Jewel Key Loop

When: April 2025

Trip Length: 2 Days

Distance: 15 miles

Trail Type: Loop

Permit: Reservations required on recreation.gov, $21 fee + $2/person/night


Route (approximate)

I’ve spent the last two winter/spring seasons guiding multi-day sea kayaking trips into the backcountry of Everglades National Park. Most of the groups I take out are initially surprised by the scenery of the trip. Guests come in with the images of alligators, snakes, and clouds of mosquitoes in their heads; most are pleasantly surprised to rather see dolphins, rays, sea turtles, and private white sand beaches. Of course, the typical picture of the “Everglades” makes up the majority of the park, which is mostly undeveloped wilderness. The latter, where the majority of backcountry camping takes place, is known as the Ten Thousand Islands region of the park.

We started our trip from a locally known launch straight into Chokoloslee Bay along the causeway. Our route was one I’ve run many times before, a loop using both the well-marked Indian Key Pass on the first day, and the unmarked but well known Sandfly Pass on the return. It makes for a great 2 day trip into the islands incorporating different passes on entry and return, lunch stops both days, and an additional ~1 mile hike on Sandfly Island.

Our start time was set for around 10am. Our high tide wasn’t until 2:15pm, which meant we’d be fighting the tide on our initial paddle out. Tides in the Everglades are relatively mild, usually around 2-3 feet. Tides in Everglades City are about an hour and a half behind the tides out in the keys here, so our high tide out in the keys was around 12:45pm. If we paddled across the bay and hugged the mangroves along the edge of the pass, we’d face less tidal resistance in the pass. Once the keys have had their high tide, we start to enter slack tide and the resistance we’d be facing would be much more mild. Once we got out of the pass and started bouncing around from island to island, we wouldn’t feel much of any tidal pull at all.

sea kayak on Chokoloskee Bay everglades
Launching into Chokoloslee Bay

The breeze we had was out of the north, which left Chokoloslee Bay nice and calm for our paddle across to Indian Key Pass. Joining me on the trip were a couple from Pennsylvania who had never been paddling or camping before showing up in the Everglades. The best way to learn is by doing! Luckily it was calm enough to help ease them into it during our paddle across the bay.

Royal tern birds Chokoloskee vay everglades
A few dozen Royal Tern taking advantage of a mud bar in middle of bay at low tide

After a seemingly long paddle across the bay, we neared the pass. As we crossed the marker designating the national park boundary, the occasional sight of styrofoam crab trap buoys vanished, and the color-coded channel markers began. We stayed tight to the mangroves on the east side of the pass and besides for the occasional bit of strong water when reaching the end of a mangrove island, paddling against the tide was manageable at a relaxed pace and we ended up paddling about 2mph in the pass. We didn’t have much traffic this late in the season besides a few commercial crabbing boats as well as the national park tour boat. One of the crabbing boats started to leave the marked channel abruptly and pointed straight at us at a steady clip, it was odd enough that one of the people I was with asked me what the boat was doing coming right at us. The boat did correct course after a several long seconds and returned to the channel; as I was watching the boat I saw a huge ray jump clear out of the water behind the boat. I usually see this about every trip out here, but it all happens so fast that I’m really not able to point it out to people before it’s gone. Such a cool thing to catch!

Royal tern in Indian key pass everglades
Royal Tern perched on a channel marker
kayak mangrove gulf everglades
First Views of the Gulf

We continued our paddle through the pass until we were able to see the gulf and branched off towards Jenkins Key, making our way to Kingston Key for lunch. Kingston Key is a nice stop on this route for lunch with a good sized beach facing the north. We ate our lunch of wraps, apples, and granola bars and took about an hour to walk around the key before finishing the final 4 miles of today’s paddle.

