One of the most memorable ways to travel is to anchor a trip around a major event. Whether it is the thrill of live sport, the pageantry of a historic festival, or the sparkle of holiday traditions, an event gives structure and meaning to your journey and turns a good trip into something unforgettable.
The catch? These trips are also among the most complex to plan. The best packages often combine hard-to-access tickets with unique cultural and culinary experiences. That is where working with a travel advisor makes all the difference. You gain insider access, VIP hospitality, and thoughtful itineraries that elevate the entire experience.
Here is some inspiration for 2026.
Wimbledon in London – June 29 to July 12, 2026
Imagine stepping onto the hallowed grounds of Wimbledon, sipping Pimm’s on the terrace, and enjoying a gourmet lunch in a private hospitality suite before taking your seat for the day’s matches. A trip like this becomes even more remarkable when paired with curated experiences across London. These may include a private morning visit to Westminster Abbey, a guided tour of Buckingham Palace’s East Wing, an after-hours walk through Windsor Castle, and appointments to design a custom fragrance or shop handbags with a stylist. This is London at its most polished and its most exclusive.
The 2026 Winter Olympics – Italy
Italy is always irresistible, and never more so than during the Winter Olympics. Picture yourself in the Dolomites. One day you are watching the world’s best skiers compete. The next day you are carving your own turns down alpine slopes. Between events, you can explore local villages, shop, and savor Italy’s culinary delights. It is a perfect blend of sport, leisure, and la dolce vita.
Ryder Cup – Ireland, September 25–27, 2026
Golf’s most electric event lands at Adare Manor in County Limerick. Days at the Ryder Cup are filled with team rivalries and dramatic match play. Evenings are for Ireland’s magic. You might spend time in Dublin’s pubs, wander Galway’s charming streets, drive the rugged Ring of Kerry, or enjoy a private tasting at a legendary whiskey distillery. Add in castle stays and you have a sporting pilgrimage with a luxury Irish twist.
Oktoberfest – Munich, Germany
Yes, you can absolutely get into the best tents without waiting in endless lines. Through advisor access, packages include reserved seats, local guides, and cultural experiences that let you enjoy Munich at its festive best. Pair the revelry with time in Bavaria’s storybook towns or a side trip to Austria for a well-rounded adventure.
Christmas Markets in Europe
Few things capture the holiday spirit like Europe’s Christmas markets. Vienna feels like stepping into a fairy tale, while Strasbourg, the self-proclaimed “Capital of Christmas,” is pure enchantment. This is also an ideal time to try river cruising. Tauck and other luxury lines offer itineraries that float you from one illuminated city to the next, with festive cheer waiting at each stop.
Formula 1 Monaco Grand Prix – May 2026
The Monaco Grand Prix is one of the most glamorous spectacles in sport. What many travelers do not realize is that a luxury cruise ship is one of the easiest and most seamless ways to experience it. Imagine watching the race from a yacht-style vessel, with Explora Journeys offering front-row access paired with curated culinary and wellness experiences.
Events Closer to Home
Anchoring a U.S. getaway around an event can be just as rewarding. Think NFL suites with all the perks, Kentucky Derby packages that go well beyond the stands, or the WM Phoenix Open. Music lovers might plan for the 2026 Country Music Awards in Nashville, which is a perfect excuse to immerse yourself in the city’s vibrant food and music scene.
And of course, for me, running half marathons with friends has become an annual tradition. Past favorites have included Napa 2 Sonoma in July, Covered Bridges in Vermont in June, and Urban Bourbon in Louisville. This year, it is Malibu in November. The experience will be made even better with a post-race recovery stay at Ojai Valley Inn, one of my most beloved wellness retreats.
Why It Works
When you build a trip around an event, you do not just go somewhere. You step into a story, surrounded by energy, culture, and community. With the right planning, these experiences expand into journeys full of private tours, local flavors, and once-in-a-lifetime access.
That is the difference between booking a ticket and crafting an event-based journey. It is not about simply attending. It is about being immersed. And that is where we come in, curating the access, connections, and details that make the trip seamless and unforgettable.
