2027 Long Weekends: How to Turn 4 PTO Days Into a Week Away

Here's the move: take a US holiday, add four PTO days, and you've got a full week somewhere epic. Below is every 2027 long weekend lined up with the SYB trip that fits it, so you can block the dates before your coworkers do.

How we count PTO: the weekdays inside the trip dates, minus the holiday. Long-haul trips (Bali, Kenya, the Philippines) can need an extra travel day.

2027 long weekends at a glance

• New Year's Day, Fri Jan 1: Nicaragua, Bali or Belize · 3 to 4 PTO days
• MLK Day, Mon Jan 18: Chamonix ski week · 4 PTO days
• Presidents' Day, Mon Feb 15: Zermatt, Nicaragua, Guatemala or the Philippines · 3 to 6 PTO days
• Easter, Sun Mar 28: Nicaragua · 4 PTO days, 2 if you get Good Friday and Easter Monday off
• Memorial Day, Mon May 31: the Sahara in Morocco · 4 PTO days
• Juneteenth, observed Fri Jun 18: Amalfi Coast, Norway or Kenya · 4 PTO days
• Fourth of July, observed Mon Jul 5: Iceland or the South of France · 4 PTO days
• Labor Day, Mon Sep 6: Amalfi Coast or Croatia · 4 PTO days

New Year's Day: Friday, January 1

The week between Christmas and New Year's is the easiest week of the year to take off. Spend it somewhere warm, with a crew.

New Year's Eve in Nicaragua
Sun Dec 27 to Sat Jan 2 · 4 PTO days
Surf lessons, a private catamaran day and the All White Party with fireworks on the beach.

New Year's Eve in Bali
Mon Dec 28 to Sun Jan 3 · 4 PTO days
The most epic adventure to finish off the year.

New Year's Eve in Belize
Tue Dec 29 to Sun Jan 3 · 3 PTO days
Reef days. Countdown nights.

More: all three New Year's Eve trips

Midnight toast, Nicaragua

MLK Day: Monday, January 18

Ski Yoga Spritz, Chamonix
Sat Jan 16 to Fri Jan 22 · 4 PTO days
A week skiing the French Alps for all levels, in a hotel five minutes from the main lift, with après every afternoon.

More: MLK weekend ski trip

Send it, Chamonix

Presidents' Day: Monday, February 15

The best long weekend of the winter, and four ways to spend it.

Swiss on the Rocks, Zermatt
Sat Feb 13 to Fri Feb 19 · 4 PTO days
A car-free alpine village, endless powder and the Matterhorn out every window.

Surf Yoga Beer, Nicaragua (singles only)
Sat Feb 13 to Thu Feb 18 · 3 PTO days
Single? Same. Spend Valentine's weekend in the surf.

Guat A Feeling, Guatemala
Tue Feb 9 to Mon Feb 15 · 4 PTO days
Volcano hikes, boat days on the lake and old colonial towns.

Islands of Palawan, Philippines
Wed Feb 17 to Tue Feb 23 · 6 work days off, door to door
Fly out on Presidents' Day night for a week of snorkeling, freediving and island hopping from Coron to El Nido.

More: Presidents' Day trips

Table for the whole crew, Zermatt

Easter: Sunday, March 28

Surf Yoga Beer, Nicaragua
Wed Mar 24 to Mon Mar 29 · 4 PTO days, 2 if you get Good Friday and Easter Monday off
Endless sun, easy waves.

Not tied to Easter? Nicaragua also runs Mar 19 to 24 and Mar 29 to Apr 3, there's a women-only week from Mar 14 to 19, and Finland brings huskies, reindeer and the northern lights from Mar 13 to 18.

More: spring break for adults

Spring break, grown-up edition

Memorial Day: Monday, May 31

Desert Dopeness, Morocco
Tue May 25 to Mon May 31 · 4 PTO days
All Sahara, all week: camels, ATVs, dunes, two nights in a desert camp and endless stars.

More: Memorial Day trips

ATV day in the Sahara

Juneteenth: Friday, June 18 (observed)

Juneteenth lands on a Saturday in 2027, so the federal holiday is observed on Friday, June 18.

Mambo Italiano, Amalfi Coast
Sun Jun 13 to Sat Jun 19 · 4 PTO days
Eat, love and spritz through the Amalfi Coast before the summer crowds land.

Fjord Almighty, Norway
Mon Jun 14 to Sat Jun 19 · 4 PTO days
Fjord hikes, white water rafting, floating saunas and an all white party, with nights in Voss and Bergen.

Safari Stylin', Kenya
Fri Jun 18 to Thu Jun 24 · 4 PTO days
Late June in the Masai Mara. We go when the herd starts to come.

Amalfi crew, flag up

Fourth of July: Monday, July 5 (observed)

The Fourth is a Sunday in 2027, so you get Monday the 5th off.

Fire & Ice, Iceland
Tue Jun 29 to Sun Jul 4 · 4 PTO days
Hike to waterfalls, volcanoes, glaciers and hot springs, then fly home with Monday off to recover.

Bonjour Cote d'Azur, South of France
Wed Jun 30 to Tue Jul 6 · 4 PTO days
Kayak the Calanques from Cassis, swim the Verdon Gorge, and spend the Fourth at a Saint-Tropez beach club.

More: Fourth of July trips

Waterfall crew, Iceland

Labor Day: Monday, September 6

Mambo Italiano, Amalfi Coast
Tue Aug 31 to Mon Sep 6 · 4 PTO days
Eat, love and spritz through the Amalfi Coast over Labor Day weekend.

Island Takeover, Croatia
Sat Sep 4 to Fri Sep 10 · 4 PTO days
The last great week of summer: workouts, boat days, cliff jumps and parties on a Croatian island.

More: Labor Day trips

Last swim of summer

FAQ

What are the long weekends in 2027?

New Year's Day (Fri Jan 1), MLK Day (Mon Jan 18), Presidents' Day (Mon Feb 15), Memorial Day (Mon May 31), Juneteenth (observed Fri Jun 18), Independence Day (observed Mon Jul 5), Labor Day (Mon Sep 6), Columbus Day (Mon Oct 11), Christmas (observed Fri Dec 24) and New Year's Day 2028 (observed Fri Dec 31). Thanksgiving is Thursday, Nov 25.

How many PTO days do I need for a week away?

Usually four. A Saturday to Friday trip over a Monday holiday only needs Tuesday to Friday off.

Can I come solo?

Yes. Almost everyone on our trips comes without a plus-one.

How does booking work?

A 20% deposit holds your spot, and the balance is due six weeks before the trip. Live dates and spots for every trip are on the calendar.