Friday - 5:00PM-11:00PM
Saturday - NOON-11:00PM
Sunday - NOON-9:00PM


Thursday - 9:00AM-5:00PM
Fri-Sat - 9:00AM-11:00PM
Sunday - 9:00AM-9:00PM
Club is closed on Tuesday and Wednesday

Regattas at The Upper Keys Sailing Club

The Upper Keys Sailing Club has a strong tradition of annual regattas, spread out in our "busy" sailing season from November through April. Most two day regattas include a day of Portsmouth racing on Saturday and PHRF racing on Sunday. We also hold Portsmouth and PHRF series throughout the year and several regattas associated with holidays. Here are our traditional Regattas held every year, along with our newer one-design and invitational regattas! Unless otherwise noted, Skippers' Meetings are at 12 noon and the first flag will be at 1:00 pm.


JUST FOR THE HALIBUT - September. A fun All Comers Regatta followed by a fish fry!

DOCKMASTERS REGATTA - November The DOCKMASTERS REGATTA celebrates our Dockmasters every year! Our Dockmasters are our club caretakers, bartenders, clubhouse managers, and hosts/hostesses for our regattas. Every dockmaster couple leaves their own distinct mark on our club, and this is their regatta and their chance to shine. Last year we had a boat building contest out of recycled materials - who knows what Joel Messamore and Kacie Bonner will come up with for this year? Dockmasters Regatta winners are immortalized with their names on the perpetual trophy, which has a proud place right over the bar.

BLACK BETSY - October or November. The Black Betsy is a destination race for PHRF boats, out to the Black Betsy Keys south and west of the UKSC. Often, cruising boats will race out and then raft up to enjoy a night on the hook.

FLAIL & SAIL - December. Golf one day - sail the next! This fun regatta combines a best-ball golf tournament on Saturday with a PHRF Race on Sunday. The scoring requires multiple calculators and some witchcraft. A very fun time is always had by all, even the non golfers and non sailors in the club!

DEAD DOGS & TIN WHISTLES - January Martin Luther King holiday weekend. This is a one-design dinghy regatta for Buccaneers and Mutineers. It started as an invitation to a Fleet Captain Regatta in 2008 and developed a life of its own! Buccs and Mutts from all over the USA escape their wintry homes and come to Key Largo to enjoy a weekend of wind and camaraderie.

COMMODORE'S REGATTA - Celebrating the current and past Commodores, this regatta is always well attended. A great regatta dinner is always included! This is one of the Club's older regattas, and has a Perpetual trophy.

COMMUNITY BANK REGATTA - A one day regatta combining Portsmouth and PHRF racing, sponsored by our local Community Bank. All local sailors invited to participate. Dinner Saturday.

BUCCANEER BLAST MARK SORENSEN YOUTH SAILING CHAMPIONSHIP - Our premier youth event attracts young Opti and Laser sailors from all over Florida and beyond! Nearly 90 youth sailors battle it out on two courses on Buttonwood Sound. Details can be found on the youth section of our website.

FLEET CAPTAIN'S REGATTA - Our Fleet Captains are responsible for the racing program at the club, so they get their own regatta too! Another of our traditional regattas with its own Perpetual Trophy on our clubhouse wall.

FORCE FIVE MIDWINTER CHAMPIONSHIPS - February - March. For several years, the Upper Keys Sailing Club has proudly hosted the Force Five Class Association Midwinters. These dinghy sailors race hard and play hard - one of their awards is for the biggest bar bill!

MARLIN CUP - March. One of our oldest regattas, the Marlin Cup races are held on the Oceanside. Held on a Sunday, there is an informal Race to Rodriguez Ken on the Saturday just before, as our bayside boats head oceanside. This is a PHRF race.

GLANDER CUP - March. This regatta is the ultimate Upper Keys Sailing Club Holy Grail! Our oldest, most prestigious regatta creates some great competition amongst the PHRF boats at the Club. Racing is held oceanside, with a celebratory Glander Cup Dinner on Saturday night. The winner skipper and crew of the Glander Cup enjoy a champagne toast, drunk out of the Glander Cup itself.