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2022 Key West Southernmost Regatta is back

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Rise of the Southernmost Regatta

  • By Dave Reed
  • August 10, 2022

Vesper

When Marty Kullman finally got home after orchestrating his weeklong Southernmost Regatta in Key West , his phone was lighting up. Texts, emails and phone messages, he says, poured in from people thanking him for pulling off the regatta. “It was off the charts how many people actually took the time to reach out and thank me for bringing us back to the best sailing we’ve done in a long time,” Kullman says. “That and the conditions we had were the highlights for me.”

The Southernmost got its start in 2021 as a getaway regatta for a small band of J/111 class owners. “That was a bit of a test run,” Kullman says. “There was a lot of connecting with city officials, the Navy, the Coast Guard and all sorts of people. Developing relationships with the right people was critical.”

Key to executing the regatta was keeping costs in check, Kullman adds. A big country music festival at the same time presented a pile of challenges with boat launching and housing, but in the end, 48 boats registered, spread across fleets of GL52s, J/111s, Melges 24s and J/70s, as well as a five-boat ORC division. Kullman was adamant the regatta should have a grassroots feel and only two races per day.

Basing operations and the nightly socials at the Galleon Marina, Kullman and his volunteer army delivered with the bare essentials. With the Omicron variant spiking (although you’d never know it on Duval, he says), there was no need to host big parties and secure city permits as in the past. “The socials started right away after sailing at the Galleon with Mount Gay Rum, there was a short awards thing outside at the Tiki Bar with the sunset, and then everyone could go on their way to team dinners or whatever. It worked out great.”

His edict for the racing itself was that it be fun, and he drove that point home numerous times to the many hard-charging professionals in attendance to keep the racing clean and easy. “We had one protest the entire week,” Kullman says. “That was between a couple of the GL52s, and they eventually worked it out between them. So, technically, no protests were heard.”

The list of naysayers is long, Kullman says, but after a week of what owners and crews agree was a classic Key West experience—proven by the explosion of in-your-face, look-at-what-you-missed social media posts—he’s ­committed to doing it again. And again.

With one running of the Southernmost under his belt, Kullman is unsure how he can continue to grow it, scale it and keep it on the down low, but “what we did is sustainable,” he says. “This is what sailing needs. If it’s the same next year, I’m sure everyone will be happy because it will be as successful, but we know already that there is strong interest from a lot of other classes. We will cap it for sure next year if we need to.”

He’ll do whatever it takes to get people excited about sailing, he says. And he’ll get back to it just as soon as his phone stops dinging. In the meantime, here’s what the winners have to say about their week of fun in the sun.

GL52 Vesper – David Team

It had been about 20 years since David Team set foot in Key West with his sailing gear, but he fondly and easily recalls the glory days of Race Week, racing with his brother in the gigantic Melges 24 fleet of the time. Doing 20 knots in a dinghylike sportboat was a much different experience than the sleepy, light breezes of Newport Beach—an experience he says is seared into his memory.

But that was then and this is now, and this year Team showed up with his GL52, Vesper , which he’s been campaigning since 2018. He’s taken the program on the road over the last few years, competing on the Great Lakes and the East Coast, and when his fellow 52 owners all pushed to put the Southernmost on the calendar, how could he possibly say no?

sailboat race key west

With most of Vesper ’s regular crew, led by all-star tactician Morgan Larson, they won five of 12 races in the five-boat fleet—not an easy task given the caliber of those in attendance. Team Vesper excelled in the big breeze of the first four days, even though conditions didn’t ­necessarily suit their boat.

“With our particular hull form, we ­actually do OK in the waves with the others, so we don’t mind it,” Team says. “Even though Vesper is a light-air boat, we were fast for the first couple of days, especially downwind.”

Good starts contributed to good ­finishes, he adds, and a lot of that was Larson’s guidance in the box. “Starting in these boats is a lot of work, and in some cases, it can almost be easier when it’s windy because the boats tend to separate a bit more,” Team says. “You have to stay a bit closer to your boatspeed so you don’t get yourself in trouble. The thing with this fleet is that no one holds back, so you can’t be late either.”

Vesper

Perfect sailing conditions aside, Team’s personal highlight of the week was a bit of piracy on the final day: “The crew snuck beers on board,” he says. “That was a good way to end it.”

