10 Shoulder Season Destinations Worth Booking Early

If you love traveling when destinations feel a little calmer and a lot more rewarding, this one’s for you. These shoulder season favorites shine when the crowds thin, the weather cooperates, and the experience feels more relaxed.

From global cities to coastal escapes, these are the places worth booking before everyone else catches on.

Orlando, Florida

When the school calendars quiet down, Orlando becomes far more enjoyable. Shoulder season brings lighter crowds, shorter waits, and gentler weather at the major theme parks. It is also the perfect time to use Orlando as a home base for golf, day trips, and easy escapes to Florida’s beaches.

Galway, Ireland

Spring and fall are ideal times to experience Galway, when crowds thin and the city’s character shines. Spring brings longer days and fresh energy, while autumn adds moody skies and glowing color.

Both seasons are perfect for coastal walks to the Cliffs of Moher, oyster season, bookshops, and Galway’s famously lively food and music scene.

Tokyo, Japan

Tokyo truly shines when the pace slows and the weather turns mild. In these in between months, blossoms or fiery leaves frame peaceful park strolls, cultural performances, and traditional bathhouses.

With cooler days and fewer crowds, Tokyo feels more intimate, making it easier to savor its neighborhoods, cuisine, and nearby mountain escapes at a relaxed rhythm.

Scottsdale, Arizona

When desert heat eases and the days turn comfortably warm, Scottsdale is at its best. Mild weather invites long poolside afternoons, desert hikes, championship golf, and evenings spent exploring galleries and Southwest-inspired cuisine, all without the peak season crowds that dominate the calendar later in the year.