Last Updated on July 25, 2025
Picture sails rising against the skyline, a warm breeze dancing off Lake Ontario, and the historic schooner When And If catching the wind as she glides into Rochester, New York. I didn’t just imagine it, I lived it.
This was an unforgettable sailing tour where peace and passion flowed on this Great Lake out of the Port of Rochester Marina in Upstate New York.
A living, breathing chapter of American history came to visit Rochester during the Harborfest on the waterfront of Ontario Beach Park. The vessel was greeted by veteran Jack Foy, who served under General George S. Patton. Patton commissioned the vessel.
“Came down to see my boss, General Patton,” the 99-year-old Foy, who served in the Battle of the Bulge, said.
As I walked along the pier and embarked on the original vessel, cozy conversations captured my heart. My love of water and boats broadened my horizon and showed me the beauty, history, and adventure not only at this destination, but the story of this schooner, the captains, and the crew on the When And If.
Casting Off
Captain Sean Flynn sounded the horn with a conch shell signaling that we had cast off and eased away from the dock in the Genesee River and crossed into Lake Ontario. The conch shell is their official signaling device approved by the Coast Guard and could ask to be blown during every inspection.
Once the motor is turned off and the sails are set, the wind propels the boat. Alignment and adjusting the sails on every voyage not only applies to sailing, but also to life. The crew allows passengers to volunteer to raise and lower the sails if you wish. Watching the crew at work was like witnessing a well-played symphony.
There’s a rhythm and harmony where the elements of nature, the design of the boat, and skills of the captain and crew come together. It takes coordination and balance to achieve an even keel and smooth motion cutting through the waves. I needed to simply observe and keep myself balanced. When I was sitting on the high side of the schooner, I was able to stay secure.
Once the sails changed direction, I was on the lower side and thought I was going to slide right into the water. I hung on with both hands and both feet. No meandering about the deck for me when it was tipped to the low side. But, oh what a ride! Just hang onto your hat. One man’s blew off and could not be retrieved.
The Legacy of When And If
This sturdy schooner constructed of double planked mahogany over black locust frames and an oak keel was built for and commissioned by General George S. Patton and designed by naval architect John Alden. It was constructed in 1939 by FF Pendleton in Wiscasset, Maine, to sail around the world.
The name was born after Patton said, “When the war is over, and If I live through it.” He did live through it. However, Patton and his wife Beatrice did not get to fulfill their dream of sailing around the world. Patton died due to complications from a car accident eight months after the capitulation of the Nazis.
In 1972, the Patton family donated the schooner to the Landmark school for children with dyslexia in Pride’s Crossing, Massachusetts. Patton himself was dyslexic, and When And If’s time there marked some of the happiest years for children at the school. Today they come sailing and visit the boat both in Massachusetts and Florida, bringing their own families to entertain them with their sea stories never forgotten from all those previous summers.
Captain Seth Salzmann was the driving force to fulfill the destiny of When And If after purchasing this magnificent vessel from winemaker and sailor, Doug Hazlitt. In 2012, efforts of preservation and restoration were underway on Cayuga Lake.
Just like the schooner needed repair and renewal, I needed healing and wholeness too. Embarking on this journey restored my health and sense of awe and adventure. I recalled a quote from Dolly Parton that said, “We cannot direct the wind, but we can adjust the sails.”
Love was in the air. I became one with the gentle rocking of the boat and rhythmic sounds of the water. Speaking of love, Captain Seth was at the wedding of Captain Sean. That is how Captain Sean Flynn knew that the When And If would be sailing on the Great Lakes and going to Rochester, New York.
Sailing Stories
With Captain Flynn at the helm, he told me his story about growing up sailing even though he lived in the landlocked state of Arkansas. He got into the nautical sport in college and said, “I didn’t even realize it could be a career.”
After college, Flynn sold everything he had and bought a boat in California. Later, he saw the When And If and fell in love with her. He worked his way up from mate to captain. From the St. Lawrence Seaway and Canadian Maritimes to Galveston, Texas, Key West, Salem, Massachusetts, and now Rochester, New York, he has sailed vast stretches of water.
Captain Flynn shared that his passion for sailing provides a sense of freedom navigating through the open water and seeing the world from a unique perspective. The wind is shifting however, and he has a new commission – a baby on the way, which will be his new adventure. Taking a Port Captain role will keep Flynn anchored at home more often so he can spend time with his wife and new bundle of joy.
The camaraderie, close quarters, and clear communication among the captain and crew breeds a family feel. They not only work together, but are there for each other in the long haul. There is definitely a love for one another and for the historic vessel.
Guests welcomed onto the When And If are treated like VIPs. The captain and crew are approachable and accommodating. Bringing guests out on the day tours, sunset sails, or private charters keeps the vessel running and maintained as well as paying the crew.
Currently, six crew members live on board full time. I met a few including Josh, Sean’s brother, when I was on the Sunset Sail. Captain Zach was at the helm on the day of my sail. I chatted with Kate Dingus, who has been sailing for seven years and aboard the When And If for two months. She said she got to know the crew at a Tall Ships Festival in New Orleans and asked, “This is your career? This is how you make a living?”
When they said “yes,” Kate applied for a job and got her captain’s license, then going from cashier to captain. Kate’s story is a testament to the transformative power of pursuing your passion.
Sailing Tips
Below deck, there is a bathroom if needed. Be careful navigating up and down the ladder. Some people tend to have motion sickness more below deck than on deck. Either way, I bring my natural remedies like essential oils to stay calm and well. Looking out at the horizon and going with the motion helps.
Remember to dress according to the weather. It’s generally about 20 degrees cooler out on the water.
There is more beyond the waterfront when you Visit Rochester, in Western New York between Buffalo and Syracuse. You’ll feel right at home. In fact, the Great Lakes is called “HOMES” representing the name of each freshwater lake: Huron, Ontario, Michigan, Erie, and Superior.
Beacon of Light
When I saw the lighthouse at the end of the Charlotte pier, I knew we had changed course and were getting ready to secure the schooner at the dock. It reminds me how lighthouses are a beacon of light not only guiding sailors to navigate their way, but leading people in life giving them hope to persevere through adversity. They represent safety, strength, and direction.
While at the Port of Rochester, there is a historic lighthouse nearby overlooking the Genesee River. The Charlotte Genesee Lighthouse was voted one of the top three landmarks in the City of Rochester.
I had the opportunity to sail the schooner twice, once by day and again at sunset. Both experiences left a lasting impression. In between sails, I had time to explore more around Rochester beyond the waterfront, starting with dinner at Hose 22, a restored firehouse. That caught my attention since my son is chief of a local fire department. Decorated with turnout gear, helmets, historic photos, and memorabilia as a tribute to these first responders who serve, the food they serve is superb.
Surrounded by arts, music, and culture, I grooved my way through the Rochester International Jazz Festival, one of the world’s leading jazz events.
I stayed at the Courtyard by Marriott located downtown. When it was time to settle into my room, I grabbed a decaf latte on the way up. It was the perfect pairing with the Stevers Chocolate Truffles that greeted me.
The highlight of my visit was being in my happy place on the water aboard the When And If, giving me a renewed vigor. With the wind in my hair and Captain Sean Flynn at the helm, I felt a connection to the vessel and the crew. The sailing experience gave me a new lease on life I’ll cherish every moment. I didn’t want to say “goodbye,” so instead, I’ll say, “I wish you smooth sailing as forward you float. May there be wind in your sails and friends in your boat.”
To Captain Flynn and the When And If crew, thank you for sailing into Rochester. You gave me another reason to say, “I love New York!”
