16 Ideas For Enjoying A Simply Luxurious Winter Holiday Season
Wednesday December 2, 2020

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Anticipation for the first ski of the season begins to simmer about mid-November when you realize that any first snow could mean the first ski is just the next day able to be enjoyed. And when that snow falls, the winter holiday season has begun in Bend. Even if sparse or no snow rests on the ground in town, 20 minutes away, the holiday playlist is turned on in the car, I bundle up with my freshly waxed skis and take the boys to the mountain for our first outing (Norman still runs alongside me, but now Oscar guards the car while he naps inside ;)).

Each year, it seems to be Thanksgiving announces the first availablility for skiing. I can remember my first Thanksgiving in Bend (I actually ventured out of town for the occasion), and when I came home, I found a foot and a half of snow on my porch. Yep, the winter season had officially begun.

However, what has changed each year as I get to know myself better and come to understand what truly makes the holidays special are the traditions, to-dos and festivities I make sure are part of my winter holiday celebration.

As we each move through our lives we begin to crystalize what activities, decorations, food, people, and events signify the winter holidays’ arrival, and thereby enable us to partake in such a way to make the season as special and as memorable as possible.

Especially being in the midst of a pandemic, it becomes all the more important to become clear about what makes the winter holidays feel like the holidays. A time of celebration, a time of joy in the everyday rituals that only happen this time of year. A time to gather (safely) and a time to just fully remember how awesome it is to be alive, to be loved and love and perhaps shake ourselves awake to what is truly important.

As I sat down over the weekend next to the fire while Norman napped away after our first outing to ski on the mountain (where the picture above was taken), I made up my list of activities and tasks for the season, tended to some gift and sale shopping and homed in on what I feel will make this year special and simply luxurious. Today I’d like to share with you 16 more ideas for enjoying a simply luxurious holiday season (visit the end of this post for past posts which share even more ideas and inspiration for the holidays) :

1.Buy the Winter Snow Pass (annual) or any necessary passes for outdoor winter activities

However you enjoy stepping outside and away from home (that is safe and within the bounds of your local health regulations), purchase the necessary passes to save time and increase ease.

I prefer to head up to the mountain in the morning, and often the shops are not open yet if I had forgotten to purchase the pass. So when November rolls around, I pop into a local ski store and pick it up whether or not we have had our first snow to decrease the amount of time it takes to be out playing in the snow (our pass is $30 for the entire winter season to enable free parking at the many Sno-Parks. This is for cross country and skate skiing as I don’t head to Mt. Bachelor for alpine skiing at ski resort).

2. Plan a day for the tree finding and decorating (& purchase a tree permit if necessary)

For $5, Oregonians can go out into the state forest and cut down their own tree. While I sometimes change the day when I will make the trek, I purchase my pass around Thanksgiving so that it is with me and ready to go whenever I choose to go hunting for the holiday tree.

Making this day an occasion has been a tradition I have kept for many years, as it is special. The rearranging of the furniture is tended to, the holiday tunes ring throughout the house and the car during the trek to the mountain, a favorite winter or Christmas movie is chosen (sometimes two), and the necessary ingredients are picked up at the store so a comfort meal can be savored once the tree is all aglow its first night.

3. Plan and shop for the gifts to give the special individuals on your gift list

The individuals on my gift list may not be long, but it is intentional, and I want to purchase something they would sincerely enjoy. Taking advantage of the holiday Black Friday and Cyber Monday deals (technically an entire weekend now of sales this year), my goal is to always have a list ready before these two days and make sure anything I need to purchase takes place just after Thanksgiving so I can relax and just enjoy each day of December knowing enough time has been given for the shipping to have time to arrive prior to the 25th (if shipping is needed).

4. Outdoor decorations

Simple or grand, wobbly lines of Christmas lights or stick straight color schemes, the simple joy and delight brought to the neighborhood when the lights and winter decor goes up is a fun task. After all, while we are inside our homes, we actually don’t have the opportunity to enjoy our creations, but we sure do when our neighbors decorate their homes. As one of the young neighbors encouraged with a sign near the neighborhood mailboxes, “Do it for the children!” Well, in that vein, we’re all children, and it so much fun to contribute and to witness each year.

This year, as you can see below, I picked up a handful of cedar garlands at Trader Joe’s as well as a pair of fresh boughs. Then, I made my own boughs. I removed their ribbon and added fresh red berries and eucalyptus as well as spruced it up a bit. A simple approach, and I was able to make it my own without breaking the bank and still bringing fresh foliage to the front porch.

5. Add a fresh wreath to the front door

While many decorations may be reusable each year, faux garlands and pinecones for example, I try to purchase a fresh wreath for the front door. This year I was a little late in ordering, but my wreath full of eucalyptus and pepperberries should arrive next week (see below). A simple luxury I treat myself to, but many of them dry very well and can be used again. For example, the one I purchased last year now will hang on my garden porch door and looks perfect framed inside the white wooden screen door without an extra cent spent.

