If you're someone who looks at the calendar every January and wonders how to squeeze more travel into a limited number of vacation days, consider this your 2027 cheat sheet.
The secret to traveling more isn't necessarily having more PTO. It's knowing how to use the days you already have.
With a little planning around U.S. federal holidays, you can turn a long weekend into a proper escape, or four vacation days into nine days away. And if you start planning now, you have a better chance of securing the hotels, flights, and experiences you actually want.
Below, I've broken down the 2027 U.S. holiday calendar, exactly which days to request off, and where I'd recommend traveling based on the time of year and how long you can realistically be away.
Because a great vacation should feel like a vacation, not a race to fit everything in.
Quick tip: These recommendations assume a traditional Monday–Friday workweek and that your employer observes the listed holidays. Always check your company's calendar before booking.
2027 U.S. Federal Holidays (Observed Dates)
New Year's Day: Friday, January 1
Martin Luther King Jr. Day: Monday, January 18
Presidents' Day: Monday, February 15
Memorial Day: Monday, May 31
Juneteenth: Friday, June 18 (observed)
Independence Day: Monday, July 5 (observed)
Labor Day: Monday, September 6
Columbus Day / Indigenous Peoples' Day: Monday, October 11
Veterans Day: Thursday, November 11
Thanksgiving: Thursday, November 25
Christmas: Friday, December 24 (observed)
Bonus: Good Friday falls on March 26, 2027. It's not a federal holiday, but some employers and schools observe it.
January: Start 2027 Somewhere Wonderful
New Year's Day: Friday, January 1
PTO Play: 5 PTO Days = 10 Days Off
Take off: Monday, January 4–Friday, January 8
Travel window: January 1–10
If you're ready to start the year somewhere other than your living room, this is an excellent opportunity to get away.
Where I'd go:
Mexico City + San Miguel de Allende: Start with Mexico City's museums, markets, restaurants, and design-forward hotels before heading to San Miguel for a few slower days.
Costa Rica: Pair the Arenal Volcano region with the beaches of Guanacaste for an ideal combination of adventure and relaxation. A self-drive trip gives you flexibility and opportunity to explore. Go through local company Vamos Rent-A-Car.
Thailand: Bangkok plus a few days at a beach resort is a wonderful way to begin the year, especially if you're looking for sunshine.
Martin Luther King Jr. Day: Monday, January 18
PTO Play: 4 PTO Days = 9 Days Off
Take off: January 19–22
Travel window: January 16–24
Where I'd go:
Cartagena, Colombia: Colorful streets, Caribbean warmth, excellent restaurants, and beautiful boutique hotels.
St. Barts or Anguilla: A winter Caribbean escape with fantastic hotels and beaches.
Scottsdale + Sedona: Desert landscapes, spas, art, and plenty of opportunities to spend time outdoors.
February: Trade Winter for Something Better
Presidents' Day: Monday, February 15
PTO Play: 4 PTO Days = 9 Days Off
Take off: February 16–19
Travel window: February 13–21
February is one of my favorite months to recommend a warm-weather escape, although there's also something to be said for embracing winter in the mountains.
Where I'd go:
Rajasthan, India: Explore Jaipur, Udaipur, and the extraordinary palace hotels of Rajasthan. Nine days makes a lovely introduction, although I'd recommend more time if possible.
Morocco: Marrakech paired with the Atlas Mountains or Agafay Desert offers culture, beautiful hotels, and an entirely different pace.
Park City or Jackson Hole: For anyone who would rather lean into winter, this is a prime opportunity for a ski vacation.
Advisor tip: Presidents' Day overlaps with school vacation schedules in many parts of the country. If you want a particular hotel or suite category, plan well ahead.
March and April: Don't Overlook Spring
There isn't a federal holiday in March or April, but that doesn't mean you should skip spring travel.
Good Friday: Friday, March 26 (for those who have it off)
PTO Play: 4 PTO Days = 9 Days Off
Take off: March 22–25
Travel window: March 20–28
Where I'd go:
Japan: Cherry blossom season typically begins in parts of the country around late March, although peak bloom varies by destination and year.
