The Ultimate Teacher’s Guide to Traveling on a School Calendar: Maximize Your Time Off!

Teachers get more vacation time than most professionals – sounds like good news, right? Well, if you’re a teacher, you already know the bad news: everyone else with kids also has those same weeks off, prices skyrocket, and popular destinations are overcrowded nightmares.

But your schedule doesn’t have to feel like the odds are against you. With some creative thinking and strategic planning, you can travel better, cheaper, and more frequently than your nine-to-five friends who only get two weeks of PTO.

Treat Professional Development Days like Mini Sabbaticals

Most school districts offer several professional development days throughout the year. Some are mandatory in-person sessions, while others let you complete requirements online or through approved conferences.

Here’s what to do: find professional development opportunities in places you want to visit. Teaching conferences take place year-round in cities across the country and internationally. Register for a multi-day conference, complete your PD hours, and extend your trip on either end.

The NEA and the ASCD host conferences in different cities each year. Language teachers can attend immersion programs abroad that count toward recertification. STEM educators have conferences at NASA facilities, national parks, and science museums.

Your district might even partially fund the trip if you frame it correctly. Conference registration, travel, and lodging for professional development may be reimbursed or covered by grants in your district.

Stack Your Sick Days Strategically

This sounds sketchy, but it’s completely legitimate. Most teacher contracts give you 10-15 sick days per year. Many districts let unused sick days roll over indefinitely or pay them out at retirement.

If you’re healthy most of the year, you can use sick days to take longer breaks without technically taking unpaid time off. You’ll need to combine timing and legitimacy, and get over your worries about faking sick. You’re using benefits you’ve earned for mental health and personal wellness, which are valid reasons to take a sick day in most contracts.

If you can, take a Thursday and Friday as sick days after a three-day weekend. That means you have nine consecutive days off. Do this twice a year and you’ve added two international trips to your calendar without touching your salary. They’re days that you are allowed to take.

Become a Travel Coordinator for Student Trips

Many schools organize international student trips during spring break or summer. These trips need teacher chaperones. If you volunteer, you typically travel for free or at a heavily discounted rate.

Companies like EF Tours and Explorica organize student trips to dozens of countries. As a group leader, your travel costs are covered based on the number of students you recruit. Bring 10 or more students, and you usually travel completely free.

• Watch this interview with teacher Cameron, who traveled around Europe FOR FREE through EF Tours!

Of course, you’re responsible for teenagers in a foreign country, and that’s work! But you’re getting a free trip to Europe, Latin America, or Asia that you’d otherwise have to spend thousands of dollars on yourself. Plus, you’re not stuck with your group 24/7 – most tours build in free time.

Leverage Teacher Exchange Programs

Fulbright Teacher Exchanges let you swap positions with a teacher in another country for a semester or full academic year. You teach in their school, they teach in yours. Both districts maintain your salary and benefits.

As with student tours, this isn’t vacation time because you’re working your regular contract in a different country – but your housing is usually arranged through the exchange, and you get to live like a local, not a tourist, for months at a time.

Other programs to check out: Teachers for Global Classrooms and bilateral exchange programs between the US and countries like France, Spain, and China. Some programs even prefer teachers with families because it helps international students see “normal” American life.

The application process is competitive but not impossible. You need classroom experience, good evaluations, and a compelling reason for wanting the exchange. Start researching programs 12-18 months before you want to go.

Take a Sabbatical Every Seven Years

Many teacher contracts include sabbatical provisions that rarely get used. After seven years of service, you may be eligible for a semester or full-year sabbatical at partial pay (usually 50-75% of your salary).

You must propose an educational purpose, such as writing a curriculum, conducting research, or pursuing advanced study in your subject area. Want to spend a year traveling through South America? Propose a project on indigenous education systems and how they could inform US teaching practices. Planning six months in Southeast Asia? Frame it as a study of educational technology adoption in developing nations.

Check your contract and union agreement. The sabbatical clause is often buried in there, unused because nobody asks for it. Administrators might initially push back, but if your proposal is solid and you’ve been a strong teacher, they may approve it.

You’ll make less money that year, but you won’t quit your job or lose benefits. And you return with fresh perspectives that make you a better educator.

• Read our tips for taking a sabbatical to reset after burnout

Work the Summer School Circuit in Other Countries

International schools need summer session teachers. These positions run from June through August, pay real salaries (not volunteer stipends), and often include housing.

Search Associates and ISS maintain databases of international teaching jobs, including summer positions. American schools in Europe, Asia, and beyond are seeking teachers for summer enrichment programs, ESL courses, and test prep.

You’re working, but you’re working in Barcelona or Bangkok. Your evenings and weekends are free, housing is covered, and you’re making money while living abroad, rather than draining your savings account.

The pay varies widely. Some positions offer $2,000 to $3,000 for a six-week session, plus housing. Others pay closer to $6,000 to $8,000. Either way, you’re earning while experiencing a new place.

Rent Out Your House During Peak Season

You live in a college town or near a major city? Your house has value to tourists during exactly the weeks you don’t want to be there.

List your place on Airbnb or VRBO during Thanksgiving week, winter break, and summer vacation. Charge premium rates when demand is highest, and use that income to fund your off-season travel.

You’ll need to prep your space, hire a cleaner between guests, and manage bookings. However, that’s a few hours of work for thousands of dollars in income. Screen guests carefully, require security deposits, and get good insurance!

