Bold But Beautiful Mistakes

Don’t learn to sail like I did. My path into the pastime was impulsive. On a Sunday afternoon in October 2021, I was browsing Facebook Marketplace in Denver when I came across what I thought was a good deal: a light blue 1978 dinghy listed for $140. On a whim, I drove to Broomfield and inspected the boat, which was missing its rudder and boom. The fiberglass hull looked solid, though, and the sails were in good condition. I didn’t know what else to look for, but I wanted a winter project, so I paid the man and towed the boat home.

As the cold weather descended, I researched the vessel, a Luger Leeward 16, and realized I could probably sell it for $1,200 with a modest investment and a lot of work. I figured if I learned to sail along the way, it’d be a bonus. I beat my $800 budget by 20 bucks, and in April 2022 at Cherry Creek Reservoir, I launched for the first time. To my extreme relief, the boat floated. Then she sailed. Then I began to learn lakemanship the hard way—teaching myself, ignorant of the local resources that might have led me to smoother waters.

Colorado’s capital may be 1,000 miles from the nearest ocean, but the state has plenty of lakes and a bevy of educational and recreational sailing opportunities. Plus, the wind here is fickle, meaning that while it’s a challenging place to learn, it’s also a good one. “We see 80- to 100-degree wind shifts all the time,” says Melissa Gorchynsky, executive director of Community Sailing of Colorado (CSC), a Front Range–based nonprofit focused on creating equitable access to the sport. “It’s like riding a unicycle on a balance beam. If someone can learn to sail here, they can sail anywhere.”

The writer on Cherry Creek Reservoir. Photo by Chayce Lanphear

My crash course in Colorado looked like flipping my boat in Grand Lake, crashing into docks at Cherry Creek Reservoir, and losing the trust of some mates I used as guinea pigs. But none of that has to happen to you. You’ll save yourself some headaches, some time, and probably some money, too, if you avoid these 10 mistakes—all of which I made but each of which ultimately taught me important lessons.

Mistake 1: Buying First (Without Doing the Research)

I approached purchasing a sailboat like Elon Musk approached buying Twitter: I thought it would be cool, but I had no idea how the thing actually worked. I’m happy with the boat I brought home, but I got lucky. I should have looked into what models would work best for Colorado’s small lakes and ever-changing winds. Here, a primer on beginner vessels for those who should probably rent first (see Mistake 4) but may share my lack of impulse control.

Illustrations by Lars Leetaru


Size: 13 feet, nine inches
Price: $500 to $1,200 used; $4,000 new
Overview: These summer-camp mainstays are hard to sink and agile enough to keep veteran sailors entertained, making them popular starter vessels that won’t get boring as their captains gain experience.
Pros: At just 120 pounds, with a removable centerboard, a Sunfish can be launched from any beach, meaning you can cruise lakes that don’t have boat launches.
Cons: Sunfish are easy to capsize, so expect to spend part of your day in the water. Thankfully, they’re just as easy to right as they are to flip.

Daysailing Dinghies

Size: 14 to 17 feet
Price: $1,000 to $3,000 used; $5,000-plus new
Overview: Countless varieties of sturdy daysailers have been manufactured over the years, many of which can fit up to four people comfortably.
Pros: Heavier than a Sunfish but still nimble, these boats can handle bigger weather and longer days on the water. They’re also trailerable, making them a good option for yachtsmen who don’t want to invest in a boat slip or stress over launching a keelboat.
Cons: While relatively stable, dinghies can still capsize, and because they have larger interiors and storage spaces, they take on water fast.


Size: 16 to 30-plus feet
Price: $2,000 to $10,000 used; $10,000-plus new
Overview: As a general rule, if your boat has a keel—a permanent, finlike structure along the bottom of the hull that counterbalances the wind—you’re looking for stiffer breezes and larger bodies of water.
Pros: Large enough for overnight and multiday outings, keelboats are unlikely to capsize and are designed to right themselves if they do.
Cons: Because a keel isn’t retractable like a centerboard on a Sunfish or daysailer, you need deeper water to launch and sail your vessel.

Mistake 2: Not Learning the Lingo

From shipshape to loose cannon, plenty of nautical terms have made their ways into our everyday vernacular, but their original meanings are often lost in translation. Knowing a few key terms will help you communicate on and off the water.

Nadtochiy/Getty Images

Boom: A horizontal pole attached to the mast and sail that pivots depending on wind direction. The boom and mainsail are controlled using a line called the main sheet.