Andalusia, Spain: Seville, Córdoba, and Granada are beautiful in spring, although Holy Week can bring significant crowds.
Washington, D.C. + Virginia Wine Country: Cherry blossoms, museums, historic hotels, and a countryside escape.
If Good Friday isn't part of your company's holiday calendar, this itinerary requires five PTO days instead of four.
May: The Unofficial Start of Summer
Memorial Day: Monday, May 31
PTO Play: 4 PTO Days = 9 Days Off
Take off: June 1–4
Travel window: May 29–June 6
Late May and early June can be a particularly wonderful time to travel before the busiest summer weeks arrive.
Where I'd go:
Portugal: Lisbon, Porto, and the Douro Valley offer a fantastic combination of food, wine, architecture, and beautiful hotels.
Greece: Athens paired with Paros, Crete, or another island is a lovely introduction before peak summer.
Italy: Florence and Tuscany, or Rome paired with the countryside, make excellent nine-day itineraries.
Advisor tip: Don't try to squeeze three or four destinations into every European vacation. Two thoughtfully selected stops can be much more rewarding.
June: Make the Most of Juneteenth
Juneteenth: Friday, June 18 (observed)
PTO Play A: 4 PTO Days = 9 Days Off
Take off: June 14–17
Travel window: June 12–20
Where I'd go:
Ireland: Dublin plus the countryside, with beautiful manor houses, coastal scenery, and plenty of excellent food.
France: Paris and Champagne, or Paris paired with the Loire Valley.
Canadian Rockies: Banff and Lake Louise for dramatic scenery, hiking, and luxury mountain lodges. Some higher-elevation trails may still have snow.
PTO Play B: 1 PTO Day = 4 Days Off
Take off: Monday, June 21
Travel window: June 18–21
For a shorter escape, consider Nantucket, Newport, or Charleston.
July: A Summer Vacation Without Using All Your PTO
Independence Day: Monday, July 5 (observed)
PTO Play: 4 PTO Days = 9 Days Off
Take off: July 6–9
Travel window: July 3–11
Where I'd go:
Croatia: Split and the Dalmatian Islands are ideal for travelers who love boating, beautiful waterfront hotels, and historic towns.
French Riviera + Provence: A classic summer pairing of Mediterranean beaches, markets, vineyards, and countryside hotels.
Montana + Wyoming: Explore Yellowstone and Grand Teton National Parks with comfortable lodges and private guiding.
Advisor tip: This is peak travel season in many destinations. Flights and premium hotel rooms can be in high demand, so earlier planning matters.
September: My Favorite Time for a European Escape
Labor Day: Monday, September 6
PTO Play: 4 PTO Days = 9 Days Off
Take off: September 7–10
Travel window: September 4–12
September is one of my favorite months for travel. Summer crowds begin to thin, the Mediterranean is still warm, and many destinations are at their best.
Where I'd go:
Greece: Paros, Milos, or Crete for warm seas, beautiful boutique hotels, and a more relaxed atmosphere.
Spain: Madrid and Rioja for art, architecture, outstanding food, and wine country.
Portugal: Lisbon paired with Comporta or the Algarve for a city-and-beach vacation.
If you're a wine lover, this is also a wonderful time to consider European wine regions, although harvest timing varies.
October: Fall Colors, Wine Country, and Culture
Columbus Day / Indigenous Peoples' Day: Monday, October 11
PTO Play: 4 PTO Days = 9 Days Off
Take off: October 12–15
Travel window: October 9–17
Where I'd go:
New England: Vermont, the Berkshires, and Hudson Valley for fall foliage, beautiful inns, and cozy restaurants.
Spain: Barcelona and Rioja, or Madrid and the Basque Country, for food and culture.
Morocco: October is an excellent time to explore Marrakech, the Atlas Mountains, and beyond.
This is also an excellent window for a shorter domestic getaway if you don't want to use all four PTO days.
