (Great)
Bonefish
Jack Crevalle
Permit
+5
US $389
Entire boat: 2 people
3 Hour Trip (PM)
FREE Cancellation 3 days notice
3 hour trip starts at 3:00 PM
Barracuda (Great)
Bonefish
Jack Crevalle
Permit
+5
US $389
Entire boat: 2 people
4 Hour Trip (AM)
In high demand Last booked: 5 days ago
FREE Cancellation 3 days notice
4 hour trip starts at 7:30 AM
Barracuda (Great)
Bonefish
Jack Crevalle
Permit
+5
US $549
Entire boat: 2 people
4 Hour Trip (Mid AM)
FREE Cancellation 3 days notice
4 hour trip starts at 9:30 AM
Seasonal trip
Oct 1 - Jun 30
Barracuda (Great)
Bonefish
Jack Crevalle
Permit
+5
US $549
Entire boat: 2 people
6 Hour Trip (AM)
FREE Cancellation 3 days notice
6 hour trip starts at 7:30 AM
Barracuda (Great)
Bonefish
Jack Crevalle
Permit
+5
US $849
Entire boat: 2 people
There are 2 people looking at this charter.

Customer reviews

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Rating

4.9
25 reviews
4.9
Boat & equipment
5.0
Captain & crew
5.0
Fishing Experience

Anglers' gallery (16)

Reviews (25)

  • Kenneth Reeves
    Kenneth Reeves
    us
    Tennessee, US
    Member since 2026
    5.0
    Verified

    Great Day on the Water

    4 Hour Trip (Mid AM) on May 29, 2026 • 3 adults

    Chandler was great! Super friendly and very helpful with the first-time fishers in our group. Put us on some barracuda, mangrove snapper, and black tip shark. Very experienced. Would be a great guide for any level of fisher.

  • Bradley Adams
    Bradley Adams
    us
    Alabama, US
    Member since 2026
    5.0
    Verified

    Great Experience

    3 Hour Trip (PM) on February 19, 2026 • 1 adult

    Captain Chandler was great. Spent time figuring out my experience level, asked me why I wanted to catch and put a plan together to go get em. Caught a beautiful 40” barracuda that captain Chandler really helped me land in the boat with his direction and coaching. Overall, great experience and I would highly recommend.

  • Judy Hambleton
    Judy Hambleton
    us
    Virginia, US
    Member since 2026
    5.0
    Verified

    February fishing trip

    3 Hour Trip (PM) on February 26, 2026 • 1 adult

    it was such a beautiful view and Chandler was fabulous. He made sure I caught fish— barracuda and mangrove snapper:) He was such a great instructor and his knowledge of the ecosystem and the area was super interesting. absolutely great time w him!

  • Timothy Costanzo
    Timothy Costanzo
    us
    Nebraska, US
    Member since 2026
    5.0
    Verified

    Best trip ever

    3 Hour Trip (AM) on February 24, 2026 • 1 adult

    Captain show me how fish different areas. Also had great conversations along the way

  • Rosanna Franco
    Rosanna Franco
    us
    Texas, US
    Member since 2025
    5.0
    Verified

    Great memories!

    4 Hour Trip (AM) on June 19, 2025 • 3 adults

    We had SO MUCH FUN! Thanks to our captain being patient and helpful with fishing techniques AND not shy about moving around to find the fish! We definitely recommend this charter 👍can't wait for the next time!!

  • Tom Law
    Tom Law
    Repeat angler
    us
    California, US
    Member since 2019
    4 trips
    5.0
    Verified

    Great fishing trip

    3 Hour Trip (AM) on May 21, 2025 • 2 adults

    Captain SRB is so talented and so much fun to be with. We caught Tarpon, Barracuda, Snapper. We had the best time. Thank you Captain SRB for such a wonderful trip. See you next year.

  • Dave Koch
    Dave Koch
    us
    North Carolina, US
    Member since 2025
    5.0
    Verified

    Great Captain, Amazing Experience

    3 Hour Trip (PM) on June 16, 2025 • 2 adults • 1 child

    I had a wonderful time and wish I could come back. Brennan 11 years old Great customer service, very knowledgeable, highest recommendation!!

  • Molly Horton
    Molly Horton
    us
    Vermont, US
    Member since 2025
    5.0
    Verified

    March fishing trip

    3 Hour Trip (AM) on March 23, 2025 • 2 adults
  • Eric Klein
    Eric Klein
    us
    Maine, US
    Member since 2026
    5.0
    Verified

    Top Notch

    3 Hour Trip (AM) on June 30, 2026 • 1 adult

    What an outstanding experience. Captain Chandler was adept at silently sneaking up on several schools of bonefish, putting me is perfect position every time. His knowledge and experience was just as impressive when we later hit the deeper waters and once again got into fish. In addition to phenomenal fishing, Captain Chandler was a superb guide as we traded stories and tales to make it a truly memorable adventure. I would recommend him to anyone, whether it be a die hard angler in pursuit of the Keys trophy fish, or a family just looking to get out into the water.

