The Smart Traveler’s Guide to Maximizing Your 2026 Time Off
- Ellie Friese
- 3 days ago
- 5 min read
Most of us start the year with big dreams of travel — the places we want to finally see, the trips we’ve been “saving for later,” the experiences we hope will shift us out of our routines. But by the time summer rolls around, reality hits: the calendar is full, schedules feel tight, and those vacation days… somehow disappear.
As a travel advisor, I see this all the time.
People want to travel — they’re just not planning with intention.
The truth is simple:
You don’t need more PTO to be able to travel. You just need to use what you already have… smarter.
With a little strategy, a few well-placed days off, and some thoughtful planning, you can turn your 2026 PTO into multiple meaningful escapes — without draining your vacation bank or feeling like you’re “wasting days.”
Let’s break down how.
Winter Escapes (January – March)
Best paired with:
✓ New Year’s weekend
✓ Martin Luther King Jr. Day
✓ Presidents’ Day
Winter can feel long — which makes it the perfect moment to use a single PTO day to create a long weekend that feels like a reset.
Where I recommend:
A long weekend in Colorado or Utah for skiing, snowshoeing, and cozy lodge vibes
A warm-weather recharge in Aruba, Curaçao, or Puerto Vallarta
A culture-forward city break in Lisbon or Seville (both mild and wonderful in winter)
PTO Strategy:
Take Friday or Tuesday off around a federal holiday → instantly creating a 4-day holiday.
→ Martin Luther King Jr. Day: Jan 19 (Mon) → Take Jan 16 (Fri) or 20 (Tue) → 4 days off
→ Presidents’ Day: Feb 16 ****(Mon) → Take Feb 13 (Fri) OR Feb 17 (Tue) → 4 days off
Travel Advisor Tip:
February fills quickly for warm-weather getaways — book early if you want boutique hotels or adults-only resorts. Also, winter is the best time to take advantage of off-season pricing in Europe.
Best for:
Travelers craving a reset — whether that’s cozy mountain vibes, warm sunshine, or a culture-rich city break without the peak-season chaos.
Spring Refresh (April – June)
Best paired with:
✓ Spring break flexibility
✓ Easter weekend (even if it’s not a federal holiday)
✓ Memorial Day weekend
Spring is one of the most forgiving and beautiful seasons to travel — mild weather, fewer crowds, and vibrant destinations coming back to life.
Where I recommend:
Portugal’s Douro Valley for wine, river views, and countryside charm
Tuscany or Umbria before the summer heat
Santa Barbara, Napa, or Sonoma for vineyard scenery
Japan (prime cherry blossom season)
PTO Strategy:
Add 1–2 PTO days to Memorial Day weekend → create a 5–6 day trip perfect for a coastal escape or extend a bit and spend 7-8 days in Europe!
→ Memorial Day: May 25 (Mon) → Take May 22 (Fri) OR May 26 (Tue); or take May 22–23 (Fri + Tue) → 4 or 5 days off
Travel Advisor Tip:
If you’re considering Europe, spring is the sweet spot. Book flights early, but keep accommodations flexible enough to lean into shoulder-season perks like lower rates and gentler crowds.
Best for:
Those who want beauty and balance — moderate temperatures, blooming scenery, and destinations that feel alive without feeling overwhelming.
Summer Adventures (July – September)
Best paired with:
✓ Independence Day
✓ Labor Day weekend
Summer brings longer days, easier schedules, and destinations that shine in warm weather.
Where I recommend:
New England: Nantucket, Maine’s coastal towns, Cape Cod
Basque Country, Spain — coastal charm, pintxos culture, and relaxed seaside living
Canadian Rockies for dramatic scenery, alpine lakes, and glacier views
Croatia’s Dalmatian Coast — ideal for island hopping, crystal-clear water, medieval seaside villages, and effortless Adriatic summer energy
Greece — incredible mediterranean waters, prime weather, and excursion or relaxation options for all parties
PTO Strategy:
→ Independence Day: July 4 (Sat) → Take July 2 (Thu) OR July 6 (Mon) → 4 days off
→ Labor Day: Sep 7 (Mon) → Take Sep 4 (Fri) OR Sep 8 (Tue); or Both → 4 or 5 days off
Travel Advisor Tip:
Summer fills fast — especially coastal and island destinations. If you’re eyeing Europe or national parks, plan at least 4–6 months ahead for the best hotel selection and flight pricing.
Best for:
Sun seekers, outdoor enthusiasts, families, and anyone who loves long days, easy travel logistics, and “let’s just go” seasonal energy.
Fall & Holiday Getaways (October – December)
Best paired with:
✓ Veterans Day
✓ Thanksgiving
✓ Christmas & New Year’s holiday weeks
Fall is one of my favorite times to travel — crisp weather, lighter crowds, and the ability to stretch PTO further thanks to consecutive holidays.
Where I recommend:
Ireland or Scotland for cozy pubs, dramatic landscapes, and the changing leaves of fall
Morocco — October and November are spectacular for exploring Marrakech, the Atlas Mountains, or coastal towns like Essaouira without the summer heat
Mexico for Día de los Muertos (Day of the Dead) or a warm beach break
Germany, Austria, or Prague + Budapest for magical Christmas markets. You can explore by river, land, or both!
South Africa for its warm spring/summer weather, lower crowds than peak season, and the ability to pair cities, wine country, and safari in one trip.
PTO Strategy:
A single PTO day around Thanksgiving or Christmas can turn a short break into a meaningful getaway — perfect for escaping holiday chaos or celebrating somewhere new.
→ Indigenous Peoples’ Day: Oct 12 (Mon) → Take Oct 9 (Fri) or Oct 13 (Tue) → 4 days off
→ Veterans Day: Nov 11 (Wed) → Take Nov 10 and Nov 12 → 5 days off
→ Thanksgiving: Nov 26 (Thu) → Take Nov 28 (Fri) → 4 days off
OR take Nov 24 + 28 (Tue + Fri) → 6 days off
→ Christmas: Dec 25 (Fri) → Take Dec 24 (Thu) or Dec 28 (Mon) → 4 days off
or take Dec 21–24 → 6–7 days off
→ New Year’s 2027: Jan 1 (Fri) → Take Dec 29–31 → 9 days off
Travel Advisor Tip:
Fall is when your PTO goes the farthest. Take advantage of built-in holidays and book early if Christmas markets or long-haul destinations (like South Africa) are on your wishlist — they fill faster than you think.
Best for:
Travelers who appreciate cooler temps, cultural experiences, holiday charm, or meaningful escapes before year-end.
The Goal Isn’t “Travel More” — It’s “Travel Intentionally”
When you zoom out and look at the year as a whole, there are so many natural opportunities to take meaningful breaks — even if you use only 1–2 PTO days at a time.
Your 2026 PTO isn’t just time off.
It’s space to reconnect with yourself, with the world, and with the people you love.
And with a little strategy, it can take you further than you think.
Ready to Plan Your 2026 Travel Intentionally?
Whether you’re dreaming of one big adventure or a few perfectly-timed long weekends, I’d love to help you outline a plan that fits your schedule, your pace, and your personal travel style.