Happy start of spring! After an intense winter here in Westchester, the warmer weather is a welcome change. As everything begins to thaw, many families are turning their attention to spring break, but I’m already looking ahead to summer.
In particular, August has been a major focus in conversations with my clients lately. In my opinion, it’s one of the best months of the year to plan a vacation, and that’s not just a personal preference. The data supports it.
August is one of the best times of year to find significant discounts on top travel destinations. Hotels, all-inclusive resorts, cruise lines, and theme park destinations all anticipate strong summer demand, but most of that demand is concentrated in July.
While we’re fortunate in New York to have a school break that extends into September, most schools across the United States resume by mid-August. As a result, travel providers roll out promotions and incentives to attract guests during the late summer slowdown.
For Westchester families, this creates a unique opportunity: access to excellent deals without conflicting with the school calendar.
With many students back in school by early to mid-August, late summer travel often comes with noticeably lighter crowds.
Beach destinations are less congested, theme parks have shorter wait times, and cruise ships feel more relaxed and spacious. For travelers who prefer a calmer, less hectic experience, this timing can make a significant difference.
If crowded environments tend to feel overwhelming, late August can offer a more enjoyable way to travel!
August also brings ideal conditions for a summer getaway. While July can bring extreme heat—especially in southern destinations—August often delivers slightly milder temperatures.
It remains warm enough for pool days and beach vacations, but with a subtle drop that can make outdoor activities more comfortable. For travelers who find peak summer heat overwhelming, this balance can be especially appealing.
Of course you have to plan a trip that works best with your own personal schedule, but if the timing works, I wholly recommend getting an August getaway on the calendar!
For many families, August creates a natural pocket of opportunity that’s surprisingly easy to plan around. Most summer camps wrap up about two weeks into the month, while school typically doesn’t resume for a few more weeks, leaving a gap that parents often have to creatively fill.
Instead of spending extra on childcare or coordinating schedules with family and friends, this window can be the perfect time to plan a getaway, especially for working parents. It’s a built-in solution that turns a logistical challenge into something to look forward to.
On top of that, many kids’ sports and extracurricular activities don’t kick back in until around Labor Day, which means fewer scheduling conflicts and more flexibility to travel without juggling multiple calendars.
Erica Terry is a Westchester resident and travel agent specializing in family travel. You can reach her at ericat@friendlikemetravel.com. She specializes in international travel, all-inclusive resorts, beach vacations, theme park destinations like Walt Disney World and Universal Orlando Resort, as well as a variety of cruise lines. Check out her Instagram page. You can also get a quote on a vacation here.
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