J/70 Dingbat – Bobby Julien

Bobby Julien, of Delray Beach, Florida, declares himself a “total newbie” to sailboat racing, but by the looks of his team’s scores at the Southernmost Regatta, you’d say he’s pulling your leg. But no, it’s true, he says. The last time he skippered a boat with a tiller, he was 13 years old. Julien can thank his three young’uns for his latest obsession. “My kids started racing six years ago, and after watching them and thinking about it for a few years, I finally decided to do it myself,” he says.

But how? And what boat?

He asked around, and all recommendations pointed to the J/70. He eventually found one in Houston, and Dingbat ’s first team hire was Alec Anderson, who solidified a squad with Chris Waters upfront and pro trimmer Will Felder on the sheets. One day of practice is all Julien got before being thrown into the J/70 madness in Miami in early January. Then it was straight to Key West for outing No. 2, a much smaller fleet and an opportunity to work on his boathandling. After two days of practice, he was in the thick of it, rifling off wins in six of 10 races. Beginner’s luck, Julien says. But for a guy who had never raced in the big breeze and waves of Key West, he may be underselling his undiscovered talent.

Dingbat crew

“It was shifty and definitely not easy to steer in the first races,” Julien says. “It takes a lot of concentration, but it was so much fun. I’m so happy I’m back into sailing.”

With less traffic to contend with, they could focus on developing boatspeed and mechanics, and his confidence skyrocketed over five days. “As a new skipper, I was very tense and stressed on the tiller on the first day, and by the end of the week I was relaxing way more,” Julien says, “more confident through the tacks and jibes. It was ugly at the beginning, but that’s what I’m learning—the art of the turn.”

The relaxing vibe of Key West was also an opportunity for the 54-year-old real estate developer to take his mind off work and put it to something else. “Everyone was there to have a good time,” is the first-­timer’s takeaway. “It was awesome. In terms of location of a regatta, it was first-class. Great atmosphere—no complaints at all. The venue itself, I now know, is beautiful. The sailing is amazing.”

ORC Interlodge IV – Gwen Fragomen

Austin and Gwen Fragomen’s Interlodge sailing team rolled into Key West with not one, but two slick grand-prix boats: the GL52 for Austin and the Botin 44 for Gwen. The squad of top-shelf pros and their state-of-the-art hardware were no match for the rest of the smaller and much older ORC boats. Interlodge IV won nine of 10 races, losing the one by a mere 3 seconds on corrected time. Some would say it wasn’t fair, but for Olympic 49erFX sailor Stephanie Roble, the results didn’t really matter. It was the experience of a lifetime being part of a big program.

Botin 44

Roble drove the 44-footer for the first day, and for the rest of the week she helmed the starts, passing the wheel to Gwen for the remainder of the race. On the last day, Gwen helmed from start to finish, which Roble says was the team’s goal for the week. “She picked up everything so quickly,” Roble says, “so everyone was really stoked on that.”

But about that first windy day: “It was an amazing experience,” Roble says. “It was an absolute blast, and I really had to pinch myself that I was driving this beautiful boat with this incredible team around me. It was a super-cool moment.”

Cool Breeze

Differences between the tiller of a 49erFX and the carbon wheel of the big speed machine were many, Roble says, especially upwind: “There isn’t much feel to it with such a small rudder. Plus, I’m so used to feeling the wind on my face, and on the trapeze, you can feel everything. Plus, this boat wants to sail upwind at 25 degrees of heel angle—I’m more used to 1 to 2 degrees of windward or leeward heel—so that took some getting used to.”

Eventually, Roble ignored the instruments and sailed the boat as if it were a skiff. “The times when we weren’t going well was when I was looking at the instruments too much,” she says. “When I focused more on the heel—feeling things, looking at the water and listening for the puff calls—is when we started going better.”

sailboat race key west

The boat is an apparent-wind machine, just like her 49erFX, so there wasn’t too much adaptation once the big kite was set. “The technique is similar,” Roble says. Turn it up, load up the rudder and send it. But don’t get greedy. “Everything is about trying to find the edge, loading the boat and then releasing it,” she says. “And when you release it, you can really feel the acceleration. It’s sensational. I remember just trying to visualize myself in the 49er, being aggressive on the wheel to keep it trucking the whole time. It was so much fun. I was honored and grateful to be part of the program.”

