The Holiday Season is Officially Here!

While many might consider Thanksgiving or December as the start of the holiday season, I personally think of Labor Day weekend as the unofficial kickoff. I like to keep things subtle until October rolls around. Once October arrives, it’s all about decking the halls—starting with Halloween decorations and gradually building up to the festive season.

In October, alongside decorating and celebrating Halloween, I continue to work on my craft projects, creating personalized cards and gifts. It’s also the perfect time to gather wrapping materials, ensuring I’m prepared for the gift-wrapping frenzy that will come. I plan to bake another batch of make-ahead cookies this month, adding to the assortment I’ve already started. With the busy holiday season approaching, I find it essential to declutter my pantry and check the freshness of my spices. Regularly updating my pantry helps me stay organized and ready for the cooking and baking that come with the festive season.

Plan Travel

During the holidays, travel can fill up quickly, so it’s wise to plan and book your trips early. Nathan and I have a tradition of taking a holiday-themed weekend trip each December. Often, we find ourselves at Walt Disney World, but a couple of years ago, we spent five festive days in New York City, soaking in all the iconic Christmas activities.

This year, we’ve chosen to spend a weekend in St. Augustine, FL. We actually made our reservation back in July to celebrate the 30th anniversary of their famous Night of Lights. St. Augustine is frequently listed among the top holiday destinations in the U.S., and we’re excited to stay in a charming Bed and Breakfast, enjoy the dazzling lights, savor the local cuisine, and take a scenic carriage ride.

Update Address List

In August, I discussed the importance of planning your Christmas card list, including the use of a spreadsheet to keep track of whom you send cards to. Now that we’re in October, it’s time to focus on gathering and confirming addresses. Tracking down missing addresses can be time-consuming, so it’s wise to use this month to finalize your list and ensure you have accurate addresses for everyone on it. This way, you’ll be all set to send out your holiday greetings without any last-minute scrambles.

Advent Activities

Advent calendars are a beloved tradition, but Nathan and I took it a step further one year by creating our own list of 25 small activities to enjoy throughout the holiday season. Each day, we open a drawer to reveal a new activity, which helps us slow down and savor the magic of the season daily. Over time, we’ve fine-tuned our list, tailoring it to our preferences.

Feel free to check out our activity list and start your own tradition. Keep in mind that since we live in Florida, our list doesn’t include winter-specific activities like building a snowman, making a snow angel, going sledding, or taking a carriage ride. To keep things fresh, we also have more than 25 activities so we can mix them up each year.

I’d love to hear about the creative activities you come up with. Please share your ideas, as we’re always on the lookout for new and exciting ways to celebrate the season!