Changes in Latitude: A California Girl Heads to Key West

San Francisco J/70 sailor and photographer Christy Usher followed her boat to Key West Race Week where she got a front-row seat for all the action on and off the water.

Quantum Key West Race Week is one of those rare regattas that’s on every sailor’s bucket list—especially because when it’s winter almost everywhere else in the world, you can go bask in the sunshine and sea breeze, test your skills against the incredible talent on the water, and enjoy the social atmosphere at the legendary dock parties and nightlife only Key West’s Duval Street can deliver.

key west race week

Welcome to Key West. Home of KWRW, the frozen concoction, spectacular sunsets, Bahamian style bungalows, and coastal cottages. Photos: Christy Usher/Christine Robin Photography.

key west race week

The flavor of Key West Race Week. Photo: Christy Usher/Christine Robin Photography.

key west race week

Team JElvis 7* takes the helm of the Christine Robin at Key West Race Week after she made the 3,000 mile trip across country from San Francisco to the Florida Keys. Photos: Christy Usher/Christine Robin Photography.

After sailing the 2016 J/70 Worlds in San Francisco in September, the sailing season had come to a close for myself and my husband on our J/70 Christine Robin. Looking ahead to our 2017 sailing schedule, we set our sights on the trifecta of regattas—Quantum Key West Race Week, Miami Sailing Week, and Charleston Race Week—but due to a business trip my husband had scheduled, we wouldn’t be able to sail at KWRW. So instead, we chartered our boat to Martin Dent’s British team JElvis 7*. I jumped at the opportunity to accompany the boat to Key West and handle logistics related to the charter.

key west race week

Christy says that as a sailor and photographer, watching and photographing the races with Sharon Green of Ultimate Sailing was the experience of a lifetime. Photo: Christy Usher/Christine Robin Photography.

It was hard at times to stand on the sidelines, watching another J/70 team prepare, rig, launch, and race my boat around the course, but luckily I ended up with one of the best seats in the house—watching and photographing the racing on the water with Sharon Green and Betsy Crowfoot of Ultimate Sailing. It was the experience of a lifetime. We couldn’t have been closer to the action if we’d been racing, and indeed, at times it felt like we were.

Changes in latitude, changes in attitude

The greatest part of any journey, however, isn’t arriving at your destination; it’s all the stuff that happens along the way. From the moment I landed in Miami, the adventure began.

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Key West is paradise found. Photo: Christy Usher/Christine Robin Photography.

key west race week

When you see this sign you know you’ve arrived in Key West! Photo: Christy Usher/Christine Robin Photography.

You could fly directly into Key West International Airport, or you could take the stunningly scenic four-hour, 110-mile drive from MIA to Key West. I opted for the latter. The route takes you across 42 bridges connecting a seemingly endless string of islands. Along the way, you’ll gaze out across some of the most picture-perfect turquoise blue water you’ve ever seen. Once you hit Highway 1, you’ll be counting down the mile markers from 110 to Zero—destination Key West.

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Roadtrip approved! The perfect rental regatta mobile, the Mercedes GLA Class: sports wagon meets SUV. Photo: Christy Usher/Christine Robin Photography.

Having done this road trip once before, years ago, I knew I wanted to rent a convertible. Unfortunately, when I arrived in Miami the rental car agency Sixt did not have the convertible Beetle I reserved available. I ended up with a Mercedes GLA Class with a super-sized sunroof—a suitable alternative to top down and the high-end luxury car features far surpassed the Volkswagen beetle I had reserved. Not only was the GLA a dream to drive, it also turned out to be the perfect regatta mobile for me once I arrived in the Keys for hauling sails, boat covers, photography gear, photographers, and sailors around town.

Island time

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For lunch I’d like, a side of sand in my toes, please! Photos: Christy Usher/Christine Robin Photography.

It’s easy to adjust to island time, and when you do, there’s plenty of time to stop at the Morada Bay Beach Café at mile marker 81.6 in Islamorada—my favorite pit stop on this trip. This charming outdoor restaurant and bar overlooking Morada Bay is casual and quaint and famous for their full moon parties.

key west race week

A slice of heaven Key lime pie. Salmon salad served up to perfection at the Morada Bay Beach Cafe. Photos: Christy Usher/Christine Robin Photography.

key west race week

Leave a message, I am on Island time. Photos: Christy Usher/Christine Robin Photography.