Melges 24 Raza Mixta – Victor Diaz de Leon

Raza Mixta tactician Victor Diaz de Leon wasn’t doing his teammates any favors on the starting line of the talent-packed 17-boat Melges 24 fleet at the Southernmost. Too much time in the J/70 was messing with his timing. “I was setting us up too early on starboard,” says the J/70 world-­champion tactician (with Peter Duncan’s Relative Obscurity ). “On the 70, you can sail those slow speeds because of the really fat keel, but the cord length on the 24’s keel is short, so when you set up too early, you slide sideways a lot. And then you’re at the mercy of others coming in from behind with speed.”

With average starts and decent pace upwind, Duncan, Diaz de Leon, Matt Pistay and Greiner Hobbs made their advances on the runs.

“It was so fun and dynamic with the waves downwind,” Diaz de Leon says. “With Erik’s trimming and Peter’s driving—that was a lot of our success because we made our money downwind with really kinetic and aggressive sailing.”

Raza Mixta

They opened their 10-race series with a third and second, but the next day they put up two wins, banking valuable points that would later come into play. “It was very shifty that day,” Diaz de Leon says. “I was able to pretty much nail the shifts with a bit of luck. I often find myself being too conservative on how much leverage I take. For the last two years I’ve consistently finished second or third, so I started thinking that I have to start trusting my gut a little bit more. That day, I thought there was more breeze on the left, and so I said, ‘Screw it, there’s more wind out left, and I’m not going to tack until we’re into it.’ I finally got it right.”

Pacific Yankee

After being runner-up in Key West ­several times, Diaz de Leon was stoked with the win for his team. “This was one of my favorite regattas ever. The sailing was amazing; the water color, the wind, the conditions were money. When it stopped a few years ago, it was such a bummer, so I was so super-excited to be back.”

J/111 Bravo – Andrew Ward

Every Sunday through the New England winter, Andrew Ward plunges into the Atlantic near his home on Shelter Island, New York. “My buddy from Sweden says it’s good for me,” he says. Invigorating as the cold shock may be, Ward is no fool. He knows the better place to take a dip in January is Key West, and that’s where he and his teammates on the J/111 Bravo found themselves scraping for every inch in the final race to win their division.

J/111

With Bill Hardesty calling tactics, Bravo won the regatta’s first two races, but then fell into a daily pattern of scoring one good race and one stinker. The second-to-last race of the regatta was their worst—a DFL—which left them facing a complex scenario going into the final one-race day. In order to beat Ian Hill’s Sitella , they had to finish ahead, with one boat between them.

“We went out early—Bill ­suggested it because our worst races were in light air,” Ward says. “So, we went out and messed around with the rig for a bit, and loosened it to power it up a little better.”

As the helmsman, Ward doesn’t remember much of the final race. He was doing his job keeping his eyes glued to the telltales. Only on the final beat, with the course shortened to an upwind finish, did he take a look around. He could see it was going down to the wire. Approaching the finish, Fireball was close behind them on starboard, but Sitella was on port, so it was hard to judge which boat was ahead. “We beat Sitella , but we had to watch it play out,” Ward says. “We were cheering on the Fireball guys, and only after they finished did my whole body just relax.”

Ward’s 90-year-old father, Sedgwick, who owns and races the boat in Shelter Island, watched it all play out from the sidelines, which made the win all the sweeter. “We’ve been racing this boat for 10 years, with a lot of seconds and thirds, so winning one was really nice, especially in Key West and especially with him watching,” Ward says. “All the firsts we got were awesome, but to go from eighth to winning in the last race—that’s my best Key West moment.”

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sailboat race key west

Published on February 9th, 2022 | by Assoc Editor

Southernmost Regatta returns in 2023

Published on February 9th, 2022 by Assoc Editor -->

Key West, FL (February 9, 2022) – After having 45 boats compete in the inaugural edition of The Southernmost Regatta last month, the second edition is now confirmed. The 2023 edition will see racing from January 16 – January 20, 2023 with 9 races planned for the regatta.

“We were thrilled with the excitement and turnout surrounding The Southernmost Regatta this year, and our team was so excited to confirm it coming back in 2023. January sailing in Key West is absolutely top-notch, and our team can’t wait to see another successful edition this year,” said Ryan Ruhlman of The Sailing Inc.

Registration is open now on Yachtscoring. The NOR is posted with likely classes including Melges 24s, J-70s, J-111s, ORC, and others based on interest.

