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Travel: How Many Nights Should You Stay?

TLDR: Daytrips, two night stays and five night stays are my preferred travel durations.

A problem I often wrestle with when planning trips is how to long to stay at a destination. Should I make the drive to the beach a daytrip, or an overnight stay? A weekend in San Diego: Go on Friday and do two nights, or just Saturday? And then on multi-week international trips, the question is usually about how many nights in each place: 4 nights in Paris, 1 in Lyon and 2 in Burgundy? Or 5 nights in Paris, 2 in Lyon and Burgundy as a daytrip?

What am I trying to do when traveling? I think the answer is something like this: Maximize the experience of being in a different place, hit minimum thresholds of pleasure and comfort, weighed against the investment of time and money.

The part about pleasure and comfort being requirements to be satisfied rather than variables to be maximized is key, and it took me a long time and a lot of suboptimal trips to learn that.

Pleasure. There's no point flying halfway around the world to maximize pleasure. Unless you have a particular fascination for the chef, the ingredients or the cuisine? I think you do the blowout Michelin dinner at home. Massages, laying on the beach, the blowout bottle of wine - best done as close to home as possible. A dessert on top of an already big meal is great on a mundane weekend, but on a trip if it means a bad nights sleep with indigestion then it's best skipped. Etc.

And comfort: Comfort is incredibly valuable up to a mostly subjective point, and beyond that it's all diminishing returns. A comfy bed in a fairly quiet, safe hotel is fantastic. Spending extra for the best of the best hotels is pointless when you'll be jetlagged and can't sleep at 3AM anyway. The second class section of the train gets there at the same time as the first class. Planning and booking 80% of the trip ahead of time is great, but going to 99% and having every last detail plotted is pointlessly restricting.

All of this as we're currently planning a trip to Europe. 3 1/2 weeks in the UK, Spain and Portugal. We're probably going to stay in quite a few different places, possibly up to a dozen. One of the questions I've been wrestling with is how long should I stay in each place? After we get a car, should I book overnights? For the cities, should I book 3 nights or 4?

I wanted to get a formula down that I could just plug in to a complex trip like this and go.

It probably won't surprise those of you who know what I nerd I am that my approach was to put all my recent trips into a spreadsheet with one row for each destination and the number of days as a column.

(Those of you who really know me will know that I already had all my trips in a spreadsheet like that)

Here's what I found, and how I'm going to plan all my travels from now on:

Daytrips. I underrate daytrips. Especially during the long summer days. The beauty of the daytrip is threefold: They're light on the logistics, especially if you have a car. They're also budget friendly, especially if you've got a taste for spendy Airbnbs and hotels. And they require the least commitment, either the (a) front or backend of a weekend with another weekend day to relax or (b) a mid-week day off.

A daytrip is the MVP of trips: Out of the house, into a new space, and if that space is within a couple hours of home then even though the driving (or the train or bus travel) can be hectic, there's also time to explore and experience a different space.

I need to take more daytrips.

Overnights. If daytrips are great because they're lightweight, overnights suffer from the opposite problem. They're the worst from a logistics-to-quality-time ratio perspective, since everything static in your pack the bags game is done whether it's for a one night stay or a ten night stay. The same applies to costs: cleaning fees, service fees, anything static is going to be at its maximum percentage of total spend on an overnight.

The worst aspect of overnights though, and what really makes them my least favorite duration, is wrapped up in this: Any day I spend flying, driving or taking a train or bus long distance, checking in to a place, checking out of a place or otherwise lugging luggage and settings things up is a measurably worse day than a day where I do none of those things.

I don't know exactly what's going on here, if it's the stress of movement or the uncertainty of setting up somewhere new, but I've talked to a lot of people about this and nobody has disagreed that they feel an elevated amount of stress and discomfort around these movement days.

And that stress or discomfort or whatever it is, it gets in the way of experiencing the place I want to experience. Which, as mentioned, is the primary motivation for traveling in the first place.

So if days of movement are to be avoided, and days with none are to be maximized, what's so bad about overnight stays becomes evident: Overnights are two days of doing the things I don't want to do and zero days of doing the things I do.

The worst worst might be an overnight on a Saturday. It's usually the most expensive night to stay anywhere, and it takes two days that are usually relaxing and makes them stressful. Blech!

Two nights. Now we're talking. I love two night trips for one important reason: That day in between the day getting there and the day getting away is almost always a great day.

I've thought about this, and tried to break down why that is, and I suspect it comes down to having two travel days bookend the one true vacation day. There's a focus that happens. All the best activities, sites, conversations, whatever get concentrated on that middle day. In the memories that follow, the middle day is the trip, the bits of the experience that live on in my mind.

Three or four nights. I won't turn down three or four nights, but when I look at the column where I wrote What Would I Do Differently, half of the three or four night stays say "stay shorter" and another significant chunk, maybe 20%, say "stay longer".

Here's what I think happens: When we stay three nights there's two of those inner days. The first one is usually good and then the second one gets contrasted with the first one. Why? I don't know, that's just what we do, or at least what I do.

I don't know why four nights doesn't work. But it doesn't. I almost always either wish I'd stayed an extra day or I'd stayed a day or two less.

Five nights. YES. Over winter break we took some time between Christmas and New Years and drove to Joshua Tree. Staying five nights in Yucca Valley allowed us to have an intense hiking day, an intense cocktails + vintage shopping day in Palm Springs, and several more relaxing days with easy hikes or sightseeing. In short, five nights in a destination gives us the opportunity to get a little bored. And getting a little bored is a great way to notice things, do something seemingly banal, and really experience the place you're in.

Another thing that happens with five nights is that we almost certainly get so see weekdays turn into a weekend or vice versa. That's an interesting thing to do anywhere, and especially in a big world city like San Francisco, New York, London, Paris.

On our upcoming trip to Europe, we're starting in London and staying five nights. Arriving on a Wednesday, we'll get to settle into the city and then see a weekend arrive, feeling the anxiousness of a Friday lunch, the excitement building in and around the pubs as five o'clock arrives, and finally the rush of a buzzing happy hour with, if April graces us with sunny weather, pubs pouring out into the street as they do in London. I've seen that the summer I worked in London 23 years ago, and I'm excited to see it again.

Six or seven nights are great, too. I think in terms of memories, there's not a lot of difference between them and five nights, so while I wouldn't hesitate to spend one more night in a great destination, I do think there's an element of diminishing returns there.

Beyond that, well, I don't have a lot of experience being in one destination longer than seven days. I suspect that there's a serious gap between a week and about six weeks, which is about the minimum amount of time you need to be in a place to feel a seasonal change, which is magical and probably pretty rare for most of us - it certainly is for me. Six weeks to three months probably does that really well.

And then, just to really get into the silly, I think the next step up is at 3-5 years which is the amount of time I was living in San Diego and then Portland before I really felt like I knew the cities, their rhythms, their mindsets and how they worked at a deep level.

Hope this helps someone out there think about how to max their days off and travel spend. It's helped me plan my current trip. Big asterisk: All this is mostly subjective, so I'm probably overrating the advantages of the timeframes I like, and conversely overrating the disadvantages of the ones I don't.

posted in Travel