PTO GUIDE · 2027
How to Maximize PTO in 2027
The best days to take off around every US holiday in 2027. Request the dates in the table and the weekend and the holiday do the rest. 2028 dates are one tap away below.
Best days to take off in 2027 (US)
| Holiday | Short break: take off | Days away | Full break: dates away | PTO days | Days away |
|---|---|---|---|---|---|
| New Year’s DayFri, Jan 1 | Wed, Dec 30, 2026 & Thu, Dec 31, 2026Wed, Dec 30, 2026 – Sun, Jan 3 | 5 | Sat, Dec 26, 2026 – Sun, Jan 3Take Mon, Dec 28, 2026 – Thu, Dec 31, 2026 | 4 | 9 |
| MLK DayMon, Jan 18 | Thu, Jan 14 & Fri, Jan 15Thu, Jan 14 – Mon, Jan 18 | 5 | Sat, Jan 16 – Sun, Jan 24Take Tue, Jan 19 – Fri, Jan 22 | 4 | 9 |
| Presidents’ DayMon, Feb 15 | Thu, Feb 11 & Fri, Feb 12Thu, Feb 11 – Mon, Feb 15 | 5 | Sat, Feb 13 – Sun, Feb 21Take Tue, Feb 16 – Fri, Feb 19 | 4 | 9 |
| Memorial DayMon, May 31 | Thu, May 27 & Fri, May 28Thu, May 27 – Mon, May 31 | 5 | Sat, May 29 – Sun, Jun 6Take Tue, Jun 1 – Fri, Jun 4 | 4 | 9 |
| JuneteenthFri, Jun 18 | Wed, Jun 16 & Thu, Jun 17Wed, Jun 16 – Sun, Jun 20 | 5 | Sat, Jun 12 – Sun, Jun 20Take Mon, Jun 14 – Thu, Jun 17 | 4 | 9 |
| July 4thMon, Jul 5 | Thu, Jul 1 & Fri, Jul 2Thu, Jul 1 – Mon, Jul 5 | 5 | Sat, Jul 3 – Sun, Jul 11Take Tue, Jul 6 – Fri, Jul 9 | 4 | 9 |
| Labor DayMon, Sep 6 | Thu, Sep 2 & Fri, Sep 3Thu, Sep 2 – Mon, Sep 6 | 5 | Sat, Sep 4 – Sun, Sep 12Take Tue, Sep 7 – Fri, Sep 10 | 4 | 9 |
| Thanksgiving (+ day after)Thu, Nov 25 | Tue, Nov 23 & Wed, Nov 24Tue, Nov 23 – Sun, Nov 28 | 6 | Fri, Nov 19 – Sun, Nov 28Take Fri, Nov 19 – Wed, Nov 24 | 4 | 10 |
| ChristmasFri, Dec 24 | Wed, Dec 22 & Thu, Dec 23Wed, Dec 22 – Sun, Dec 26 | 5 | Sat, Dec 18 – Sun, Dec 26Take Mon, Dec 20 – Thu, Dec 23 | 4 | 9 |
Assumes a Monday–Friday week plus the holidays most US companies give, the same rules as our PTO calculator. The MLK Day, Presidents’ Day and Juneteenth rows only work if your company gives that day. The best New Year’s Day break starts Wed, Dec 30, 2026 — those PTO days come out of your 2026 allowance.
Questions
What is the best way to maximize PTO in 2027?
Put your PTO days next to weekends and paid holidays. Thu, May 27 and Fri, May 28 off before Memorial Day give you 5 days away. Four days around most Monday holidays give you nine.
Does this work for 2028?
Yes — the table above switches to 2028, and there's a full guide for it. The same rules apply: weekends plus the holidays most US companies give. 2028 Memorial Day is Mon, May 29, so Thu, May 25 and Fri, May 26 off give 5 days away.
Which holidays does this table assume?
Weekends plus the holidays most US companies give: New Year's Day, Memorial Day, July 4th, Labor Day, Thanksgiving, the day after Thanksgiving and Christmas. Each row also counts that row's own holiday, so the MLK Day, Presidents' Day and Juneteenth rows assume your company gives that day.
Why do some dates fall in the year before?
New Year's Day often lands on a weekend or a Friday, so the best break starts in the last week of the year before. The best New Year’s Day break starts Wed, Dec 30, 2026 — those PTO days come out of your 2026 allowance.
What if I work weekends or get different holidays?
The table assumes a Monday to Friday week. Use the PTO calculator to choose your own company holidays, block months you can't travel and map every trip your PTO can hold. It plans this year and next.
Turn the dates into a trip
Save these windows in Days IRL to see places that fit, what they could cost and who can come.
Also planning 2028? How to maximize PTO in 2028.