Centerboard or keel: Beneath every boat is either a retractable centerboard or a fixed keel. Both provide stability and counter the horizontal force of the wind to propel the boat forward and prevent it from capsizing.

Helmsman/helmswoman: The person helming the boat, which means they’re either steering the vessel or are in charge of its direction. The captain does not always take the helm.

Knot: Hundreds of years ago, sailors would tie a series of knots into a long rope with a log at one end, then toss the log in the water and count the knots as they were pulled through their hands to measure their speed. Today, one knot is about 1.15 miles per hour.

Lines: Speaking of ropes, sailors call them lines—and there can be dozens of them on a sailboat. The two most common are halyards, which raise the sails, and sheets, which trim them.

Point of sail: The angle of your boat compared to the direction of the wind. There are seven points of sail. When a boat is perpendicular to the wind, it is on a beam reach—the fastest point of sail. The only point in which a boat cannot move forward is when it faces directly into the wind, which is called irons.

Port and starboard: Deceptively simple, port is the left side of the vessel and starboard the right when facing the bow. If you turn toward the stern, port and starboard will switch relative to your body but stay the same relative to the boat.

Tack and jibe: Unless the wind is blowing in the exact direction sailors need to go, they must navigate with turns known as tacks and jibes to harness the wind. Tacks are used when the wind is coming more from the bow; jibes are used when the wind is blowing more from the stern.

Tiller: Typically, this is a long wooden handle that controls the rudder and steers the boat. Many larger sailboats have a steering wheel instead of a tiller.

Mistake 3: Not Looking at a Map

Map illustration by Sean Parsons

Just minutes after buying my vessel, I began worrying that having a sailboat in Colorado might be like owning a snowmobile in Texas. It took some research to learn which local lakes allowed sailboats and which had boat ramps, but I eventually found places to catch the wind across the state. Colorado has plenty of sailable water, but these 11 lakes and reservoirs, featuring marinas, public boat ramps, and large communities of mariners, stand out as local favorites.

1. Blue Mesa Reservoir

Location: Gunnison
Surface Acres: 9,180
Why Sailors Love It: Nearly 20 miles long, Blue Mesa is Colorado’s largest body of water. It’s served by two marinas, Elk Creek and Lake Fork, and its size allows sailors to cruise open-water-style, meaning they don’t have to continually change course to avoid accidentally beaching their crafts.

2. Carter Lake

Location: Larimer County
Surface Acres: 1,100
Why Sailors Love It: Surrounded by the Rocky Mountain foothills and swaths of public land, this reservoir is a serene place to float. It’s also home to Carter Lake Sailing Club—the oldest organization of its kind in the state—which has an impressive lineup of races and events, including its 70th anniversary celebration this month.

Chatfield Reservoir. Steve Krull Sailing & Yachting/Alamy Stock Photo

3. Chatfield Reservoir

Location: Littleton
Surface Acres: 1,479
Why Sailors Love It: Chatfield is the largest waterhole in the Denver metro area, and as the home of the Colorado Sail and Yacht Club, it boasts one of the state’s most active racing and recreational sailing communities.

4. Cherry Creek Reservoir

Location: Aurora
Surface Acres: 850
Why Sailors Love It: With two sailing schools, this urban lake is an educational hub for the Front Range sailing community. But it’s not all classwork: The Denver Sailing Association usually hosts more than 140 races each year at Cherry Creek, going deep into the fall.

5. Grand Lake

Location: Grand Lake
Surface Acres: 515
Why Sailors Love It: Colorado’s biggest and deepest natural lake features panoramic vistas of the Never Summer Mountains. The ever-shifting winds created by those peaks give newbies a serious challenge and longtimers something to get amped about.

6. Lake Dillon

Location: Summit County
Surface Acres: 3,233
Why Sailors Love It: Lake Dillon, sometimes called Dillon Reservoir, is nestled into the Tenmile Range at 9,017 feet, making it cold and challenging due to the swirling mountain wind. But with a 30 mph speed limit and a ban on swimming and watersports like wakeboarding, sailboats reign. That supremacy attracts one of the largest concentrations of sailpower in the state.

Lake Granby. Getty Images

7. Lake Granby

Location: Granby
Surface Acres: 7,256
Why Sailors Love It: As Colorado’s third-largest body of water, this reservoir just down the road from Grand Lake offers plenty of room for the competitive race series hosted by Lake Granby Yacht Club on summer Saturdays.

