How to Turn Presidents’ Day Weekend into a Romantic Valentine’s Getaway (With Just One PTO Day)
Valentine’s Day falls on a Saturday in 2026 which sounds perfect... until you realize it lands right in the middle of a regular weekend. Blink, and it’s over.
But this year, there’s a smart travel trick hiding in plain sight: Presidents’ Day falls on Monday, February 16 — giving you a built-in long weekend. Add just one PTO day on Friday, February 13, and suddenly you’ve got a 5-day window to take a proper romantic escape.
Whether you’re craving sunshine or snowflakes, here’s how to turn a typical holiday weekend into a mini-vacation you’ll both actually remember.
Your 5-Day Romantic Escape Plan
PTO Day: Friday, February 13, 2026
Valentine’s Weekend: Saturday, Feb. 14 + Sunday, Feb. 15
Bonus Holiday: Monday, February 16 (Presidents’ Day)
Back to Work: Tuesday, Feb. 17
That’s five days to travel, reconnect, and celebrate — without needing a full week off or using half your vacation days.
OPTION 1: Warm & Sunny — A Romantic Escape to Puerto Rico
Why it works: No passport needed, quick flights from most major U.S. cities, and a perfect mix of culture, beaches, and nature. It’s an easy choice if you’re looking to swap February’s chill for golden-hour cocktails and ocean views.
Sample 5-Day Itinerary for Puerto Rico
Day 1 (Friday)
Arrive in San Juan. Check into a stylish boutique hotel in Old San Juan or Condado. Stroll the colorful streets, then enjoy rooftop drinks with a view before dinner at a local gem.
Day 2 (Saturday – Valentine’s Day)
Spend the day exploring El Yunque National Forest — hike to waterfalls, take in the views, and stop for roadside empanadas. Head back for a couples massage and a romantic beachside dinner.
Day 3 (Sunday)
Take a catamaran out to the nearby islands of Vieques or Culebra. Think white sand, crystal-clear water, and no crowds. Pack a beach picnic or snorkel hand in hand.
Day 4 (Monday – Presidents’ Day)
Slow it down. Sleep in, sip coffee on your balcony, then explore the art and flavors of Santurce. Cap the trip with a visit to the glowing bioluminescent bay in Fajardo — a magical finale.
Day 5 (Tuesday)
Fly home feeling sun-kissed and truly recharged.
Stein Eriksen Lodge in Park City | Image Provided by Partner
OPTION 2: Cozy & Romantic — A Fireside Getaway in Park City, Utah
Why it works: Whether you ski or not, Park City offers dreamy mountain views, walkable charm, and just the right dose of luxury. Perfect for couples who want to lean into winter romance — fireplaces, hot tubs, and all.
Sample 5-Day Itinerary for Park City
Day 1 (Friday)
Fly into Salt Lake City and drive to Park City. Check into a cozy mountainside lodge or charming boutique inn. Enjoy a welcome dinner and evening soak in the hot tub.
Day 2 (Saturday – Valentine’s Day)
Hit the slopes at Deer Valley or Park City Mountain, or opt for a guided snowshoe adventure. Book a fireside couples massage and toast to your love with a candlelit dinner.
Day 3 (Sunday)
Spend the day browsing Main Street’s art galleries, shops, and local cafés. Add in a sleigh ride through the snow or sip wine at a cozy speakeasy.
Day 4 (Monday – Presidents’ Day)
Relax. Sleep in, brunch, then head to the spa or take a scenic gondola ride. Wrap up your trip with a chef’s tasting dinner or a private meal in your suite.
Day 5 (Tuesday)
Head home with that glowing, just-had-a-real-break energy.