6. Order the holiday greeting cards early

I thoroughly enjoy the tradition of thoughtfully choosing the holiday card, personalizing it in some way and carving out an afternoon to sit down (next to the tree perhaps!) and write a short personal note to each person on my list, people who I often only hear from and they from me, once a year.

As our life journeys move our lives to and from different towns, our travels introduce us to new friends, this seasonal connection is invaluable for letting them know we still hold them fondly in our minds and hearts even if we are not able to see them as often as we might have done in the past.

This year I purchased my cards from Minted.com as they offer a long list of independently designed cards from small and single-entrepreneurial owned businesses. Currently, they are still having a sale – 25% off, +free shipping with BF2020 (this may have changed, but take a look at their recent sale promo code).

7. Indoor decorations

My indoor decorations are few and last yea I made a significant edit, donating anything that no longer fit how I enjoy decorating (this created more free space on the storage shelves as well), but I love the festive cheer they bring to the home. I usually wait until the day I bring my tree home, so to entirely change the interior aesthetic in one swoop of energy. From the mantle, tabletops, and stockings hanging above the fireplace, these details gradually have become more customized to my life journey, and in so doing bring even more warmth and cosy into the house.

8. Plan a New Year’s Eve and/or Day tradition

2020. I think we are all ready for this year to be done. Of course, we don’t know what awaits in any new year, but perhaps we step forward with more gratitude for what we may have taken for granted when 2020 arrived. However you feel about the arrival of the new year, make the shift into 2021 one that works for you. My New Years plans have always been rather quiet, so this year won’t change too much. And I am perfectly fine with that. But with that said, I am making plans as I want something to look forward to. Do what you can to make your own plans for something to look forward, for something to hope for – a fresh start, a clear-eyed beginning.

9. Tend to the paperwhites and other winter bulbs

New this year, I have welcomed paperwhite narcissus bulbs into my home, and I cannot wait to enjoy their brilliant white blooms as the new year begins. Symbolic, simple and beautiful.

10. Make a small sweet treat for neighbors

Depending upon where you live and what your connections are to your neighborhood, making a sweet treat for either your neighbors or close friends and family to be delivered (make an occasion of it and add a bundle of festive tunes while you commute to each house – or however you are delivering them – perhaps just to the post office :)).

11. Plan and shop for once-a-year holiday meals, treats and sweets

Every year around the holidays certain dishes, desserts and drinks are enjoyed, and only once a year do they make an appearance. Waiting 12 months to savor such specialties is worth it and makes that first bite or sip all the more wonderful. Tune in on Saturday December 12th to discover three of my holiday favorite recipes when I will step into the kitchen for the first holiday episode of The Simply Luxurious Kitchen.

12. Keep an eye open for holiday linens and decor which fit your home holiday decor

It seems I often forget what I need until right before the holiday occasion arrives when it comes to particular dishware, linens and so on. However, I am getting better at keeping a look out for beautiful, eye-catching decor details that can be purchased for great deals during this time of year. In time, what we use and need finds its way into our lives if we gradually and thoughtfully bring one item into the home this year and another the next or throughout the year. Have patience and have fun. The more you begin to get to know how you enjoy entertaining and celebrating, the more clear you will be as to what to purchase.

13. Find a way to give, help, volunteer in a way that works for you

Understandably, volunteering may look a little bit different this year, but it all depends upon your community, what those in your local area need and how you can help. Explore the local newspaper, online postings, local hospital, shelters, etc. and ask what is needed during this time. Make a decision to give in a way that allows you to feel safe but also give what you can. More and more volunteering and helping is shifting to the virtual world at the moment, so perhaps someone needs a tutor or simply someone to talk to. Most importantly, simply be there for your friends and family. Extending kindness during this time of year is a reminder of what we all want the entire year.

14. Find a great playlist or two or three and start playing what puts you in a festive mood

I shared my holiday playlist a couple of years ago, and I still play and enjoy it each December (from jazz to pop to classical to contemporary to you name it, I’ve included it – in terms of being simply luxurious :)). I will also turn on KUSC’s holiday classical music station. There is something toe-tapping and comforting about turning on music that delights the spirit. Whether we are in the car heading up to the mountain to play in the snow, sipping a hot cup of chocolat chaud while staying inside or welcoming guests into our homes, holiday music is a must. 🙂

15. Watch, enjoy and explore holiday films and series (known and new)

From favorites such as Grumpy Old Men (you don’t think it is holiday at first, but it is entirely set during the winter season and oh so funny!) to Love, Actually, even You’ve Got Mail (they celebrate Christmas during a handful of scenes!), I will play these films frequently during the course of December. Also, I enjoy finding a new film or series each year, and this year, I stumbled across (as shared in last Friday’s This & That) Dash & Lily on Netflix. I will admit, I binged the entire 7-8 episode series last weekend and loved it. Delightful, entirely set during the Christmas season in New York City AND largely set in the Strand bookstore. The last detail sold me completely on the storyline. Loved it. Highly recommend.

But just in case those films or shows don’t speak to you, check out this list of 12 Simply Luxurious Holiday Films to Enjoy Each Year.