8. Lake Nighthorse

Location: Durango
Surface Acres: 1,490
Why Sailors Love It: Consistent winds make Nighthorse one of the easier places to sail in the state, and the La Plata Mountains that flank it are a beautiful backdrop.

9. Lake Pueblo

Location: Pueblo
Surface Acres: 5,399
Why Sailors Love It: Lake Pueblo State Park has been a boating and angling mecca for southern Coloradans since the completion of the Pueblo Dam in 1975 created its namesake reservoir, which features two full-service marinas and one of the region’s longest sailing seasons.

10. Ruedi Reservoir

Location: Near Basalt
Surface Acres: 1,000
Why Sailors Love It: As home to the Aspen Yacht Club, Ruedi is one of the only sailing hubs on the Western Slope. The narrow lake is surrounded by the Sawatch Range, which helps forge famously unpredictable winds that keep sailors alert.

11. Union Reservoir

Location: Longmont
Surface Acres: 736
Why Sailors Love It: Union Reservoir is the lone lake on the Front Range that only allows wakeless boating, so you won’t have to deal with powerboats speeding by. Plus, it’s just a 45-minute drive from downtown Denver.

Mistake 4: Not Renting First

Getty Images

Purchasing your own vessel is not necessarily the best first step—especially if that boat is missing some key parts like mine was. And while sailing schools will put you in their boats during lessons, there are precious few places to rent in Colorado. That’s mostly due to the likelihood that an overconfident rookie (like me) could put a hole in the boat. As CSC’s Melissa Gorchynsky says: “The five scariest words in the English language are: ‘I know how to sail.’ ”

That doesn’t mean you can’t find a boat to borrow, though. Dinghies can be rented at Colorado WaterSports’ Roxborough Cove location on Chatfield Reservoir ($50 for two hours), and Victoria Sailing School’s Why Buy Club is essentially a timeshare for the school’s fleet of keelboats on Cherry Creek, Chatfield, Carter, and Dillon. Packages there range from $660 for five outings to $1,150 for a full membership with unlimited reservations and no blackout dates for the three daily slots. But you’ll have to take the American Sailing Association’s (ASA) Basic Keelboat Sailing and Basic Coastal Cruising classes through the school first.

Dillon Marina also offers keelboat rentals, but there’s a mandatory refresher course (Wednesdays and Saturdays from 9 a.m. to 10 a.m.; $95) and written exam, even if you’re currently certified by the ASA or U.S. Sailing. Rental prices start at $174 for two hours, depending on the time of year. You could also try to befriend a few sailors. Just show up at the docks with a case of beer, explain that you’re looking to learn, and offer to help with any menial tasks.

Mistake 5: Going It Alone

Plenty of people learn the way I did: with help from Sailing For Dummies, YouTube, and advice from knowledgeable friends. Then again, plenty of people embarrass themselves the way I did, too. And once you’ve capsized and been forced to swim after your sandals, you’ll wish you’d sought out formal instruction.

A CSC camper. Photo courtesy of Community Sailing of Colorado

Victoria Sailing School

Background: Victoria Sailing School, Colorado’s oldest and largest such institution, offers courses at Cherry Creek Reservoir, Chatfield Reservoir, and Carter Lake, and it’s a family affair: Erica Cook, daughter of founder James Cook, runs it with her husband, Tibor Van den Wildenbergh.
What It Offers: In addition to Basic Keelboat Sailing (ASA 101; $445) and Basic Coastal Cruising (ASA 103; $669)—the minimum certifications you need to rent and captain anything bigger than a dinghy—Victoria also offers courses on basic maintenance, provisioning, and navigation.

Community Sailing of Colorado

Background: Since 1994, CSC has helped make this pricey pastime accessible by partnering with youth-serving nonprofits such as Big Brothers Big Sisters and Boulder’s Thorne Nature Experience.
What It Offers: CSC provides adult clinics open to all ($55 for four hours) as well as summer camps for kids ages five to 17, youth scholarships to reduce the financial barrier for families who need the flexibility, and an adaptive program for folks living with physical and sensory disabilities. “Sailing can be very white-washed and very yacht-clubby,” Gorchynsky says, “so we focus on groups of people who wouldn’t typically have access to sailing.”

