Islamorada, Florida Keys

Islamorada charters from the family that wrote the book on Keys fishing.

Four boats, one family. Deep sea trips aboard a 55 foot Hatteras, overnight swordfishing, evening shark runs, and sunset cruises, all out of Islamorada. Founded by the sons of Bob Epstein, the Miami Herald's legendary fishing editor. Real rates below. No surprises at the dock.

Veteran owned. Active duty, veterans and their families ride at a discount on every boat in the fleet.

Deep Sea Half Day$1,4754 hours · 55' Hatteras
Evening Shark Trip$1,0003 hours · 5 pm departure
Overnight Swordfish$3,500Overnight · 30 miles out
Sunset Cruise$5752 hours · tritoon

Four boats,
one family dock.

Two big Hatteras sportfishers, a nimble bay boat, and the party barge. Every trip runs on the right hull for the water.

53' Hatteras Sportfisher

Poppa Wahoo Too

The sister ship, wearing wahoo stripes down her hull.

Up to 6Deep seaEvening sharks

23' Barletta Tritoon

Poppa Toon

The easy button, for days that call for drinks instead of drag.

Up to 6Sunset & sandbarResort pickup

Trips and rates, posted in plain sight.

Every trip includes rods, reels, tackle, bait, licenses, ice and cleaning of your catch. No fuel surcharge, no per-person add-on at the dock.

Hands on the rod and reel, hooked up offshore aboard the Poppa Wahoo
4 hours · 7 am

Deep Sea Half Day

$1,475Up to 6 guests

The reef and the wrecks minutes from the dock: grouper, snapper and kingfish.

More ways out on the water
The Poppa Bay running the shallow nearshore water off Islamorada

Nearshore & Reef

From $1,050
4, 6 or 8 hours

Snapper and mackerel on the bay boat. Calm water, lighter tackle, good with kids.

Guests and their dog watching the sunset from the Poppa Toon in Islamorada

Sunset Cruise

$575
About 2 hours

Flat water, cold drinks, and an Islamorada sunset from the best seat in the Keys.

Bahamas and Bimini runs, eco tours and chef-catered dinner cruises are built to order. Call and tell us what you are picturing.

(954) 326-7360

What's running right now?

It's September: mutton snapper and yellowtail are steady on the reef, and grouper season opens on the structure. Every photo below came off our decks.

Mutton snapper held up boatside on a Poppa Wahoo charter
Mutton snapper on the deck
A mutton snapper at the dock
Yellowtail snapper in the bucket after a reef trip
Yellowtail snapper fresh off the reef
A table of yellowtail snapper at the dock
Black grouper held up by an angler
Grouper and mutton snapper together at the dock
A kid with his first grouper
Crew holding a bull mahi
Two mahi on the deck
A pair of mahi at the dock
Mahi mahi held up boatside
Extra large wahoo on the bow
Wahoo hung at the dock
The group with a wahoo at the rail
A group with their wahoo
Blackfin tuna held up on deck
Blackfin tuna at the transom
A pair of blackfin tuna
Sailfish held boatside before release
Sailfish at the rail before release
King mackerel held up on deck
King mackerel at the rail
Shark boatside on the evening trip
Shark alongside the boat at sunset
Amberjack held up on the transom
Amberjack on the deck
Expand

The Poppa Wahoo running out of Islamorada.

Mentored by legends. Now running your trip.

The collective's captains came up under names like Stu Apte, Flip Pallot, Lefty Kreh, and Ted Williams. Capt. Brian Epstein leads the fleet, backed by two of the most decorated captains in the Upper Keys. The business behind them is family-run and veteran-owned.

Co-owner · USCG 100 Ton Master Capt. Brian Epstein Forty years on Upper Keys water, backcountry to blue, and a proven tournament captain. Follow on Facebook
Fleet legend Capt. Skip Bradeen Best Charter Boat Captain in the Upper Keys fourteen years running. Fished Mantle, Newman and Bradshaw.
Fleet legend Capt. George Clark Jr. Thirty years guiding these islands, and one of the faces of Discovery Channel's "The Fish Guyz."
Captain Capt. Shane Gore Bio to come from the dock. Years on the water, the boat he runs, and what he is known for.

Capt. George Clark Sr. is George's father, and the Clarks have been fishing these islands together since 1973. The collective carries his name alongside Poppa's, because the same two families taught each other this water.

And the crew that makes it run: Capt. Rick Martin II and Gabriela Urbina, with mates Wyatt, Tyler and Ricky earning names in the reviews below.

Owner · U.S. Air Force, Retired

David Epstein

Bob's son, and the reason there is a fleet at all. David is a retired United States Air Force veteran, rated 100 percent disabled, and an emergency management specialist. He and Brian bought the boat in late 2024 to take their dying father fishing one more time. They did not make it, so they named her for him and put Islamorada's best captains on the bridge. David runs the money and the logistics, not the boat.

Veteran owned, and veterans ride for less. Active duty, veterans and their families get a discount on any charter in the fleet. Mention it when you call and it comes off the trip.

