Always Somethin' Charters – Vessel 2 

4.9/5 (24 reviews)
 
State licensed
 1801 North Roosevelt Boulevard, Key West, FL 33040, United States

Always Somethin' Charters – Vessel 2 

State licensed
Key West, FL, United States
18 ft
3
4.9/5 (24 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

Trip availability and prices

Trip Date:
Group Size:
Select date to see availability
July 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
3 Hour Trip (AM)
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)
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 is 1 person looking at this charter.

Customer reviews

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Rating

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

Anglers' gallery (16)

All reviews (24)

Frequently mentioned
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Showing 15 of 24 reviews
Eric Klein
Eric Klein
us
Maine, US
Member since 2026
5.0
Verified
Top Notch
3 Hour Trip (AM) on June 30, 20261 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 🤙🏼

Bradley Adams
Bradley Adams
us
Alabama, US
Member since 2026
5.0
Verified
Great Experience
3 Hour Trip (PM) on February 19, 20261 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 🤙🏼

Judy Hambleton
Judy Hambleton
us
Virginia, US
Member since 2026
5.0
Verified
February fishing trip
3 Hour Trip (PM) on February 26, 20261 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!

Always Somethin' Charters
Response from Charter operator

Awesome! so glad you enjoyed your time! It was a pleasure having you aboard and we appreciate the review. Tight lines and we will see 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, 20263 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 🤙🏼

Chet Richter
Chet Richter
us
Sealy, TX, US
Member since 2025
5.0
Verified
October fishing trip
3 Hour Trip (PM) on October 13, 20252 adults

We had the best time on our fishing trip. Srbo was extremely helpful and genuinely wanted us to have the best experience possible. He was very knowledgeable in the areas we fished in. We've been on lots of fishing trips and this was truly one of THE BEST! We will definitely use Srbo again when we are back in the area!

Always Somethin' Charters
Response from Charter operator

Thank you so much! it was awesome having you guys out there! I’m very thankful you guys enjoyed a beautiful day on the water. I am looking for to the next one, tight lines my friends 🤙🏼

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
Always Somethin' Charters

Key West, Florida, United States

ID & license verified
819 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

ID & license verified
819 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

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

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

Compare similar fishing charters

Current
Always Somethin' Charters – Vessel 2
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State licensed
4.9
(24)
18 ft
Group size 1 - 3
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+6
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US $549