PaddlePin

Florida Keys Paddling With Kids: Three Launches, and SUP or Kayak

A launch that suits a family on a calm morning can be the wrong call by lunchtime. Here are three Keys paddles we have researched, what makes each one manageable, and the conditions that should change your mind about the board.

Compiled from PaddlePin’s researched location records

The short answer

  • Newest paddlers, smallest kids: the 1.5-mile mangrove loop at Curry Hammock in Marathon. It is the only route in this guide PaddlePin rates beginner, and the only one you can abandon quickly.
  • A first Keys paddle with rentals on site: the mangrove trails at John Pennekamp in Key Largo.
  • Older kids, settled weather, a destination: the crossing from Indian Key Fill to Lignumvitae Key — kayak or canoe, not a board.
  • Wind decides, not the calendar. Every one of these opens onto exposed water within a few hundred yards of shelter.

Is it a SUP day or a kayak day?

Owning boards changes the question. When you rent, you decide where to go and the concession decides what you paddle. When the boards are already on the roof, the decision moves to the morning of, at the launch, in whatever the wind is doing.

The useful framing is not “are we paddleboarders or kayakers”. It is: where do we want to go, and which craft makes sense there today? Three things push the answer toward a kayak — wind, distance from shelter, and how far you would have to get back if a child stops paddling. A board is slower to make ground into wind and has a standing rider acting as a sail. In protected mangrove water none of that matters much. On an open crossing it decides the day.

A launch existing does not tell you the water is protected. Two routes from the same parking lot can be completely different paddles, which is the single most useful thing to know before driving to the Keys with boards.

Key Largo · Upper Keys

John Pennekamp: mangrove trails, with rentals on site

Pennekamp has something most Keys launches do not: a dedicated mangrove-paddling network, several miles of marked trails that lead out into Largo Sound. Board, kayak and canoe all work here, and there are two launches — one near the education classroom and one behind the Snorkel Shed for rented craft — so arriving without gear is a plan rather than a problem.

Inside the mangroves the water is protected and the boat traffic is somebody else’s. Largo Sound is not. Motorised traffic in the Sound is on the record for this location, along with changing weather and the ordinary difficulty of keeping track of where you are inside a trail network that looks the same in every direction.

Firsthand

We paddled this as a family in two tandem kayaks rented in the park, staying mostly inside the mangroves. As beginners it was relaxing rather than intimidating. What stuck was the moment we left the mangrove shelter: the open water was immediately, noticeably harder. Same park, same afternoon, a different paddle.

Two practical notes from the record. Check the Florida Department of Health advisory before water contact, and take the current trail map from the concession rather than trusting distances published elsewhere — including older ones of ours.

Florida Keys · Monroe County · Mangrove trails / Largo Sound

A dedicated mangrove-paddling network in Key Largo with several miles of trails leading through mangroves and into Largo Sound.

Not yet ratedDifficulty: Not yet rated
1 routeEstuary
High confidence

Islamorada · Middle Keys

Lignumvitae Key: a real crossing, and not one for boards

This is the most ambitious paddle in the guide and the one to be most honest about. From the public ramp at Indian Key Fill it is a 2.84-mile roundtrip across shallow seagrass flats to Lignumvitae Key, where a tropical hardwood hammock and the historic Matheson House are the reason you went. There is a shorter option: a 1.84-mile out-and-back into the mangrove creek entrance, without the island landing.

PaddlePin lists this one for kayak and canoe. Not because a board cannot cross flats, but because the record for this route is wind on open flats, channel navigation and sun exposure with no shade for the whole crossing — and those are the conditions where a board stops being the forgiving choice. Morning, on a light-wind day, is the guidance on the record. Leave a float plan and use the designated kayak landing.

The compensation is the water. Clear enough to watch the seagrass go past, with manatees and wading birds as ordinary sightings rather than lucky ones.

Florida Keys · Monroe County · Lignumvitae Key waters / Lower Matecumbe seagrass flats and mangrove creeks

A 2.84-mile roundtrip from Indian Key Fill across shallow Keys flats to Lignumvitae Key, with optional mangrove-creek exploration and an island botanical/historic destination.

Not yet ratedDifficulty: Not yet rated
2 routes1.8 miSeagrass flats, Estuary, Creek
High confidence

Marathon · Middle Keys

Curry Hammock: the one rated for beginners

If one paddle in this guide is built for a family finding out whether they enjoy this, it is the 1.5-mile Little Crawl Key loop. It is the only route here PaddlePin rates beginner, and the reasons on the record are the reasons that matter with children aboard: the loop stays close to the launch, it is protected mangrove water for most of its length, and it is short enough to turn back if the wind gets up.

Board or kayak both work. The variable to watch is tide rather than wind: at very low tide the mangrove tunnel can be too shallow to pass, and the record suggests treating tide as a route-selection input rather than a footnote — skip the tunnel and paddle the sandbar east of the launch instead. Beyond the mangroves there are grassy flats, sandbars and short open-ocean sections, which is where the exposure comes back.

Florida Keys · Monroe County · Florida Bay / Atlantic coastal waters

A compact Florida Keys paddle with mangrove-tunnel and Deer Key loops, a sandbar about a third of a mile out and short open-water sections. Conditional go: the mangrove route depends on water level, so plan a fallback before you launch.

Beginner+ unrated routesDifficulty: Beginner
3 routes0.3–1.5 miSeagrass flats, Estuary, Ocean
High confidence

What to check the morning you go

Five questions, in the order they change your plan. Wind speed and direction, because it decides craft before it decides route. Tide, because in the Keys it decides whether a route exists at all. Which launch, because parks here often have more than one and they open onto different water. How far from shelter the route takes you. And whether anyone in the group would struggle to get back against the wind that is blowing when you turn around.

None of that is exotic knowledge. It is just harder to assemble standing in a car park with three impatient people than it looks from a kitchen table, which is why it is worth doing the night before.

Keeping the paddle afterwards

PaddlePin the app is the other half of a day like this: it records the route you actually paddled, lets you drop and name a pin out loud at a sandbar or a tunnel mouth worth remembering, and keeps each paddle with your photos as something you can reopen next season. It works offline once you are on the water.

Get the app$4.99

PaddlePin.com is free to use. PaddlePin for iPhone is a separate $4.99 app that records your paddles — it does not import routes from this site.

What this guide does not tell you

Only the Curry Hammock loop carries a difficulty rating. The routes at Pennekamp and Lignumvitae have not been assigned one, and we would rather show that gap than round it up to “beginner” because the water looks calm in photographs. Each location page says which of its facts have been verified and when.

Nothing here replaces checking conditions, closures and regulations on the day. PaddlePin is a paddle journal and route memory tool — not a marine navigation or emergency app.

Paddled these with kids and know something we have missed? How we research explains what we do with a correction.

More Florida water: explore every researched location, or go back to all guides.