Reservations are not required for lunch or dinner and you’ll enjoy your meal right on the beach with sand in your toes under the sway of the coconut palm trees. As if the ambiance isn’t enough, they also served up the best salmon salad of my life, cooked and seasoned to perfection, and the fruits and greens could not have been more flavorful and fresh. After lunch, I retired to the nearby Adirondack chairs to soak up more sunshine, blissfully and literally “wasting away” my afternoon Jimmy Buffet style.

January’s best were in Key West

Quantum Key West Race Week attracts some of the best boats and sailing talent from all over the world racing in the hottest classes, from the TP52s and J/111s, to the J/70s, C&C 30s, and more. Three separate racecourses hosted nine different sailboat classes all competing for the Key West Championship title in their respective divisions.

Some 100 professional and Corinthian boats from the North America, South America, and Europe were registered in the 30th annual event, including Carlo Alberini’s J/70 Calvi Network, who has won the last two KWRW events, Dan Cheresh’s Extreme2 in the C&C 30 class, and Quantum Racing in the TP52 fleet, the first of six TP52  Superseries regattas.

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The stunning TP52 Class. Photo: Quantum Key West Race Week/


I’ve been a dinghy sailor most of my life, only recently graduating to the “larger” 22-foot J/70. Getting up-close on the racecourse with the incredible TP52s was an eye-opening experience for me. I’ll never forget the moments we’d glide up next to those beautiful 52-foot beasts for a photo op, our powerful powerboat barely able to keep up, the wind howling, the water splashing and crashing, and the sailboats groaning under the load of the wind in their sails.

The TP52s aren’t just stunningly beautiful sailboats; they’re also incredibly photogenic with sleek lines and intricate artwork on both the hull and sails.

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The TP52s sport creative art on their hulls and sails. Photo: Key West Race Week/

key west race week

A sampling of the winner’s circle: Quantum Racing in the 52 Super Series, Skeleton Key in the J/111 Class and New England Ropes in the J/70 Class. Photo: Quantum Key West Race Week/

Former J/70 world champion Tim Healy took home the Key West Race Week title on New England Ropes without winning a single race but finishing no lower than 10th in the 38-boat J/70 fleet. Quantum Racing started their season well with a Key West title, as did Extreme2 in the C&C 30 fleet and Peter Wagner’s San Francisco-based J/111 Skeleton Key. Click here for complete results.

“Although there were a number of boats that posted good scores, the main competition for Skeleton Key in the J/111 series was from Shamrock, Spaceman Spiff, and Velocity. With such close racing, we didn’t obtain the lead in the series until the last race on Thursday,” said bowman John Collins. “Our ultimate goal is to win the J/111 worlds, which will take place at the StFYC in the San Francisco Bay in August 2017.”

Being the proud boat owner that I am, I was bragging at dinner one evening that the U.K. team sailing my boat had scored a second place that day, to which one of my dinner companions, Craig Leweck of Scuttlebutt replied, “Christy, you are like a horse owner, cheering your horse on from the sidelines.” I couldn’t have said it better myself.

The après-sail

key west race week

The view from the Waterfront Brewery a.k.a. race headquarters never got old. Photo: Christy Usher/Christine Robin Photography.

Key West Race Week’s main social events, post-race discussions, and awards were held at the hip Waterfront Brewery, ideally located in the heart of old town with spectacular views of the historic seaport. The Brewery also hosted the Regatta Bar, which offered daily Mt. Gay Rum and Red Stripe beer socials. Augmenting the Regatta Bar socials was Key West’s infamous midweek Blender Dock Party.

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Hooligans on and off the water. Photos: Christy Usher/Christine Robin Photography.

