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Sir Winston Churchill was a voracious traveler, having visited various European countries as well as Cuba, Sudan, India and South Africa by the time he was twenty-five (and that’s before the turn of the last century). His granddaughter, Celia Sandys, has written extensively about these journeys, most notably in her books Churchill: Wanted Dead or Alive, which chronicles Sir Winston’s daring escape from Boers’ captivity in South Africa in 1899, and Chasing Churchill, her most latest memoir which was recently turned into a three-part documentary for PBS. This fall, travelers will be able to retrace the famous premier’s steps in Europe and Africa, on two special journeys, arranged in collaboration with the Chicago-based Churchill Centre, led by Sandys.

The first tour, scheduled for September 7-12, will be a cruise on board the Christina, Aristotle Onassis’ fabled yacht on which the sixteen-year-old Celia embarked on her first journey with her grandfather in 1959 (the summer when Onassis and opera singer Maria Callas began their doomed affair). Guests will board in Naples and travel to Capri, Syracuse, Malta and Palermo. Speakers aboard will include Allen Packwood, the keeper of the archives at Churchill College Cambridge and a great expert on the premier minister, Patrick Jephson, who was the private secretary for Princess Diana for eight years and, of course, Sandys, a charming, approachable host who is open to sharing her memories of traveling with her grandfather. From $1,540 per person per day.

The second itinerary, scheduled October 20-27, will explore Morocco, a destination Churchill loved and visited many times, including four days in Marrakech and three in Ouarzazate. Churchill once described Marrakech as “the loveliest spot in the world,” even convincing Roosevelt to drive there with him after the Casablanca Conference in 1943. Highlights of the trip will include a guided visit of the Majorelle gardens, where Sandys’ grandfather spent hours painting, a cooking class at La Maison Arabe, a hosted dinner at a beautiful private home and La Mamounia, if the legendary hotel has reopened by then. Says Sandys: “These are not ‘study tours.’ I chose places that my grandfather visited and we will talk about his travels and tell anecdotes, but the tour will also include some of my own favorite spots and, of course, some tourist essentials. The point is to make them journeys of a lifetime.” From $5,950 per person.

Chasing Churchill Tours can be booked through Admiral Travel (www.admiraltravel.com). In June 2009, Sandys is planning a trip to South Africa.

Read a Q&A with Sandys about traveling with her grandfather.