Dillon Marina Sailing School

Background: At more than 9,000 feet of elevation and flanked by ski resorts, Lake Dillon is a rarefied place to learn to sail. The instructors at Dillon Marina help novices navigate the occasionally rough waters in a fleet of keelboats.
What It Offers: Basic group lessons (from $110) and private lessons ($154 for two hours) as well as ASA 101 certifications ($450).

Peaks and Tides Sailing School

Background: Katie James and her partner, Scott Frazer, were living on a 33-foot sailboat when they realized the lessons they were learning would be useful to others. “To test a relationship, there’s nothing quite like sailing,” James says.
What It Offers: A dynamic youth program as well as ASA 101 and 103 courses taught on Durango’s Lake Nighthorse. They also teach an advanced cruising class on the Gulf of California.

Nautilus Sailing

Background: Tim Geisler initially launched a sailing school on Blue Mesa Reservoir but has since left local waters behind and taken the program global, operating classes in locales such as Tahiti, the Caribbean, Mexico, and Spain.
What It Offers: Greenhorn sailors get a week of immersive ASA education as they eat, sleep, and live aboard one of Nautilus’ catamarans or monohull sailboats.

Mistake 6: Not Knowing Your Knots

When you step aboard a sailboat for the first time, you’ll notice the sheer number of different knots. Learning them all takes time, but the bowline is a good place to start: It will turn the end of your line into a loop and is often called the King of Knots because of its strength and utility.

Mistake 7: Underestimating Colorado’s Weather

Colorado may be famous for sunny days, but as any local knows, its weather is as erratic as it comes. “The Rockies completely interrupt everything,” says 9News meteorologist Chris Bianchi. Because wind can hit from any direction, boat captains have to be amateur meteorologists. With that in mind, here are a few local phenomena to keep on your weather radar.

Sailing on Lake Dillon. Arina Habic/Alamy Stock Photo


Wind gusts are common in sailing, but they really tend to sneak up onyou in Colorado. If you’re unprepared, you could be knocked off course at best or end up swimming in some very cold water at worst. You can account for incoming gusts by watching for ripples on the water’s surface and either steering into the gusts or loosening your sails so they simply flap in the wind instead of capturing the breeze.


These small, intense columns of sinking air can create strong gusts. They typically form in the afternoon along with thunderstorms, so if you see dark clouds rolling in, get off the water. “It can be terrifying when the lake pretends to be an ocean,” says Katie James of Peaks and Tides Sailing School. “I’ve had six-foot waves crashing over my bow.”


Boulder’s Upslope Brewing may make a good lager for lake days, but in sailing, an upslope is when the mountains force warm air to rise and cool. This usually creates gusts and precipitation, but the attendant wind can also make for great sailing conditions. With so many Colorado lakes flanked by mountains, the upslope effect is common during summer afternoons after the sun has heated the air all morning.

Katabatic Wind

Basically the inverse of upslope flows, these downslope winds often form in the evening as air on top of mountains cools, becomes heavier, and is forced downhill by gravity. When this happens, sailors can often enjoy steady breezes that aren’t too extreme.

Getting “Dillon’d”

When sailing downwind, meaning the wind is at their backs, captains often raise a spinnaker, a sail that acts like a massive kite to speed the boat along. But on Lake Dillon, the wind swirls so much that it’s common for two boats to be sailing downwind directly at each other—a phenomenon referred to as getting Dillon’d. “You think: Wait, that doesn’t make sense,” says Mike Digitis, a winner of the 2022 Dillon Open. He’s right: It doesn’t, but that’s sailing in the Rockies for you.

Mistake 8: Ducking the Competition

Racing on Lake Dillon. Courtesy of Colorado Sail and Yacht Club

You may not feel ready to captain a race boat just yet, but crewing on one is a great way to learn fast. From just-for-fun club competitions that help mariners keep their skills sharp to regionally competitive regattas where sailors can qualify for national competitions, there’s a Colorado contest for every skill level.

