Jennifer Singleton

The Balmoral in Edinburgh is special to me for both its timeless elegance and its unbeatable location right in the heart of the city on Princes Street. Sitting at the gateway to the Royal Mile with views of Edinburgh Castle, it perfectly blends historic charm with modern luxury. It’s a hotel that truly feels woven into the fabric of the city, making every stay feel distinctly and unmistakably Edinburgh. Walking out the front doors, you’re immediately surrounded by history, shopping, dining, and some of the most iconic sights in Scotland.

Naples will always hold a special place in my heart. I was born and raised here, and I still call it home today. I’ve been visiting this stretch of beach since I was a kid, back when it was the beloved Naples Beach Club. As a Four Seasons Preferred Partner, I absolutely had to check out the transformation into the new Naples Beach Club, A Four Seasons Resort. It’s been incredible to see such a meaningful place reimagined with the Four Seasons touch while still honoring the spirit of the original.

JW Marriott Starr Pass Resort & Spa is such a beautiful desert escape. It’s surrounded by mountains, cacti, and those incredible Arizona sunsets. We were upgraded to a room with a stunning view overlooking the pool and mountains, and one morning we even spotted a small group of deer wandering by just outside. It was such a peaceful moment that really set the tone for how calm and restorative this resort feels.

Fairmont Jasper Park Lodge holds such a special place in my heart especially just after the Christmas holidays, when the snow still blankets the cozy cabins and the festive lights shimmer across the frozen lake. There’s something peaceful and grounding about this spot in Jasper National Park, surrounded by mountains and nature at its quietest. I love skating on the lake, then warming up by the fire afterward, and seeing the resort’s friendly golden retriever who’s there daily to greet guests always makes it feel even more like home. It’s one of those places that makes you slow down and simply enjoy winter.

Fairmont Banff Springs truly feels like stepping into a winter fairytale. Nestled in the heart of the Canadian Rockies, it’s surrounded by snow-covered peaks, frozen waterfalls, and the cozy charm of Banff town. The grand castle-like architecture, warm fireplaces, and stunning mountain views make it feel both luxurious and comforting. It’s a place where you can unwind, explore, and feel completely swept up in the magic of winter.

Fairmont Chateau Lake Louise is one of those places that feels magical in every season. I’ve been lucky to visit in both summer and winter, and each has its own charm but winter truly transforms it into a wonderland. The trees dusted with snow, the mountains standing tall around the frozen lake, and the sound of sleigh bells as you ride to a frozen waterfall where ice climbers scale the glittering walls all make it unforgettable. Returning to the hotel for hot cocoa while watching skaters and hockey players glide across the ice is the perfect ending to a dreamy winter day.

The Four Seasons Fort Lauderdale feels like an instant escape, even though I live just a few hours away. It’s the perfect weekend getaway. It’s close enough to be easy, but far enough to feel like a true change of pace. I love how it blends sleek, modern luxury with breezy coastal charm, where mornings start with ocean views and evenings end with world-class dining. Every stay leaves me feeling refreshed, pampered, and already planning the next visit.

The Westin Grand Cayman holds a special place in my heart for its unbeatable location right on Seven Mile Beach, where the water is as blue as I remember it every time. It’s a place where my days naturally fall into a happy rhythm of beach walks, ocean swims, and sunset sails. I love that it’s relaxed enough for barefoot lunches yet polished enough for memorable dinners, all with the warm, easy charm of the Cayman Islands. Every visit feels like coming back to a familiar, sun-soaked friend who’s always ready to welcome me home.

Vail has a way of making you feel like you’ve stepped into a European alpine village without ever leaving Colorado. Inspired by the charming ski towns of the Alps, Vail’s Bavarian-style architecture, cobblestone streets, and cozy cafés give it a storybook feel and nod to its German and Austrian heritage. In winter, it transforms into a snow-dusted wonderland, with the sound of après-ski music drifting through the village and the scent of fresh pretzels and schnitzel wafting from warm, welcoming restaurants. Of course, it’s home to some of the best skiing in North America, from the legendary Back Bowls to wide, gentle greens perfect for beginners, but there’s just as much magic off the slopes. Whether you’re here for world-class skiing, strolling through boutiques, or soaking in the après scene, Vail delivers the best of alpine charm right here in the Rockies.

Hilton Waikoloa Village on the Big Island is more than a resort—it’s an experience. Ride a tram or boat to explore the lush oceanfront grounds, snorkel in the lagoon, visit dolphins, or float down the lazy river. The saltwater lagoon is naturally fed by the ocean, allowing sea life like fish and turtles to come and go freely. You can even paddleboard or snorkel under the manmade waterfall, where sea turtles gather to eat. With a luau, multiple restaurants, a spa, golf, and cultural activities, it’s Big Island adventure all in one place.

Grand Hyatt Kauai is one of those places where you show up and immediately start wondering how to extend your stay... forever. The pools go on forever, there’s a saltwater lagoon you can float in like a very relaxed pineapple, and the grounds are so pretty it feels like Mother Nature had a glam team. We wandered through tropical gardens, got lost (in a good way), and somehow ended up at the spa more than once—oops. Honestly, if you’re looking for laid-back luxury with a side of mai tai, this is your spot.

Our Four Seasons Hualālai escape was pure Big Island magic from start to finish. I keep returning to this dreamy corner of Hawaii because, quite simply, it’s my favorite place in the world. We snorkeled in the King’s Pond. It’s actually a lava-carved aquarium. We loved gliding past bright fish in the clearest water imaginable. Afternoons were for lounging by the quiet pool, where ocean breezes, chilled pineapple, and warm aloha seemed to float in the air. And as the sun melted into the Pacific, we’d sit on our lanai with tiki torches flickering and waves rolling in, feeling like the rest of the world had quietly slipped away.

Maui will always have a piece of my heart, and the Four Seasons makes it feel like a dream you never want to leave. I kayaked straight from the beach to swim alongside humpback whales in early March. When floating in the water, hearing their songs echo around me as if they were just a few feet away, was one of the most surreal and beautiful moments of my life. The spa is pure bliss, and their robes are so soft and cozy I had no choice but to buy one to bring the feeling home. Dinner at Spago, especially their legendary Peking duck, is a must, and the breakfast spread is a total highlight. You can’t beat lunch or dinner at Ferraro’s, where I spotted whales leaping in the distance during the day, and again at sunset, jumping across the horizon like it was part of the show.

I’ve done this trip twice and would go again in a heartbeat—it’s that special. I’ve seen everyone from 5-year-olds to 90-year-olds loving every minute, because if you’ve got a sense of adventure, this journey is for you. Each day, you’re off the ship exploring a new island—walking alongside giant tortoises, snorkeling with sea lions, and spotting blue-footed boobies up close. The small-group feel, expert naturalist guides, and amazing food, combined with a ship that’s both comfortable and relaxing, make it one of the best multigenerational trips out there—equal parts exciting, educational, and totally unforgettable.

Hawai'i is really special to me for a lot of reasons. First off, the nature is just unbelievable — whether it's the beaches, waterfalls or all the lush greenery, I’m always in awe of how beautiful it is. Every corner feels like a little piece of paradise. It’s also a place where we’ve made so many great memories as a family. From beach days to exploring hidden spots, it’s just the perfect place to relax and spend time together. And I can’t forget the history — it’s rich with culture and traditions that make it feel so unique. The Hawai'ian vibe is like no other, and I always leave feeling like I've learned something new and connected with the spirit of the islands.