Stress-Free Holiday Planning

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The 30-60-90 Day Guide

The holiday season is a time of joy, family, and festive celebrations. However, it can also be a time of stress, especially if you’re not prepared. But fear not, dear reader! We’ve got a 30-60-90 day plan to ensure that your holidays are smooth, organized, and most importantly, enjoyable.

90 Days Out: The Foundations

1. Setting a Budget: Before anything else, determine how much you’re willing to spend. This includes gifts, decorations, food, and any travel expenses.

2. Draft a Guest List: Are you hosting? Decide on your invite list now. This helps with planning the meals and seating arrangements later.

3. Gift Ideas: Start listing down gift ideas for everyone. Consider online shopping to avoid last-minute shipping woes. Remember stocking stuffers and small gifts for service workers like hairdressers, postal workers, and delivery drivers.

4. Start DIY/Homemade Gifts and Decorations: Personally made items can add such a wonderful touch to your holidays. Starting them now will ensure that they are perfect for the recipient.

5. Order Custom Made Gifts: Vendors advertising Custom Made gifts usually have longer manufacturing and shipping windows during the holiday season. Beat the rush to ensure your personalized gift is ready on time.

6. Gather Addresses for Holiday Cards: Time to review your friends and family’s addresses for any relocations or additions. Now is also a great time to pick out the perfect holiday card photo or schedule a photo session.

7. Book Travel: You’ve worked hard all year and the holidays can be stressful, now is a great time to book your holiday escape. Prices skyrocket as the holidays approach.



60 Days Out: Setting Things in Motion

1. Declutter Your Home: Taking down Halloween decor and eliminating any additional clutter will give you the extra space needed to set the stage for your holiday decorations

2. Deep Clean Your Home: Now that you have your spaces decluttered, let’s get to work on a good old-fashion deep clean before you decorate your home.

3. Plan Your Menu: For any hosting duties, decide on appetizers, main courses, desserts, and drinks.

4. Check your Bar Stock: replenish any low or old bottles to ensure your festive cocktails are ready for your guests.

5. Order Subscription Box Gifts: Subscription Boxes have become a popular and fun way to celebrate the holidays. With so many great options there is sure to be one to fit everyone on your list. Most boxes have a 30 or 60 day ordering window so be sure to subscribe early to ensure holiday delivery.

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6. Order your holiday cards: If you are planning photo cards or holiday letters, this is the perfect time to place your order or write a rough draft.

7. Start Decorating: It’s time to get those boxes of decorations out of storage and create your holiday style!


30 Days Out: Final Preparations

1. Finalize RSVPs: Send out reminders to guests to confirm their attendance.

2. Wrap Gifts: Begin wrapping the gifts you’ve purchased. Add tags so you don’t forget whom they’re for!

3. Set Up Decorations: Brighten up your living space with festive decor.

4. Address and Mail Cards: Enjoy your new decor while addressing your holiday cards and prepping them for mailing.

5. Order Online Items: If you’re shipping items directly to your recipient, ordering before the 15th will most likely ensure delivery before the big day.

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6. In-Store Shopping and Gift Cards: Now that most of your gift buying is complete, it will be a breeze to finish up any last minute or unexpected gifts that are needed. As a last resort, gift cards are always appreciated!

7. Advanced Prep Idea: Prep any side dishes that can be frozen ahead of time, such as casseroles and side dishes.

8. Cookie Exchange: Participating in a cookie exchange at work or with friend can give you a great opportunity to add a variety of holiday treats without all of the work. You bake a large batch of your favorite cookie recipe and divide the batch to share among the group. Each person will leave with several different kinds of cookies and treats for their holiday entertaining.

9. Create a Shopping List of Meal Items: It’s time for your final shopping list. Double check ingredients and measurements to make sure all items are ready for the big day! Splitting cooking and/or shopping responsibilities with family and friends will help keep your holiday running smoothly.

Task/Chore90 Days60 Days30 Days
Gift Planning
Set a Budget
Create a List of Gift Ideas
Start any DIY or Homemade Gifts
Order Subscription Box Gifts
Order Any Online Items to be Delivered
In-Store Shopping and Gift Cards
Decorating
Declutter Your Home for Holiday Prep
Deep Clean
DIY or Crafted Decorations
Set Up Decorations
Wrap Gifts
Entertaining
Draft Guest List
Plan Your Menu
Restock Bar
Prepare Freeze-ahead Dishes
Participate in a Cookie Exchange
Create Shopping List of Meal Items Needed
Review Times and Oven Temperatures for Dishes
Miscellaneous
List of Addresses for Cards
Choose Holiday Card Photo
Order Cards
Address and Mail Cards
Book Holiday Travel


Final Thoughts

With this 30-60-90 day planning guide, you’re not only prepared but also spaced out your tasks to ensure minimal stress. By the time the holiday season is in full swing, you’ll be able to kick back, relax, and savor every moment, knowing everything is taken care of.

Happy Holidays!

***Affiliate Disclosure ***

Land2Shore LLC participates in various affiliate marketing programs, which means we may get paid commissions on editorially chosen products purchased through our links to retailer sites. Our editorial content is not influenced by any affiliate partnerships, and all opinions expressed here are our own.

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Kirsten Hoskins and Nico Rossi

Hello Friend!
Originally from the Midwest, Nico is a professional fine dining chef and Kirsten is a full-time blogger/digital marketer. In 2020 we decided to reinvent ourselves in the beautiful Florida Keys and have not looked back!

Consider us your friends to bounce questions to about travel ideas, lifestyle, vacation locations, food or things to do in the Florida Keys and we'll be sure to answer through email or post.

Let's explore together!

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Land2Shore LLC participates in various affiliate marketing programs, which means we may get paid commissions on editorially chosen products purchased through our links to retailer