Leavewise finds every hidden long weekend, holiday bridge, and calendar gap — so you get more time off without burning a single extra PTO day.
See exactly how many vacation days you're leaving on the table.
Round numbers for a quick preview — the planner recalculates from your real holidays and year.
See the flow
Leavewise compresses the full leave-planning loop into one surface, so you stop bouncing between holiday tabs, spreadsheets, and booking searches.
Best Fit
Built for people trying to squeeze more life from a finite PTO balance.
Stretch a small leave budget into longer breaks without manual calendar math.
Find windows that line up with teammates, family schedules, or shared trip plans.
See good leave windows and booking context together instead of in separate tabs.
Useful when your local holiday rhythm changed and your instincts have not caught up yet.
Journey
Three inputs. One plan. Maximum life.
Pick your country and enter how many PTO days you have.
We cross-reference every public holiday, weekend, and bridge day to find windows where 1–2 PTO days unlock 5–10 days off.
For each optimized window we surface flight deals for those exact dates — already aligned to your schedule.
Toolkit
More than a calculator — a complete planning toolkit.
Every holiday bridge, gap, and long weekend found automatically. Our algorithm maximizes time off per PTO day.
See live flight prices for your exact windows. Spot cheaper departure dates and book directly.
One-click .ics download drops your PTO plan straight into Outlook, Google Calendar, or Apple Calendar.
Adjust PTO on individual windows and watch the rest rebalance in real time. You stay in charge.
Example-style windows Leavewise can surface for the US in 2026 (exact dates shift with Easter and other holidays).
Two holiday anchors create a spring break that feels much bigger than the PTO spend.
A reliable late-May trip block that uses Memorial Day as the anchor.
A short Thanksgiving bridge that punches above its weight for domestic or short-haul travel.
Office workers who stopped leaving PTO on the table.
Quotes are shortened composite examples for illustration, not recorded customer interviews.
“I had 12 PTO days. Leavewise turned them into 5 separate trips by finding bridge days I never would have spotted.”
“Saved me 2 PTO days on our family Thanksgiving trip just by shifting the window one day. That's a free long weekend.”
“The flight deals for each window are clutch. Booked a round-trip to Lisbon for $380 on dates I wouldn't have considered.”
Everything you want to know before you start.
Yes, completely free — no account, no paywall, no "premium tier". The tool runs entirely in your browser.
The planner is built for the United States (including state-level public holidays) and South Korea right now. More countries are on the roadmap. You can still add your own company holidays manually.
Yes — the holiday data includes substitute holidays, so in years where Seollal, Chuseok, or holidays like Foundation Day land on a weekend, windows are computed from the days you actually get off.
The optimizer considers every public holiday, weekend, and bridge opportunity in your year. It ranks windows by PTO efficiency (days off per PTO day) and respects your total budget. You can fine-tune individual windows after.
Your planner settings are saved locally in your browser so they persist across sessions — no account, no server-side database of your plan. We may load Google Analytics and Microsoft Clarity when those tools are enabled for the site; both help us understand traffic in aggregate. We do not sell your personal data.
Currently Leavewise is designed for individual planning. You can share your optimized plan via a link or by downloading the calendar file (.ics).
In-depth, sourced guides on leave, holidays and travel
November is Buenos Aires in full spring -- jacarandas blooming, 65–75°F weather, and flights 25–35% below the January peak. Patagonia is just opening. Here is the math and the Veterans Day bridge.
Read →Aug 4, 2026The US has no federal bereavement leave law, but a growing number of states do. Here's what you're actually entitled to, how it varies by employer and country, and how bereavement leave interacts with your annual PTO.
Read →Aug 4, 2026Cruise lines move ships between the Caribbean and the Mediterranean twice a year. These 12–16 night transatlantic repositioning sailings are priced 40–55% below equivalent Med itineraries. Here is how to pick one, when to book, and how to bridge it with US holidays.
Read →A printable calendar with every holiday and optimized window highlighted. No spam, unsubscribe anytime.
See exactly which days you're leaving on the table — in 30 seconds.
No account. No catch.
Find my missing days