Wednesday, June 25, 2025
Travelers are craving deeper cultural connections. They’re also seeking slower, more meaningful journeys—ones that feel intentional, authentic, and personal. And according to Classic Vacations CEO Melissa Krueger, this shift is just the beginning. As travelers crave more than just sightseeing, they’re trading jam-packed itineraries for immersive moments. They want local stories, cultural depth, and experiences that leave a lasting mark.
Meanwhile, Melissa Krueger sees this evolution unfolding across every destination—from the cobbled streets of Turin to the tranquil villas of Turks & Caicos. Classic Vacations is watching it happen in real time. The demand for slower, more meaningful journeys is rising fast.
But what exactly are travelers choosing now? How are deeper cultural connections reshaping luxury, family, and sustainable travel? And what does it mean for the future of tourism?
This isn’t just a trend—it’s a transformation. And Melissa Krueger is leading the conversation. Keep reading, because this insight could change how you plan your next journey.
In an exclusive conversation, Melissa Krueger, CEO of Classic Vacations, offers a deep dive into the evolving landscape of global travel and how her company is aligning with shifting traveler behaviors and emerging market trends.
Maui’s Recovery
Melissa highlights a 3.8% increase in visitor arrivals to Maui, attributing it to a respectful return by travelers who waited for the right time. She emphasizes that guests are now more mindful, supporting local businesses, choosing cultural and sustainable experiences, and taking advantage of competitive summer rates. Hawaii, seen as a safe and meaningful destination close to home, continues to attract Americans amid global unrest.
Italy’s Rising Popularity
Italy is experiencing a 40% increase in bookings, driven not only by Rome’s 10% growth due to the 2025 Jubilee Year, but also by a growing desire to explore lesser-known destinations. Travelers are venturing to Turin, Umbria, Orvieto, Bologna, and other cultural hubs in search of more authentic and immersive experiences. Italy has transitioned from a once-in-a-lifetime destination to an annual tradition for many Americans.
Luxury Caribbean Travel Trends
Destinations like St. Barts and Turks & Caicos are seeing consistent demand for privacy, exclusivity, and personalized experiences. Villas are top choices, offering luxury and space. Melissa notes the importance of curated add-ons—such as yacht charters, private dining, and nature-based adventures—which enhance the overall experience and appeal to the high-end segment.
Asia’s Comeback
Destinations like Japan and Thailand are regaining traction, thanks to expanded flight options and policy changes. Melissa explains that while these changes haven’t shifted confidence in the destinations themselves, they have made access more convenient and cost-effective. Word-of-mouth from early-returning travelers is playing a major role in encouraging broader interest.
The Rise of “JOMO”
The Joy of Missing Out (JOMO) trend is influencing itinerary planning. Rather than rushing to see it all, travelers now seek longer stays, slower travel, and deeper connections with their surroundings. For luxury travelers, it’s about maximizing meaningful moments and embracing cultural richness without the stress of overpacking schedules.
Multigenerational Family Travel
More families are returning to the same villas and resorts annually to create continuity, reduce planning stress, and deepen emotional connections. Properties that offer villa-style accommodations with hotel services are increasingly popular, allowing families to enjoy privacy alongside high-touch amenities. These resorts are also expanding their offerings to cater to multiple age groups.
Smart Travel Hacks
Melissa recommends open-jaw flights for efficiency in multi-city itineraries and services like Luggage Free to simplify ski trips and extended holidays. She advises travelers to pack light, leave room for local purchases, and travel with essentials that enhance comfort. Her personal staples include her MZ Wallace tote, Le Prunier beauty oil, and a Drowsy Sleep silk mask.
Sustainable and Meaningful Travel
Classic Vacations champions responsible travel, promoting the TOURISM CARES Meaningful Travel map, which highlights community-led, Indigenous-owned, and cultural experiences. These real-time tools help travelers and advisors make ethical travel decisions that support local communities. Melissa herself uses the map for her own trips, including her upcoming visit to Maui, showcasing her commitment to values-aligned tourism.
This interview offers a comprehensive view of how Classic Vacations is helping travelers explore the world with intention, style, and purpose.
Maui’s recovery: What specific factors do you believe are driving the 3.8% increase in visitor arrivals to Maui, and how are travelers engaging differently with the island post-disruption?
Maui holds a special place for us — Classic Vacations was founded in Hawaii in 1978, so the islands are in our DNA. The 3.8% increase in visitor arrivals reflects more than just numbers; it shows that travelers feel it’s the right time to return. They gave the island the respectful space it needed, and now they’re coming back in ways that are more mindful — supporting local businesses, choosing cultural experiences, and prioritizing sustainable stays. Rates are also incredibly competitive this summer, which is helping to drive demand. And with unrest in other parts of the world, Hawaii continues to offer American travelers a beautiful, meaningful, and safe destination that feels close to home.