As far back as 1984, sailor Terry McSweeney has hosted a hugely successful dock party to foster good will and camaraderie among the fleet. Terry hasn’t been in Key West in recent years, so his Melges 32 boat partner Trey Sheehan of Hooligan, part of the Flat Stanley Racing program, has dutifully taken over the responsibility of hosting the Blender Dock Party. Sheehan, as the owner of Hooligans Irish Pub in Put-In-Bay, OH, is an ideal host since he has access to the commercial grade supplies required to host a party of this magnitude. To give you an idea of exactly how popular this party is, at least two commercial blenders have been burned thru since 1996.

The blender, it should be mentioned, travels nationally and internationally in its own custom fabricated Igloo cooler (with seat belts and rivets hastily fashioned after the plastic hinges and snaps disintegrated) usually with its own whisper-quiet Honda generator, since it has been known to take down the electrical service at numerous yacht clubs and marinas over the years. Before the worst can happen, there’s a familiar hum and high-pitch whirl that signals the neighbors to turn off their own power consumption in anticipation of a rum-laden Mudslide or the popular Creamsicle.

Brain freeze is a very serious side effect, and morning-after hangovers usually earn team Hooligan at least one clear pass on a tight crossing the next day. About 12 years ago, the Galleon Marina asked Trey to move the party after the sheer number of attendees sunk the floating docks. Damage to under-engineered docks and blown fuses has always been handled with a generous frozen compensatory donation.

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The Green Parrot was always packed with sailors. Photo: Christy Usher/Christine Robin Photography.

When the docks were underwater and the blender had blacked out the marina, the sailors headed over to the Green Parrot where they carried on with live music into the early hours of the morning.

Off the water

I arrived in the Keys on the evening of the Morada Bay Beach Café’s Full Moon Party. It’s a must-do in the Keys, so after checking into my hotel in Key West, I doubled back to Islamorada.

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A little full moon party never hurt nobody. Photos: Christy Usher/Christine Robin Photography.

Though it was January, it felt like a warm summer night with a gentle sea breeze and no humidity. Tiki torches light the grounds of the Beach Café and entertainment abounds all evening with fire throwers, bands, DJs, stilted acrobats, bonfires in the sand, and an impressive fireworks show.

The catalyst for my trip to Key West was Race Week, but a postponement on shore was an opportune time to do some sightseeing around the island.

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“Now Hiring: Must Love Seashells” was the sign in this shop. Christy says she was tempted to apply! Photos: Christy Usher/Christine Robin Photography.

In contrast to being the arterial of Key West’s nightlife, during the day Duval Street is lined with charming stores, shops, and cafes. My favorite shop, Fanta-Sea offers quintessential coastal living charm at its best.

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That iconic kiss. Photos: Christy Usher/Christine Robin Photography.

I also enjoyed visiting the newly installed statue of the iconic kiss between a World War II sailor and nurse in 1945. The famous moment in U.S. history is often referred to as “the kiss that ended World War II.” And with such a large military presence still in Key West, the statue and tribute seem fitting on the island.

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The sunrises are just as memorable as the sunsets in Key West. Photo: Christy Usher/Christine Robin Photography.

It’s a good idea to get up early to enjoy the sunrise and avoid the tourists at the buoy marker for the southernmost spot in the U.S., on the southern end of Duval Street. On the north end is Mallory Square, the best place to watch the sunset.

Where the sailors stay

Key West offers numerous lodging options with its plethora of quaint and charming 19th and 20th-century residences and buildings. The more recently constructed Galleon Resort and Marina has been the lodging of choice for KWRW sailors for many years thanks to its easy access to boat slips in the marina.

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The Galleon Resort and Marina is favorite of sailors. Photos: The Galleon Resort and Marina.

key west race week

Bahamian charm at the Truman Annex. Photo: Christy Usher/Christine Robin Racing.

The Truman Annex, with its Bahamian-style bungalows and townhomes, is a great location if you’re looking for a VRBO. Both housing options are conveniently located within walking distance of shopping, restaurants, bars, and local attractions.

Vitamin sea in the Florida Keys

Key West Race Week was the thrill of a lifetime; an opportunity to indulge my passions of sailing and photography in a tropical paradise with friends old and new and an up-close look at the “fresh and frightening” action (as Sharon Green calls it) on the TP52 racecourse. One thing I know for sure, is that a little vitamin sea in the Florida Keys is just what every sailor needs.

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