Did you know most Americans get two weeks of PTO per year and yet dream of seeing the world in a much bigger way? The good news: with a little planning, you can stretch those days into long, restorative escapes. In this post, I’ll show you how to maximize your holiday travel in 2026 by pairing PTO with key U.S. holidays for high-reward breaks.

Let’s get those requests on the calendar early. Below are three long-weekend trip ideas with exact dates to help you get the most from your time off.

WINTER VACATION | TOTAL TIME OFF: 5-6 DAYS

Gray skies, post-holiday blues, and chilly mornings? It’s the perfect time to book something warm—or a snowy escape that feels intentional.

Holiday: New Year’s Day – Thursday, January 1, 2026
PTO: Take Friday, January 2
Weekend Days: Saturday, January 3 and Sunday, January 4
Return to Work: Monday, January 5

Five Days Away: Ideas for Your Escape
Want to stay closer to home? Cozy up in Jackson Hole or Park City, ski all day, then unwind fireside with a glass of wine and a view.

Passport ready? Escape to Portugal’s Algarve for a peaceful, sunlit getaway with fresh seafood, cliffside walks, and charming boutique hotels.

SUMMER GETAWAY | TOTAL TIME OFF: 10 DAYS

July 4th falls on a Saturday in 2026, so the holiday will be observed on Friday, July 3—making it perfect for a well-timed summer sabbatical.

Holiday: Independence Day (Observed) – Friday, July 3, 2026
PTO: Take Monday, July 6 through Friday, July 10
Weekend Days: July 4–5 and July 11–12
Return to Work: Monday, July 13

Ten Days Away: Ideas for Your Escape
Want to stay stateside? Head to coastal Maine for lobster rolls, sailboats, and seaside serenity.

Passport ready? Take a slow journey through the French Riviera and Provence, with lavender fields, rosé terraces, and stylish seaside stays.

FALL BREAK | TOTAL TIME OFF: 9 DAYS

Thanksgiving is always a good time to make a break for it, especially if you’d rather swap small talk and turkey for warm sand or crisp European air.

Holiday: Thanksgiving – Thursday, November 26, 2026
PTO: Take Monday, November 23, Tuesday, November 24, Wednesday, November 25, and Friday, November 27
Weekend Days: November 21–22 and 28–29
Return to Work: Monday, November 30

Nine Days Away: Ideas for Your Escape
Want to stay domestic? Napa Valley in late fall is a dream! Harvest season brings fewer crowds, rich reds, and golden vines for the perfect escape.

Passport ready? Visit Spain’s Andalusia region. Seville, Granada, and Córdoba shine in cooler temps, offering the perfect blend of culture and cuisine.

Need help turning these dates into dream-worthy escapes?
Let’s design your 2026 travel calendar together.