Italy’s boom: With Italy’s bookings up 40%, what’s fueling the demand for lesser-known destinations like Turin, and how do these compare to established favorites like Rome and Milan in traveler behavior?
Italy has always been a favorite for American travelers — what once felt like a once-in-a-lifetime trip has really become more of a once-a-year tradition for many. Bookings are up 40%, with Rome seeing 10% growth, thanks in part to the 2025 Jubilee Year. But what’s really driving demand is this natural inclination to go beyond the major cities. Travelers — couples, multigenerational families, and solo explorers alike — are extending their stays to places like Umbria, Assisi, Orvieto, Bologna, and Turin, looking for deeper cultural connections and more meaningful, immersive experiences outside the usual tourist path.
Luxury Caribbean demand: What trends are you seeing in traveler expectations when booking upscale destinations like St. Barts and Turks & Caicos in 2025?
We’re seeing continued strong demand for luxury Caribbean getaways, especially in St. Barts, Turks & Caicos, Antigua, and St. Lucia. Travelers are looking for privacy, personalized service, and curated experiences — villas remain hugely popular in both St. Barts and Turks, offering that perfect mix of space and luxury. In St. Barts, day yacht charters and securing the right restaurant and beach club reservations are a must. In Turks, travelers love pairing villa stays at places like COMO Parrot Cay, The Shore Club, or The Palms with private yacht outings, kayaking, or even horseback riding in the water. It’s all about creating that seamless, high-touch experience.
Asia’s comeback: What role have expanded flight options and policy changes played in restoring traveler confidence in destinations like Japan and Thailand?
Expanded airlift and evolving policies have definitely played a role — not so much in creating confidence in the destination itself, but in making travel more convenient and accessible. More flights mean greater supply, which helps with pricing, and as more people go, it reinforces that sense of attainability. We’re naturally influenced by the actions of others, so seeing friends, family, and peers return to places like Japan and Thailand makes these destinations feel even more doable and inviting.
The shift to “JOMO:” How is the “Joy of Missing Out” trend reshaping itinerary planning, and what are some examples of slow travel experiences that are resonating most with your clients?
We’re seeing what people call the “Joy of Missing Out” take hold, but for luxury travelers, it’s really about right-timing travel so it can be experienced as it’s meant to be — with cultural richness and authenticity. These are people who work hard and value the time they set aside for holiday. They don’t want that time taken from them by overwhelming crowds or rushed itineraries. Instead, they’re choosing longer stays, nature-focused retreats, and experiences that let them slow down and connect deeply with a place because true luxury is about how it feels, not how much you fit in.
Family travel traditions: Why do you think more families are returning to the same villas and resorts year after year, and how are these properties adapting to multigenerational needs?
By nature, we crave tradition and certainty — and with so much we can’t control in our daily lives, families work hard to create that sense of consistency through their vacations. Returning to the same villa or resort year after year simplifies planning and helps maximize time together. Sometimes trying something new is exciting, but it can also mean more work. Properties that offer villas within a hotel setting do a fantastic job of making it special for families, blending privacy with services and amenities that make it easy to come back again and again. These places are evolving, too — with flexible accommodations and activities designed to meet the needs of every generation.
Melissa’s travel hacks: Could you elaborate on how practices like open-jaw flights and shipping gear ahead are transforming the travel experience in terms of cost and convenience?
Traveling well really comes down to preparation. I always recommend open-jaw flights — flying into one city and out of another — especially for multi-stop European itineraries. It saves time, money, and energy. For ski trips or longer getaways, many of our clients now ship gear ahead using services like Luggage Free to avoid airport hassle. And a big tip: don’t overpack. Leave space to buy locally — most destinations have shops that are perfectly suited to the climate and style, and supporting small businesses is always the right thing to do. I always pack a foldable bag for those extra purchases and make sure I know where the local farmers market is. And of course, the right travel products help — my MZ Wallace Chelsea Top Handle Tote, Le Prunier beauty oil, and Drowsy Sleep silk mask are always with me to make the journey more comfortable. It’s all about removing friction so you can truly enjoy the experience.
Sustainable travel: How is the TOURISM CARES Meaningful Travel map being used by clients in real-time, and can you share any standout success stories of community-led experiences making a big impact?
At Classic Vacations, we believe travel can and should be a force for good when done thoughtfully. Tools like the TOURISM CARES Meaningful Travel map help make that easy as it highlights small, community-run businesses that are not only the heart of a destination but also its storytellers. Travelers use the map in real time to plan experiences that have real impact, like booking with Indigenous-owned outfitters, visiting heritage farms, or joining cultural workshops that give back. I’ve been to Hawaii more than a dozen times, and this summer as I head to Maui, I’m looking at what’s on the map — it’s helping me make this trip different, more meaningful, and unique. More and more of our advisors are using this alongside their usual planning tools to help clients align their values with their travel choices.
