“Where the Figawi?” More than likely, you are probably thinking “What is the Figawi?” Unless you are from the Northeast or are well-versed in the sailing world, it’s likely you may have never heard this term before. Fear not, I’ve compiled the ultimate guide to everything you need to know about the legendary race and highly-anticipated party weekend known as Figawi.
Table of Contents
The Race
The Figawi Race is a world-renowned sailing regatta that takes place annually on Memorial Day Weekend in Massachusetts. It is the Northeast’s first major regatta of the summer sailing season. Each year, over two hundred sailboats of all sizes and thousands of sailors (or wannabe sailors like me!) participate in the race. The 25-mile race starts in Hyannis Port on Cape Cod and finishes at the entrance to Nantucket Island Harbor. 2019 will be the 48th Annual Figawi Race Weekend!
The Legacy
The first Figawi race took place in 1972 as an informal competition between 3 friends. Legend has it that Bob Horan, Joe Horan, and Bob Luby were having drinks one night at Baxter’s Boathouse in Hyannis Harbor. A friendly argument ensued about whose boat was the fastest of the three. They decided to settle the dispute by racing from Hyannis to Nantucket.
As any New Englander knows, the weather can be fickle and foggy and apparently the fog was quite thick that day. At some point during the race, blinded by the fog and with no GPS on board, one of the competitors shouted “Where the f*ck are we?” Of course, this was said in a thick Boston accent so it sounded more like “Where the Figawi?” And thus the name, and tradition, of Figawi Race Weekend was born.
The Schedule
Friday
The fun-filled weekend starts off on Friday of Memorial Day Weekend with registration from 3-8 PM, as well as the Annual Figawi Kick-off Party held at the Hyannis Yacht Club. Sailors from all over the country reconnect and gather for a buffet dinner, drinks, and entertainment. This is also where you get first dibs on the Figawi merchandise for sale (except for the infamous red hat – more on that later).
Pro-tip: Parking at Hyannis Yacht Club for the weekend, as well as drinks at the kick-off party, can ONLY be paid for in cash. Avoid this rookie mistake by hitting the ATM before coming to the party!
The night of revelry continues with the unofficial post-kick-off party bash at Baxter’s Boathouse, in Hyannis Harbor. There’s inevitably a good crowd and fun to be had here – but remember to take it somewhat easy on the adult beverages if you are sailing in the morning!
Saturday
It’s Race Day! The regatta starts from the Hyannis Port Jetty at 10 AM, with staggered start times according to each boat’s rating continuing until 12 PM. The boats make their way across the Nantucket Sound and cross the finish line mid-afternoon. The start and finish of the race is fast-paced and exciting. But there is actually a fair amount of downtime during the middle of the race! I may or may not have been lulled into sleep by the waves.
Pro-tip: If you are not racing, head to Brant Point Lighthouse to watch the parade of sailboats make their way to the Nantucket Boat Basin after crossing the finish line!
One of my favorite parts of Figawi weekend is the camaraderie amongst the sailors. This is evidenced by the party that takes place in the Boat Basin after the race has finished. Sailors and non-sailors alike swarm the docks and make their way from boat to boat, catching up with friends and more than likely making new ones!
For racers, the Competitor Party at the Figawi Tent on New Whale Street in town starts at 7 PM. There is a live band, free-flowing drinks, dancing, and other revelry. Make sure to hold on tight to your bracelet because that is your ticket for entry! For the non-racers, unfortunately bracelets are only available for purchase ahead of time by race competitors. But don’t worry, there are plenty of other options for fun during Figawi weekend (keep reading below).
Sunday
It is well-worth making your way to the tent for the Joke Telling Session from 9-11 AM. That is, if you can muster up the energy to get up that early after the tent shenanigans from the night before. The Figawi Bloody Mary acts as a much-needed “hair of the dog” remedy. The first year I raced I didn’t attend the joke telling session and ended up regretting it. The jokes are equally offensive to all races, genders, and religions and no subject matter is off limits. It is definitely one of the highlights of the weekend and an event you can’t really find anywhere else.
At 11:30 AM, the Figawi High School Invitational takes place in the Nantucket Boat Basin, and there is a Memorial Day parade through town starting at 1 PM. Sunday afternoon is usually filled with more party-hopping in the boat basin, shopping in town, or perhaps a much-needed nap.
Sailors make their way back to the Figawi Tent in time for the awards ceremony starting at 5 PM. Trophies are given out to the winners and top finishers of all 13 classes that competed in the race. There is also an award given to a well-deserving volunteer, and an award given to the team that most embodied the spirit of Figawi (either on land or on the sea).
The Sunday festivities conclude with a Wrap-Up Party held for competitors starting at 7 PM in the Figawi Tent. The Sunday night tent party is a déjà vu of the night before with a live band, dancing, drinks, and more debauchery. Just remember that there is still a sail back to Hyannis the following morning!
Monday
All good things must come to an end. On Monday morning, willing sailors participate in the “Redux Race” from Nantucket Harbor back to a neutral point near Hyannis. For those still standing, there is a Farewell Party held at Baxter’s for new and old friends to gather one more time before parting ways.
The Charity
Members of the Figawi organizing committee capitalized on the growing popularity of Figawi Race Weekend and added a Charity Ball as a way to give back to the local communities. The first black-tie ball took place in 1987 and continues to be held annually in Hyannis the Saturday before Memorial Day Weekend. The proceeds from the ball go to local charities and over $2 million have been donated to date.
