Always Somethin' Charters – Vessel 2 

4.9/5 (17 reviews)
 
State licensed
 1801 North Roosevelt Boulevard, Key West, FL 33040, United States

Always Somethin' Charters – Vessel 2 

 
State licensed
4.9/5 (17)
 Angler's Choice
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1801 North Roosevelt Boulevard
Key West, FL, United States
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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.

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Rating

4.9
17 reviews
5
16
4
1
3
0
2
0
1
0
4.9
Boat & equipment
4.9
Captain & crew
4.9
Fishing Experience

Anglers' gallery (13)

February fishing trip
Best trip ever
Best trip ever
Great Experience
Great memories!
Great memories!
+7

All reviews (17)

Filter
Showing 15 of 17 reviews
Bradley Adams
Bradley Adams
5.0
Verified
New
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.
Review media 0
Reported catch:
Great Barracuda
Mangrove Snapper
Response from Captain
February 23, 2026
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 🤙🏼
0
Judy Hambleton
Judy Hambleton
5.0
Verified
New
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!
Review media 0
Response from Captain
March 1, 2026
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 🤙🏼
0
Chet Richter
Chet Richter
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!
Response from Captain
October 16, 2025
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 🤙🏼
0
Timothy Costanzo
Timothy Costanzo
5.0
Verified
New
Best trip ever
3 Hour Trip (AM) on February 24, 20261 adult
Captain show me how fish different areas. Also had great conversations along the way
Review media 0
Review media 1
Response from Captain
February 26, 2026
Thank you so much! 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 🤙🏼
0
Tyler Hebert
Tyler Hebert
5.0
Verified
absolute FANTASTIC time
3 Hour Trip (AM) on December 11, 20252 adults
Capt Tyler was nothing but THE MAN. Hooked us up to a variety of fish, very knowledgeable of the area and where and where not to go- had a fantastic time and just booked another trip. Will 100% always book through these guys.
Response from Captain
December 12, 2025
Thanks so much! I’m happy you enjoyed your time on the water! It was a pleasure having you aboard! Tight lines my friend and we will see you tomorrow!🤙🏼
0

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
March 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
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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
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US $389
Entire boat: 2 people
3 Hour Trip (PM)
FREE Cancellation 3 days notice
3 Hour Trip
starts at 3:00 PM
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US $389
Entire boat: 2 people
4 Hour Trip (AM)
FREE Cancellation 3 days notice
4 Hour Trip
starts at 7:30 AM
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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
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US $549
Entire boat: 2 people
6 Hour Trip (AM)
FREE Cancellation 3 days notice
6 Hour Trip
starts at 7:30 AM
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US $849
Entire boat: 2 people
There are 5 people looking at this charter.

Rating

4.9
17 reviews
5
16
4
1
3
0
2
0
1
0
4.9
Boat & equipment
4.9
Captain & crew
4.9
Fishing Experience

Anglers' gallery (13)

February fishing trip
Best trip ever
Best trip ever
Great Experience
Great memories!
Great memories!
+7

All reviews (17)

Filter
Showing 15 of 17 reviews
Bradley Adams
Bradley Adams
5.0
Verified
New
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.
Review media 0
Reported catch:
Great Barracuda
Mangrove Snapper
Response from Captain
February 23, 2026
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 🤙🏼
0
Judy Hambleton
Judy Hambleton
5.0
Verified
New
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!
Review media 0
Response from Captain
March 1, 2026
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 🤙🏼
0
Chet Richter
Chet Richter
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!
Response from Captain
October 16, 2025
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 🤙🏼
0
Timothy Costanzo
Timothy Costanzo
5.0
Verified
New
Best trip ever
3 Hour Trip (AM) on February 24, 20261 adult
Captain show me how fish different areas. Also had great conversations along the way
Review media 0
Review media 1
Response from Captain
February 26, 2026
Thank you so much! 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 🤙🏼
0
Tyler Hebert
Tyler Hebert
5.0
Verified
absolute FANTASTIC time
3 Hour Trip (AM) on December 11, 20252 adults
Capt Tyler was nothing but THE MAN. Hooked us up to a variety of fish, very knowledgeable of the area and where and where not to go- had a fantastic time and just booked another trip. Will 100% always book through these guys.
Response from Captain
December 12, 2025
Thanks so much! I’m happy you enjoyed your time on the water! It was a pleasure having you aboard! Tight lines my friend and we will see you tomorrow!🤙🏼
0

FAQs about Always Somethin' Charters – Vessel 2

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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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