Heads & Tails Fishing Charters
Heads & Tails Fishing Charters
Booked with us before? You may qualify for a Loyalty Discount. Sign in to check.
Welcome aboard Heads or Tails, our 26-foot World Cat 246—the perfect platform for exploring the waters of Key West. This stable, comfortable catamaran accommodates up to six guests and is powered by twin 150 HP Suzuki outboards, delivering a smooth, reliable ride whether you're fishing the backcountry, chasing reef species, or cruising to a secluded sandbar after the rods are put away.
The boat is fully equipped for a productive and enjoyable day on the water, featuring GPS, fish finder, a trolling motor with Spot-Lock for precise positioning, and plenty of rod holders. You'll also find an easy-to-use Armstrong boarding ladder, a spacious cooler stocked with ice and bottled water, and a private portable marine toilet inside the console. For guests on a combo trip who want to cool off after fishing, we also carry a 10-foot floating water hammock that's perfect for relaxing at a sandbar.
Your captain holds a USCG 100-Ton Master's License and has spent a lifetime boating and fishing the Florida Keys. With extensive local knowledge of the backcountry, nearshore waters, and hidden spots around Key West, every trip is tailored to your group's goals. Whether you want to target local species, introduce the family to fishing, or combine a few hours of fishing with sightseeing and a sandbar stop, your captain will customize the experience to make the most of your time on the water.
Whether you're looking for a fun day of light tackle fishing, a family-friendly adventure, or a combination fishing and sandbar charter, Heads or Tails offers a relaxed, personalized experience showcasing the very best of Key West.
Welcome aboard Heads or Tails, our 26-foot World Cat 246—the perfect platform for exploring the waters of Key West. This stable, comfortable catamaran accommodates up to six guests and is powered by twin 150 HP Suzuki outboards, delivering a smooth, reliable ride whether you're fishing the backcountry, chasing reef species, or cruising to a secluded sandbar after the rods are put away.
The boat is fully equipped for a productive and enjoyable day on the water, featuring GPS, fish finder, a trolling motor with Spot-Lock for precise positioning, and plenty of rod holders. You'll also find an easy-to-use Armstrong boarding ladder, a spacious cooler stocked with ice and bottled water, and a private portable marine toilet inside the console. For guests on a combo trip who want to cool off after fishing, we also carry a 10-foot floating water hammock that's perfect for relaxing at a sandbar.
Your captain holds a USCG 100-Ton Master's License and has spent a lifetime boating and fishing the Florida Keys. With extensive local knowledge of the backcountry, nearshore waters, and hidden spots around Key West, every trip is tailored to your group's goals. Whether you want to target local species, introduce the family to fishing, or combine a few hours of fishing with sightseeing and a sandbar stop, your captain will customize the experience to make the most of your time on the water.
Whether you're looking for a fun day of light tackle fishing, a family-friendly adventure, or a combination fishing and sandbar charter, Heads or Tails offers a relaxed, personalized experience showcasing the very best of Key West.
Select date to see availability
Trip availability and prices
| Su | Mo | Tu | We | Th | Fr | Sa | |
|---|---|---|---|---|---|---|---|
Customer reviews
Rating
All reviews (1)
FAQs about Heads & Tails Fishing Charters
- US $650 per group - AM Half Day Fishing (4 hours)
- US $650 per group - PM Half Day Fishing (4 hours)
- US $950 per group - Full Day Fish (8 hours)
- US $950 per group - Full Day Fish, Sandbar and Swim (8 hours)
- Toilet Marine portable toilet inside console
- GPS
- Fishfinder
- Wireless trolling motor
- Rods, reels & tackle
- Lures
- Catch cleaning & filleting
- Fishing license
- Nearshore fishing
- Offshore fishing
- Reef fishing
- Wreck fishing
- Light tackle
- Bottom fishing
- Trolling
- Spinning
- Amberjack
- Barracuda (Great)
- Cero Mackerel
- Grouper (Black)
- Grouper (Goliath)
- Grouper (Red)
- Snapper (Lane)
- Snapper (Mangrove)
- Snapper (Mutton)
- Snapper (Yellowtail)
Your captain
Capt. Zachary runs trips out of Key West aboard 26' Worldcat Center console. The crew has you covered if you wish to try bottom fishing, spinning, trolling, or other techniques. The only way to learn is to join them on the water.
Capt. Zachary runs trips out of Key West aboard 26' Worldcat Center console. The crew has you covered if you wish to try bottom fishing, spinning, trolling, or other techniques. The only way to learn is to join them on the water.
Real catches by this captain
What is the boat like?
What kind of fishing will you do?
Which fishing techniques you can try
Which amenities are available onboard
How cancellations work
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.
What the listing policies are
Pickup not included
Transfer to/from departure site is not included in trip rates.
How you can pay
When the captain confirms your trip, FishingBooker charges your credit card a 20% 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
Bank transfer
When paying the remaining balance with a credit card, an additional 2.5% charge will apply.
What’s biting in Key West right now
Amberjack
Barracuda (Great)
Grouper (Black)
Grouper (Red)
Snapper (Mangrove)
Snapper (Mutton)
Snapper (Yellowtail)Compare similar fishing charters
State licensed4.5(8)24 ftGroup size 1 - 41 - 4
+94 hour trip • 4 personsUS $700
State licensed5.0(11)22 ftGroup size 1 - 41 - 4
+44 hour trip • 4 personsUS $750
Federally permitted5.0(2)25 ftGroup size 1 - 41 - 4
+54 hour trip • 4 personsUS $750
State licensed5.0(20)26 ftGroup size 1 - 61 - 6
+64 hour trip • 2 personsUS $695
