Planning a luxury vacation in the United States this May? You’re in for a treat! May is one of the best months to explore the US, offering warm weather, stunning landscapes, and vibrant cultural experiences—not to mention plenty of unique, luxurious travel opportunities. From enchanting coastal towns to breathtaking national parks, we’ve curated a list of 25 exclusive and unforgettable destinations for affluent travelers seeking unique experiences.
Whether you’re drawn to the charm of New England, the vibrant culinary scenes of the South, or the dramatic vistas of the West, this list has something for everyone. Get ready to explore the USA like never before!
Northeast Region
Destination 1: Newport, Rhode Island
Experience the elegance of Newport in spring. Wander through its historic mansions that feel plucked from the Gilded Age, and treat yourself to a luxurious seaside lunch at a waterfront bistro. Don’t miss the iconic Cliff Walk for breathtaking views of the coast.
Destination 2: Bar Harbor, Maine
Bar Harbor offers a quintessential New England experience. Indulge in fresh lobster at a high-end restaurant, then stroll through Acadia National Park, where forests meet the ocean. The crisp May weather and blooming flora make it the perfect time to visit.
Destination 3: Hudson Valley, New York
If you’re a fan of art and wine, Hudson Valley is your dream destination. Exclusive wine tastings, boutique inns, and art galleries await. Drive along scenic country roads surrounded by lush, blossoming landscapes.
Southeast Region
Destination 4: Charleston, South Carolina
Walk the cobblestone streets of Charleston and take in its charming pastel homes. Book a culinary tour for a taste of the city’s iconic Lowcountry cuisine, and relax at one of its many luxurious boutique hotels.
Destination 5: Savannah, Georgia
Savannah’s romantic southern charm sets it apart. Stay at a high-end inn with views of centuries-old oak trees draped in Spanish moss. Take a private historical tour to learn about the city’s rich past.
Destination 6: Miami, Florida
For a splash of excitement and opulence, Miami is the place to be. Enjoy premier beachfront accommodations and dine at Michelin-starred restaurants before exploring the city’s thriving art and nightlife scenes.
Midwest Region
Destination 7: Chicago, Illinois
May is a delightful time to visit the Windy City. Watch stunning sunsets over Lake Michigan, enjoy rooftop cocktails with views of the skyline, and immerse yourself in cultural activities like the Art Institute of Chicago.
Destination 8: Mackinac Island, Michigan
Step back in time on Mackinac Island, where cars are replaced with horse-drawn carriages. Stay at the luxurious Grand Hotel, and indulge in high tea on the veranda with panoramic views of the lake.
Destination 9: Kansas City, Missouri
Kansas City offers a surprising mix of jazz, art, and barbecue. May marks the start of festival season here, making it the perfect time to experience the city’s cultural vibe while staying at a swanky hotel downtown.
Southwest Region
Destination 10: Santa Fe, New Mexico
Art lovers will find paradise in Santa Fe. Explore the Georgia O’Keeffe Museum, and stroll through vibrant artist markets. Treat yourself to a spa retreat at one of its world-class resorts.
Destination 11: Grand Canyon, Arizona
Nothing beats the sight of the sun setting over the Grand Canyon. For a truly luxurious experience, book a helicopter tour or stay in an upscale lodge nearby for unobstructed canyon views.
Destination 12: Austin, Texas
Austin is where luxury meets eclectic vibes. Think five-star resorts and gourmet barbecue. Attend a live music event downtown, then cap off the night at a posh cocktail lounge.
West Coast Region
Destination 13: Napa Valley, California
Napa in May offers picturesque vineyards and ideal weather for wine tasting tours. Enjoy exclusive pairings at renowned wineries and unwind in one of Napa’s luxury boutique hotels.
Destination 14: Carmel-by-the-Sea, California
Carmel is a charming coastal town filled with art galleries, unique shops, and gourmet restaurants. Walk along its pristine beaches or stay at a romantic inn overlooking the ocean.
Destination 15: Portland, Oregon
May brings out the best in Portland’s vibrant gardens and buzzing coffee culture. Explore the Japanese Garden, and enjoy farm-to-table dining in the heart of this creative city.
Mountain States Region
Destination 16: Jackson Hole, Wyoming
For those seeking adventure with a touch of elegance, Jackson Hole is perfect. Go hiking in the Grand Teton National Park, then unwind in style at a high-end mountain retreat.
Destination 17: Aspen, Colorado
Aspen isn’t just for winter getaways. Visit in May for scenic hiking trails, wildflower views, and luxurious spa treatments at five-star resorts.
Destination 18: Montana’s Luxury Ranches
Experience sophisticated wild west vibes at a luxury guest ranch in Montana. Horseback riding, fly fishing, and farm-to-table dining make for an unforgettable vacation.
Pacific Northwest Region
Destination 19: Seattle, Washington
Explore Seattle’s gourmet coffee houses, Pike Place Market, and trendy rooftop bars. Take a ferry ride to Bainbridge Island for a serene escape from the urban hustle.
Destination 20: Columbia River Gorge, Oregon
Revel in the beauty of waterfalls and wildflowers in the Columbia River Gorge. Opt for a luxurious river cruise to fully appreciate this lush and dramatic landscape.
Unique Destinations Across the USA
Destination 21: Yosemite National Park, California
Explore Yosemite’s iconic vistas with a guided tour. Stay at an upscale lodge near the park and enjoy activities tailored to luxury travelers.
Destination 22: Sedona, Arizona
Sedona’s red rock landscapes are at their most captivating during golden hour. Enjoy holistic spa treatments or hot air balloon rides for a one-of-a-kind experience.
Destination 23: Key West, Florida
Relax island-style in Key West with beachfront resorts, private snorkeling trips, and plenty of fresh seafood dining options.
Destination 24: Outer Banks, North Carolina
The Outer Banks is ideal for a tranquil getaway. Enjoy coastal luxury with private beach houses and yacht excursions through pristine waters.
Destination 25: Lake Tahoe, California and Nevada
Spring blooms beautifully in Lake Tahoe. Take a scenic drive along the lake, or indulge in water activities, followed by evenings at a cozy (yet luxurious) lakeside lodge.
Plan Your Dream May Vacation Now
Whether you’re after breathtaking coastline views, serene mountain retreats, or vibrant cultural scenes, the USA offers endless luxury travel opportunities in May. Each of these destinations promises to deliver unforgettable experiences tailored to affluent travelers.
Don’t wait to plan your next adventure. Step into the world of experiential travel and make May 2025 truly extraordinary!
