Passalacqua | Lake Como, Italy

I understand why most people want to vacation in summer. I also understand the appeal of a table at eight o’clock, a concierge who isn’t performing triage, and the occasional radical freedom to decide what I’m doing tomorrow sometime tomorrow.

Which is why I’ve begun pushing back against one of travel’s most persistent assumptions: that the most popular time to visit somewhere must also be the best time to experience it.

For decades, we’ve planned around “peak season.” We want the Amalfi Coast when the beach clubs are buzzing, Paris when the days stretch late into the evening, Tuscany beneath an impossibly blue sky.

And there is absolutely nothing wrong with any of that.

But peak season and peak luxury aren’t necessarily the same thing.

Because if luxury is about more than perfect weather—if it is also about time, attention, access, spontaneity and that increasingly rare feeling of not having to rush—then September and October start to make a very compelling case for themselves.

The Gleneagles Hotel | Perthshire, Scotland

September has always felt like a reset.

Maybe it’s the back-to-school blues, but September always makes me want to go somewhere.

Conveniently, it’s also when some of the world’s most desirable destinations start getting really good. The summer crowds thin, the pace changes, and suddenly the places we fought so hard to visit in July have room to breathe again.

The Colony Hotel | Palm Beach Florida – September 14th

Hospitality has to breathe.

The best hotels in the world are very good at making full occupancy look effortless.

Behind the scenes, of course, everyone is moving at full speed. Every suite is occupied. Every dinner table is spoken for. The concierge desk is juggling dozens of requests. The pool attendant has heard “any chance of two chairs together?” since breakfast.

Exceptional service still happens. But there is a difference between hospitality delivered beautifully under pressure and hospitality with enough room for something unexpected to happen.

Go a little later and the rhythm changes.

There is time for an actual conversation with the concierge instead of a transaction. The restaurant manager may suddenly have that table you wanted. Someone mentions a vineyard you hadn’t considered, makes a phone call, and by afternoon you’re on your way.

These aren’t necessarily grand gestures. In fact, the best ones rarely are.

They’re the small moments when someone has enough time to notice what might make your day better.

That, to me, is luxury.

You can change your mind again.

There is something faintly absurd about spending thousands of dollars to travel somewhere beautiful and discovering that every minute of your supposedly carefree vacation needed to be decided six months ago.

Tuesday, 12:30: lunch.

Tuesday, 3:00: beach club.

Tuesday, 7:45: cocktails.

Tuesday, 8:30: dinner.

Do not be late. Do not change your mind. And heaven help you if it rains.

During the busiest weeks of summer, good planning is essential. I will always believe that. But there is a point at which planning stops creating freedom and starts eliminating it.

Travel used to contain more happy accidents.

A lunch ran long because nobody wanted to leave. Someone told you about a little town nearby. You stayed by the pool instead of visiting the museum. You canceled dinner because the hotel bar was too much fun.

September and October can give some of that back.

And perhaps one of the greatest luxuries in modern travel is simply having enough space in the itinerary to say, “Actually, let’s do this instead.”

The September harvest at Castiglion del Bosco | Montalcino, Tuscany

Places become themselves again.

Something else happens after summer.

Paris goes back to work.

Tuscany harvests.

Wine regions stop looking like scenery and become working landscapes again. Restaurants that spent summer serving an international parade of visitors begin filling with familiar faces. Scottish estates light their fires. Small towns settle back into routines that have very little to do with who has arrived for the week.

The destination exhales.

This doesn’t mean tourists disappear. Nor should they. But the balance shifts.

There is a difference between visiting a place while it is performing beautifully for visitors and experiencing it while ordinary life is happening around you.

No surprise here, I prefer the latter.

You begin noticing morning rituals instead of sightseeing queues. You hear more of the local language at the next table. Markets feel like markets rather than attractions. Dinner feels less like securing one of the city’s most coveted reservations and more like joining the evening already in progress.

The place hasn’t become quieter simply for your benefit.

It has become itself again.

Cliveden House | Taplow, United Kingdom – November 10

The hotel becomes part of the story.

Summer creates a peculiar kind of pressure.

The weather is perfect. The days are long. You have come all this way.

Surely you should be doing something.

So we leave beautiful hotel rooms to sightsee. We hurry through breakfast because there is somewhere to be. We walk past gorgeous bars on our way to dinner somewhere else. We book magnificent resorts and then feel vaguely guilty if we spend an entire afternoon enjoying them.

Fall gives us permission to linger.

Adare Manor | County Limerick, Ireland

Breakfast can become brunch without anyone checking the clock. A gray afternoon makes the spa seem like an excellent plan rather than an extravagant use of precious sightseeing hours. Drinks beside the fire become the evening’s first event. Maybe the second one, too.

