How to get the most days off from your PTO in 2027
Last checked 2026-11-15
The trick is to spend PTO on the workdays that sit between a holiday and a weekend. A Thursday holiday needs one PTO day on Friday to become four days off. A Monday holiday plus four PTO days becomes nine days. With all 11 federal holidays and 10 PTO days, you can get 40 days off in 2027. With a typical private-sector list of seven holidays, the same 10 days give 34.
Best breaks with 1 PTO day
| Days off | Dates | Book |
|---|---|---|
| 4 | Fri, Jan 1 – Mon, Jan 4 New Year's | Mon, Jan 4 |
| 4 | Fri, Jan 15 – Mon, Jan 18 MLK Day | Fri, Jan 15 |
| 4 | Fri, Feb 12 – Mon, Feb 15 Presidents' Day | Fri, Feb 12 |
| 4 | Fri, May 28 – Mon, May 31 Memorial Day | Fri, May 28 |
Best breaks with 2 PTO days
| Days off | Dates | Book |
|---|---|---|
| 5 | Fri, Jan 1 – Tue, Jan 5 New Year's | Mon, Jan 4, Tue, Jan 5 |
| 5 | Thu, Jan 14 – Mon, Jan 18 MLK Day | Thu, Jan 14, Fri, Jan 15 |
| 5 | Thu, Feb 11 – Mon, Feb 15 Presidents' Day | Thu, Feb 11, Fri, Feb 12 |
| 5 | Thu, May 27 – Mon, May 31 Memorial Day | Thu, May 27, Fri, May 28 |
Best breaks with 3 PTO days
| Days off | Dates | Book |
|---|---|---|
| 6 | Fri, Jan 1 – Wed, Jan 6 New Year's | Mon, Jan 4, Tue, Jan 5, Wed, Jan 6 |
| 6 | Wed, Jan 13 – Mon, Jan 18 MLK Day | Wed, Jan 13, Thu, Jan 14, Fri, Jan 15 |
| 6 | Wed, Feb 10 – Mon, Feb 15 Presidents' Day | Wed, Feb 10, Thu, Feb 11, Fri, Feb 12 |
| 6 | Wed, May 26 – Mon, May 31 Memorial Day | Wed, May 26, Thu, May 27, Fri, May 28 |
Best breaks with 4 PTO days
| Days off | Dates | Book |
|---|---|---|
| 9 | Sat, Jan 16 – Sun, Jan 24 MLK Day | Tue, Jan 19, Wed, Jan 20, Thu, Jan 21, Fri, Jan 22 |
| 9 | Sat, Feb 13 – Sun, Feb 21 Presidents' Day | Tue, Feb 16, Wed, Feb 17, Thu, Feb 18, Fri, Feb 19 |
| 9 | Sat, May 29 – Sun, Jun 6 Memorial Day | Tue, Jun 1, Wed, Jun 2, Thu, Jun 3, Fri, Jun 4 |
| 10 | Fri, Dec 24 – Sun, Jan 2, 2028 Christmas, New Year's | Mon, Dec 27, Tue, Dec 28, Wed, Dec 29, Thu, Dec 30 |
A 10-day plan for 2027
This is what the PTO planner picks with the federal holiday list, 10 PTO days and breaks of at least four days.
| Days off | Dates | PTO |
|---|---|---|
| 4 | Fri, Jan 1 – Mon, Jan 4 | 1 |
| 4 | Fri, Jan 15 – Mon, Jan 18 | 1 |
| 4 | Fri, Feb 12 – Mon, Feb 15 | 1 |
| 4 | Fri, May 28 – Mon, May 31 | 1 |
| 4 | Thu, Jun 17 – Sun, Jun 20 | 1 |
| 4 | Fri, Jul 2 – Mon, Jul 5 | 1 |
| 4 | Fri, Sep 3 – Mon, Sep 6 | 1 |
| 4 | Fri, Oct 8 – Mon, Oct 11 | 1 |
| 4 | Thu, Nov 11 – Sun, Nov 14 | 1 |
| 4 | Thu, Nov 25 – Sun, Nov 28 | 1 |
Tips that matter more than the math
- Request the popular weeks early. The days around Thanksgiving and between Christmas and New Year's go first on most teams.
- Check your company's own list. If you do not get Juneteenth or Veterans Day, the best bridges move. Enter your real list in the planner.
- Watch for observed days. In 2027, Christmas is observed on Friday, Dec 24 and New Year's Day 2028 on Friday, Dec 31, which makes the last week of the year unusually cheap.
- Ask whether unused PTO carries over or pays out. If it is use-it-or-lose-it, plan the last days before the deadline.