#1 Moloka‘i, Hawaii
The understated elegance of Moloka‘i is often overshadowed by its more famous Hawaiian siblings. If you’re looking to experience Hawaii with a touch of exclusivity, Moloka‘i offers just that. The island boasts plenty of beachfront vacation villas with personalized services that will make you feel like you’ve discovered Hawaii’s best-kept secret. Being only the fifth largest out of the eight major islands, Moloka‘i is more underdeveloped but that means visitors can experience pristine natural wonders along with more authentic Hawaiian experiences. Plus, it’s only a 90-minute ferry ride from Maui!
I’d recommend visiting between April and October to enjoy the island’s balmy weather and avoid the winter crowds. Do not miss a visit to the Halawa Valley for a serene hike that ends at a breathtaking waterfall. And for those who love history wrapped in luxury, the Moloka‘i Museum and Cultural Center offers fascinating insights with a touch of class. Cap off your day with a private sunset cruise, where you can sip champagne as you glide past the island’s pristine shores.
#2 Sedona, Arizona
Sedona, with its dramatic red rock formations and spiritual vibe, is a paradise for luxury seekers who also enjoy a bit of adventure. L’Auberge de Sedona is the epitome of luxury here, nestled at the banks of Oak Creek in the heart of Sedona, offering world-class spa treatments and award-winning dining.
March through May are ideal months to visit, offering pleasant temperatures and vibrant wildflowers. Alternatively, visit in the fall to experience the red rocks against the backdrop of golden foliage. For a luxurious touch of mysticism, book a private jeep tour to the vortex sites believed to possess healing energy. Wine enthusiasts can indulge in tastings at the nearby Verde Valley Wine Trail. And don’t forget to book a hot air balloon ride at dawn—nothing says luxury like floating above the desert in a wicker basket.
#3 Block Island, Rhode Island
Block Island is the epitome of underrated luxury, offering a slice of New England charm with an upscale twist. Picture this: you’re lounging on the unspoiled sands of Mansion Beach, cocktail in hand, with the Atlantic Ocean serenading you in the background. Getting there is part of the adventure, with a scenic ferry ride from Point Judith (under an hour) or a quick flight from the mainland. Once you arrive, explore the island’s 17 miles of pristine coastline, visit the historic Southeast Lighthouse perched dramatically on Mohegan Bluffs, or indulge in some retail therapy at chic local boutiques. Wrap up your day with a gourmet seafood dinner at The Surf, where you can dine with your toes in the sand and the sunset as your backdrop.
Summer, from June to August, is the perfect time to visit, when the island blooms with vibrant wildflowers and the weather is ideal for beachside relaxation.
#4 La Jolla, California
La Jolla, often dubbed the “Jewel of San Diego,” offers a sophisticated coastal retreat in Southern California. I love the iconic La Valencia Hotel, with its pink stucco facade and Mediterranean flair, epitomizes old-world glamour and modern luxury. Spring and fall are the best times to visit, avoiding the peak summer crowds while still enjoying warm, sunny days.
I’d recommend starting your day with a visit to the La Jolla Cove, perfect for a morning snorkel or just to admire the picturesque coastline. The Birch Aquarium offers an upscale educational experience, ideal for a cultured afternoon. For dinner, head to George’s at the Cove, where you can savor award-winning cuisine with panoramic ocean views. And for a truly luxurious evening, don’t miss a performance at the Conrad Prebys Performing Arts Center. La Jolla is included in my roundup of best road trip getaways outside of Los Angeles, read more here!
#5 Bar Harbor, Maine
Bar Harbor is the gateway to Acadia National Park and a haven for those who appreciate refined luxury with a touch of rugged nature. The there are plenty of historic and charming B&B’s offering sumptuous accommodations and full-service spas overlooking the ocean. Late spring to early fall (May to October) is ideal for experiencing the region’s natural beauty and avoiding the harsh winter chill.
Be sure to drive up to Cadillac Mountain for the first sunrise in the U.S. and breathtaking views that will start your day in the most magnificent way. Take a luxurious yacht tour around Frenchman Bay, where you might spot seals and bald eagles. End your day with a lobster dinner at the elegant Reading Room Restaurant, known for its fresh seafood and impeccable service.
