Tell us how many PTO days you have and which holidays your employer gives. We find the blocks that turn the fewest days off into the most days away, then show destinations that fit each one.
10 PTO days, 42 days off
Nov 21 to Nov 29, 2026 · Thanksgiving, Day after Thanksgiving
9 days off3 PTO days
Destinations that fit this window:
Fares appear here as we see them.
Dec 25 to Dec 27, 2026 · Christmas Day
3 days offno PTO needed
Destinations that fit this window:
Fares appear here as we see them.
Jan 1 to Jan 3, 2027 · New Year's Day
3 days offno PTO needed
Destinations that fit this window:
Fares appear here as we see them.
May 29 to May 31, 2027 · Memorial Day
3 days offno PTO needed
Destinations that fit this window:
Fares appear here as we see them.
Jul 3 to Jul 5, 2027 · Independence Day
3 days offno PTO needed
Destinations that fit this window:
Fares appear here as we see them.
Sep 4 to Sep 6, 2027 · Labor Day
3 days offno PTO needed
Destinations that fit this window:
Fares appear here as we see them.
Nov 20 to Nov 28, 2027 · Thanksgiving, Day after Thanksgiving
9 days off3 PTO days
Destinations that fit this window:
Fares appear here as we see them.
Dec 18 to Dec 26, 2027 · Christmas Day
9 days off4 PTO days
Destinations that fit this window:
Fares appear here as we see them.
Save your home airport and we'll email you when a fare there is genuinely worth a look.
| Holiday | Options |
|---|---|
| Thanksgiving Thu Nov 26, 2026 | No time off needed: 4 days (Nov 26 to Nov 29, 2026) Take Wed Nov 25 off, get 5 days (Nov 25 to Nov 29, 2026) Take Tue Nov 24 and Wed Nov 25 off, get 6 days (Nov 24 to Nov 29, 2026) Take Mon Nov 23, Tue Nov 24 and Wed Nov 25 off, get 9 days (Nov 21 to Nov 29, 2026) |
| Day after Thanksgiving Fri Nov 27, 2026 | No long weekend with 3 or fewer PTO days. |
| Christmas Day Fri Dec 25, 2026 | No time off needed: 3 days (Dec 25 to Dec 27, 2026) Take Thu Dec 24 off, get 4 days (Dec 24 to Dec 27, 2026) Take Wed Dec 23 and Thu Dec 24 off, get 5 days (Dec 23 to Dec 27, 2026) Take Tue Dec 22, Wed Dec 23 and Thu Dec 24 off, get 6 days (Dec 22 to Dec 27, 2026) |
| New Year's Day Fri Jan 1, 2027 | No time off needed: 3 days (Jan 1 to Jan 3, 2027) Take Thu Dec 31 off, get 4 days (Dec 31 to Jan 3, 2027) Take Wed Dec 30 and Thu Dec 31 off, get 5 days (Dec 30 to Jan 3, 2027) Take Tue Dec 29, Wed Dec 30 and Thu Dec 31 off, get 6 days (Dec 29 to Jan 3, 2027) |
| Memorial Day Mon May 31, 2027 | No time off needed: 3 days (May 29 to May 31, 2027) Take Fri May 28 off, get 4 days (May 28 to May 31, 2027) Take Thu May 27 and Fri May 28 off, get 5 days (May 27 to May 31, 2027) Take Wed May 26, Thu May 27 and Fri May 28 off, get 6 days (May 26 to May 31, 2027) |
| Independence Day Mon Jul 5, 2027 | No time off needed: 3 days (Jul 3 to Jul 5, 2027) Take Fri Jul 2 off, get 4 days (Jul 2 to Jul 5, 2027) Take Thu Jul 1 and Fri Jul 2 off, get 5 days (Jul 1 to Jul 5, 2027) Take Wed Jun 30, Thu Jul 1 and Fri Jul 2 off, get 6 days (Jun 30 to Jul 5, 2027) |
| Labor Day Mon Sep 6, 2027 | No time off needed: 3 days (Sep 4 to Sep 6, 2027) Take Fri Sep 3 off, get 4 days (Sep 3 to Sep 6, 2027) Take Thu Sep 2 and Fri Sep 3 off, get 5 days (Sep 2 to Sep 6, 2027) Take Wed Sep 1, Thu Sep 2 and Fri Sep 3 off, get 6 days (Sep 1 to Sep 6, 2027) |
| Thanksgiving Thu Nov 25, 2027 | No time off needed: 4 days (Nov 25 to Nov 28, 2027) Take Wed Nov 24 off, get 5 days (Nov 24 to Nov 28, 2027) Take Tue Nov 23 and Wed Nov 24 off, get 6 days (Nov 23 to Nov 28, 2027) Take Mon Nov 22, Tue Nov 23 and Wed Nov 24 off, get 9 days (Nov 20 to Nov 28, 2027) |
| Day after Thanksgiving Fri Nov 26, 2027 | No long weekend with 3 or fewer PTO days. |
| Christmas Day Fri Dec 24, 2027 | No time off needed: 3 days (Dec 24 to Dec 26, 2027) Take Thu Dec 23 off, get 4 days (Dec 23 to Dec 26, 2027) Take Wed Dec 22 and Thu Dec 23 off, get 5 days (Dec 22 to Dec 26, 2027) Take Tue Dec 21, Wed Dec 22 and Thu Dec 23 off, get 6 days (Dec 21 to Dec 26, 2027) |
| New Year's Day Fri Dec 31, 2027 | No long weekend with 3 or fewer PTO days. |
How this works: weekends and the holidays you pick are free days off; any other weekday inside a block is a PTO day. Holiday dates follow the US federal calendar (OPM), including the observed day when a holiday falls on a weekend. Many employers do not give every federal holiday, so choose the ones yours does. The plan only counts days inside the blocks it shows.