Second Generation Fishing Charter

Key West, Florida
Book Now Meet Your Guide
Key West Drag Ripping

About Your Guide

Profile photo of Captain Experiences guide Rob Delph

Rob Delph

Independent Guide
Talkative
Instructional
Beginner Oriented
Laid-back
Adventurous
Quality
Capt. Rob has over 30 years of fishing and boating experience. His father Ralph was a champion tournament angler, and he passed his passion and experience down to Rob. Captain Rob holds an IGFA World Record for a 38lbs, 12oz King Mackerel on 4lbs. test line! The angler's name was Jerry Mathews. If you're looking for an awesome charter fishing experience in Key West, book a trip with Rob and see what it's all about!

About Your Guide

Profile photo of Captain Experiences guide Rob Delph

Rob Delph

Independent Guide
Capt. Rob has over 30 years of fishing and boating experience. His father Ralph was a champion tournament angler, and he passed his passion and experience down to Rob. Captain Rob holds an IGFA World Record for a 38lbs, 12oz King Mackerel on 4lbs. test line! The angler's name was Jerry Mathews. If you're looking for an awesome charter fishing experience in Key West, book a trip with Rob and see what it's all about!
Scroll for more

Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?
1154lbs Bluefin Tuna on stand up tackle.
If you were cooking for all your friends what would you cook?
Snapper and Grouper
What’s your favorite band?
Scorpion
What’s your favorite movie?
StarWars series

Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?
1154lbs Bluefin Tuna on stand up tackle.
If you were cooking for all your friends what would you cook?
Snapper and Grouper
What’s your favorite band?
Scorpion
What’s your favorite movie?
StarWars series
What’s your favorite sports team?
UFC
What’s your drink of choice?
Monster Zero Ultra
What was your last halloween costume?
Unicorn security guard
What do you want for Christmas this year?
Another Year!!!
How did you get started guiding?
Father
What makes you different from other guides?
We take pride in keeping our boat in the best shape.
Scroll for more

Second Generation Fishing Charter Trips

Choose a trip to get started
Bucket List
The Captain Experiences team chose this trip as one for the bucket list.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Dry Tortugas Fishing Trip

100% (11) Guided by Rob
36 ft 1 - 6 People From $2,800
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Key West

Second Generation Bay Boat

100% (11) Guided by Rob
25 ft 1 - 8 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Key West Fishing Trip

100% (11) Guided by Rob
36 ft 1 - 6 People From $2,400

Don't see what you're looking for?

Contact us to create a custom trip for you and your group.

Contact Us

Recent Reviews of Second Generation Fishing Charter

5.0
based on 6 reviews

Jodie

Verified Review

The best

Jodie

Verified Review

The best
Scroll for more

Lee

Verified Review

We had an absolutely unforgettable day on the water with Captain Mason! Our family of six—ranging from more "seasoned" to children—was treated to a private fishing excursion that truly exceeded all expectations.

From the moment we stepped on the boat, the Mason made us feel completely at ease. He was incredibly accommodating, making sure each of us was comfortable, engaged, and having a great time. Whether it was adjusting for the kids' needs, helping with baiting...

Lee

Verified Review

We had an absolutely unforgettable day on the water with Captain Mason! Our family of six—ranging from more "seasoned" to children—was treated to a private fishing excursion that truly exceeded all expectations.

From the moment we stepped on the boat, the Mason made us feel completely at ease. He was incredibly accommodating, making sure each of us was comfortable, engaged, and having a great time. Whether it was adjusting for the kids' needs, helping with baiting hooks, or offering fishing tips to the beginners among us, his patience and positive energy never wavered.

What stood out the most was how safe and inclusive he made the entire experience. Every member of the family felt like part of the crew. He kept a watchful eye on everything while still creating a laid-back, fun atmosphere. We never once felt rushed or out of place—just fully present and enjoying every moment.

He also went above and beyond in every possible way—from extending our time a bit when the fish were biting to showing us local wildlife and secret spots only a seasoned pro would know. It truly felt like a one-of-a-kind adventure curated just for us.