16. Don’t forget the pets!

Norman and Oscar’s stockings are hung by the fire as well as stuffed full of goodies (which we shop for together on a special day – they love going to the pet food store for this annual trip of treat shopping), and this year they have even been spoiled with doggie advent calendars from my mom (yep, she loves her granddogs just as much as she loves her grandkids – thank you mom!).

Wishing you a wonderful and festive and full of reasons to celebrate holiday season.


TSLL’s Holiday Gift Guide: 40+ French & British-themed & Extra Festive Finds (2020)

Thesimplyluxuriouslife.com | The Simply Luxurious Life

18 thoughts on “16 Ideas For Enjoying A Simply Luxurious Winter Holiday Season

  1. Shannon, thank you for such thoughtful suggestions. I am looking forward to adding some of these to my holiday season. I would love to know more about the doggie advent gift you mentioned. I realize we are already into to advent however, if this is something still available I know my fur babies would enjoy this treat. Thank you so much and blessings to you and yours.

  2. What great ideas! I’ve been having paperwhite bulbs for the last couple of years and love this. Just yesterday, I was at Trader Joe’s (LOVE their annual holiday treats featured at this time of year) and purchased my paperwhite in a glass vase (usually plant them in soil) so a new twist on an annual tradition.

  3. Wonderful post! Great ideas how to relish in the winter holiday season. I LOVE winter..I strive to make every day cozy. I am about finished the Christmas list, including the 2 cats and new addition adopted dog..I have no idea if he knows about presents, but the cats are well versed and will probably show him. This year will look a bit different, but I made adjustments. My daughter is on campus for her senior year of college so it isn’t safe for her to join us, but I am making a second carbon copy of the christmas eve dinner for her and her roomates to enjoy. I can drop it off along with her gifts. I figure, soon enough, the holidays will look different with my kids growing up and flying the nest, so this is just practice to find new traditions!

    1. Hi Michelle,
      That is a great attitude and approach to the necessary changes this holiday season. Thank you the reminder that change is constant and we can choose to find something positive in a challenging situation.

    1. Cannon, I think you will enjoy it. Notably, it is a young cast, high school characters, which initially caused me to not explore it. But I am so glad I did as it is precisely the younger cast that makes this storyline absolutely enjoyable. 🙂

  4. Loved this post !
    Making celebration plans is always part of the fun , and especially this year , when many of us will be celebrating very differently because of the virus.
    Music, candlelight, flowers, snuggly throws, decorating our homes and our trees, writing Christmas cards and letters, choosing films and books to enjoy, are all things we can do , even if we are by ourselves.
    Everyday can still be special if we choose to make it so , while remembering that not everyone might have that choice, because of illness, homelessness , loss of livelihood, or liberty .
    Remembering that we can make a difference , and helping in whatever way we are able to ,by small acts or bigger ones .
    We may never know what a difference our smile, words or actions can have to make someone’s day , blessings come in all sizes and fit everyone ?❤️
    Thank you for sharing Shannon , enjoy all your preparations ?⭐️

  5. Love this list, Shannon!
    Though not a Scrooge, I tend to not get too involved in the December holidays. This year, however, I find myself actively searching out ways to celebrate. New twinkle lights, a trip to the thrift shop to pick up some decorations, and lots of Christmas music have been enjoyed.
    Though I missed out on my annual tradition of a tea advent calendar (the only true tradition I am dedicated to every year), I have picked up several seasonal treats at Trader Joe’s.
    Paperwhites and New Year’s plans sound like the perfect way to keep savoring & celebrating being alive and well. Thank you.

    1. It sounds like you are tailoring the holidays to what brings you joy. So happy to hear. It really needs to be more intrinsically driven and less driven by external expectations. I hope you have a wonderful December and start to the new year. Thank you very much for sharing. 🙂

  6. Some lovely ideas. I was particularly taken with your thoughts on New Years day. I always think it can be a bit flat after the jollity of Christmas so I have been inspired to create a tradition for this day. I suspect it will involve delicious food but pondering on a few other thoughts. Thank you Shannon.

    P.S I’m intrigued that you’re allowed to tell your own tree.

    1. Nicola, Oh, I do hope you find a way to celebrate that is something you look forward to regardless of what others may be doing. Since doing that in my own life, it has brought far more joy. 🙂

  7. I especially loved your point about outside decorations and lights as a neighborly gesture of good cheer. Our neighborhood started lighting up as Diwali approached and many took advantage of unseasonably warm weather to string up lights before Thanksgiving, and as the days shorten, I now have something to look forward to on our late afternoon walks instead of lamenting the loss of daylight on yet another day of quarantine. I just need to convince my dog that he has nothing to fear from the giant, blowup reindeer on the lawn around the corner!

    1. Julie, thank you so much for sharing!! It sounds like you have a very festive and welcoming neighborhood and oodles of good cheer! Your pup sounds a bit like my Oscar. He has his doubts about all of these bright things that weren’t there just a few months ago. ? Wishing you many good evening strolls. ??

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