Outback with Jack

Outback with Jack Fully customized charters on a 26 foot tritoon. Fishing, sandbar, and snorkeling. FAQ

How many people can go? Up to six. What are the prices? Call for pricing.
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They are private charters, so prices are for the boat. Where are you located? Sugarloaf Marina at 17015 overseas highway. 13 miles outside of key west. What do you do on the charters? It’s a tour through the maze of creeks, sandbars, flats, and reefs known as the back country. We snorkel, fish, and explore the numerous sandbar islands in the area. What is included? I provide coolers, ice, snorkel

gear, fishing tackle, licenses, beach chairs, and floats. Are kids welcome? Absolutely! Kids and dogs are more than welcome aboard. Can we byob? Yes, the marina is fully stocked with beer, seltzers, and soda. What kind of boat? I’m currently using a twin engine, 23-foot Bennington tri toon for these trips.

Had to cut today's trip short but we got it done. Some early morning snorkeling followed by a surprisingly good snapper ...
09/06/2026

Had to cut today's trip short but we got it done. Some early morning snorkeling followed by a surprisingly good snapper bite. Spent a little time at the sandbar before the pyrotechnics started and we tucked tail.
Made it back to Sugarloaf just ahead of the white squall.

Backcountry fun with new friends from Big Pine Key. Had to do a little storm dodging but we stayed in the clear almost a...
09/05/2026

Backcountry fun with new friends from Big Pine Key. Had to do a little storm dodging but we stayed in the clear almost all day. Couple of little sprinkles were welcome this time of year.
Young Riley showed the guys how it's done and put on a mangrove snapper clinic. She couldn't keep them off the hook.
Did some snorkeling afterwards and found a few wayward bugs.
Finished the day soaking at the sandbar before cruising back to Sugarloaf.

A postcard at every turn. That's the only way to describe today. Had a wonderful afternoon with Brandy and company. Girl...
09/04/2026

A postcard at every turn. That's the only way to describe today. Had a wonderful afternoon with Brandy and company. Girls trip 2026.
They put a nice catch of snapper together quickly and we headed out for lobster. It's been a little slow lately but we found some beauties today. Saw an abundance of sea life as well.
The extreme low tide allowed us to utilize some gulf sandbars that are rarely exposed. Aside from having no one around, the water was much cooler than the main sandbars.
The ladies found sand dollars while Mullet chased everything that moved.
A perfect day all around.

It was a special day in the backcountry for me. By chance I had two schoolmates from Sugarloaf elementary on the same sh...
09/03/2026

It was a special day in the backcountry for me. By chance I had two schoolmates from Sugarloaf elementary on the same shared trip. One of which I hadn't seen in nearly 35 years. Was really cool to catch up on the last few decades. Man it goes by fast. Had some awesome new friends aboard as well. They caught a nice pile of snapper and spent time at multiple sandbars.
Pretty as it gets out there.

Sandbars, snapper, and sunshine in the backcountry today. Fish were popping the surface and we had the beach all to ours...
09/01/2026

Sandbars, snapper, and sunshine in the backcountry today. Fish were popping the surface and we had the beach all to ourselves for hours. Even managed to find a few lobster. Absolutely perfect

Returning friends and some new ones on today's shared charter. Snappers were snapping and we caught our limit easily. Gr...
08/27/2026

Returning friends and some new ones on today's shared charter. Snappers were snapping and we caught our limit easily. Grabbed a few bugs after fishing and spent the remainder of the day relaxing at the sandbar.

I love Mondays in the backcountry. Only saw a handful of boats in six hours. Lobsters were few and far between but they ...
08/24/2026

I love Mondays in the backcountry. Only saw a handful of boats in six hours. Lobsters were few and far between but they were BIG.
Had to snare a few that would have been tough to get in a net. After the morning snorkeling session we broke out the rods.
Put a nice pile of snapper in the cooler on a 30 minute bite. Headed to the sandbar next to wind down and chill in the current. Huge thanks to Brandy and Steven for spending another day with us and bringing awesome new friends along. See ya soon!

Perfect day with good time retuning friends. Had a real light current so fishing was tough. Caught enough for a couple o...
08/21/2026

Perfect day with good time retuning friends.
Had a real light current so fishing was tough. Caught enough for a couple of meals and then focused on lobster. Had a good crawl this week. Rocks that were empty opening day had fresh gulf bugs on them today. Took what we needed and spent the remainder of the afternoon soaking at the sandbar.

Good times with great people in the backcountry today. We fished for a couple of hours until the sun forced us into the ...
08/18/2026

Good times with great people in the backcountry today. We fished for a couple of hours until the sun forced us into the water. Grabbed some big lobsters and managed to catch not one but two hogfish with a net and tickle stick. Both were a little short and went back but that was a first....and second for me.
The water is amazing right now and loaded with life. In a short snorkeling session we saw huge snapper, parrotfish, pork fish, yellow jacks, conch, hogfish, nurse sharks, and the full array of tropicals. Lots of large stone and spider crabs around as well. All in four feet of water.

Update: No longer available Just had a cancellation for August 22nd. Day is wide open.Let's go fishing!305 394 7032
08/18/2026

Update: No longer available

Just had a cancellation for August 22nd.
Day is wide open.
Let's go fishing!
305 394 7032

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Sugarloaf Shores, FL
33042

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