Is spontaneity dead?

When my husband tells our origin story – the first weekend we went away together – it always begins with how I proposed we go to Palm Springs for the weekend. Even though he couldn’t afford it, he had just received a new credit card with a $5,000 limit, and called his travel agent, Jimmy at Altour Travel, to see if he could find him a flight. Jimmy’s ‘You met a girl’ line is always a part of it, complete with an American Italian accent (think Tony Soprano). Not to turn this into a ‘remember the good old days’ story, but back then, you talked to people, and they helped you with a task you wouldn’t have been able to do on your own. You wanted to go to a restaurant for dinner, you called and made a booking.

We recently moved to the Upper East Side, which is a more old-school New York neighbourhood. It’s so refreshing to see Italian and French restaurants that nobody has ever heard of, cafés that aren’t part of a chain, and even several culty Japanese restaurants. Perhaps more exciting is that we can usually walk in, or call up while having cocktails at home to see if they have a table in, say, an hour, and they do. After 20 years of living in a different part of the city, where we would have our reservations planned out, or just suffer through mediocre neighbourhood dining, this was an epiphany.

Over dinner with friends last week, we collectively complained about how seemingly impossible it is to go anywhere – every cool place you want to go to never has a table. And now even the bar area has to be reserved. Remember when you could just walk into a bar, sit on a stool and talk to the bartender or the person next to you? Friendships were forged, people fell in love and lives changed. Sure, that can happen from a reserved seat as well, but if anything, energy is slightly faded because you’d already planned to be here a month ago.

My husband and I had joined a club once. We loved the way Casa Cipriani looked and got sucked into membership. But after only going two or three times in one year, we didn’t renew; who wants to eat the same menu every time you go out to dinner? Initiation fees in the last couple of years have become so exorbitant. Why do that when you could opt to redo your kitchen and have people over, serve champagne and order from your favourite restaurant instead?

I’d say the final straw for spontaneity happened when it became possible to book everything on our phones and we stopped talking to people as much as we used to. I was so thrilled to have the tools to book all of my travel and, as a self-proclaimed control freak, I still am. But I never loved booking restaurants online. With restaurant apps, there is no chance for any personal exchange. And worse, any change in the number of diners means potentially having to cancel the reservation or pay a cancellation fee for the no-show. While I’m happy that restaurateurs have more financial stability, I miss the days when you could actually be spontaneous. When I go to Edinburgh next month, I know exactly where I’ll be eating (The Palmerston, by the way!) because we’ve booked it that far out. And if I run into friends when I’m in town and want to invite them to dinner, it’s unlikely I’ll be able to grow the table.

On New Year’s Eve in New York, a dear friend of mine and his partner walked into Le Rock, Via Carota, I Sodi and Commerce Inn (all hot ticket tables) to see if they could get a last-minute table, and finally succeeded at the last one. I mean, the audacity! In today’s world, it’s a bold move to have no plan and be willing to end up at a place that is just fine and perhaps not on the cool list.

One of my favourite modes of travel is the road trip – and I love to leave at least a few days with no hotel plan, because who knows if we’ll end up spending two extra hours in some antique mall and falling behind schedule. I discovered Hotel Tonight on one such road trip and it freed me up so much, knowing that it’s possible to find a place to lay your head, even if it’s not the ‘best’ place.

With all the planning, the freedom to do whatever we want, when we want, feels like a true luxury. And it is decidedly so: in some cases, having a full-fare airline or train ticket usually means you can change your plans without penalty. But for me, when friends call up last-minute to see whether we’re in town, and we’re all happy to go to the not-hot restaurant but the good one where we, without a reservation, easily land a table for four, then that’s pure bliss.

The spontaneous person rulebook

1. Keep a running list in your notes (not in your maps) of places that are classics – great restaurants that are solid, but not the new hot spot. Since these aren’t the places that everyone is talking about, they won’t be top of mind unless you keep a list. You will likely be able to just walk in or, at the very least, get a same-day reservation.

2. Use notifications for last-minute reservations, both for flights and restaurants. While the Resy app may be partly to blame for how difficult it is to get into a restaurant with everyone booking in advance, if you sign up to be notified when a reservation becomes available, you might also need to be very spontaneous to take advantage of it. The same goes for flights: sign up to be notified about a flight route, airline and fare that you’re interested in.

3. Map out all the hot spots in town and take a walking tour of them to see if you can just walk in! As it will likely be a no, be prepared to improvise a Plan B on the spot.

4. Gift yourself time. Plan an itinerary for a trip in great depth and then, at the last minute, cancel it. You have just gifted yourself some free time, and you can take that trip another time when it suits.

5. Plan for no plans. Designate a weekend to be completely free of obligations and then book something based on what’s available within your budget – which could be a staycation or something further afield. A friend of mine always says, ‘Have a party, don’t plan a party,’ because planning is stressful and time-consuming, and if you overthink it, you’ll probably end up not doing it. Go on a trip, don’t plan a trip!

A version of this article appears in the June 2025 Travel Issue of Wallpaper*, available in print, on the Wallpaper* app on Apple iOS, and to subscribers of Apple News +. Subscribe to Wallpaper* today.