Cassidy understands that travel should be a relaxing and soul-enriching journey.

Cassidy’s formative experiences in hospitality began during her summers working at Nantucket’s exclusive Yacht Club and the Westmoor Club. Here, she mastered the art of exceptional service and honed the skills necessary for success in the industry. Over the past decade, she has continued to nurture these skills through her background in hospitality management while maintaining her lifelong connections in Nantucket. Cassidy’s recent work organizing global corporate and leisure travel for C-level financial executives has further enriched her expertise.

This foundation, combined with her passion for travel, culture, and art, has allowed Cassidy to specialize in creating high-quality experiences tailored to her clients’ unique interests, all crafted with care. Cassidy’s approach to travel planning centers around meticulous design driven by passion and purpose. The relationships she builds with her clients allow her to tailor each trip while splashing her eye for luxury, adventure, and style into every detail.

Whether her clients desire champagne with a view of Madrid’s Palace from the Jardines de Sabatini balcony or seek the raw energy of a caravan journey through Tanzania’s Ngorongoro Crater – to everywhere in between – Cassidy understands the delicate balance between comfort, experience, and family. Her innate ability to craft special experiences, characterized by attention to detail and excellence, is what every client can expect.

What has been your most memorable travel experience to date?

Hemingway once said, ‘I never knew of a morning in Africa when I woke up that I was not happy.’ I can personally attest to the magic of this continent — its people, nature, culture, and the circle of life. There is no rawer experience than embracing the thrill of the hunt or feeling empathy and connection when invited into the tribal home of the Venda people to learn about their culture.

During a mother-daughter trip, I had the privilege of meeting Blessed, our caretaker and tour guide, for whom I will be forever grateful while staying at Victoria Falls Island Lodge in Zimbabwe. It’s challenging to express in words, but once you travel to Africa and experience the warmth and kindness of its people, you will understand what Hemingway articulated better than I ever could.

Which destinations or hotels do you go back to again and again? Why?

The Savoy in Madeira, Portugal, is a destination in itself. However, it’s Madeira, the island as a whole, that truly stands out; you can find everything: beaches, mountains, nature walks, hiking, Michelin-starred dining experiences, but most importantly, you can connect with the locals. I haven’t traveled to any other place on Earth where you can enjoy all of these experiences, and the best part is that they are all just 30 minutes apart from each other.

This island, located 600 miles west of Portugal, holds a special place in my heart. While you’re there, don’t miss the opportunity to have an intimate dinner at Terreiro Fire Pit at The Savoy, or immerse yourself in history at Reid’s Palace, a Belmond Hotel.