How to Plan "The Holiday" (Your Version)

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Advisor - Sarah Roof
Curated By

Sarah Roof

  • Boutique Travel

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  • Cotswolds

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Advisor - How to Plan "The Holiday" (Your Version)
Curator’s statement

If you, like me, can't get enough of cozy, romantic movies every holiday season--then this one is for you. The Cotswolds in England have always felt like the perfect setting for a cozy and romantic Christmas, much like the one in "The Holiday". With its charming honey-stone cottages, cobbled streets and beautiful countryside, it’s hard not to fall in love with this place during the holiday season. Picture wandering through small villages with twinkling Christmas lights, popping into a cozy pub for mulled wine or curling up by a crackling fire. It’s a destination that just feels like the holidays (and "The Holiday")—relaxing, intimate and full of that special festive magic that makes everything feel a little bit more heartwarming.

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Day 1: Arrive and explore London

You simply can't kick off your holiday without exploring the Christmas magic of London! Some of my top recommendations would be to grab a coffee or hot chocolate at Ralph's in the heart of Bond Street and explore the streetlights and decked-out department and designer stores like Fortnum & Mason, Dior, Chanel and Annabel's in Mayfair.

If crowds aren't really your thing, you can pop into a cozy pub like one of Mr. Fogg's iconic locations for some mulled wine and festive music. During this time of year, London has no shortage of things to do. Christmas markets, ice-skating rinks, traditional sightseeing and more make it a true winter wonderland — and there's even one of those, too.

Day 2: Afternoon tea and the English countryside

It wouldn't be a true UK adventure without a spot of afternoon tea, would it? Have a cozy morning sleep-in to get rid of the jet-lag and then head out for afternoon tea at one of London's most iconic spots. Personally, I recommend Brown's Hotel for a luxurious 5-star festive experience, but there are so many others to choose from as well! Some other tried-and-true favorites include Sketch, The Ritz and The Lanesborough.

Following your afternoon tea, it's time to get your rental car and head out into the English countryside. Only about 1.5 hours from London, the Cotswolds beckons (because it's time to check in!) Although driving on the left can be intimidating at first, you really will need your own car to get around the villages of the Cotswolds. Unfortunately, you can't have timeless, charming tiny villages and Uber. Don't worry though, as soon as you get on the M4, it's pretty much a straight shot. All you have to do is follow the crowd!

Now, many (if not all) hotels in the Cotswolds offer festive packages that cover an entire itinerary and meals--usually starting on Christmas Eve and running through the day after Boxing Day. So, if you're truly here for the holidays, once you check in, all you have to do is sit back and let yourself be dazzled by your chosen hotel's festive plans. Enjoy your festive Christmas Eve (or other December day!) dinner and wind down by one of your hotel's crackling fires (there's sure to be many to choose from).

Day 3: Cozy + Christmas

If you selected a Cotswolds Christmas package stay like we did, that means today is Christmas! (Even if you're following this itinerary outside of Christmas, today is for pure relaxation.) Have a delicious hotel breakfast in your pajamas, because you're not changing today. Afterward, treat yourself to a cozy bath, an afternoon nap, a coffee and reading by the fire, a Christmas movie marathon, you name it! Today, the world is your relaxation's oyster. After all, the holidays can be so full of hustle and bustle that many times we miss out on spending true time with those who matter most to us. That's what today is for.

After you've spent the day relaxing, you can decide to get all dressed up (or don't - stay in those PJs!!), enjoy the lovely Christmas dinner at your accommodation before you retreat for yet another luxurious slumber.

Day 4: A boxing day adventure

Whether it's Boxing Day or not, you simply must get out and explore the English countryside today! A Boxing Day walk is a traditional family activity in the UK. It's a time to get outside, enjoy the fresh air and get some exercise after all those Christmas biscuits! Borrow some wellies (think: rainboots) and get the local experience of exploring the area on foot. Throughout the area, you'll find the Cotswold Way. It is a 102-mile (164 km) walking trail following the western edge of the Cotswold Hills that winds through rolling hills and honey-colored stone villages. Now, no need to wear yourself out too much! A Boxing Day walk could always just be to the nearest village pub. Once you're finished, you can head back for another cozy bath or afternoon spent by the fire before yet another sumptuous dinner, likely hosted by your hotel (or one in a nearby village).

Day 5: Exploring the villages

Now that most of the shops have re-opened from the holidays, it's time to get out and explore! The Cotswolds are dotted with the cutest villages, each one with their own special charm. Some favorites include:

  • Bibury, where you can check out the gorgeous view in the heart of town at The Swan.

  • Bourton-on-the-Water, a sleepy little village marked by its collection of boutique shops along the river.

  • Cheltenham and Cirencester, which both boast incredible Christmas markets before the holiday season ends.

  • Stow-on-the-Wold, another village filled with the cutest pubs and boutique shops you can find.

  • My personal favorite, Upper and Lower Slaughter (home to some of the cutest, witchiest homes in the area) and Slaughters Manor House or Lords of the Manor Hotel. Here you can experience an incredible afternoon tea.

Advisor - Sarah Roof

Travel Advisor

Sarah Roof

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