Logistics & Support

9 Mile Paddle – WOW. How long will that take? Is this something a first time paddler can handle? What do I need to carry with me?

We know you will have a lot of questions about the Islander Regatta and we’ve anticipated many of them with answers below. The Islander Regatta is not a race: it’s a paddling adventure for non-motorized boats. That’s right: you & your boat will make it around the island solely on your own power.

Water Support

Members of US Coast Guard Auxiliary Flotilla 66 provide regatta safety zone support around the paddlers, alerting other boaters at times to lower their speed and give way to the paddlers and kayakers. Pictured here is Coxswain Ray Procopio with crew members Matt Smith and Mike Moore on board (not pictured), all members of Flotilla 66.


Shallow Water Support

Local resident boat owners, such as Ron Love, Jacob Love, Allen Ward, and Warner Ward (some of whom are pictured here) follow paddlers during the circumnavigation. Their shallow draft boats allow them closer access to shore and to participants as needed.


Some Experience Required

Although the water is generally calm around Gwynn’s Island, by its very nature, open water paddling can be unpredictable. The 9-mile distance can take experienced paddlers as little as 2 hours or as long as 4 hours to complete in the calmest situation. Given those two factors, the Islander Regatta is not suited for many first-time paddlers. Average completion time is 3 hours, allowing for 2 rest breaks.

Safety/ Support crew can – at their discretion – ask a participant to withdraw from the Islander Regatta & guide them to the shore if they believe a paddler is as risk due to inexperience. Once underway, paddlers should gauge their comfort level and return to the start/ finish area if they feel unsure/ unsafe with the conditions. The first 3 miles in Milford Sound tend to be the most tranquil – offering several creeks and coves to explore. Let that be your journey if you are unable to complete the full circumnavigation!



PFD required. Each participant in the Islander Regatta must wear or carry a PFD (personal flotation device) during the event at all times.

Recommended equipment – a waterproof carrier for your mobile device, whistle, water/ liquid (enough for a 3-4 hour workout), snacks.


Participant Waiver – Required at Registration

During the registration process participants will be required to read and sign a waiver. A summary of the waiver conditions is provided below as a preview (subject to change). The Islander Regatta is limited to participants ages 14 & older; anyone under the age of 18 will need a parent/ authorized guardian signature.

Physically Able. I have read the event description, understand the course conditions and believe myself capable of completing the self-powered paddle around Gwynn’s Island.

Self Conduct & Race Crew Instructions. I agree to adhere to the school and council rules of conduct and sportsmanship while participating in this event. I will follow instructions of the race crew including – but not limited to – the keeping the required equipment (PFD) with me during the event.

Medical Insurance Waiver. I understand that neither the Islander LLC nor the Mathews Outdoor Club provide any registrant medical or hospitalization insurance whatsoever, and hereby waive any and all claims against the Islander LLC, the Mathews Outdoor Club or any other person affiliated with these entities and sponsors for injuries sustained while watching or participating in this event or traveling to and from event.

Health Precautions. I acknowledge that certain health risks are inherent with public activities and that the event organizers will provide reasonable safety precautions (such as providing space/room for social distancing) at the event start/finish areas. While the participants are not within the start/finish areas, it will be each participant’s responsibility for adhering to the safety precautions.

Photography Waiver. I agree that photographs taken of my child or me while participating in this activity may be used for publicity.


The Islander Regatta is a great opportunity for sightseeing: paddlers are in close proximity to the shoreline during the trip around Gwynn’s Island.