Hi Reader,

One of the most common questions we get before a big trip: should we go during the holidays or avoid them entirely? The honest answer is that it depends. But “it depends” is actually useful advice when you know what questions to ask.

The two big ones: Do crowds energize or exhaust you? And are you likely to find half the city closed? Your answers will tell you more than any travel calendar ever will.

Hawai’i: The Holidays Worth Planning Around

In Hawai’i, certain holidays are genuinely worth building a trip around. Lei Day on May 1st brings beautiful celebrations across O’ahu, with lei competitions, hula performances, and a sense of community that feels deeply local rather than performative.

Kamehameha Day in June draws parades and ceremonies honoring King Kamehameha I, with the most significant celebrations on the Big Island and O’ahu. These are the kinds of cultural moments that give a trip its story. Learn more in our Hawai’i travel guide.

France: Watch the May Holiday Cluster

France at Christmas or Easter can be quietly spectacular. Markets still running, fewer crowds than high summer, Paris or Lyon feeling genuinely lived-in. But if your dates fall in early May, pay close attention.

May 1st (Labor Day) and May 8th (VE Day) are both public holidays, and many restaurants, shops, and museums close for both. Landing in Paris for a week that bridges those two dates can mean unexpected dead ends. We’ve seen it trip up even experienced travelers. This guide to planning a France trip covers what to know before you book.

Italy (and France): The August Calculus

Ferragosto (Assumption Day, August 15th) is the peak of European summer holiday season, and the crowds in Italy and France during the two weeks surrounding it are not a rumor. European vacationers, American summer trips, and the holiday itself stack on top of each other. If August is your only option, lean into smaller towns and coastal villages rather than Rome or the Amalfi Coast.

That said, Italy rewards the curious traveler in other seasons. Liberation Day in late April and Republic Day in early June bring fireworks, military parades, and a palpable sense of national pride to cities across the country. And the harvest festivals scattered through autumn are among the most genuinely convivial experiences in Italian travel. For more details, check out our Italy travel guide.

A Note on the Palio di Siena

The Palio runs twice a year, in July and August, and it is one of the most visceral, historic spectacles in all of Europe. We’d never tell you to skip it. But go in knowing: the city of Siena is effectively at capacity. Book accommodation months out, expect standing-room conditions, and give yourself a full day on either side to actually see the city when it exhales.

The Key to Holiday Travel

Holidays abroad fall into three categories: the ones worth traveling for, the ones that create logistical headaches, and the ones that change the character of a place. Knowing which is which (before you book) is the key.

When you’re ready to plan a trip that accounts for all of it, we’d love to help you think it through.