And when you have chosen your hotel well, staying in isn’t missing the destination.

It is part of experiencing it.

Some hotels, in fact, become better characters in colder weather. The grand lobby suddenly makes sense. The library gets used. The fireplace becomes more than decoration. The bar that seemed slightly too dark in July becomes exactly where you want to be at five o’clock in October.

Which brings us to another point.

It isn’t just about hotels.

Some of the best arguments for going later happen at sea.

Four Seasons Yachts

The same shift happens at sea. Some of the Mediterranean’s newest luxury yachts are sailing well beyond the traditional summer crush. Four Seasons I, for example, spends September and October moving through the Rivieras, when places like Portofino, Saint-Tropez and the Mediterranean coast begin settling into a different rhythm.

The water still sparkles. Lunch can still stretch well into the afternoon. But days ashore become less about navigating peak-summer intensity and more about actually enjoying where you have arrived.

You aren’t arriving after the season.

You’re simply arriving for a different version of it.

The Colony Hotel | Palm Beach, Florida

The icons can make more sense.

There is another advantage to going later that luxury travelers sometimes hesitate to talk about: value.

Not bargain hunting. Not choosing somewhere simply because it is less expensive. But recognizing that the same travel budget can occasionally buy a very different experience once the calendar changes.

This is when some of the names we already know and love become particularly interesting. The Colony in Palm Beach as the season begins to turn. Nemacolin when Pennsylvania’s Laurel Highlands are putting on their fall show. And, perhaps most intriguingly, Passalacqua on Lake Como, which is extending its 2026 season through the holidays rather than closing its doors when summer ends.

Imagine Lake Como without the midsummer crush: crisp mornings, long lunches that can still happen beside the lake, new olive oil, white truffles, and one of the world’s most celebrated hotels settling into an entirely different rhythm. Passalacqua itself calls fall and winter the season for dolce far niente—the sweetness of doing nothing—and I’m inclined to agree.

The point isn’t to chase a deal. It is to recognize opportunity. A room category that felt extravagant in July may suddenly be within reach. Staying the extra night may make sense. Or perhaps the same budget buys the legendary 5* hotel instead of the 4* down the road.

Sometimes going later doesn’t mean compromising on luxury.

It means getting more of it.

Perfect weather may be overrated.

We spend an extraordinary amount of energy trying to engineer blue skies. Understandably—nobody books a vacation hoping for rain.

But perfect weather doesn’t always make the best stories.

Paris in the rain is still Paris. Scotland without a little fog would almost feel suspicious. And the first snow in the Alps may completely change your plans—and make the day better because of it.

Sometimes a little weather is exactly what gives a place its atmosphere—and the supposedly imperfect day becomes the one you remember most.

Give me a beautiful hotel with a fire, a storm outside, and a great lobby bar, and I’m a happy girl.

Ashford Castle | Cong, County Mayo, Ireland

Also, the clothes are better.

There’s something about fall that simply makes travel feel more glamorous.

Boots and jackets come out. Fires are lit before dinner. Hotel bars become places you actually want to linger, and long lunches have a funny way of turning into cocktails.

Fall has its own rhythm—and I’ll take it over fighting the summer crowds any day.

The Gleneagles Hotel | Perthshire, Scotland – October 31st

There’s just something about sweater weather.

Travel has seasons just as fashion, entertaining, and design do, and there’s something particularly satisfying about experiencing a destination just as the way it looks, tastes, and feels begins to change.

If all of this sounds like an elaborate justification for a 70-pound suitcase and martinis at four o’clock, I’m not entirely denying it. In fact, I’m probably planning around both—and starting an OOTD board as we speak.

Nemacolin | Farmington, Pennsylvania

So why are we always going in June?

I am not suggesting we abandon summer.

There are places I want in July precisely because they are glorious in July. There are family schedules, school calendars and traditions that make summer travel make sense. Sometimes you want the beach club buzzing, the Mediterranean warm and dinner beginning long after sunset.

Go.

But perhaps we should stop assuming that the most popular time to visit a place automatically delivers its most luxurious experience.

Because real luxury isn’t simply getting the reservation everyone else wants.

It is being able to change it.

It isn’t always having the perfect weather.

Sometimes it is having nowhere you need to be when the rain begins.

And sometimes the greatest luxury isn’t getting into the world’s most desirable places when everyone else wants to be there.

It’s knowing when those places become themselves again.

Oceania Marina | Mediterranean – October 24th

Convinced?

Then perhaps the only question left is “Where to go?”

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