A ticket can get you into the stadium, the theater or the ballroom. But some of the most interesting travel experiences begin with what happens before the doors open or after everyone else has gone home.
An appointment with a Parisian fashion house. A chef’s table in Aspen that turns into an evening among friends. A costume fitting before a Venetian masked ball. A closer look at the enormous balloons that will float above Manhattan on Thanksgiving morning.
These are the trips that require more than booking a hotel and buying a ticket. They require time, thoughtful planning and sometimes relationships that take years to develop.
Here are four occasions worth putting on the calendar.
Paris: Beyond the Front Row
Paris Fashion Week, March 1–9, 2027; Haute Couture Week, January 25–28, 2027
Imagine taking your seat at a Paris fashion show, then exchanging the runway for an entirely different side of the industry.
Upstairs in an atelier, the conversation turns from the collection everyone has just seen to a piece designed for one person. Fabrics are brought out, measurements taken, and the process of creating something entirely your own begins.
The following morning might bring another extraordinary appointment: a private viewing of Coco Chanel’s apartment above the historic boutique at 31 Rue Cambon.
These are the possibilities that make Paris during Fashion Week so compelling. The shows are spectacular, but the craftsmanship, history and people behind them are just as fascinating.
The distinction between Fashion Week and Haute Couture Week matters. For someone whose dream is a bespoke couture creation, January’s couture calendar provides a particularly fitting starting point. For someone drawn to the energy of the wider fashion industry, March’s ready-to-wear shows offer a different experience.
Neither a front-row invitation nor private access to a designer’s atelier or Chanel’s apartment is a standard bookable experience. Each would require specific approval and confirmation. But a trip can still be built around private shopping, exceptional fashion exhibitions, specialist guides and appointments with designers or maisons that welcome private clients.
And then, of course, there’s Paris itself: a suite at Hotel de Crillon or Le Bristol, dinner at a restaurant you’ve been trying to visit for years, and enough time between appointments to enjoy the city.
Aspen: After the Last Tasting
FOOD & WINE Classic, June 18-20, 2027
Aspen in summer has an entirely different personality from its winter counterpart. The mountains are green, the terraces are full, and for one weekend the town becomes a gathering place for chefs, winemakers and people who take considerable pleasure in a very good meal.
The FOOD & WINE Classic is the reason to go. Days revolve around tastings, chef demonstrations and conversations about everything from rare vintages to what belongs on the perfect dinner menu.
But imagine what the weekend could become after the official programming ends.
You’re at an intimate gathering when one of your favorite Michelin-starred chefs arrives carrying a leg of jamón ibérico over one shoulder and a magnum of Champagne in the other. Soon, they’re carving and pouring for the room. Dinner becomes an evening that nobody is particularly eager to end.
That’s the kind of spontaneous-feeling experience that makes a food-focused trip memorable. Although an evening with a particular chef would need to be commissioned and confirmed, rather than assumed to come with festival access.
There is plenty to build around the festival itself. Stay at The Little Nell, spend a morning in the mountains, arrange a private wine tasting or add a few days for a more leisurely Colorado escape.
The festival fills the calendar. The best moments may be the ones that never appear on it.
Venice: An Invitation to the Ball
Venice Carnival January 30–February 9, 2027
Venice during Carnival is a city that knows how to put on a performance.
Elaborate costumes move through narrow streets. Masked figures appear in palazzo windows. Arriving somewhere by boat suddenly feels less like transportation and more like making an entrance.
But the most interesting way to experience Carnival may be to become part of it.
Begin with an appointment to select or commission a traditional Venetian costume. There is an entire world of craftsmanship behind the elaborate gowns, capes and masks, and the preparation can be nearly as enjoyable as the evening itself.
Then comes the ball.
A private water taxi delivers you to a historic palazzo, where dinner, music and dancing unfold beneath frescoed ceilings. For 2027, Venice’s official Carnival Dinner Show is scheduled at Ca’ Vendramin Calergi on selected dates, providing a confirmed starting point for planning a formal evening.
The next morning offers a beautiful contrast. Before the day’s crowds gather, explore Venice with a private guide, visit an artisan’s workshop or cross the lagoon for a long lunch.
For a hotel, I’d look at Aman Venice or The Gritti Palace. Both fitting settings for a trip built around one of the city’s most theatrical traditions.
New York: Thanksgiving, Behind the Scenes
November 26, 2026 — the 100th Macy’s Thanksgiving Day Parade
Most people experience the Thanksgiving Day Parade from the sidewalk or their living room. For a trip to New York, I’d build the experience around what happens on both sides of Thanksgiving morning.
Start with the balloons.
The evening before the parade, the enormous characters are inflated on the Upper West Side, transforming the surrounding streets into a remarkable preview of the next day’s spectacle. The public balloon inflation viewing is a wonderful experience in its own right. A genuinely private behind-the-scenes visit, however, would require separate authorization and should never be assumed.
Then comes Thanksgiving morning. A parade-facing suite or a premium viewing experience means watching the balloons float past Manhattan without spending hours securing a place along the sidewalk. Exact sightlines and access depend on the property and package booked.
This year has particular significance: Macy’s is celebrating its 100th parade, with special balloons and commemorative elements planned for the occasion.
I’d round out the trip with a Broadway show, an exceptional Thanksgiving dinner and a few days enjoying New York as the holiday season begins.
It’s a particularly appealing multigenerational trip: children get the magic of the balloons, while adults get a New York weekend with considerably more to it than standing along the parade route.
With Thanksgiving approaching, though, this is the itinerary to inquire about first. The most desirable parade-facing accommodations and premium viewing arrangements are limited.
The Trip Around the Event
What connects these four experiences isn’t simply access.
It’s the opportunity to see a familiar destination from an entirely different perspective: Paris through its fashion houses, Aspen through its chefs, Venice through its Carnival traditions, or New York through one of its most beloved celebrations.
Sometimes the extraordinary moment is planned months in advance. Sometimes it comes from leaving enough room in the itinerary for something unexpected.
Either way, the event is only the beginning.
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