5.0 across every published charter review
"We caught 19 keepers! The boat was luxurious and comfy. Captain George was the best!!"
SonyaCharter guest · May 2025
More from the dock

"Booked a 4 hour charter for snorkeling and the sandbar with Shane and had an amazing day. Sea turtles, snorkeling near the lighthouse, even shelling on the sandbar. The boat was very comfortable. All around perfect day!"

DawnGoogle review · August 2026

"After 30 plus years using another guide, we went out with Rick on the 25 footer. Could not have been happier with the trip."

ChristopherApril 2026

"Clean, spacious, and top of the line gear. The crew had us on fish all day and cleaned everything at the dock."

StephanieMarch 2025

"Full day trip: trolled up tuna and mahi, then deep dropped for vermilion and yellowtail. A perfect mixed bag."

Junofull day charter

"Great boat! Great crew!"

Troy JonesMarch 2026
Sebastian the Ibis, the Miami Hurricanes mascot, holding a fishing rod aboard a Poppa Wahoo Collective boat Sebastian the Ibis posing with an angler on the transom, wake behind
Yes, that is Sebastian

When the Hurricanes go fishing, this is the boat.

The University of Miami brought its tournament to Islamorada and Sebastian the Ibis rode the bow with us all day, rod in hand, zero fish cleaned. When a whole athletic program picks a fleet for its day on the water, that tells you something. Book the same boats, same captains, same water.

Before there was a fleet, there was Poppa.

Bob Epstein, Miami Herald fishing editor, with President George H. W. Bush
Bob Epstein with President George H. W. Bush.

Bob Epstein covered Keys fishing for the Miami Herald for decades, and everyone on the Islamorada docks called him Poppa. When he passed in January 2025, his sons David and Brian built a charter fleet worthy of his name.

2025Founded in tribute to Bob Epstein
4 boatsFrom a 55' Hatteras to a sandbar tritoon
5.0Across every published charter review
Read Poppa's story
A wahoo laid across the bow of Poppa Wahoo Too on clear water off Islamorada

The fish the boats are named for. Wahoo run the Islamorada humps and the deep edge from late fall into spring. They hit at 50 miles an hour, they do not fight long, and they are the best eating fish that swims. Every one that comes over the rail gets filleted at the dock before you leave.

There is a chef on the boat. He starts before you get back.

Most charters hand you a cooler and a sandwich. There is a professional chef aboard Poppa Wahoo cooking while you are still fishing: fresh ceviche from what just came over the rail, hot plates out of the galley, and a spread that turns a long day offshore into something closer to a dinner party with rods.

He is a licensed captain as well as a professional chef, so he works the boat when the bite is on and the galley when it is not. Ask about the chef-catered option when you book.

Fresh ceviche prepared on board from the day's catch The chef torching steaks in the galley aboard Poppa Wahoo The chef finishing fresh crudo from the day's catch in the galley
Also ours

The Islamorada Shrimp Shack

The Collective owns the Shrimp Shack, the Old Florida seafood joint on the Overseas Highway that Guy Fieri put on Diners, Drive-Ins and Dives. Bring in what you caught with us and the kitchen will cook it for you. It is the shortest possible trip from the reef edge to your plate.

Know before you go.

What is included, how booking works, and what to expect at the dock. Anything else, call and a captain will pick up.

(954) 326-7360
Everything you need to fish: the boat, fuel, captain and mate, rods and tackle, live bait, fishing licenses, bottled water, and light snacks. Your catch is cleaned and filleted at the dock. Catered meals and charcuterie can be added to any trip.
Both Hatteras sportfishers carry up to 6 guests. Poppa Bay fishes up to 4 anglers, and the Poppa Toon handles relaxed cruising groups. Tell us your headcount and we will match the boat.
No. The boats carry the licenses that cover every guest on board. Show up, step on, fish.
Very. Families are a big part of what the collective does, and the nearshore and cruise trips are built for mixed groups. Bring life vests for the little ones and we will handle the rest.
Want the offshore box fish, go deep sea on the Hatteras. Want a thrill after dinner, the evening shark trip. Want the fish of a lifetime, the overnight swordfish. Calm water with kids, nearshore on Poppa Bay. No fishing at all, sunset or sandbar on the Toon. Still stuck? Call and describe your group.
The fleet docks at Three Waters Resort and Marina, 84001 Overseas Highway, Islamorada. Nearshore trips on Poppa Bay depart from Square Grouper at 80461 Overseas Highway. Your confirmation spells out exactly where to walk.
A deposit holds your date and the balance is settled at the dock. Cancellations are free up to 30 days before the trip, and weather or mechanical calls made by the captain are refunded in full. Exact terms are confirmed with your booking.
Tipping is customary in the charter world when the crew takes care of you: 15 to 25 percent of the trip price, handed to the captain or mate at the dock.

Questions? Start here.

Rates and trips are all posted above. If you want to talk through a date, a group, or something custom, send it over and a captain gets back to you directly.

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Prefer to talk? Call or text (954) 326-7360. Open daily, 6:00 AM to 5:00 PM.