Dana Freeman Travels: Cruising with Grandma (excerpt)

....In 2018, Dana Freeman was named one of the “10 Travel Influencers Changing How We Vacation” by Porthole Cruise Magazine, and she was also selected as one the “30 Bloggers and Travelers to Follow for Summer Vacation Advice” by Travel Pulse.

Dana has had a diverse career path to get to where she is today as a travel writer and influencer, but her passion for travel can be traced in a straight line back to her grandmother. Somewhat before her time, Dana’s grandmother, Mildred, was an itinerant traveler dating back to the forties and fifties. After a divorce, her grandmother vowed to continue traveling, and cruising was particularly conducive to traveling solo; accordingly cruise travel developed into a passion for “Gram.” It was not unusual, even in the fifties, for Mildred to save up her money, put her kids in summer camp, and go on a cruise. Mildred also frequently traveled professionally in her medical administration career. She introduced Dana to travel, first by having Dana accompany her on a business trip to Greece, and then sshortly thereafter taking her on her first cruise—just the two of them. Consequently, Dana became addicted to travel as a young teen, and that passion for travel has morphed into a passion for travel writing, and Gram forever speaking through her as what Dana refers to as “her travel muse.”

In 1980, “Gram” decided to share her love of travel with her four grandchildren by inviting each one of them to accompany her on a trip of their choice. Each year Gram planned a trip with one grandchild to go anywhere in the world that they wanted to visit. Dana was the oldest of her grandchildren and got to travel with Gram first. 12-year old Dana knew Gram’s true passion was cruising—and that was her pick to travel with her. “I wanted to see why she loved cruising so much,” Dana said. In August 1980, Gram and Dana embarked on the Holland America Line SS Veendam on a cruise to the Caribbean.

In 2010, 91-year old Gram—known as Great Gram to Dana’s two children, daughter Callahan, 8, and son Flynn, 11—expressed an interest in resurrecting the tradition she had started 30 years earlier of traveling with Dana and the other grandchildren. Gram told Dana, “I want to take your kids out on a trip like I did when you were children.” What an audacious thing to want to do at 91. Not surprising given Gram’s longtime love for cruising, and her independent attitude. (Gram continued in her career until well into her eighties, only stopping due to failing eyesight.) Dana was very hesitant to let the kids go on a cruise with Gram alone. Gram would be 92 by the time she traveled with the great grandkids. Dana told her, “I don’t think that it’s fair to put on the kids the burden of something happening to you. And they are a lot to handle.” Gram responded, “Ok fine, why don’t we all just go. I’ll take you all.” After Gram quickly reached that compromise, Dana’s concern was alleviated. She assumed this would be a one-time event. “I thought she would take my children, my husband and myself on a cruise because that is what she really wanted to do and we felt like she could not do it herself anymore and it would be done. Gram’s passion was cruising and that’s what she wanted to do.”

In August 2010, virtually 30 years to the day of 12-year old Dana’s first cruise with Gram, Dana, her husband Andrew, son Flynn, daughter Callahan and Great Gram embarked on the Windstar Windsurf in Barcelona, Spain to Nice, France. Aside from a cruise in Mexico with her parents as a young teen on Sitmar Cruises (now P & O Holidays), for Dana it was the first time cruising in almost 25 years. Flynn and Callahan, and Andrew, would get to experience their first cruise on one of the world’s most exclusive vessels. “It sort of spoiled them rotten going on the Windstar Cruise line as their very first cruise!” With a capacity of only 310 passengers, the five-mast, seven-sail, 6-decks Wind Surf yacht was the flagship of the luxury Windstar fleet—its largest and most well-appointed craft. The Freeman family and Gram were “somewhat of a square-peg-in-a-round hole” on the grand Wind Surf. “We were definitely an anomaly; even for my demographic in the mid-forties, I was not the typical Windstar cruiser. My kids were the only kids on ship. So as a family we were definitely seen as an oddity. Gram was the oldest on the ship and my kids were the youngest.” Nevertheless, Dana described the Wind Surf cruise as incredible. So, much so that Great Gram and Dana’s family decided to take another cruise the next year. “When we got home from the trip—I don’t even think Gram’s luggage was unpacked—Gram said, let’s go again; so where are we going next year.” It turns out Cruising with Grandma became a tradition—beginning with Gram at 92-years old and taking place over the successive four years—of Gram taking Dana, Andrew, Flynn, and Callahan on a cruise. Not just any cruise; Gram was partial to small luxury craft. So, after first experiencing Wind Surf, the Freemans got to experience a Mediterranean cruise on Seabourn, another cruise line that Gram was very fond of....

Read the complete amazing saga of Cruising With Gram in Chapter 5, Dana Freeman Travels, The Joy of Cruising. Available now...