How to Turn Long Weekends Into Family Vacations in 2026 (Without Using All Your PTO)
- alyh95
- Jan 20
- 3 min read
How to Turn Long Weekends Into REAL Family Vacations (Without Burning All Your PTO)
For many families, the biggest barrier to travel isn’t desire — it’s time off work and school.
The good news? You don’t need to take weeks off or pull kids out of school for long stretches to enjoy meaningful vacations. One of the smartest (and most underrated) ways to travel is by planning around long weekends and federal holidays.
With a little strategy, you can turn just a few PTO days into longer getaways that actually feel like a vacation — whether that’s Disney, Universal, a cruise, or an all-inclusive resort.
Why Long Weekend Travel Works So Well for Families
Planning trips around long weekends allows you to:
Miss fewer school days
Use less PTO from work
Spread travel costs out over time
Still enjoy 4–9 night trips that don’t feel rushed
This strategy works especially well for:
Walt Disney World & Universal Orlando trips
Cruises (short or extended sailings)
All-inclusive resorts in the Caribbean & Mexico
Shoulder-season travel when crowds are lighter
Best Long Weekends to Travel in 2026 (and How to Maximize PTO)
Here are some of the best long weekend opportunities in 2026, plus exactly how much PTO you’d need to take to stretch each one:
February 14-17 - Presidents' Day: Perfect for a short cruise, quick Disney or Universal trip, or a warm-weather escape.
May 22-26 - Memorial Day Weekend: A great kickoff to summer — ideal for all-inclusive resorts or a longer theme park stay... or even a shorter cruise!
June 13-21 - Extend the Juneteenth Long Weekend: One of the best opportunities of the year. With smart planning, this is perfect for cruises, Europe, Alaska, or a full Orlando split stay at the theme parks.
July 3-6 - Happy 250th, America!: Short and sweet — great for short cruises, beach trips, or theme park getaways with summer energy.
September 5-13 - Extended Labor Day Vacation: Another excellent chance to travel longer with fewer crowds — especially for Disney, Universal, or Caribbean trips.
Pro Tip: If you're worried about hurricane season in the Caribbean, plan for Aruba or Curacao -- they're outside the hurricane belt and hardly see rain, let alone a hurricane.
November 21-29 - Thanksgiving Weekend: Thanksgiving is one of the most popular travel weeks of the year, especially for cruises and theme parks — planning early is key.
Bonus: If you or your kiddos are off on November 30 as well, that could even be a 10-Day Vacation (or just some added flexibility for your planning purposes).
Pro Tip for Northeastern/Mid-Atlantic Residents: Did I mention that cruises sail from New York and New Jersey year round? So no need to deal with airfare if those ports are driving distance for you -- talk about a win-win!!
December 23-28 - Christmas Weekend: Holiday magic at Disney, Universal, cruises, or tropical resorts — with surprisingly efficient PTO use.
Why Planning Early Makes a Big Difference
When families plan these trips early, they often get:
Better availability for popular dates
More resort and cabin options
Easier flight schedules
Smaller payments spread over more months
Less stress as the travel date approaches
Long weekends and holiday weeks are some of the first dates to sell out, especially for family-friendly destinations.
The Bottom Line
If you want to travel more — without exhausting your PTO or disrupting school schedules — long weekend planning is one of the smartest strategies out there.
You don’t need to have every detail figured out right now. Even identifying which long weekend could work for your family is enough to start the conversation.
If you’d like help turning one of these long weekends into a trip that actually fits your family’s travel style, I’d love to help you explore options and timing. A little planning now can make a big difference later.
Comments