Exploring the World by Sailboat

The following is adapted from Wandering the World by Peggy Simonsen.

“I must go down to the seas again, to the lonely sea and the sky,

And all I ask is a tall ship and a star to steer her by…”

— John Masefield

From excursion ships to kayaks and most every type in between, I don’t count a trip complete without at least a tour boat on the water at some point. I like to travel in boats, not on them. For example, I am happiest in a Zodiac, close to the water and wildlife, or in a kayak, managing my own path through the water, and especially in a small sailboat, maybe diving off to snorkel. But I have also had wonderful experiences on excursion ships in parts of the world where a small boat couldn’t or shouldn’t go. As you will see later in this chapter, I am not a cruise ship person, traveling on the ship as a traveling hotel.

I grew up living near White Bear Lake in Minnesota, the “Land of 10,000 lakes.” We played in the water all summer, swimming, diving off rafts, and sailing little Sunfish boats with the intent to tip them over in order to right them again. White Bear Lake was the town where the scows were designed and built, so sailing was just what we did. We also canoed and “gunnel-jumped,” which is balancing on the edges (gunnels) with another person with the intent of bouncing the competitor off. In college, I earned my Water Safety Instructor (WSI) certificate and worked as a lifeguard and swimming instructor at a Girl Scout camp, at a camp in Maine, and at a beach near my house. And I monitored the beach in a rowboat, so I could get to any kid quickly who was going underwater.

As an adult living in Illinois and not near little lakes, sailing and being in or near the water became a goal of our vacations, and we finally owned a large enough sailboat to handle sailing and racing on Lake Michigan. The saying about sailing is, “Hours of boredom interspersed with moments of sheer terror!” But I don’t experience either extreme; I find sailing challenging and also restful.

Sailboats

One of the first sailing vacations my husband and I took was to the British Virgin Islands with friends. We chartered a “bareboat,” meaning we had the boat without a crew; we were the crew. It was a forty-foot Beneteau monohull with four cabins and heads (boat bathrooms). That was my first experience with snorkeling, and I loved it! This was in 1987, and the coral and tropical fish were spectacular. The Caribbean water was turquoise and clear, and the little atolls we anchored by were mostly uninhabited by humans except for the occasional few seen at a beach bar. One afternoon, we had to choose if we wanted conch or mutton for dinner. Not a fan of conch, I ordered mutton only to see a little goat pulled across the floor of the bar, hung from a nearby tree, and slaughtered. I ate dinner on the boat that night! But we were hooked on warm-water sailing.

Racing

We also came home and bought a larger boat (C&C 38) to sail and race on Lake Michigan. We harbored in Waukegan, a suburb north of Chicago, and participated in buoy races plus the occasional distance race from Chicago to Waukegan (about twenty-eight miles) with a crew. My husband became an excellent racer, and I got good as a driver, where I could focus on steering the racing line while Bill was the tactician and oversaw the crew and all the sail changes.

It was obvious that the next trip to the Caribbean would be to race. One spring, we flew to Saint Martin to join the Heineken Race Week. We chartered a boat from the Moorings with friends from Illinois who were experienced racers. We quickly found out that some of our competition were company teams on rented boats, for which they bought new sails. (Chartered boats tend to have functional sails, not high-tech racing sails.) They had team uniforms with their company names on them, and our ragtag crew just wore whatever shorts and T-shirts we had brought. Others were experienced ocean racers from the East Coast and Europe. The first race was from the Dutch side of the island (Sint Maarten) to the French side (Saint-Martin), with an obligatory party that evening. The second day was from the French side back to the Dutch side, with competition for the best party. The third day was around the whole island, and we were elated to beat the company boats! No one expected people from Illinois to win, for heaven’s sake.

Over the years, we competed in the Chicago to Mackinac Race, which was started over one hundred years ago by the Chicago Yacht Club. It goes the full length of Lake Michigan, 333 miles as the crow flies. But one rarely can sail as the crow flies; the wind determines how straight a line you can hold. Depending on the size of the boat, it can take up to three days and nights, and the weather can be cooperative, but usually, it’s a challenge. Lake Michigan is considered a bathtub for waves because it is long and narrow, and when the wind blows from the north over the whole fetch of the lake, the waves can be eight feet or more. They are choppy because they break off one shore, then bounce back to break on the opposite. In July, when the Mac race is held, there can be horrendous thunderstorms adding to the challenge. Boats have been dismasted, had their sails torn, and more seriously damaged.

For one race, Larry Ellison, Founder of Oracle, shipped his seventy-foot sailboat to Chicago for the Mac race and bragged that he was coming to sail the pond only to find out how challenging the lake can be. He ate his words, but he did have a respectable time with the rest of the “sleds” (seventy-foot boats). Milwaukee is not even a quarter of the way to Mackinac Island, but we were passed by the sleds (our boats were half that size), even though we started an hour earlier.

One year following the Mac race, we continued to sail in the North Channel of Lake Huron, exploring the Northwoods along the shores of Drummond and Manitoulin Islands. The islands are forested rocky shores with very few towns or other sailors. We had provisions on the boat, of course, but a special treat was from a local resident who made pies from fruit in her yard and sold them to sailors like us stopping at a local dock.

For more stories on adventure travel you can find Wandering the World on Amazon.

Peggy Simonsen has been a sailor, skier, and nature lover most of her life. As the owner of an international consulting company, she has traveled for both business and pleasure, experiencing more than sixty countries and all seven continents. Now a retired widow, she continues to seek adventure in far-flung parts of the world with family and friends — not just to observe, but to participate in all life has to offer.

Peggy is also the author of Promoting a Development Culture in Your Organization, about using career development as a change agent, and Career Compass, on managing your career in the twenty-first century. At home, she serves on the board of two conservation organizations and cultivates her Illinois wooded yard with native plants.