Ok, let’s start by stating the obvious. You do need to kayak to be able to attempt this event. There is a committing sea leg to undertake at the outset of the journey, followed by a good few miles of sheltered Keys paddling to reach the get-out. It’s a long day in the boat for any paddler, before you’ve added on the cycling and running legs. As such, we can’t allow people who have never been in a boat before to undertake this event. Which means we have laid out some guidance on what we expect regarding the level required to undertake the challenge. It’s not meant to be intimidating or out of reach and anyone who has done some paddling will be able to achieve this level quickly, with some refreshment of skills. If you have never paddled, you can get there too, but you will need to take some tuition and/ or spend some time in the boat between now and the event. You can learn more about the level of paddling skill we expect below. One thing is for sure – this is a superb kayak leg and the opportunity to traverse this section of uninhabited Keys is certainly very unique. Its entirety is rarely travelled along and certainly not in such an outstanding event format such as this.

Kayaking skill level required for this event

We expect that you will be able to:

  • Be comfortable and have had some experience in a solo enclosed sea or touring kayak (or a double, if that is what you select).
  • Be confident steering a straight course and the various strokes to be able to turn your craft efficiently.
  • Be comfortable sitting in a kayak for extended distances.
  • Be able to exit your craft under control, should you capsize and to be able to call for help.
  • Please note that sit-on-top kayaks, whilst providing good paddling experience, are not used or permitted in this event.

Rates for kayak rental are covered here.

The nature of the distance and the conditions experienced on our sensational kayak leg dictate that sea kayaks are the catch of the day here. Whilst this event could be attempted with a sit-on-top, it’s a very long way for such a craft and frankly, we wouldn’t recommend it. Therefore we advise closed-cockpit single of double sea kayaks. We will be renting both types of craft. 
We will permit supporters’ vehicles to the kayak drop-off and take-out locations at appointed times. These will be released nearer to the time. 
Yes. We will have a transfer service available from Key Largo to get your craft into the water and out again. You do however need to get it to Key Largo. 
Nope. It won’t sink but it will take you light-years to do the distance. 
Makes it more exciting! This is generally very sheltered paddling but there is an open sea leg, there are currents at play and the sea is always susceptible to the action of tide, swell and wind. We will operate within defined safety parameters and keep a keen eye on the forecast. Many contingencies will be place, together with a robust safety plan, safety paddlers, coastguard liaison and motor-powered craft. If we deem it too rough, we will pull the kayak leg, or shorten it. But we will absolutely set out to achieve the full traverse if weather permits.
If you really have bitten off more than you can chew, we’ll give you a tow to the next Pit Stop location. If you do have to abandon, our craft will pluck you and your craft from the water. We really hope it doesn’t come to that but that’s what we are there for, if required. 


The bike stage is all on smooth tarmac and as you would expect in the Keys, is for the most-part extremely flat, except where you go up and over large bridges. Even then, it’s hardly any ascent at all! Check out the ride here! As such, this is classed as an easy bike. However, with 33 miles of kayaking in the arms and legs and a 13 mile run ahead, this is not to be underestimated. There may be a headwind and 100 miles is still 100 miles. But you will be rewarded with great views, fresh sea air, occasional sightings of birds and marine life around you and hopefully, a good fast ride along a very unique and historic stretch of the US Highway network.


You can walk or run the foot stage. We have designed the format of this event so that the final half marathon foot route will be suitable for fast or slower paces. Open her up and lay down a fast, flat half marathon time (we’ll be impressed with any PBs!) or just kick back, take your foot off the gas and enjoy the final miles into Key West, along some of the most spectacular sections of the Overseas Highway. Upon journey’s end, dip those battered feet into the Ocean and enjoy a brewski – you’ve earned it!