“With such a successful inaugural edition, we kept hearing from all the competitors about how much fun they had both on and off the water. So we were excited to keep the racing in Key West alive for another go in 2023,” said Regatta Chairman Marty Kullman.

sailboat race key west

Andrew Ward, winner of the J-111 class in 2022 said, “Key West is my favorite place to sail in the winter with warm blue waters and perfect sailing conditions. We can’t wait to go back in 2023.”

Event information

Source: Event media

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Key West Boat Races.

Key West Boat Races: 2022 World Offshore Championships

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Last Updated on November 3, 2023 by Boatsetter Team

Key West Offshore World Championship might be best described as the Indy 500 of powerboat racing, and it truly is a festival of speed on the water. Slated for Sunday through Sunday, Nov. 6-13, the 41st annual event in Key West, Florida , features three days of racing action pitting the top U.S. and international powerboat teams competing for a world championship title in multiple classes.

Here’s what to expect at the 2022 Key West Boat Races:

  • When: November 6-13, 2022
  • Where: Key West, Florida; Truman Waterfront, Duval Street, Mallory Square
  • What: Four races scheduled per day (Wednesday, Friday, and Sunday), featuring boats from multiple classes.
  • Enhance your Race Week Experience with a boat rental: Explore Boats in Key West

Between race days fans can view the boats and teams up close in the Truman Waterfront Race Village and view the teams testing on the water. Nightly social events for race teams and fans include multiple concerts, a traditional Duval Street party with race boats on display, and a Sunday night awards ceremony.

Explore All Available Boat Rentals in Key West, FL

Key West Boat Races.

Event Schedule

Kickoff parade.

The week kicks off with the ‘World’s Fastest Boat Parade’ of race boats down the island’s famed Duval Street beginning at 4pm Sunday, Nov. 6.

Race Schedule

The excitement builds throughout the week with racing action scheduled for: Wednesday, Nov. 9; Friday, Nov. 11; and Sunday, Nov. 13 . Four races are scheduled per day featuring boats from multiple classes.

  • Chief among them are the hotly contested Super Cat and Class 1, whose boats can reach up to 140 and 160 mph, respectively, on a 4.4-mile-per-lap course that features both rough and calm water conditions.
  • Teams accumulate points in each race toward the championship, so the drama builds throughout the week.

Duval & Greene Powerboat Street Party

Starting on Friday at 7 p.m ., the intersection of Duval Street and Greene Street will be blocked off to cars, and instead filled with powerboats hauled in and parked on their trailers right in the middle of the streets. Come up close and personal with these massive race boats, and snap a picture with one!

Boats and Boots Concert

The anticipated entertainment highlight is Saturday night’s Boats and Boots concert with country star Eddie Montgomery of Montgomery Gentry fame; musician/PGA golfer John Daly, and headliner Brian Kelley, who co-founded the renowned duo Florida Georgia Line .

Viewing Areas: Where to Watch the Races

The racing series provides an unparalleled experience for spectators. Boats can come within 50 yards of the Truman Waterfront grandstand area, providing fans with breathtaking displays of speed and power.

  • Fans can observe the action on race days from several areas on the Truman Waterfront including a VIP grandstand and hospitality tent with a water shuttle transportation service.
  • Other popular viewing areas include Key West’s Mallory Square and harborfront hotels.

Tickets and information on all-inclusive VIP spectator packages for the Truman Waterfront grandstand and hospitality tent are available at Key West Offshore World Championship .

  • General-admission tickets are $25 for a single day or $53 for a three-day pass.
  • Admission is free for kids 12 and under and for veterans and active military with a proper ID.

Own a Boat? Let your boat pay for itself. List, rent, earn — Only at Boatsetter.

Charles Plueddeman

Charles Plueddeman  is a self-employed writer and photographer based in Wisconsin. A staff editor and contributor to  Boating Magazine  since 1986, he is the author of its “Off My Dock” column. In the marine realm he specializes in engine technology and trailerable boats. His editorial work has appeared in many national publications, including  Popular Mechanics, Men’s Journal, Playboy, Popular Science, Cycle World,  and  Harley-Davidson Enthuisast .

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Sail Racing

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Besides being known for great food and music, Key West is also known for its perfect sailing conditions. And what better way to experience sailing than aboard the Schooner  America 2.0  for a race! 

Unlike most traditional schooners, Schooner  America 2.0  was built for both speed and comfort. We would love for you to experience our her grace and style, and our crew’s incredible service at one of our annual race events.