New Belgium Timberline Cruiser Regatta

It’s a stretch to call this race on Lake Dillon a, well, race because winning has little to do with speed. Points are awarded if you can hit floating checkpoints, impress a mermaid with your singing voice, or don the best pirate garb. Free; August 19

Trailer Sailor Rally

Lake Pueblo Sailing Club invites anyone with a sailboat they store on a trailer to explore its home waters. There will be some racing during the weeklong event, but mariners can also enjoy the boat parade, night cruises, a gear swap, and barbecues. $60; October 1 to 6

Beer-Can Races

Various fleets (boats of the same design or class) gather each week during the warmer months at Cherry Creek, Chatfield, Lake Dillon, and other lakes for friendly competition. They’re forgiving places to start racing. Some marinas will publish schedules online, but sometimes you’ll need to call and ask. Then just show up, says local sailor Mike Digitis. “Someone will take you out,” he says. Free; various dates

Colorado Governor’s Cup Regatta

Chatfield Reservoir hosts the Governor’s Cup, the last major event of Colorado’s racing season, each October. While it’s a competitive race, the late-season weather means it’s often a small affair, and sailors have to be extremely careful in the cold water; capsizing at this time of year can be fatal. $115; October 14 and 15

Carter Lake Open Regatta

Scheduled for the first weekend of June every season, Carter Lake’s regatta is one of the first held in the Rockies each year, so it attracts competitors from across the region who are eager to start the season with a win.

The Dillon Open Regatta

At 9,017 feet above sea level, this is considered the world’s highest regatta—and in Colorado, it’s the most cutthroat. Nearly 100 boats enter each year, the most of any regatta in the state, and the event draws sailors from across the country and even from international waters. $100 to $150; August 25 through 27

Mistake 9: Not Having the Correct Gear

The Centennial State may be landlocked, but that doesn’t mean local gear companies don’t have a handle on water-related necessities.

Courtesy of The North Face

North Face Valle Vista (Men’s, Women’s)

You could buy a purpose-built spray jacket designed to protect you from storm-driven gales, but it’s not necessary. A breathable rain shell, such as the new Valle Vista from the North Face, based in Denver, is perfect for warm days when Colorado’s cold snowmelt is splashing into your boat. $170

Zeal Optics Caddis Polarized Sunglasses

Polarized shades are essential for boating because the sun can reflect off the water at odd angles. To fend off wayward rays, look for wraparound-style sunnies, like these plant-resin frames from Boulder’s Zeal Optics. $159

Osprey Dry Sack

If you’re bringing your phone, wallet, and keys aboard, you’d better have a waterproof place to stash them. Cortez-based Osprey makes dry sacks in sizes ranging from six to 30 liters. $18 to $28

Sea to Summit Bilge Pump

Buckets are a classic, if backbreaking, way to bail water when it inevitably crests the bow, so upgrade to a bilge pump. This double-action version from Sea to Summit, which has its U.S. headquarters in Boulder, can remove nearly a half-liter of water with every stroke. $30

Mistake 10: Capsizing

Just when I was beginning to feel like a real sailor, Colorado offered me a dose of humility. I had no choice but to accept it.

Illustration by Lars Leetaru

I’d been told that the fastest way to learn to sail is on the smallest boat in the coldest water. After all, the message went, an unexpected gust can teach an underprepared captain crucial, if not entirely welcome, lessons.

I was that captain on Grand Lake last summer. The forecast had called for a mild morning with winds of just two to five miles per hour—essentially a newbie sailor’s dream—before a bigger system was expected to blow through in the afternoon. The air temperature was 80 degrees; the water only 50. After about an hour, just as my friends and I had nearly been lulled to sleep by the temperate weather, the wind gusted up to 15 knots. I suddenly found myself fighting with the tiller and sail to maintain control. We rocketed toward the middle of the 400-foot-deep lake, tilting over so far that I had to sit on the far side of the boat and lean back over the water to counter the force in our sails. It wasn’t enough. I saw my friends fall in first. Then, in a disastrous baptism, I plunged in beside them.

Both of my friends were treading water when I surfaced, but the boat was on its side. We grabbed the life jackets I should have made sure we were all wearing, then I fought to pull the dinghy upright. It only took a minute, but it felt like 10. My fingers were numb, my heart was pounding, and I was racing time as my companions bobbed next to me. In water with temperatures that low, cold shock can kill in minutes. Fortunately, all that was lost to the deep that day was my phone, some spare equipment, and a bit of my dignity.

Embarrassed as I was, I was even more thankful. Although I had been unprepared for the forecasted weather that day, I won’t be caught off guard again. And I’ll keep in mind that a captain is responsible not only for the boat, but also for the safety of everyone on board.

This article was originally published in 5280 August 2023.
Jay Bouchard
Jay Bouchard
Jay Bouchard is a Denver-based writer and a former editor on 5280's digital team.