  • Kingston key everglades
  • Kingston key everglades
  • crab everglades

We left Kingston Key after lunch and continued on our route. Jack Daniels Key is between Kingston and Jewel, and it is a spot I commonly see dolphins on trips. No luck today in Jack Daniels Cove, but in the narrow gap on the north side of the key, we spotted our first sea turtle of the trip. We were able to get a few feet from the little guy when it noticed us approaching and dove down out of sight. We exited the narrow gap and saw what we had been looking for in the first place, dolphins! A few hundred feet or so to the northeast, we could see fins, splashing, and hear blowholes. They must have been feeding as they repeatedly charged the mangroves; we hung out for several minutes and watched from afar, surfacing and splashing. We got our fill of the dolphins and continued toward Jewel Key. After clearing another narrow gap in the route, we spotted an osprey up in its nest. Finally, Jewel Key was in front of us. We circled the island to the sheltered landing spot on the east side of the key where we pulled in our kayaks and unloaded our gear.

mangrove narrow kayak everglades
Narrow sections like this are my favorite sections to paddle
osprey everglades
Osprey Nest near Jewel Key

I setup my tent, our community area, and helped my guests setup their tent and we took a few minutes to relax on the beach. Another group on a tour pulled up in a motorized skiff to check out the lightning whelk tree. Their guide invited us to listen in and we learned a few neat fun facts that I’m looking forward to sharing with the next group I bring along to Jewel Key. Our new friends departed and I started gathering firewood for the night. We relaxed a bit more on the beach and I brought out the national park trivia game I always bring along to pass the time until dinner and sunset. Tonight’s menu was chicken quesadillas cooked on the fire, as well as a bottle of champagne to cap off the night. We called it a night around 9:30 and retreated to our tents as the wind was dying down and the sand flies started coming out.

jewel key shell tree everglades
Lightning Whelk Tree
jewel key everglades
Dropping tide on Jewel Key
jewel key everglades
Snapped this pic of my guests watching the sunset from Jewel Key

The islands are notorious for their resident racoons. I had one sniffing around my tent in the middle of the night that woke me up. Smacking on the side of the tent a few times and making some noise scared it off, and otherwise had a quiet night. The following morning we had a breakfast of oatmeal and yogurt before packing up and pushing off around 9am, this time with the tide in our favor. With the tide pushing us in we made it to Sandfly Island via Sandfly Pass around 10:30am where we checked out the hiking trail loop and set up our table for lunch on the dock.

jewel key sandlfy pass everglades
Leaving Jewel Key
Sandfly pass mangrove everglades
Paddling through Sandfly Pass
  • Sandfly island kayak
  • Sandfly island dock
  • sandfly island dock
  • sandfly island gumbo Limbo tree
  • Everglades ruins sandfly island
  • sandfly island trail boardwalk
  • sandfly island well

We made quick work of our paddle back after pushing off from Sandfly Island. Our paddle across Chokoloskee Bay was still, without any wind and only a few boats off in the distance. We arrived back at our takeout location around noon, emptied out our boats and loaded up the trailer for the short drive back. Another trip in the books! This was my final multiday trip of the season, my last until November, and my 32nd overall in the Everglades. It was a bittersweet end to the season, and I look forward to whatever this summer brings as well as next season down in the ‘glades!

everglades chokoloskee bay
Final view of Chokoloskee Bay from our takeout location
Gear List
Kayak: Wilderness Systems Tempest 170
Tent: Kelty Wireless Freestanding Car Camping Tent, 2 Person
Sleeping Pad: Sea to Summit Ether Light XT Extra-Thick Insulated Sleeping Pad
Sleeping Bag: Sea to Summit Boab Synthetic Sleeping Bag
Pillow: REI Campwell Camp Pillow
Chair: NEMO Equipment Moonlite Reclining Camp Chair
Table: ALPS Mountaineering Aluminum Roll-Top Camp Table
Headlamp: Paria Outdoor Comet Rechargeable Headlamp
Stove: MSR Pocketrocket 2
Cooking Pot: Sea to Summit Frontier Ultralight Camping Cooking Pot
Trowel: Sea to Summit Collapsible Pocket Trowel
First Aid Kit: NOLS Med Kit 4.0
GPS Watch: Garmin Instinct 2 Solar
Camera: Google Pixel 6a
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