November: Two Excellent Opportunities to Get Away
Veterans Day: Thursday, November 11
PTO Play A: 1 PTO Day = 4 Days Off
Take off: Friday, November 12
Travel window: November 11–14
Where I'd go:
New York City: Restaurants, theater, galleries, and a beautiful hotel.
Charleston: Historic neighborhoods, excellent food, and mild fall weather.
Santa Fe: Art, galleries, desert landscapes, and wonderful spas.
PTO Play B: 4 PTO Days = 9 Days Off
Take off: November 8–10 and November 12
Travel window: November 6–14
For a longer trip, consider Mexico, the Caribbean, or a cultural escape to Spain.
Thanksgiving: Thursday, November 25
PTO Play: 4 PTO Days = 9 Days Off
Take off: November 22–24 and November 26
Travel window: November 20–28
If your employer already gives you the Friday after Thanksgiving off, you only need three PTO days.
Where I'd go:
Vienna + Prague: A wonderful opportunity to enjoy the beginning of Europe's Christmas market season. Confirm individual market opening dates before booking.
South Africa: Cape Town and the Cape Winelands, where late spring brings beautiful weather for exploring.
Mexico City: Art, food, architecture, and a fantastic restaurant scene.
Thanksgiving can also be a good opportunity for families to travel together, particularly if everyone has overlapping school and work schedules.
December: The Best PTO Opportunity of the Year?
Christmas: Friday, December 24 (observed)
PTO Play A: 4 PTO Days = 9 Days Off
Take off: December 20–23
Travel window: December 18–26
Where I'd go:
Austria + Germany: Christmas markets, festive hotels, historic towns, and winter traditions.
Switzerland: Alpine villages, mountain resorts, and spectacular winter scenery.
Caribbean: Anguilla, St. Barts, or the Bahamas for anyone dreaming of sunshine instead of snow.
PTO Play B: 4 PTO Days = 10 Days Off
Take off: December 27–30
Travel window: December 24–January 2, 2028
Here's where things get especially interesting.
Christmas Day falls on a Saturday in 2027, so the federal holiday is observed on Friday, December 24. New Year's Day 2028 also falls on a Saturday, meaning the federal holiday is generally observed on Friday, December 31, 2027.
If your employer observes both dates, taking just four days off between Christmas and New Year's gives you 10 consecutive days away.
Where I'd go:
India: Rajasthan, Mumbai, or a longer itinerary combining culture, architecture, and extraordinary hotels.
Thailand: Bangkok and the islands for a warm-weather holiday.
South Africa: Cape Town and the Winelands, with the option to extend into safari country if you have more time.
This is one of the busiest and most expensive travel periods of the year, particularly for luxury hotels and premium flights. It's worth planning well in advance.
A Few Things to Remember Before Booking Your 2027 Vacation
A clever PTO calendar is only part of the equation.
The right destination depends on the season, flight schedules, how much time you have, and what you actually want from your vacation.
A four-day getaway to Charleston is very different from a nine-day vacation in Europe. And while nine days might sound like plenty of time, long-haul flights and time-zone changes can make a packed itinerary feel rushed.
This is where working with a travel advisor makes a difference.
I help clients think through the entire experience, from choosing the right destinations and hotel combinations to arranging transfers, private guides, restaurant reservations, and those special experiences that make a trip memorable.
Through my preferred hotel partnerships, clients may also receive additional amenities and benefits at participating properties, depending on the hotel and rate.
The goal isn't simply to travel more. It's to make the time you have count.
Ready to Put Your 2027 Vacation Days to Good Use?
Whether you're planning a quick long weekend, a European summer vacation, a milestone celebration, or a two-week escape over the holidays, now is the time to start looking at the calendar.
Some of the best hotel rooms, guides, and experiences are booked many months in advance, especially around major holidays.
Let's make those vacation days count. Start Planning Your 2027 Travels
Holiday dates are based on the U.S. Office of Personnel Management's published federal holiday schedule. PTO recommendations assume a Monday–Friday workweek and employer-observed holidays. Individual company policies may vary.