  • Ricky Bybee
    Ricky Bybee
    us
    Florida, US
    Member since 2023
    5.0
    Verified

    Fishing with Srbo

    4 Hour Trip (AM) on August 22, 2026 • 2 adults

    Chandler, our Capt, was a most gracious host. He was informative, knowleable and a great stiry teller. He put us on fish right away and ensure the action never stopped. I highly recommend Chandler if your coming down to fish the flats. Booking my next trip now!

Rating

4.9
25 reviews
4.9
Boat & equipment
5.0
Captain & crew
5.0
Fishing Experience

Anglers' gallery (16)

All reviews (25)

Frequently mentioned
Showing 1 – 5 of 25 reviews
Eric Klein
Eric Klein
us
Maine, US
Member since 2026
5.0
Verified
Top Notch
3 Hour Trip (AM) on June 30, 2026 • 1 adult

What an outstanding experience. Captain Chandler was adept at silently sneaking up on several schools of bonefish, putting me is perfect position every time. His knowledge and experience was just as impressive when we later hit the deeper waters and once again got into fish. In addition to phenomenal fishing, Captain Chandler was a superb guide as we traded stories and tales to make it a truly memorable adventure. I would recommend him to anyone, whether it be a die hard angler in pursuit of the Keys trophy fish, or a family just looking to get out into the water.

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 🤙🏼

Ricky Bybee
Ricky Bybee
us
Florida, US
Member since 2023
5.0
Verified
Fishing with Srbo
4 Hour Trip (AM) on August 22, 2026 • 2 adults

Chandler, our Capt, was a most gracious host. He was informative, knowleable and a great stiry teller. He put us on fish right away and ensure the action never stopped. I highly recommend Chandler if your coming down to fish the flats. Booking my next trip now!

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 🤙🏼

Kenneth Reeves
Kenneth Reeves
us
Tennessee, US
Member since 2026
5.0
Verified
Great Day on the Water
4 Hour Trip (Mid AM) on May 29, 2026 • 3 adults

Chandler was great! Super friendly and very helpful with the first-time fishers in our group. Put us on some barracuda, mangrove snapper, and black tip shark. Very experienced. Would be a great guide for any level of fisher.

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

Thank you! It was awesome having you aboard and I’m thankful you enjoyed your time on the water, Tight lines and we will catch you on the next one 🤙🏼

Bradley Adams
Bradley Adams
us
Alabama, US
Member since 2026
5.0
Verified
Great Experience
3 Hour Trip (PM) on February 19, 2026 • 1 adult

Captain Chandler was great. Spent time figuring out my experience level, asked me why I wanted to catch and put a plan together to go get em. Caught a beautiful 40” barracuda that captain Chandler really helped me land in the boat with his direction and coaching. Overall, great experience and I would highly recommend.

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

Thank you! We appreciate that! It was awesome having you aboard and I’m thankful you enjoyed your time on the water, tight lines my friend, and we will see you on the next one 🤙🏼

Kristen Stone
Kristen Stone
Repeat angler
us
North Carolina, US
Member since 2018
2 trips
5.0
Verified
Fishing with Srbo
3 Hour Trip (AM) on June 27, 2026 • 3 adults

Lot’s of fun! Captain Chandler put us on the fish everywhere we stopped!

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 – Vessel 2

Always Somethin' Charters – Vessel 2 offers the following trips to customers:
  • US $389 per group, additional US $49 per person after 2 guests - 3 Hour Trip (AM) (3 hours)
  • US $389 per group, additional US $49 per person after 2 guests - 3 Hour Trip (Late AM) (3 hours)
  • US $389 per group, additional US $49 per person after 2 guests - 3 Hour Trip (PM) (3 hours)
  • US $549 per group, additional US $49 per person after 2 guests - 4 Hour Trip (AM) (4 hours)
  • US $549 per group, additional US $49 per person after 2 guests - 4 Hour Trip (Mid AM) (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 – Vessel 2, you can expect the following amenities onboard:
  • GPS
  • Fishfinder
  • Live bait well
  • Ice box
  • Radar
Trips booked with Always Somethin' Charters – Vessel 2 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 – Vessel 2 offers the following types of fishing:
  • Inshore fishing
  • Nearshore fishing
  • Flats fishing
  • Backcountry fishing
Always Somethin' Charters – Vessel 2 offers the following fishing techniques:
  • Light tackle
  • Heavy tackle
  • Bottom fishing
  • Trolling
  • Jigging
  • Popping
  • Fly fishing
  • Handline
Top targeted fish species with Always Somethin' Charters – Vessel 2 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
853 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
853
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

  • Great Day on the Water
    Kenneth R.
    Kenneth R.
  • Best trip ever
    Timothy C.
    Timothy C.
  • Great Experience
    Bradley A.
    Bradley A.
  • Great memories!
    Rosanna F.
    Rosanna F.
  • Great fishing trip
    Tom L.
    Tom L.
  • March fishing trip
    Molly H.
    Molly 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
2020
Boat manufacturer
Sterling
Boat type
Skiff
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
Handline

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

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State licensed
4.9
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