Stepping off the transatlantic ship in Rotterdam, wearing a velvet hat, white gloves, high pointy toed heels, a garter belt holding up nylon stockings, and beige suit perfectly pressed, I lugged a plaid suitcase filled with the 'right' outfits ready to embark on a three month European tour in the summer of 1958. I expected windmills and wooden shoes, longed for picturesque towns of narrow cobblestone streets lined with leaning buildings shaped by time. I found a continent shaped by war. When I took off my high heels and nylon stockings to slip my feet into fleece lined walking shoes, my Gypsy Boots, when I stored my packed plaid suitcase in London to substitute a small rucksack with one change of clothes, when I fearfully held out my arm to flag down my first car, I stepped into a strange dream. One that enfolded me and sent me in a new direction, an irrevocable moment when I walked across a boundary my old self couldn't cross. Living for a dollar and a half a day, I hitchhiked 25, 000 miles, from Lapland to the Canary Islands, from East Germany to Greece, through Tito's Yugoslavia and Franco's Spain. A year and a half later, on the way home, I barged into Castro's revolution in Cuba on a freighter bound for Mexico. Gypsy Boots is a journey that describes a time when women's ambitions were limited to nursing, teaching or taking dictation. It took place on a continent still in shock from war and trying to cope with poverty, dictators and the impositions of the Iron curtain, where people were willing to share their customs and voice their challenges to a naive American. This turns into the adventures of an innocent abroad who hitchhiked from the conventions of her past into a new era.