Highly recommend this charter to anyone looking for a fun, family-friendly, and expertly guided day on the water. Can’t wait to book again next time we’re in town!
Scroll for more

Kip

Verified Review

Everything about our trip was outstanding! The boat, the Captian, Captain Carlson was fantastic. He wanted fish for every one of us on the boat even more than we wanted to catch! He worked so hard to load the boat and that we did!!! One of the best charters I have even been one. We all can’t wait to come back again and do it all over again!

Kip

Verified Review

Everything about our trip was outstanding! The boat, the Captian, Captain Carlson was fantastic. He wanted fish for every one of us on the boat even more than we wanted to catch! He worked so hard to load the boat and that we did!!! One of the best charters I have even been one. We all can’t wait to come back again and do it all over again!
Scroll for more

Blaine

Verified Review

We had a great time with mason-fun day on the water

Blaine

Verified Review

We had a great time with mason-fun day on the water
Scroll for more

Patrick

Verified Review

Mason was phenomenal. Easy to talk to, engaging, great at teaching, and fun to be with… we got Mahi-Mahi and an exotic. We had a blast and will go fishing with Mason again soon!!!

Patrick

Verified Review

Mason was phenomenal. Easy to talk to, engaging, great at teaching, and fun to be with… we got Mahi-Mahi and an exotic. We had a blast and will go fishing with Mason again soon!!!
Scroll for more

Robert

Verified Review

Second Generation fisherman Rob was absolutely the best. He knew where to go close to the Harbor to put us on the fish. Highly recommended.

Robert

Verified Review

Second Generation fisherman Rob was absolutely the best. He knew where to go close to the Harbor to put us on the fish. Highly recommended.
Scroll for more

Potential Target Species

Color-coded seasonality below is based on .
View Full Species Seasonality Chart »
  • Get it while it's HOT!
  • This species is in play.
  • You might get lucky (as long as things are in-season).
  • Couldn't tell ya! (no data)

Techniques

Artificial Lure Fishing
Bottom Fishing
Cut Bait Fishing
Deep Dropping
Drift Fishing
Fly Fishing
Heavy Tackle Fishing
Jigging
Kite Fishing
Light Tackle Fishing
Live Bait Fishing
Sight Casting
Topwater Fishing
Trolling

Types of Fishing

Deep Sea
Inshore
Nearshore

Second Generation Fishing Charter Photo Gallery

Key West Drag Ripping
Key West Fishing Trip
March 18th, 2025
Key West, Florida
Key West Drag Ripping
Key West Fishing Trip
March 18th, 2025
Key West, Florida
Key West Drag Ripping
Dry Tortugas Fishing Trip
April 9th, 2023
Key West, Florida
Second Generation Bay Boat
Second Generation Bay Boat
May 2nd, 2025
Key West, Florida
Second Generation Charters
Dry Tortugas Fishing Trip
April 23rd, 2024
Key West, Florida
Second Generation Bay boat
Second Generation Bay Boat
May 19th, 2024
Key West, Florida
Black Grouper Fishing in Key West, Florida
Key West Fishing Trip
March 18th, 2025
Key West, Florida
Key West Drag Ripping
Dry Tortugas Fishing Trip
May 16th, 2022
Key West, Florida
Tarpon Fishing in Key West, Florida
Second Generation Bay Boat
May 20th, 2024
Key West, Florida
Second Generation Bay boat
Second Generation Bay Boat
May 19th, 2024
Key West, Florida
Mutton Snapper Fishing in Key West, Florida
Key West Fishing Trip
March 18th, 2025
Key West, Florida
Mutton Snapper Fishing in Key West, Florida
Dry Tortugas Fishing Trip
May 16th, 2022
Key West, Florida
Second Generation Bay boat
Second Generation Bay Boat
April 25th, 2024
Key West, Florida
Second Generation Bay Boat
Second Generation Bay Boat
May 2nd, 2025
Key West, Florida
Fishing in Key West, Florida
Second Generation Bay Boat
April 25th, 2024
Key West, Florida
Mahi Mahi Fishing in Key West, Florida
Dry Tortugas Fishing Trip
May 16th, 2022
Key West, Florida
Book Now

Enter to Win a

$500 DAMN GOOD GIFT CARD

Gift Card

Sign up to win $500 towards ANY trip. Winners drawn monthly.

By subscribing, you agree to receive marketing communications from Captain Experiences. To opt-out, click the unsubscribe button at the bottom of our emails. Privacy Policy and Terms & Conditions