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Episode 6 Caitlynn Bailey-Cummings

On Italy, Dolce Far Niente & Thoughtful Travel

Caitlynn Bailey-Cummings is a travel guide, writer, mother, and lifelong learner. After 15 years of travelling to Italy, she founded DOP Italian Travel, a consultancy that helps other thoughtful travellers plan their own trips to Italy. Caitlynn has lived in Rome, Cortona, Perugia, and Alberobello; she’s travelled to 19 of the 20 Italian regions; and she can’t get enough. Italy has gotten under her skin, and now it’s her mission to share her love and knowledge with others who also might wax poetic about drinking a glass of Sagrantino while the sun slinks behind undulating Umbrian hills. 


DOP Italian Travel can help enrich your next trip to Italy with advice on crafting your ideal itinerary, restaurant recommendations, Italian culture prep, language practice sessions, and pre-trip experiences in Calgary (Canada) such as authentic meals prepared by an Italian chef in your home and food and wine masterclasses. Caitlynn will show you hidden gems, help customize your itinerary, and get you excited and prepared while you count down the days until take-off.


Caitlynn has an MSc in Creative Writing from the University of Edinburgh and has written a novel, short fiction, poetry, drama, nonfiction, and, most recently, a travel memoir entitled Ida and I, the story of two foreign women travelling the length of Italy, 176 years apart.

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