Our stunning, black-hulled, 105-foot sailing yacht is a tribute to the first Schooner  America,  the namesake and winner of the first America’s Cup in 1851. And true to her predecessor, Schooner  America 2.0  has won over 30 races in the past 8 years! 

So grab your tickets! A sailing race is something that you must experience while staying in Key West!

Stern of the schooner America 2.0 with the sails raised and the Captain Turned around waving while sailing for a Key West Wreckers Race

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All hands on deck!  If you enjoy a good sailboat race, it is an absolute must for you to sail on board the Schooner America 2.0 for the Key West Schooner Wharf Bar Wrecker’s Cup Race! 

A little history…back in the days of old Key West, ships from afar often ran aground on Sand Key Reef. When all the scallywags in Key West heard there was booty to be had, they jumped in their boats and raced to the reef. The first one there could claim the ship’s cargo! Arrggh!

Today, we celebrate this Key West tradition annually with a set of monthly races from January to April. It all starts with the firing of the cannon at 1:00 PM.  Enjoy the excitement aboard Schooner  America 2.0  as we race to defend our title of fastest schooner in Key West!

One round of beer, wine, champagne, and a boxed lunch are complimentary with your ticket purchase. Purchase a Beverage Package during the booking process, or additional drinks for credit card purchase while on board.  (Call us directly to save 6% online processing fee)

A large schooner sailing in Key West with the sun peaking through the sails for a Key West Sunset Sail

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Enjoy the best sunset sail in Key West on the Schooner America 2.0!  Take in the vibrant colors of Key West’s famous sunset as you sip complimentary champagne.  On this Key West Sunset Cruise, you will magically glide through the crystal clear surrounding waters whilst being taken care of by our professional and friendly crew.

This two-hour Key West sunset cruise features complimentary champagne, wine, beer, soft drinks, and water and passed hors d’oeurves- veggie crudite, cheese and crackers, and shrimp cocktail. There is a cocktail bar on board for purchase. Sit back and relax while Schooner America 2.0 plies effortlessly through the turquoise green Key West sailing waters and off towards the horizon for the quintessential Key West Sunset experience!  (Call us directly to save 6% online processing fee)

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Storm Trysail Club

Next Race: January 9, 2025

An annual 160 mile race in Florida held each winter.

The Fort Lauderdale to Key West Race began when crews delivering boats to start the St. Petersburg to Fort Lauderdale Race in the '70s decided to stop for a drink (or two) in Key West on the way. In the days before yacht tracking, getting there faster meant more time on Duvall Street without the owners knowing! It organized in 1975 and evolved into one of the premiere distance races in North America, ultimately giving birth to the fabled Key West Race Week in the '80s because no one wanted to leave! Today, racers from around the country still enjoy the warm waters of the Gulf Stream in February and the unique hospitality of Key West at the finish line.

LATEST NEWS

January 7, 2022

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47th Lauderdale to Key West Race

Congrats to Rear Commodore Andrew Weiss’ on his new Italia 11.98 Christopher Dragon for taking ORC honors.

January 25, 2021

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Fort Lauderdale Race 2021

Photo: SORC Sailing ... It was a very light Fort Lauderdale Race in 2021 but at least sailors were able to participate! Congrats to the SORC for a successful event and Commodore Ed Cesare on the First to Finish.

In Partnership with:

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NOTICE BOARD

VIA YACHT SCORING

NOTICE OF RACE & REGISTRATION FOR 2022 IS POSTED

Storm Trysail Club

stormtrysailclub

Dedicated to blue water sailing. Sponsor of inshore, distance, and offshore sailboat races. Supporter of the interests and needs of sailors.

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ABOUT THE EVENT

Proud Partnership with Lauderdale Yacht Club & SORC

sailboat race key west

Highlight of the Winter Season

The course shall be from the starting line, south to the Miami Sea Buoy (“RW Mo (A) Whistle”) leaving it to starboard; then to the Key West Sea Buoy (“RW Mo(A)”) located south of Key West, leaving the following marks and a continuous line connecting them to starboard. Note that the continuous line is not always indicative of the boundary of safe water for navigation, and does not include the course from the Key West Sea Buoy to the Finish.

EVENT LOGISITCS

Next Race: January 2022

REGISTRATION

Registration is done via Yacht Scoring before the event and check in begins on Thursday afternoon.

First signal for each course will be at 1000 Friday. Class assignments and starting times will be available online and will be announced at the Skippers Meeting.

