The 2026 Holiday PTO Calendar: How to Turn US Holidays Into Real Vacations (With Trips You Can Book)
If you’re someone who has to “borrow” holidays to make travel happen, this is your cheat sheet.
Below you’ll find the 2026 US federal holiday dates plus exact PTO moves to turn them into 3–4 day long weekends or 9–11 day trips—with trip ideas sized to the number of days you’ll actually have. And yes, I can book every one of them for you as well as plan the best time to book certain trips.
Quick tip: When a holiday lands on a Monday or Friday, you’re one smart PTO day away from feeling like a genius. Also if you can fly on a day following or before the actual weekend, you’re likely to find better flight prices and less chaos at the airports.
2026 US Federal Holidays (Observed Dates)
New Year’s Day: Thu, Jan 1
MLK Day: Mon, Jan 19
Presidents’ Day (Washington’s Birthday): Mon, Feb 16
Memorial Day: Mon, May 25
Juneteenth: Fri, Jun 19
Independence Day (Observed): Fri, Jul 3
Labor Day: Mon, Sep 7
Columbus Day: Mon, Oct 12
Veterans Day: Wed, Nov 11
Thanksgiving: Thu, Nov 26
Christmas Day: Fri, Dec 25
Bonus (often off, not federal): Some employers observe Good Friday (Fri, Apr 3, 2026).
The Best PTO “Plays” + Trips to Book (2026)
Each section includes:
The PTO move
How many days you actually get
Trip ideas that fit the window
January: New Year’s Day (Thu, Jan 1)
PTO Play A: 1 PTO → 4-day reset
Take Fri Jan 2 → Thu–Sun (Jan 1–4)
Bookable trip ideas (4 days):
Montreal (passport required): food + cozy hotel + spa circuit
Charleston: low-country dining + shopping + quick carriage strolls
Scottsdale: desert wellness, hiking, pool time even in winter
PTO Play B: 6 PTO → 11 days off
Take Fri Jan 2 + Mon–Fri Jan 5–9 → Jan 1–11
Bookable trip ideas (10–11 days):
Mexico City + San Miguel de Allende (culture + design + easy pairing)
Portugal: Lisbon + Douro Valley (city + wine country, no frantic pace)
Thailand light: Bangkok + beach (if you want winter sun, done right)
January: MLK Day (Mon, Jan 19)
PTO Play: 4 PTO → 9 days off
Take Tue–Fri Jan 20–23 → Jan 17–25
Trip ideas (9 days):
Costa Rica: volcano + beach (Arenal/La Fortuna + Guanacaste)
French Caribbean (St. Barts / St. Martin): peak season, book early
London + Cotswolds: city culture + countryside decompression
February: Presidents’ Day (Mon, Feb 16)
PTO Play: 4 PTO → 9 days off
Take Tue–Fri Feb 17–20 → Feb 14–22
Trip ideas (9 days):
Japan sampler: Tokyo + Kyoto (great weather, high demand—plan ahead)
Morocco: Marrakech + Atlas Mountains + a coastal tag-on
Ski escape: Park City / Jackson Hole / Aspen (best rooms sell out early)
May: Memorial Day (Mon, May 25)
PTO Play: 4 PTO → 9 days off
Take Tue–Fri May 26–29 → May 23–31
Trip ideas (9 days):
Italy “easy mode”: Rome + Amalfi OR Florence + Tuscan countryside
Greece shoulder-season: Athens + an island (less chaos than peak summer)
California dream: Napa/Sonoma + Big Sur (slow-luxury road trip)
June: Juneteenth (Fri, Jun 19)
PTO Play A: 4 PTO → 9 days off
Take Mon–Thu Jun 15–18 → Jun 13–21
Trip ideas (9 days):
Ireland by castles: Dublin + countryside (iconic, romantic, easy to tailor)
Paris + Champagne: city + bubbles, perfect “milestone” trip
National Parks (with comfort): Jackson + Tetons, or Sedona + Grand Canyon
PTO Play B: 1 PTO → 4-day weekend
Take Mon Jun 22 → Jun 19–22
Trip ideas (4 days):
Nashville (with a chic hotel + food focus)
Santa Fe (art + desert air + spa)
Martha’s Vineyard / Nantucket (start-of-summer energy)
July: Independence Day Observed (Fri, Jul 3)
PTO Play: 4 PTO → 9 days off
Take Mon–Thu Jun 29–Jul 2 → Jun 27–Jul 5
Trip ideas (9 days):
French Riviera + Provence (this is the time—book hotels early)
Pacific Northwest: Seattle + San Juan Islands + wine country
Croatia: Split + islands (if you want peak summer, we do it smart)
September: Labor Day (Mon, Sep 7)
PTO Play: 4 PTO → 9 days off
Take Tue–Fri Sep 8–11 → Sep 5–13
Trip ideas (9 days):
Greece sweet spot: fewer crowds, warm sea, great value
Portugal + beaches: Lisbon + Comporta/Algarve
Safari (if it’s on your list): late summer can be fantastic depending on region
October: Columbus Day (Mon, Oct 12)
PTO Play: 4 PTO → 9 days off
Take Tue–Fri Oct 13–16 → Oct 10–18
Trip ideas (9 days):
New England fall: Vermont + Hudson Valley (cozy-luxury, not basic)
Spain: Barcelona + countryside (wine, design hotels, markets)
Morocco (again): October is a great time to go
November: Veterans Day (Wed, Nov 11)
PTO Play A: 2 PTO → 5 days off
Take Thu–Fri Nov 12–13 → Nov 11–15
Trip ideas (5 days):
NYC staycation (Broadway + spa + restaurants you can’t get into)
DC (museums + dining + boutique hotels)
Austin (food + live music + a Hill Country add-on)
PTO Play B: 4 PTO → 9 days off
Take Mon–Tue Nov 9–10 + Thu–Fri Nov 12–13 → Nov 7–15
Trip ideas (9 days):
Caribbean kickoff: Turks & Caicos / Anguilla / Antigua
Mexico beach luxe: Riviera Maya done right, or Los Cabos
London + countryside (holiday lights begin)
November: Thanksgiving (Thu, Nov 26)
PTO Play A: 1 PTO → 4 days off
Take Fri Nov 27 → Nov 26–29
Trip ideas (4 days):
Miami: sunshine + design hotels + great dining
Palm Springs: pool + desert calm
Savannah: charming, walkable, easy
PTO Play B: 4 PTO → 9 days off
Take Mon–Wed Nov 23–25 + Fri Nov 27 → Nov 21–29
Trip ideas (9 days):
Christmas markets (early): Vienna + Prague
Thailand / Vietnam (excellent weather window)
South Africa city + winelands (Cape Town + Stellenbosch)
December: Christmas (Fri, Dec 25)
PTO Play: 4 PTO → 9 days off
Take Mon–Thu Dec 21–24 → Dec 19–27
Trip ideas (9 days):
Switzerland winter: Zurich + mountains (ski or non-ski cozy)
Caribbean peak week: book early for best rooms
Warm-weather reset: Mexico / Bahamas / Aruba
How I’d help you book these (so it’s actually easy)
The entire point of a PTO strategy is less stress and more value:
securing the best rooms (and perks when available),
building a smooth routing plan,
adding the “wow” touches: drivers, hard reservations, guides, and time-saving logistics.
If you want to get something on the books, start with a Trip Consultation (and yes, I offer quick “Pick My Brain” sessions too).
