
Islamorada Fishing Charters From the Family That Wrote the Book on Keys Fishing
4.6 on Google, 11 reviews
Four family-run boats out of Islamorada, for deep sea days, evening shark trips, overnight swordfish, sandbar days and sunset cruises. Run by Brian and David Epstein, sons of Miami Herald fishing editor Bob Epstein. Every rate is posted up front.
Veteran owned. If you serve or served, you and your family ride at a discount on every boat.

Questions first? Call or text (954) 326-7360
Trips and rates
Every fishing rate includes your captain and mate, rods, tackle, bait, licenses, ice and your fish cleaned at the dock, with no fuel surcharge. Want a Bahamas run or a chef-catered dinner cruise? Call or text and it gets built for you.






Your boat for the day
Two big Hatteras sportfishers for blue water, a quick bay boat for calm-water fishing, and a tritoon for the sandbar and sunset. You get the right hull for the day you want.
Named for Poppa, run by his sons
Bob Epstein covered Keys fishing for the Miami Herald for decades. His sons David and Brian built this fleet in his name, so your trip runs with captains who have fished these waters for decades. Read Poppa's story
Capt. Brian EpsteinCo-owner, USCG 100 Ton Master40 years on Keys water, tournament captain
Capt. Skip BradeenBest charter captain in the Upper Keys, 14 years runningTop 50 Captains in the World, Salt Water Fisherman
Capt. George Clark Jr.30 years guiding the KeysDiscovery's "The Fish Guyz"
Capt. Shane GoreCaptainSandbar and snorkel daysTheir day, in their words
We caught 19 keepers! The boat was luxurious and comfy. Captain George was the best!!
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!
After 30 plus years using another guide, we went out with Rick on the 25 footer. Could not have been happier with the trip.
Clean, spacious, and top of the line gear. The crew had us on fish all day and cleaned everything at the dock.
Full day trip: trolled up tuna and mahi, then deep dropped for vermilion and yellowtail. A perfect mixed bag.
Great boat! Great crew!
Ready to book?
From $575 Private trips for up to 6, posted rates
Straight off the boats







A chef on board
You fish, the chef cooks: ceviche from what just came over the rail and hot plates out of the kitchen on Poppa Wahoo. Ask for the chef-catered option when you book.
Back on land, the Islamorada Shrimp Shack, part of the Collective and seen on Diners, Drive-Ins and Dives, cooks your catch. Visit the Shrimp Shack
Know before you go
What is included in the price?
Everything you need to fish: the boat, fuel, captain and mate, rods and tackle, live bait, fishing licenses and ice. Your catch is cleaned and filleted at the dock. You can add catered meals or charcuterie to any trip.
How many people can come?
Up to 6 on either Hatteras. Poppa Bay fishes up to 4, and the Poppa Toon takes up to 6 for the sandbar or the sunset.
Do I need a fishing license?
No. The boat's licenses cover everyone aboard.
Are kids welcome?
Yes. Families are welcome, and the nearshore and cruise trips are built for mixed groups. Tell us the ages when you book.
Which trip should we pick?
Want a full fish box, go deep sea on the Hatteras. Want a thrill after dinner, take the evening shark trip. Chasing a swordfish, the overnight trip. Calm water with kids, nearshore on Poppa Bay. Just want to float, the sunset cruise or the sandbar on the Toon. Still deciding? Let the trip card at the top pick for you.
Where do trips leave from?
Your boat leaves from Three Waters Resort and Marina, 84001 Overseas Highway, Islamorada, FL 33036. Nearshore trips on Poppa Bay leave from Square Grouper at 80461 Overseas Highway.
How do deposits and cancellations work?
A deposit holds your date, and it is refundable up to 24 hours before your trip. Your exact terms come with your booking.
Should we tip the crew?
It is customary when the crew takes care of you: 15 to 25 percent of the trip price, handed to the captain or mate at the dock.
Poppa Wahoo
Poppa Wahoo Too
Poppa Bay
Poppa Toon