A course from the Miami Sea Buoy to the Key West Sea Buoy. However, the continuous line is not always indicative of the boundary of safe water for navigation so vigilance is required.

The Awards Presentation and After-Race Party will be held on Saturday which will be TBD based on local regulations.

Schooner Jolly Rover

An Authentic Key West Sailing Experience!

Come sail Key West’s most photographed ship – the Jolly II Rover , a square-rigged topsail schooner! A Key West sailing adventure aboard the Schooner Jolly II Rover takes you back in time on a classic 80’ tall ship to an era of pirates, rum runners and privateers seeking freedom and solitude. Their spirit of independence lives on daily on the Jolly II Rover.

Roling Thunder Happy Hour from James Papagno on Vimeo .

The crew from Active Perspectives and Bombarda Rum chose the Rover to set the stage for their latest investment video. They were kind enough to create a short director’s cut for us to use. Cheers gents! (see the full video here )

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Sunset Sail

A top Key West attraction is the Jolly II Rovers famous “Red Sails in the Sunset” 2 hour sunset sail! Take in a memorable sail of Key West’s most famous sights while the sun works its magic turning the sky brilliant colors. With our distinctive red sails and being the only square rigged tall ship in Key West, the Jolly II Rover is the focal point as we sail past the Mallory Square Sunset Celebration. Help raise the sails, fire the cannons, and take your turn at the wheel for an authentic tall ship sailing experience.

More Info Book online now!

sailboat race key west

Key West Day Sail

Our daily 2-hour afternoon sailing tour fits perfectly into your Key West sightseeing trip. Enjoy an exciting Key West sailing adventure on the glistening crystal blue waters, with the Rover’s signature red sails flying! Look for the abundant Florida Keys wildlife both in the air and sea. Find your inner pirate and join the crew while you hoist the sails, steer the ship and fire the cannons!

  • Private Charters

Searching for a truly unique Key West sailing experience that is all your own? Charter your own private Key West tall ship sailing adventure. Whether its a few hours to celebrate a special event or an all day adventure, tell us where you want to go and what you want to experience, then climb aboard! For memories of a lifetime, charter a sunset wedding or an overnight excursion. Boca Grand is only 12 miles outside of Key West and is in a world of it’s own. You can even charter the Jolly II Rover for a private party dock side or anchor overnight experience.

Kimberly Klimek

Experiences

Key West Experiences

sailboat race key west

Key West Lighted Boat Parade

Join the Crew of the Jolly II Rover and parade through the Historic Seaport of Key West showing off the ships holiday décor! Enjoy a starry night, a festive atmosphere and thousands of twinkling lights on this entertaining evening cruise. Bring your own choice of food and beverages, bottled water snacks of crackers and cheeses included.

sailboat race key west

Key West Wreckers Race

The “day of wreckoning” reenacts times in Key West history when wreckers raced to a disabled ship, rescued the crew and laid claim to the cargo! Today, there is nothing to rescue except bruised egos from the last race. Join the Schooner Jolly II Rover for a day of rivalry, fun and radio insults on the high seas! Enjoy an exciting sailing adventure among a multitude of sailing vessels all competing for fun!

sailboat race key west

Key West Civil War Days

Join the crew of the Schooner Jolly II Rover for this very exciting and famous, annual Battle of the Schooners!! Re-enactors in period costume will be onboard as the Schooner Jolly II Rover defends its position in the harbor against opposing forces from both land and sea! This is a very popular and very exciting event. Seating will be limited to 16 passengers and ear protection will be provided to all passengers.

sailboat race key west

Currently operating year round out of the Historic Seaport of Key West, Florida, the Schooner Jolly II Rover is the only square rigged, topsail schooner contracted with the Florida National Boy Scouts of America High Adventure Sea Base Program. The Jolly II Rover provides boy scout troops with week long sailing, snorkeling and fishing adventures in the beautiful waters of the lower Florida Keys through the months of June, July and August.

sailboat race key west

Over the years, the Schooner Jolly Rover has been featured in countless magazines, newspapers and blogs for our iconic red sails and legendary sunset cruises. Read them here.

sailboat race key west

Like us on Facebook

Join us on facebook here ., frequent sailor discount.

Many locals as well as visitors are repeat sailors. And we love seeing familiar faces, so we offer $15 off your second sail and your third sail is FREE!

*Within 30 days.

Where to Find Us

Click here for the map.

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305-304-2235  BOOK ONLINE

© 2024 Schooner Jolly Rover.




