Getting the most out of your PTO in 2025

How to turn 15 days of PTO into 49 days of bliss because!! fuck!! working!!

When it comes to paid time off, I’d like to think of myself as somewhat of an expert. Some people are pros at meeting deadlines or leading team projects. Me? I’m a pro at taking time off. At this point, I’m a gold medalist in this Olympic sport.

In fact, the last time I had a full-time job with one of those shiny unlimited PTO policies, my manager had to pull me aside and very gently remind me that “unlimited” doesn’t actually mean “all the time.” The company ended up re-writing their PTO policy because of me (sorry I took 20 days off in one year!), but hey, don’t offer it if you don’t actually mean it!

working to live > living to work

I’m not saying get yourself in trouble, but if you want to turn 15 measly days into nearly seven weeks of bliss in 2025, you’re in good hands. I’m going to show you how it’s done, without getting put in time out.

The key here is getting your PTO requests in early so you can have coverage from other teammates, who are probably behind in thinking about their vacation plans for next year.

Step 1: Map It All Out (Yes, Right Now)

Planning your time off in advance is the secret sauce to maximizing your days. Use this guide to identify the best windows for booking flights, lodging, and maybe even squeezing in that dream trip you’ve been eyeing on Pinterest.

And remember: Everyone loves time off, especially during the holidays. So, put in your requests as soon as you’re done reading this. Today isn’t too early.

Step 2: Be Strategic with Your Days

What’s better—three days off here and there, or a full nine-day stretch that feels like a real getaway? Exactly. I’ll outline each federal holiday and how to maximize it, but if you’re tight on PTO, prioritize those longer stretches. Let’s get into the play-by-play.

January

New Year’s Day: January 1st
Kick off 2025 by taking January 2nd and 3rd off. Here’s what you get:

• 5 days off in a row

• 2 days of PTO used

Where to spend it:

• Faena, Miami: Because you deserve sunshine in January.

Martin Luther King Jr. Day: January 20th
Take January 17th off and you’ll get:

• 3 days off in a row

• 1 day of PTO used

Where to spend it:

• La Valise, Tulum: Close enough for a quick trip, but unplugged enough that it feels worlds away.

February

Presidents’ Day: February 17th
Turn this into a 5-day weekend by taking February 14th and 18th off. Bonus: It’s also Valentine’s Day, so you can start your trip with roses and champagne.

• 5 days off in a row

• 2 days of PTO used

Where to spend it:

• The Ritz Paris: Because a five day romantic weekend in the city of lights never hurts.

• Palm Heights, Cayman Islands: Enjoy a wellness focused trip with your loved one on a gorgeous beach.

May

Memorial Day: May 26th
Book May 23rd or May 27th off to enjoy a four-day weekend. Whether you’re hitting the beach or just want to stay home for an extra Netflix binge, it’s all up to you.

• 4 days off in a row

• 1 day of PTO used

Where to spend it:

• The Dewberry, Charleston: Eat yourself into a southern food coma and take in the stunning homes.

June

Juneteenth: June 19th
Take June 20th off, and enjoy a four-day weekend.

• 4 days off in a row

• 1 day of PTO used

Where to spend it:

• Fairmont, Banff: Immerse yourself in nature and breathe in the beautiful mountain air.

July

4th of July: July 4th
With July 4th falling on a Friday, just add July 3rd or 7th for a four-day weekend. Easy.

• 4 days off in a row

• 1 day of PTO used

Where to spend it:

• Good Hotel, Antigua, Guatemala: Who needs fireworks and American pride when Antigua is surrounded by three volcanoes?

September

Labor Day: September 1st
Turn that into a three-day weekend. Not much strategy needed here, but it’s the perfect excuse to squeeze in one more beach trip.

• 3 days off in a row

• 0 days of PTO used

October

Columbus Day/Indigenous Peoples’ Day: October 13th
Another three-day weekend up for grabs. No need to take more time now unless you’ve got leftover PTO burning a hole in your pocket. Save those days for the big ones in November and December.

• 3 days off in a row

• 0 days of PTO used

November

Veterans Day: November 11th
Take off the four days before Veterans Day, and you’ve got yourself a 9-day vacation. Yup, that’s right.

• 9 days off in a row

• 4 days of PTO used

Where to spend it:

• The Belmond, Rio de Janeiro: Plenty of time to check out the southern hemisphere and to add some warmth to the beginning of winter.

Thanksgiving: November 27th
Take just November 28th off for a quick 4-day holiday.

• 4 days off in a row

• 1 day of PTO used

Where to spend it:

• Hotel Nantipa, Costa Rica: I’ve never been more thankful than when I’ve started the day surfing.

December

Christmas: December 25th
Christmas falls on a Thursday, so take off December 26th, and the week of Christmas turns into 9 full days off.

• 9 days off in a row

• 4 days of PTO used

Where to spend it:

• Fleming’s, London: London during the holiday season is absolutely magical. It makes NYC look WEAK.

The Grand Total

If you follow this guide, you’ll have turned 15 days of PTO into a whopping 49 days off in 2025. That’s almost 1.5 months of time to explore the world, rot at home, or do whatever the hell makes you feel alive.

Here’s your cheat sheet:

• January: New Year’s and MLK Day - 8 days (3 PTO used)

• February: Presidents’ Day - 5 days (2 PTO used)

• May: Memorial Day - 4 days (1 PTO used)

• June: Juneteenth - 4 days (1 PTO used)

• July: 4th of July - 4 days (1 PTO used)

• September: Labor Day - 3 days (0 PTO used)

• October: Columbus Day - 3 days (0 PTO used)

• November: Veterans Day and Thanksgiving - 13 days (5 PTO used)

• December: Christmas - 9 days (4 PTO used)

Good luck, get your requests in, and thank me later!