PTO Planner
Plan your time away around your work calendar, trips, and available PTO.
Sep 2026 – Nov 2026
September 2026
- Sep 25–29 · Pinehurst Long Weekend
- Sep 5–8 · Chicago City Break
- Sep 7 · Labor Day
October 2026
November 2026
- Nov 26 · Thanksgiving
- Nov 27 · Day after Thanksgiving
Found in your email & calendar
Vakairos grouped these confirmations into likely trips. Demo data.
Found in your email · High confidence
Looks like a trip.
Chicago · Mar 12–15
- Tampa → Chicago · Southwest 2210Mar 12
- Chicago Athletic Association HotelMar 12–15
- Chicago Symphony OrchestraMar 14
2 PTO days recommended
Found in your calendar · Medium confidence
Looks like a trip.
Nashville · Nov 12–15
- Calendar: “Out of office — Nashville”Nov 12–15
- Ryman Auditorium showNov 13
2 PTO days recommended
Make your PTO go further
You have 10 unplanned PTO days. 5 long-weekend opportunities line up with company holidays.
Nov 21–29
Thanksgiving opportunity
Take 3 PTO days, get 9 days away
Pair two company holidays with three PTO days.
Feb 12–15
Presidents' Day long weekend
Take 1 PTO day, get 4 days away
One Friday off turns the holiday into four days.
May 29 – Jun 6
Memorial Day opportunity
Take 4 PTO days, get 9 days away
Stretch the holiday into more than a week away.
Jun 17–20
Juneteenth long weekend
Take 1 PTO day, get 4 days away
A Thursday off makes an easy four-day trip.
Jul 1–5
July 4th window
Take 2 PTO days, get 5 days away
Your July calendar has a 5-day window for just 2 PTO days.