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2000-2024
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IMAGES

  1. sailboat-race-key-west2

    sailboat race key west

  2. 'Sailboat Race, Key West Florida, USA' Photographic Print

    sailboat race key west

  3. First Sanctioned Key West-to-Cuba Sailing Race in 50 Years Begins

    sailboat race key west

  4. Key West Super Boat Races 2016

    sailboat race key west

  5. Sailboat Race Key West FL Wall Art, Canvas Prints, Framed Prints, Wall Peels

    sailboat race key west

  6. Key West Race Week Organizer Discusses Event Cancellation

    sailboat race key west

VIDEO

  1. Speed Boat Parade, Key West

  2. 🔴 REPLAY Key West Boat Races

COMMENTS

  1. Key West

    Offshore powerboat racing at the 2024 Key West Offshore World Championships in Key West, FL. Race World Offshore & the APBA national series.. Skip to content. My Account; Media Requests; Top Menu. 305-800-RACE. Race World Offshore. ... Designed to guide you through the adrenaline-fueled twists and turns of offshore boat racing. Additionally ...

  2. The Southernmost Regatta

    5 Days of Racing. The Southernmost Regatta offers 5 consecutive days of high-quality racing on the picturesque blue waters of Key West, FL. The event is open to One Design and ORC Racing / Cruising Keelboats. Our plan is to provide a two races a day on two course, a One Design Course and an ORC Course. We will also offer one distance race a day ...

  3. Key West Schedule

    2024 Race Schedule. Marathon FL - April 26th - 28th, 2024 Ocean City MD - June 7th - 9th, 2024 Clearwater FL - Sept. 27th - 29th, 2024 Key West FL - Nov. 3rd - 10th, 2024. 2024 RWO Results.

  4. Fort Lauderdale Key West Race

    Live Results. Past Race Archives. The Fort Lauderdale to Key West Race began when crews delivering boats to start the St. Petersburg to Fort Lauderdale Race in the '70s decided to stop for a drink (or two) in Key West on the way. In the days before yacht tracking, getting there faster meant more time on Duvall Street without the owners knowing!

  5. Bone Island Regatta

    Bone Islad Regatta Sailboat Race to Key West. Bone Island Regatta. Home About NOR Entries 2024 Photos Contact Final Results 2024 Save the Date. 15th Annual Bone Island Regatta race to key west May 14-17 2025. Track The 2024 Race ... Boca Ciega Yacht Club's newsletter ...

  6. Offshore World Championships

    Offshore World Championships: November 3th - 10th. Race World Offshore is thrilled to host teams and offshore racing enthusiasts in Key West for the incredible Offshore World Championship, sponsored by Performance Boat Center.As the leading Offshore Racing Sanctioning body in the U.S., our dedicated team is committed to delivering an unforgettable week.

  7. 2022 Key West Southernmost Regatta is back

    Related Articles Southernmost Regatta at Key West The J/70s and J/111s enjoy classic racing conditions in Aquamarine waters At the end of a 113.0 mile-long Florida Keys, the Southernmost Regatta offerred sailors amazing weatehr, surrounded by shimmering turquoise waters. Posted on 29 Jan Southernmost Regatta Powered by Sailing Inc Six fleets came out to play in Key West On a little chain of ...

  8. Rise of the Southernmost Regatta

    The Southernmost got its start in 2021 as a getaway regatta for a small band of J/111 class owners. "That was a bit of a test run," Kullman says. "There was a lot of connecting with city ...

  9. Southernmost Regatta returns in 2023 >> Scuttlebutt Sailing News

    Andrew Ward, winner of the J-111 class in 2022 said, "Key West is my favorite place to sail in the winter with warm blue waters and perfect sailing conditions. We can't wait to go back in 2023."

  10. Key West Worlds Day No. 1—Dominance Carries Over

    Key West Worlds Day No. 1—Dominance Carries Over. At the first day of competition at the 42nd annual Race World Offshore Key West World Championship presented by Performance Boat Center, the winners in virtually every class put on a superior display of dominance, setting the stage for three days of heated competition in the southernmost city ...

  11. REPLAY Key West Boat Races

    Replay of live boat racing video from the Key West Offshore World Championship. Truman Waterfront Cup. Race day #1 starts at 10am on Wed Nov 8 2023. Race ...

  12. Race World Offshore

    Race World Offshore. 18,077 likes · 46 talking about this. Race World Offshore, LLC is a professional offshore powerboat racing organization based in Key West, Florida.