The Hat
The infamous “Figawi hat” is the most coveted souvenir from the race – partly because it cannot be bought, only earned (or stolen!). Mount Gay Rum embroiders hats with the name and date of each of the 140 regattas they sponsor worldwide, including Figawi. The red and yellow baseball caps made their debut for Figawi in the late 1970s and have been a sought-after item ever since.
However, only 3 hats are included in the Skipper’s Bag given to the captain of each registered boat. Each crew is made up of 8-12 team members on average, so even if you sail in the race you are still not guaranteed to get a hat! I was a lucky recipient of a hat in the first Figawi race I sailed in 2016. I think the captain took pity on me because I almost went overboard on one particularly gnarly tack! It’s a badge of honor to receive a Figawi hat, and I treasure mine and the memories it brings with it.
As with most things on Nantucket, new and shiny items do not always outrank items of tradition and prestige. And so, the older the date embroidered on the Figawi hat, the more bragging rights the proud owner has since this shows how long they’ve been participating in the storied Figawi Race Weekend.
It has also become a tradition for the local island teens to devise schemes to steal these highly-prized hats off the heads of unsuspecting sailors! So if you are lucky enough to own a coveted Figawi hat, I recommend holding onto it tight!
The Party Scene
Long before I got the chance to sail in Figawi starting in 2016, I made an annual pilgrimage to Nantucket for Memorial Day Weekend to partake in the “other” side of Figawi. Though non-sailors can’t attend the tent parties (unless you finagle a bracelet from a race competitor), there are plenty of other festivities taking place around the island. So you definitely don’t have to have sailed in the race to have a good time during Figawi weekend! In fact, I’m not so sure many of the visitors to the island during Figawi weekend even realize that there is a sailing race taking place!
I must warn you, however, that you either need to have a local island connection to get you in the back entrance to one of these bars, or be prepared for a VERY long wait in line. With that in mind, here are the top spots on the island to find the fun:
While the Straight Wharf is actually a fancy restaurant at dinnertime, it transforms into an outdoor hotspot during the day over Figawi weekend and a dance club after hours every weekend during the summer. Actually, it’s not unusual to see a full-on dance party at noon on Sunday during Figawi. Make sure to order their signature drink, the Goombay Smash, or a Life Is Good while you’re there. And if you make it to last call, you’ll be serenaded with Sinatra’s “Summer Wind” to end your night.
This bare bones structure in Harbor Square is also the epicenter of Figawi weekend. Sandwiched between the Straight Wharf and The Tavern, there is a never-ending line to secure a spot in this open-air bar in the shape of (you guessed it) a gazebo. If you make it in, you can’t miss their signature mudslides (ask for it to be made with Tito’s and real Kahlua!).
Ok, so this is not technically a “hot spot.” Oddly enough, even though The Tavern is part of the Harbor Square trifecta alongside the Straight Wharf and the Gazebo, it rarely draws a crowd. The Gazebo is actually part of the Tavern but there are different lines to get into each building. So, if you aren’t in the mood to stand in line for the entire day, you can easily grab a drink at The Tavern and watch the shenanigans at the Gazebo and Straight Wharf from afar while sitting on their outdoor patio.
Cru Oyster Bar is in the absolute perfect location for Figawi, at the end of Straight Wharf (the actual wharf itself, not the eponymous restaurant). Cru has floor-to-ceiling windows on three sides that overlook Nantucket Boat Basin and the harbor. And the party has been known to spill outside onto the boats docked in the slips parallel to the restaurant. Cru tends to draw a trendy “see-and-be-seen” crowd and you can bet that magnums of rosé will be popping in abundance over Figawi weekend.
Cisco Brewery is a year-round favorite for locals and visitors alike who come to sample their ever-expanding selection of craft beers. This mid-island compound on Bartlett Road is actually also home to Nantucket Vineyards and the Triple Eight Distillery. These three buildings surround a courtyard filled with picnic tables, food trucks, and a stage for daily live music. Everyone from babies to grandparents to four-legged furry friends are welcome at Cisco.
Sample the latest craft beer release from the brewery, sip the made-fresh-daily sangria from the winery, or try a Figawi Wowie or Blueberry Lemonade from the distillery. Or head over to the outdoor Tiki Bar and order a “Blue-Haired Lady,” which is a Grey Lady beer with a Triple 8 blueberry vodka floater. Trust me, it is delicious!
Pro-tips: Take advantage of the free Cisco shuttle that makes regular rounds from the Visitor Center on Federal Street in town to the brewery. And make sure to bring cash to tip the driver and for the $5-10 cover you’ll be charged at the entrance!
You can’t come to Nantucket and not experience a night out at The Box. The Box is a no-frills, dive bar located mid-island (yes, Nantucket has a dive bar!). For Figawi weekend in particular, you’ll need to show up super early to avoid the line that will inevitably form down the street. There’s usually a $20 cover and a live band every weekend night. Although if you get there early enough, you can avoid a cover and kill time playing pool or shuffleboard until the band comes on.
Pro-tip: After-party plans are usually made outside the Box after last call if you want to keep the party going until the wee hours of dawn!
Is sailing in Figawi on your bucket list?
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