In June of 2005, Kris and Tony Crimi set sail from Bayfield, Wisconsin in pursuit of a dream - a dream that would span three years and take them to nearly 50 islands in the Caribbean Basin. Those three years would fill their lives with memories too numerous to count, adventures few of us ever experience, and friendships that will last the rest of their lives.

At the time, the Crimi’s lived in St. Paul and both worked at the University of Minnesota - Kris as a Production Scheduler in the Print Department and Tony in Veterinary Anesthesia at the Veterinary Teaching Hospital. High School sweethearts, they had married young, raised two daughters together, and had been empty-nesters for many years. They were a couple with more time to dream big.

When the girls were young, the family enjoyed boating on the myriad of Minnesota lakes and they spent time together skiing and fishing from powerboats. As the girls got older, Kris and Tony found themselves at the lakes without the children more frequently and Tony was becoming increasingly intrigued by the sailboats he saw on the lakes they visited.

During one lake excursion, Kris and Tony were invited to leave their powerboat at the dock and to help crew on a sailboat competing in a local race. As Kris recalls, “That’s all it took. Tony was hooked.”

Soon the powerboat was sold and the Crimi’s acquired their first small sailboat. They both loved the feeling and the challenge of sailing and they soon graduated to a larger sailboat. With time and experience, they gained the confidence to fly down to the Caribbean and charter sailboats.  Sailing between islands on their rented boats soon spawned the dream. “That’s when the whole dream got hatched,” explains Tony. “We told each other that someday we were going to return to the islands on our own boat.”

Fifteen years later, that time had come and they were ready to go.

The June morning they left Bayfield, Kris was 55 and Tony 57. Their boat was a 34 foot Catalina bearing the name, “Ticketoo.”  They had both retired in February four months earlier. The intervening months between leaving their jobs and departing Bayfield were a whirlwind of goodbye visits with family and friends, the sale of their home and vehicles, a trip to Henderson County to purchase a lot for a new home to be built in Flat Rock upon their return from their adventure, and the arduous task of deciding what personal belongings to put into storage and which to discard.

The trip may have been their dream, but this dream involved logistical challenges of the highest order. “What do you take?”, remembers Tony. “How do you stay in touch with people? What do you do with your mail? How do you pay your bills? What do you do for health insurance?  A lot of people say they are just going to pull up and go do it. Just sail away. But very few do, because the logistics are just so overwhelming.”

Once underway, Kris and Tony immediately faced dramatic adjustments. For Kris, she remembers the close quarters. “You've got two people on a 34-foot boat and yeah, we had been married for a long time, but it's still an adjustment. It's a small space!”, she laughs.

For Tony, it took some time to get used to living in a permanent state of uncertainty. “You're constantly in places where you don't know where anything is. Like, where do I buy food? Where do I get water? Where do I get fuel?”

The first leg of their journey involved sailing across Lake Superior, to Lake Huron, on to Lake Erie, and then traversing the Erie Canal to the Hudson River.  “The Erie canal has 35 locks that you go through and we had never been through a lock before and then, all of a sudden, we’ve got 35 of them to deal with.” 

The Crimi’s sailed down the Hudson and past New York City. From there they continued down the East Coast traveling in both the Atlantic Ocean and via the Inter-coastal Waterway. During that time they successfully weathered 20 tropical storms by seeking safe harbors and waiting for the weather to move through. 

Sailing quickly put work-life into perspective. “When I was working, I complained about having to deal with the same problems day after day,” remembers Tony. “Well, you realize that you would love to go back to knowing what your problems would be every day. Because with sailing, you just never knew what was next.”

After 6 months of sailing, the Crimi’s finally reached port just north of Miami. From there, they would set sail for the Bahamas and begin to leapfrog from island to island along the eastern edge of the Caribbean Basin. For the next six months, their itinerary took them From the Bahamas to Turks & Caicos to Puerto Rico to the Virgin Islands, on to St Martin, Barbuda, Antiqua, Guadeloupe, Martinique, St. Lucia, Barbados, Grenada, Tobago, and ultimately to Trinidad just off the coast of Venezuela.

At that point, Kris and Tony had traveled 5000 miles over the course of 12 months. They had seen some of the most spectacular vistas of their lives, gotten to know some of their fellow “cruisers” sailing in the Caribbean, and settled into a daily existence of wind, water, (mostly) sunshine, and the freedom to go and do whatever they chose. They also survived a few of the biggest challenges of their lives along the way.  In the process, they learned that when living on a sailboat, you really couldn’t have spectacular moments without accepting the difficult moments. “There were times when you felt like it was the best day of your life. But for every day like that, you paid for it with days that were kinda miserable,” says Tony.

Bad weather, broken equipment - even getting run over in their inflatable dinghy by a powerboat (no serious injuries) - were part and parcel of the journey. Tony laughs now that the photos of their trip only show the good times. “We don’t have pictures of the really sh***y times because we were too busy trying to stay alive and to keep the boat in one piece!”

In August of 2006, they had completed their first sailing season and they flew back to Minnesota to avoid hurricane season in the Caribbean. They returned to their boat which had been stowed in Trinidad in late October and spent their 2nd sailing season cruising between Trinidad and Guadalupe and all the islands in between. “ It's like traveling in a RV. You might drive every day for a week, but you also might spend a week somewhere. There were places that we just loved and we would stay there for a couple of weeks. You’d spend time in places with friends and it was just a whole community.”

In the summer of 2007, they stored Ticketoo in St Lucia and returned home to wait out another hurricane season. Ironically, the strongest storm of the season, Hurricane Dean, hit St Lucia but their boat survived unscathed. Their third and final sailing season involved a farewell tour of some favorite islands, more time with the good friends they made along the way, and then a trip back up the east coast to the Chesapeake Bay. There they sold their water-borne home and the Crimi’s three-year sailing adventure was officially over.

Returning to land was an adjustment. Kris missed “the wind in my face. Our community of friends. Jumping in the water whenever you felt like it.  In the Tobago keys when we were anchored, you would get up in the morning, put on your swimsuit (or not), have a cup of coffee, and you would jump in and enjoy snorkeling. That was awesome”

For Tony, the return to “civilization” was something of an assault on his senses.  Being away from the commercial nature of American culture had been enjoyable. “Here, from the minute you get up in the morning until you go to bed at night, you're subject to advertising all day long. So the lack of exposure to consumerism on the boat - I miss that.”

And what was their favorite place?  Kris refuses to answer. “I’m not going to answer that. All of them! They were all different in one way or another and the people were wonderful.  The most interesting food was Trinidad. The best diving was Saba. The best party-ing was Martinique and St Kitts. But everwhere was just great.”

After three years, thousands of miles on the water, and hundreds of stories of life on a sailboat, Kris and Tony returned to land in Flat Rock where they proceeded to build a new home and yet another new life.

They loved every moment of the adventure, but they would not try it again.  “It’s like asking people our age,” says Tony, “‘Would you ever have kids again?’  Well yeah, I love my kids and that was a great chapter in our lives. But now at 72, do I want to have kids again? No. Physically it is just too hard.”

For now, Kris and Tony can focus on their kids, 8 grandchildren, and 3 great-grandchildren. And regale them all with stories of adventure and discovery on the voyage of a lifetime.