  13. Key West Boat Races: 2022 Preview Guide

    When: November 6-13, 2022. Where: Key West, Florida; Truman Waterfront, Duval Street, Mallory Square. What: Four races scheduled per day (Wednesday, Friday, and Sunday), featuring boats from multiple classes. Enhance your Race Week Experience with a boat rental: Explore Boats in Key West. Between race days fans can view the boats and teams up ...

  14. Key West Florida Nov. 10-14th

    The event that begins Sunday, November 7th, starts with the world's fastest boat parade. Teams from around the world will kick off the week-long event with a 4 o'clock parade down Duval Street. ... the Duval Street Party for a better experience and to spread out all these great race teams across the city blocks of Key West. For the second ...

  15. Key West Worlds Finale: Twice As Nice

    In Bracket 600, the Key West based 25-foot Baja, Power House Racing, with Nelson Sawyer and Damon Marotta, Jr., took the hometown win by grabbing checkered flags in both races. Second went to the 26-foot Corsa, Gerard Marine/XINSURANCE , and the smallest boat in the fleet, the 21-foot Superboat, Jackhammer , placed third.

  16. Key West Sailing Race: Day Sail, Wreckers Race and more!

    Sail Racing. Book Now Call to order 305-293-7245. Besides being known for great food and music, Key West is also known for its perfect sailing conditions. And what better way to experience sailing than aboard the Schooner America 2.0 for a race! Unlike most traditional schooners, Schooner America 2.0 was built for both speed and comfort.

  17. Ft Lauderdale

    An annual 160 mile race in Florida held each winter. The Fort Lauderdale to Key West Race began when crews delivering boats to start the St. Petersburg to Fort Lauderdale Race in the '70s decided to stop for a drink (or two) in Key West on the way. In the days before yacht tracking, getting there faster meant more time on Duvall Street without ...

  18. Key West Sailing Adventure and Sunset Sails

    A Key West sailing adventure aboard the Schooner Jolly II Rover takes you back in time on a classic 80' tall ship to an era of pirates, rum runners and privateers seeking freedom and solitude. Their spirit of independence lives on daily on the Jolly II Rover. Roling Thunder Happy Hour from James Papagno on Vimeo.

  19. SORC

    The SORC mission is to lead the expansion of offshore competitive sailing in South Florida by providing the highest level of race organization, management and promotions for those that enjoy the sport of ocean sailing. The SORC is a Florida non-profit organization driven by a select group of volunteers that bring professional event management ...

  20. Wide Open Throttle Key West! Powerboat Races High Volume ACTION

    The Best Boat Passes, Jumps and Action from Key West at the Race World Offshore World Championship Boat Races!Merch:https://teespring.com/stores/zipzappowerS...

  21. 2024 Lauderdale to Key West Race

    Yacht Scoring is a featured packed 100% web based regatta administration and scoring system that simplifies the task of competitor registration, event management, competitor and media communications while providing results in near-real time to competitors and the World following your event on the internet. ... 2024 Lauderdale to Key West Race ...

  22. Racers to circle Key West during 12-mile Paddle Classic

    The 12-mile distance around the island of Key West will become a saltwater racecourse for competitors on paddleboards and self-propelled watercraft during the 2024 Key West Paddle Classic. The annual race, presented for the final time by the Florida Keys adventure tour company Lazy Dog, is scheduled Saturday, Sept. 28.

  23. RWO 2024 Schedule: A Thrilling Season of Races Ahead

    Key West: November 3-10. The grand finale awaits in Key West, where the culmination of the season unfolds against the stunning backdrop of this iconic location. Teams will battle it out for supremacy, navigating the turquoise waters with skill and precision. Key West promises to be a fitting end to a spectacular season of boat races.

  24. Cuban migrant boat arrives in Florida Keys, Border Patrol says

    A wooden fishing boat rests on Sombrero Beach in the Florida Keys Tuesday, Sept. 17, 2024. The U.S. Border Patrol says 43 people from Cuba, who the agency says are migrants, arrived on the vessel.

  25. 2022 Results

    September 23rd - 25th, 2022. We want to express our sincere gratitude to Ocean City for their support of RWO. Teams and fans had a wonderful time and we encourage you to plan your next vacation and visit Ocean City to enjoy their beaches, adventures, events and more! Click here to learn more. ATTENTION Race Teams: Please register at least 2 ...