Teach English Online From Anywhere

You can work your regular teaching job and earn extra money teaching ESL online during your off-hours. That side income funds your travel.

Companies like VIPKid and Cambly hire certified teachers to teach English to students abroad via video chat. Most pay between $15 and $25 per hour, and you can set your own schedule.

Teach 10-15 hours per week during the school year, save that money, and you’ll have $5,000-$10,000 extra for summer travel. Or teach remotely while you’re actually traveling, turning your trip into a working vacation that pays for itself.

You already have the qualifications, and most platforms prefer certified teachers. Your classroom experience makes you more competitive than other applicants.

Use Teacher Discounts

You know about museum discounts – here are a few travel discounts most teachers don’t know exist:

Road Scholar has educational travel programs with financial assistance available for educators.

Many airlines offer teacher discounts during non-peak times. You have to call and ask – they don’t tend to advertise them online. Southwest has offered educator rates at various times, and you can also explore third-party providers like CheapOair for educator discounts and special offers.

Hotels near national parks and educational sites frequently offer discounts for teachers year-round. Marriott, Hilton, and IHG properties near Smithsonian facilities, national parks, and historic sites often offer discounts of 10-15% if you show your teacher ID and mention that you’re planning educational activities. Call your preferred hotels before booking to see if they have discounts available – remember, not everything is posted online!

Even cruise lines like Norwegian have teacher discounts! Our advice? Start a Pinterest board of your dream vacations, and for any booking opportunity that requires payment (hotels, cruises, theme parks, etc.), type the brand name plus “teacher discounts” into a search engine and see what comes up. Even if you don’t see a current offer, you can still call and ask!

Build a Teacher Travel Network

Other teachers in your district have the same schedule constraints and the same desire to travel. So, it could be fun to start organizing group trips!

When you travel as a group of 6-10 teachers, you get group rates on tons of things – flights, hotels, tours, even restaurants. You split costs on rental vehicles and vacation rentals. You have built-in travel companions who understand your schedule and budget. And groups often get upgrades that solo travelers don’t have access to.

Create a shared Google Doc or private group where your fellow teachers can share travel deals, coordinate trips, and compare notes on destinations.

The Calendar Arbitrage Strategy

Your spring break doesn’t align with everyone else’s spring break. If your district takes spring break the first week of March, you’re hitting destinations two weeks before the major spring break rush that happens in mid-to-late March. There are lower prices, smaller crowds, and similar weather.

The same logic applies to winter break. If your break starts just before Christmas, you’re traveling during the absolute peak chaos. If your break starts in mid-December, you can return before New Year’s when return flights cost half as much.

Look at neighboring districts’ calendars. If they’re off when you’re working, their vacation destinations will be cheaper during your breaks. Teachers in northern states can visit Florida during their March break, while schools in the south are still in session.

Turn Your Classroom into a Travel Fund

This sounds crazy, but teachers who post their classroom supply needs on DonorsChoose can redirect some of their own salary toward travel.

If donors cover more of your classroom expenses, the money you would have spent buying supplies out of pocket goes straight into your travel fund instead. You’re not gaming the system – you’re getting your classroom funded the way it should be, by not personally financing a government employer’s supply shortage.

The Year-Round School Advantage

If you teach at a year-round school with multiple breaks throughout the year, you have the ultimate travel advantage. You get 3-4 weeks of vacation spread across the calendar when almost nobody else is off.

Year-round schedules typically break in October, January, March / April, and summer. October travel is cheap and uncrowded. January (after the holiday rush) is a deal-seeker’s paradise. Your April break misses Easter weekend.

Teachers with traditional schedules often struggle to compete. You’re traveling when everyone else is working, paying half what they’ll pay during their limited vacation windows. If you have the option to move to a year-round school in your district, the travel benefits alone make it worth considering.

Negotiate Your Contract’s First and Last Days

In many districts, the teacher contract year is longer than the student year. You might have 190 student contact days but 200 contract days, with the extra days being professional development, planning, and meetings.

Some administrators may allow you to compress those extra days if you have a valid reason. Instead of spreading 10 PD days across the year, propose doing them all in August before school starts. Suddenly, your summer extends another week.

Or negotiate to complete end-of-year duties remotely. If you can grade finals and close out your classroom from anywhere with wifi, you could leave town while you’re technically still on contract.

This requires good relationships with administration and a track record of reliability. But teachers who ask often get more flexibility than those who assume the answer is no.

Ready to Travel? Stop Thinking like a Tourist!

The biggest shift teachers need to make isn’t about finding cheap flights or maximizing days off, but rather changing how you think about travel entirely.

You have summers off, which comes to 10-12 weeks. Instead of taking one expensive two-week trip to Europe, consider spending six weeks in a more affordable Southeast Asian country, where your costs are far lower. Get a short-term apartment, not a hotel, and live like a local.

Stop maximizing days off and start maximizing value. Your schedule is better for slow travel, deep experiences, and budget-conscious adventures than the typical American worker’s schedule. And of course, if you do want more ideas about maximizing your vacation days and getting creative with time off, read our guide to getting way more than your standard PTO!

About the Author

As the editor-in-chief of Frayed Passport, my goal is to help you build a lifestyle that lets you travel the world whenever you want and however long you want, and not worry about where your next paycheck will come from. I've been to 20+ countries and five continents, lived for years as a full-time digital nomad, and have worked completely remotely since 2015. If you would like to share your story with our community, or partner with Frayed Passport, get in touch with me using the form on our About page.

Featured image by Look Studio on Unsplash