Winter in London: Cozy 5-Day Guide

I recommend taking the overnight flight to London to reduce the risk of jet lag and make the most of your valuable vacation time. You'll likely land at London's Heathrow airport in the early to mid-morning hours. The fastest way into the city is by taking the Heathrow Express train that leaves directly from inside each terminal every 15 minutes and drops you at London's central Paddington Station. Your chauffeur will be waiting to take you to your hotel to drop off your bags or take advantage of early check-in (subject to availability) to freshen up in your room. A direct car transfer for the ~1 hour drive from Heathrow to Central London for families with young children or those with lots of luggage is also a wonderful option.

If you're still feeling peckish after the breakfast served on the flight, I recommend stopping by your hotel's lobby restaurant for a quick bite. But don't fill up too much, because today's plans are for a traditional Afternoon Tea at Soho House's Dean Street Townhouse. The fireplace and cozy deep sofas in the tea room of this centrally located hotel and restaurant are the perfect place to curl up and get in the British spirit for the rest of your trip. While the food and tea are every bit as exquisite as those at the Ritz, this is a much more casual tea service with no dress code. It is a perfect stop for a travel day.

After tea, browse through the vintage shops and local brand stores in the winding streets of Soho. Tonight, catch a show at one of the world-class West End theaters. Grab a classic fish and chips at Rock and Sole Plaice and head back to your hotel for a bit of an early night.

Now that you're settled in, enjoy complimentary breakfast at the hotel restaurant or indulge in room service to really let the vacation vibes set in. I like to use my second day in a location to get the lay of the land and see all the major sights. I find that this makes the rest of my trip feel much more comfortable. It also lets me prioritize where in the city I want to explore most or pose for a couple of pictures.

No trip to London is complete without a visit to good old Big Ben and Parliament Square. The Palace of Westminster (on which Big Ben sits) is a stately and elegant monument to British architecture and history. Set against the typically periwinkle gray skies of London in the winter, it is quite mesmerizing. Westminster Abbey is also here and is worth a visit.

From here, hop on a ferry at Westminster peer and take a 30-minute scenic cruise down the River Thames. While on board, enjoy a warm mulled wine and take advantage of the leisurely pace to relax while the sights of London float by. Shortly after passing under London Bridge, hop off the ferry at Tower Bridge Quay to tour the Tower of London. See the controversial but magnificent Crown Jewels up close and personal.

By now, you're probably getting hungry. Take a quick 15-minute walk or bus ride across London Bridge to get to Borough Market under the shadow of the iconic Shard skyscraper. Here you'll find everything from fresh fruits and vegetables to local English wine merchants to Spanish tapas. There are also some great sit-down restaurants in the surrounding side streets. I recommend literally following your gut, as most places here are quite good.

From lunch, hop back on the ferry heading further east to Greenwich. Home to the beautiful Old Naval College and Queen's House, Greenwich is also a very cozy and intimate village that feels like it's straight out of a storybook. Be sure to stop by the Chapel of St. Peter and St. Paul while your at the Naval College for some truly gorgeous frescoes and woodwork (plus it's free!). Take a stroll up the hill at Greenwich Park to visit the Prime Meridian at the Royal Observatory to straddling the Eastern and Western Hemispheres at the same time. This is also one of my favorite views of London from the south.

Take the train back to the hotel for a quick afternoon nap to recharge. Or, if you're not the napping type, stop by Daunt Books and curl up with a cozy read.

Dinner tonight is at Bob Bob Ricard Soho, an all-booth, only in London, maximalist fantasy with "Press for Champagne" buttons at each table. This might not be the most memorable food you'll have in London, but it is a unique experience that demonstrates the flamboyance and diversity that has thrived in London for most of its history.

Now that you've covered a broad stretch of the city, it's time to focus in on the things you like to do. Days three, four, and five are interchangeable depending on your preferences and the specific days you're visiting. If a place or a neighborhood caught your attention on Day 2, reach out for personalized recommendations or let them come to you by exploring on foot. In the mood for some shopping? Stop by Harrod's in Knightsbridge for the ultimate in luxury and elegance. Be sure to spend some time admiring the magnificent architecture of this Grade II historically listed building. I recommend coming in the late afternoon when its lights will be on for the ultimate cozy London vibes.

Take a nice walk down the side of Hyde Park and past Wellington Arch on your way to Buckingham Palace (only worth a quick stop for some pictures) and St. James's Park. St. James's is my favorite park in central London. It has a surprising array of birds and beautiful natural landscaping. You'll feel like you're in the British countryside. St. James's Cafe is also a wonderful stop for a quick coffee and a treat.

By now you'll be close to where you started Day 2 in Parliament Square. Double down on your favorite spot from that introductory visit or, if you're looking for something new, visit the Churchill War Rooms underneath the Cabinet Offices. You'll need to book a tour to visit (I can help arrange this), but it's well worth setting some dedicated time aside to experience the secret headquarters from which Winston Churchill helped lead the Allied forces in a moment of great tragedy and triumph for the world. You'll be able to see actual maps used in planning the war effort, and tour where Churchill slept to be ready 24/7 to react to news from the front.

The Victoria & Albert Museum is a huge art museum with an exquisite permanent collection and some of the best exhibitions I've ever experienced at any museum. It's worth having your travel advisor arrange a private tour of the museum to fully appreciate the scale and impact of the collection. If you'd rather make this a shorter stop, be sure to visit the Islamic Middle East hall (Room 42) for some of the most exquisite carpets in the world.

Take a 15-minute stroll through picturesque Kensington past historic mews and stately mansions for lunch at Locanda Ottoemezzo (note that they're only open for lunch Tues-Thurs). This cafe is right out of Italy and has superb panini. While you're nearby, take a quick peak at Kensington Palace to see if you can spot any junior royals. Then make your way down bustling Kensington High Street to the Design Museum. Here you'll find an anthology of humans' best work from calculators to lamps, from maps to street signs and everything in between.

Hop on a double-decker bus and enjoy the views of Kensington Gardens and Hyde Park on your way back to the hotel to freshen up for the night.

Tonight is a perfect opportunity to experience the nightlife of one of the world's buzziest cities. Pop downtown to Swift Soho's downstairs reservations-only bar for a fantastic whisky list and finely crafted cocktails in a cozy leather booth or velvet armchair. Right around the corner, Ronnie Scott's. A mainstay in the London jazz scene and has plentiful cozy seating to settle in for a nice long night or for a quick stop before you step back out on the town.

If bar snacks aren't enough to hold you over, stop by dimly lit steakhouse Blacklock Soho for excellent prime cuts and craft cocktails served from trolleys tableside.

Your last full day in London should be about revisiting the places you think you missed or fell in love with and want to experience again. I often recommend dropping the pressure of seeing one more place on the last day. Traveling isn't about seeing all of a city or destination, but rather about making memories that matter and having fun. Give yourself a day to revel in what you've loved the most about this unique and spectacular city.

I also always recommend a massage on the last day of a trip (especially if you have an earlier morning flight). It helps to lock in that post-vacation bliss and prepare yourself for the flight home. The coziest option is Aire Ancient Baths, right off The Strand. Alongside your massage, you can enjoy thermal baths with modern appointments in a historic location. If you're more into ultimate luxury and pampering, Claridge's London in ritzy Mayfair is a stunner.

Relaxed and refreshed, head back to your hotel for your final night away feeling better than ever.