5 Romantic Cities to Visit This Winter

By Amanda Wowk

January 26, 2023

Whether it’s a trip to celebrate Valentine’s Day, practice self-love, or simply turn up the heat on winter, here are five cities that up the romantic ante—and are perfect for visiting in the chilly months of the year. 

1. Ljubljana, Slovenia

Kicking off the list is the city with love—that’s ‘ljub’—right in the name: Ljubljana, Slovenia. And you will fall in love with this beautiful city. 

Winter itinerary: Stroll the charming streets of Ljubljana; sip local wine from one of the country's three wine regions—Primorska, Podravje, and Posavje; and dine on local fare. Rented a car? Head to Hiša Franko, helmed by chef Ana Roš, one of the world’s 50 best restaurants. 

2. Paris, France 

The quintessential city of love, Paris shines for a wintertime trip. Fewer crowds mean more room to cozy up at a table for two—with a view of the Eiffel Tower, of course. 

Winter itinerary: If this is your first time in Paris, immerse yourself in what the city has to offer: world-class museums, restaurants, shopping, and more. If this isn’t your first time, dig deeper into what’s a meaningful experience to you. Love to cook? Book a cooking class with a local chef. Love French wine? (Girl, same.) Find a wine tour, like Paris Wine Walks, to learn about the myriad wine-producing regions of France. There’s much to be explored in the City of Light. 

3. San Diego, California 

From the city to the sea, San Diego lures visitors with its year-round sunny disposition. So, a winter getaway to this Southern California beach town is kind of a no-brainer. Hint, hint. 

Winter itinerary: By day, rent a Pedego electric bike and pedal your way around Balboa Park—a beautiful 1,000-acre park home to museums, botanical gardens, and the San Diego Zoo. By night, head to Kettner Boulevard for a romantic meal at hotspots like Juniper & Ivy, Kettner Exchange, and Herb & Wood

Want more trip inspo? Check out our City Break: San Diego guide

4. New York, New York 

While you might not think of winter as a romantic time in NYC, hear me out: There’s Central Park covered in a fresh layer of snow (swoon, right?); less expensive accommodations (which your wallet will love); plus NYC Restaurant Week and NYC Broadway Week—meaning you can dine before showtime at a doubly discounted rate. 

Saving money on once-in-a-lifetime experiences? So in style. And so New York. 

Winter itinerary: Check out NYC Restaurant Week for participating restaurants and to book your table. Ditto for NYC Broadway Week. Not visiting during those dates? You can always check TodayTix for discounted Broadway shows all winter (and year) long. 

DYK? TripIt helps you save money on travel—from tracking when airfare drops in price to displaying the cost of local transportation options. Learn more. >

5. Orlando, Florida

According to TripIt data, Orlando consistently ranks as a top destination for U.S. travelers. 

Between the warmth, world-renowned theme parks, and overall magical vibe, it’s easy to see why many spend the most romantic day of the year there. (It’s a top destination for getting engaged and married, too!)

And the weather this time of year? It’s called the Sunshine State for good reason, plus there’s much—much!—less humidity compared to the other three seasons.

Winter itinerary: Head to the Orlando Museum of Art to check out the traveling “Don’t Ask Me Where I’m From” exhibition, followed by dinner at Knife & Spoon

Want more date night ideas? Check out our City Break: Orlando guide.