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top tips for planning fall and winter travel (1)
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Anna Marie

Top Tips for Planning Fall & Winter Travel

The process of preparing for your fall and winter travel can bring joy and anticipation. PullOverandLetMeOut offers a selection of valuable suggestions to assist you in organizing your upcoming escape.
A woman sipping coffee outside
Hi, I’m Anna Marie. I’m a wife, mother, Irish dancer, and pug mom living in North Carolina. I also love to travel. Come along for the ride! If you see something you like, don’t be afraid to say, ‘Pull over and let me out.’

Fall and winter vacations can be extremely rewarding because they allow you to experience cozy settings, festive events, and beautiful scenery. It’s also a wonderful time to enjoy destinations during the off-season. However, there are a few things you should keep in mind to ensure a smooth journey. Here’s a list of top tips to help you make the most of your upcoming fall and winter travel:

a pond where the trees have leaves beginning to change
First fall colors at Shelton Vineyards in Surry Co. North Carolina

1. Choose Your Destination Wisely

It goes without saying, but choosing the best destination for fall and winter travel requires careful consideration of where you want to go. Research destinations that are known for their fall foliage or winter charm. Consider factors like weather, activities, and cultural events during your chosen time frame.

2. Book in Advance

Popular fall and winter destinations tend to fill up quickly, so book your accommodations, flights, and activities early to get the best options and prices. Some popular fall and winter destinations may book a year in advance, so the sooner you know your plans, the more likely you’ll be able to book the exact destination you’re interested in visiting.

What better way to enjoy the fall colors than sipping wine in the mountains?

3. Stay Flexible with Plans

Sometimes you just have to roll with it. While planning is important, weather conditions during the fall and winter can be unpredictable. Have a backup plan for indoor activities or alternative attractions in case of unexpected changes.

4. Research Seasonal Events

Look into local fall festivals, harvest markets, Halloween events, Thanksgiving parades, Christmas markets, and New Year’s celebrations at your destination. These can provide unique experiences and memorable moments. These events can also make booking accommodations challenging so keep this in mind while you research (see tip #2). 

Busch Gardens in Williamsburg, Virginia, has become a cherished autumn retreat for us. The yearly Howl-O-Scream event they host injects excitement into the amusement park experience, while the park itself boasts stunning beauty amidst the fall season. Likewise, it is so close to Colonial Williamsburg, Jamestown, and Yorktown that it makes for an excellent weekend excursion.

Busch Gardens Howl-O-Scream PullOverAndLetMeOut collage
Howl-O-Scream is a fun fall getaway at Busch Gardens in Williamsburg, VA

5. Embrace Cozy Accommodations

Choose accommodations with warm features such as fireplaces, hot tubs, and comfortable lounging areas. These amenities can add an extra layer of comfort to your trip. After a long day, nothing beats returning to a cozy inn or B&B and snuggling by the fireplace. Find these lodgings and you will have a successful vacation.

6. Check Operating Hours

Some attractions, restaurants, and shops might have adjusted hours during the off-peak seasons. Make sure to confirm their operating hours before you go. You don’t want to be like the Griswold family and discover Wally World is closed!

7. Visit Off-Peak Attractions

While popular attractions are a must-see, consider visiting lesser-known spots to avoid crowds and have a more intimate experience. I love visiting North Carolina’s Outerbanks in the winter because, there is little traffic, the beaches are empty, and the ocean breezes are cool and invigorating.

woman at the beach in winter flying a kite
Winter is perfect for kite-flying on North Carolina's OBX!

8. Capture the Beauty

Fall foliage and winter landscapes offer stunning photo opportunities. Be sure to bring a good camera or have your smartphone ready to capture the breathtaking scenery. If you’re planning on capturing amazing pictures, consider booking a photography tour of your destination. It will give you an entirely different perspective and some incredible photographs to cherish.

9. Research Local Cuisine

Autumn and winter are ideal seasons for indulging in hearty comfort foods. Investigate regional dishes and restaurants known for their seasonal offerings, and revel in your destination’s culinary delights. Taking a food tour of your destination is also a great way to experience the local flavors while learning about the culture.

10. Travel Insurance

Because winter weather can cause delays and cancellations, consider purchasing travel insurance to safeguard your investment and provide peace of mind. You may also want to book fully refundable hotel stays in case you need to make changes. 

11. Pack Accordingly

Planning fall and winter travel also means planning to pack accordingly. Layering is key for both fall and winter trips. Pack clothes that can be easily mixed and matched, as well as essentials such as warm outerwear, gloves, scarves, and hats. Don’t forget to bring rain gear. Be prepared, as the old scout adage goes.

12. Engage in Outdoor Activities

Make the most of the cooler months by engaging in outdoor activities that capture the distinct charm of autumn and winter. Enjoy brisk hikes through colorful foliage, cozy campfires with friends and family, or the thrill of winter sports like skiing and ice skating. Plan ahead of time by locating rental equipment at your destination so that you can travel light.

A collage of pictures of a woman carving a pumpkin with goats
Carving pumpkins with goats!

13. Embrace Relaxation

Fall and winter vacations can be a great time to slow down and relax. Prioritize self-care and take in the peaceful atmosphere. Find a spa destination or book a couples massage to fully relax and pamper yourself.

14. Check for Seasonal Discounts

When planning fall and winter travel, keep in mind certain lodgings, points of interest, and excursions could potentially provide reduced rates during the less busy periods. Make sure to make the most of these cost savings. Beyond excellent bargains, you might also come across fewer crowds, enabling you to relish your experiences even more.

Planning fall and winter travel is fun and exciting. The realm of splendid options for remarkable vacations and weekend retreats is vast. Armed with these extra suggestions, you’ll be aptly prepared to maximize the enjoyment of your fall and winter escapades, whether you’re immersing yourself in snowy vistas or savoring the captivating autumn allure of your selected location.

Wherever you travel this fall and winter, I wish you Happy Travels!

Cool weather travel is invigorating!

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