Dione Bailey

Raffles Bali is the kind of property that reminds you why you fell in love with travel in the first place. Perched above the gentle curve of Jimbaran Bay, spread across 23 hectares of untouched hillside, and comprising just 32 private villas, it manages something genuinely rare: the grandeur of a world-class resort matched by hospitality that feels personal, unhurried, and completely sincere. This isn’t a property that simply meets expectations—it consistently anticipates them. For clients who want Bali at its most refined without sacrificing soul, this is where I would send them first, every time.

Slovenia captured my heart with its intimate scale and outsized beauty—a country where you can have breakfast beside alpine lakes, lunch in vineyard-draped hills, and dinner in a medieval castle, all within a few hours' drive. This itinerary follows a carefully choreographed progression from the otherworldly turquoise waters of the Soča Valley through the fairytale setting of Lake Bled to Ljubljana's living-room warmth and finally to the sun-drenched wine country that rivals Tuscany. It's a destination that rewards those who look beyond the postcard views to discover a culinary scene punching far above its weight, where Michelin-starred chefs work with ingredients foraged that morning and winemakers pour their stories along with their wines.

Having lived in Tel Aviv for several incredible years, I was fortunate to have the natural wonders of Jordan and Israel just a drive away. This itinerary captures a very special trip that my husband, in-laws, and I took, connecting some of the region's most iconic and contrasting landscapes: the awe-inspiring, hand-carved history of Petra, the vast, cinematic desert wilderness of Wadi Rum, and the otherworldly experience of the Dead Sea—the lowest point on Earth. The journey created a profound travel experience that offered historical immersion, deep connection to nature, and moments of pure wonder.

Riga, Latvia’s capital on the Baltic Sea at the mouth of the River Daugava, is a cultural hub where history and modernity coexist. As my mother’s birthplace, walking its cobblestone streets makes me feel deeply connected to my family’s past. The city is renowned for its wooden buildings, Art Nouveau architecture, and medieval Old Town. Affordable and welcoming, Riga offers surprises like hidden courtyards, local treats like pīrāgi, and fascinating stories behind its grand facades.

I had a second home in Healdsburg for over five years, using it as my weekend escape from city life. Over that time, I hosted countless friends and family, exploring every corner of the town and far beyond. My favorite part was being able to stroll to the square for a wine tasting followed by dinner at one of the many available options. I’ve sipped and swirled my way through Healdsburg’s many festivals, but two stand out: Pigs & Pinot in March—hosted by Charlie Palmer at Hotel Healdsburg—and Pinot on the River, a celebration of my favorite grape. If you can’t tell, I’m a pinot noir devotee.

Penang is a vibrant blend of cultures, flavors, and history that comes alive on every street corner. From its UNESCO-listed George Town, bursting with colorful shophouses and street art, to its legendary food scene where Chinese, Malay, and Indian influences collide, the island is a feast for the senses. I love the way the pace slows just enough to savor an afternoon tea in a grand hotel, followed by evenings filled with rich flavors and local charm. Penang offers that rare combination of world-class dining, fascinating heritage, and warm hospitality.