In Praise of the Shoulder Season: Or, How I Learned to Stop Sweating and Love Traveling Like a Functional Adult
Comporta Beach, Portugal, in the Late Spring— No Crowds. - Photo by Michelle Orr
There is a particular kind of traveler I see every July. You know the one. They've just spent $30,000 to stand in a line that wraps three times around the Colosseum, in 99-degree heat, behind a bachelorette party from Ohio. They are wearing the wrong shoes. They have a sunburn shaped like the strap of a tote bag. They are, in their own words, "making memories."
Master Travelers, I am here to gently suggest there is another way.
It is called shoulder season, and it is the single greatest open secret in travel. It's the time of year when the weather is still flirting with perfection, the locals haven't yet fled their own cities in horror, and you can actually get a table at the place everyone told you was "impossible." It's roughly April–May and September–October, give or take a country, and it is — I cannot stress this enough — when smart people go.
Here's why I'm evangelical about it:
The light is better. This is not a metaphor. Photographers will tell you that summer light is harsh and flat, and your vacation photos will look like everyone else's vacation photos. Shoulder season light is golden, soft, forgiving. You will look like you have a skincare routine. You don't, but no one needs to know.
The locals like you again. In August, when you ask a Roman where to eat, the answer is a long stare and possibly a hand gesture I cannot reproduce in a family-friendly blog. In May, that same Roman will walk you four blocks to her cousin's trattoria and personally introduce you. Same person. Same city. Different month.
Hotels actually answer the phone. In peak season, the best rooms at the best hotels were booked eleven months ago by a hedge fund manager who has not yet decided if he's coming. In shoulder season, you can call on a Tuesday and get the suite with the terrace. I have done this. It is glorious.
You spend less and get more. Rates drop. Upgrades flow. Restaurants have availability at 8 p.m. instead of 5:30 or 10:45. Your money goes further, which means you can spring for the cooking class, the private boat, the second bottle of wine that you absolutely will regret tomorrow.
Now, the destinations. These are my four shoulder season love letters.
ITALY
Venice without the crowds is a dream….. this was April 2nd, so a bit chilly!
Going to Italy in August is a personal choice, and sometimes you don’t have a choice, I get it. But…..Italy in May or late September through October is the country at its absolute best. The duomo is not a sauna. The Amalfi Coast is not overrun by Instagram Influencers. You can walk into a small enoteca in Florence at lunch and the owner will pour you something he is genuinely excited about, instead of the house red he's been ladling out to tour groups since June.
Mid September - October in particular is sneaky-good. The light in Tuscany goes from gold to honey. The olive harvest is happening, which means brand-new oil, peppery enough to make you cough, on warm bread. Truffle season starts in Piedmont. The Veneto is empty. You can actually see the floor of St. Mark's Basilica without queueing behind 400 cruise passengers in matching lanyards. And if the coast is what you are seeking, the waters are still warm!
JAPAN
Everyone wants Japan in cherry blossom season, and I understand the impulse, but those two weeks are the most expensive, most crowded, and most weather-roulette period of the year. The blossoms last about eleven minutes and then it rains.
And try not to consider going in the summer months, heat and humidity will make you want to cry! Mnay moons ago, when I was working for Godiva as their Marketing Manager, we stopped-sell chocolate in Japan June-August because the melting point of the chocolate— temps in Japan turned the chocolate into soup.
Go in late October or November instead. The autumn foliage — kōyō — is, and I say this having seen a lot of trees on a lot of continents, more spectacular than the cherry blossoms. Kyoto in November is a religious experience. The maples at Tofuku-ji look like the temple is on fire in the most beautiful possible way. The food shifts to autumn — matsutake mushrooms, hairy crab, persimmons — and the weather is cool enough that you can actually walk for six hours without dying.
May is the other quiet winner: post-Golden Week, pre-rainy season, lush, comfortable, with the added bonus that most other tourists have already gone home to talk about cherry blossoms.
GREECE
Santorini in July- Can’t walk in Oia when the ships come in. May and September, now we are talking!
Greece in August is, I'm sorry, a logistical nightmare staged inside a hairdryer. The islands are full, the ferries are full, Mykonos is full of people who think they invented Mykonos, and the temperature flirts with three digits.
Late May, early June, or September — that's the move. Santorini without the cruise ship disgorgement. Crete with its restaurants still focused on locals. The water in the Aegean has warmed up but not yet become bathwater. You can hike in Naxos without filing a heat-related insurance claim. Mid-September is my personal favorite — the sea is at its warmest, the crowds have thinned, and the light slants in a way that makes every whitewashed wall look like a postcard you'd actually keep.
Also, and this is important: in shoulder season, the family-run taverna on the harbor still has the table by the water at sunset. In August, that table was reserved by a man named Reginald in February.
PORTUGAL
Lisbon without the crowds …. I didn’t even have to photoshop people out of the picture!
Portugal has been having a moment for roughly a decade now, and the moment has gotten a little loud. July and August in Lisbon mean lines for the tram, lines for the pastéis, lines for things you didn't know had lines. And want to go to the Algarve? Ok, but you will be with a lot of Europeans on Holiday, it’s one of their top destinations.
April, May, or late September into October is where the magic lives. Lisbon's hills are kinder when it's 72 degrees instead of 95. The Algarve beaches are warm but not packed. The Douro Valley is staggeringly beautiful in October — harvest season, the terraced vineyards turning copper, port houses pouring vintages that you'd pay triple for stateside. The seafood is better when the kitchen isn't drowning. The Pousada you wanted? Available. And Comporta? A dream waiting for you to wake up and go!
May in the Alentejo, with the wildflowers and the cork oaks and the empty roads, may be the most underrated week of travel in all of Europe. I will die on this hill, ideally while drinking a glass of Esporão.
THE CATCH
There isn't one, really. (Planning in advance, that’s probaby it!) Shoulder season requires only that you do not insist on traveling during the same two weeks as every schoolteacher and finance bro on the planet. If you have that flexibility — and most of my clients do — there is no reason to keep paying peak prices for peak misery.
So next time someone tells you they're going to Santorini in August, smile politely. Wish them well. And then book yourself a flight for mid-September, when the island is still warm, still beautiful, and blissfully, gloriously, yours.
Thank me when you get back, because you know this is the answer to those peak-time crowds!