10 The Stay Guide: Grand Cayman

Grand Cayman blends barefoot luxury with polished Caribbean style, offering Travel Advisors a full spectrum of hotel experiences along the island’s famous Seven Mile Beach. In this episode, Michelle Orr of Master Travel and Andrea Duvall of Andrea Duvall Travel Design share firsthand insights from recent stays and site visits across the island, including Hotel Indigo, The Westin, Black Urchin, Palm Heights, Kimpton Seafire Resort + Spa, and The Ritz-Carlton, Grand Cayman. They compare each property’s setting, guest experience, and ideal client fit, from design-driven boutique stays to all-encompassing family resorts. Their perspective highlights how beach access, aesthetics, service, and social atmosphere define each hotel’s sweet spot. Travel Advisors will come away with clear, experience-based guidance to match every client type confidently in Grand Cayman.

Key Takeaways

  • Compare and contrast Hotel Indigo and Palm Heights vibrant onsite energies, from standout food to speakeasies

  • How The Westin’s beachfront location, renovated rooms, and exceptional spa create value for families and Marriott loyalists.

  • Which hotels to send privacy-seeking travelers

  • Why Kimpton Seafire and The Ritz-Carlton represent Grand Cayman’s all-around and ultra-luxury tiers, and how to help clients choose between them.

About the guest: 

Michelle Orr is the founder and CEO of Master Travel, a Virtuoso Certified agency based in Greenwich, Connecticut. Recognized by Condé Nast Traveler as a Top Travel Specialist from 2023 to 2025, Michelle brings a deeply personal, experience-driven approach to designing tailor-made journeys around the world, from African safaris to European getaways and Caribbean escapes.

Andrea Duvall is the owner of Andrea Duvall Travel Design, an independent travel design firm focused on curated, design-forward journeys. Her nuanced understanding of Caribbean destinations helps clients navigate options confidently, from emerging boutique hotels to established luxury icons.

Whitney Shindelar

Undiscovered Sunsets was a long time in the making, even if I myself didn’t realize it. During my time at the University of Northern Iowa, I studied abroad in New Zealand. Upon graduating, I bought a one-way ticket to France, lived with a French family and studied with classmates from Turkey, China, Russia, Germany, Italy, and everywhere in between. In 2010 I began teaching English as a foreign language. This job quickly took me to China, where English teachers were in high demand and within three years, I began working in a 5-star hotel, speaking Mandarin throughout most of my day. In total, I lived abroad for 7 years.

I consider Undiscovered Sunsets to be the perfect mélange of my personal experience traveling the world and my professional experience working in the hospitality industry.

I look forward to designing your next adventure!

Next
Next

09 The Stay Guide: Amsterdam