City breaks remain an incredible escape for couples because they offer the perfect blend of intensity and ease: an exhilarating mix of new culture, world-class dining, and iconic sights, yet with moments of rest and relaxation all in one.
Discover the best luxury city breaks for couples this winter, knowing that any break is made profoundly better by the curated expertise and insider knowledge of our Luxury Travel Specialists. These five destinations promise refined warmth, timeless charm, and unforgettable shared moments.
Chicago
![Chicago city skyline against blue sky]()
Chicago
Chicago in the winter months is an absolute must. I would recommend doing it as a four-day city break so that you have some time to explore. I took an unforgettable Architectural River Cruise, saw the skyscrapers and iconic architecture, and loved shopping on Magnificent Mile. There are also some legendary blues and jazz clubs that are well worth a visit.
I stayed at
Pendry Chicago, which is perfectly positioned in the Loop, steps from the Magnificent Mile and Chicago's cultural highlights. It's set within the iconic 1929 Art Deco Carbide & Carbon building, with stylish interiors and vibrant dining.
- Elyse, Luxury Travel Specialist
Why Visit in Winter?
- Christmas shopping for yourself or loved ones on Magnificent Mile
- Warm up with some of Chicago's famous dishes, like the deep-dish pizza or Chicago hotdogs
Helsinki
![Architecture of Helsinki]()
Helsinki
Finland's capital is at its best during the winter, offering a fabulously festive city break. Its cosy culture and charming atmosphere make it the perfect place for winter, with cobbled streets, festive markets, and historic landmarks. It's also a great base from which to venture further into Finland's arctic allure, with Lapland as an extension.
Why Visit in Winter?
- Short daylight hours add to the magic with spectacular light displays
- Browse the crafts of the Helsinki Christmas Market
- Twin this city break with Lapland and discover a true winter wonderland
Marrakech
![Market stalls in the evening]()
Jamaa el Fna, Market place, Marrakech
Marrakech boasts the perfect balance of winter warmth and city exploration. This short-haul dose of sunshine reaches highs of around 22°C this time of year, and the sunny yet mild days are perfect for wandering the souks or exploring palaces away from the peak crowds. The short flight time and no time difference also grant unmatched convenience that is perfect for a city break. You can truly make the most of your time in-destination.
Why Visit in Winter?
- Milder temperatures mean it's a more comfortable climate, yet still sunny
- Visit Inara Camp for an evening desert experience
- Warming and flavourful, Moroccan cuisine is perfect for winter
New York
![Looking up at christmas tree between two skyscrapers in New York City]()
Christmas in New York
Christmas in New York is a bucket-list staple. These iconic city streets have graced our screens in many a seasonal movie, making it the vision of a winter city break. Time your 2025 trip for the 3rd of December to see the lights switch on, though there are winter delights throughout the season.
With the buzz of Manhattan at your doorstep,
Pendry Manhattan West is ideal for a city break. This sleek, understated hotel offers sophisticated style and easy access to the best of NYC.
- Macy's is perfect for Christmas shopping
- Go ice skating at the world-famous Rink at Rockefeller
Dubrovnik
![View of the blue coast from terracotta rooftops]()
Dubrovnik from the city walls
Outside of peak season, Dubrovnik transforms from a bustling tourist destination into a remarkably quiet, living city. The reduced crowds reveal a peaceful retreat that is perfect for couples, set against a backdrop of stunning architecture, red-tiled roofs, and the golden glow of the winter sun-ideal for your photo album.
The cooler temperatures invite a hand-in-hand walk around the city walls, where you can take in the breathtaking views of the clear, dramatic Adriatic coast without the summer rush, making it a serene and intimate experience. Similarly, the cafes and restaurants are now tailored to locals over tourists, giving you a more personal and genuine immersion in the city's coastal life and culture.
Why Visit in Winter?
- The cable car up Mount Srd grants a breathtaking view of the coast with the low winter sun
- Visit from December to early January for the Dubrovnik Winter Festival