October always gets me thinking about three things: all things cozy, holiday season rounding the corner, and where to escape when cozy turns into cold.
Between fall-focused outings, upcoming holiday celebrations, and a calendar that somehow keeps moving faster, it’s easy to put vacation planning on the “I’ll get to it later” list.
But this is a great month to turn “we should go somewhere” into something to look forward to. Whether that’s a winter beach escape, a spring break adventure, or the big 2027 trip you’ve been talking about for years, let’s start putting the pieces together.
🚐 Life on the Road
Fall is my favorite of all seasons for so many reasons, and I scheduled our travel around the season. Just like I planned, the season has already found us up here in Quebec City! Being this far north means we’re getting an early taste of the season, and it feels like the perfect way to kick off our first fall as a full-time traveling family.
Next we’re starting to head south, chasing the changing leaves and hoping to stretch out my favorite parts of fall along the way. After a first month filled with stormy weather, camper projects, our first border crossing, and finding our new life rhythm, it’s fun to let the season help shape where we go next.
One of my favorite parts of life on the road is having the chance to slow down and enjoy these transitions together. This chapter is all about following the colors and seeing what we discover along the way.
💻 What’s Keeping Me Busy This Month:
October is all about looking ahead. Here are a few trips worth getting on the calendar:
- Holiday & winter getaways: If a last-minute trip is still on your wish list for Thanksgiving, Christmas, or New Year’s, let’s talk through your dates, priorities, and available options. The holidays have a way of sneaking up on us, so let’s see what’s possible while there’s still time to make it happen.
- Spring Break 2027: Before the holiday to-do list takes over and more resorts book up, pull out those school calendars! Having your dates and an idea of who’s coming gives us a starting point for finding the right fit.
- Summer 2027 adventures: That family trip to Europe, Alaskan cruise, or long-awaited getaway with the grandparents deserves time and thoughtful planning.
- Group trips & celebrations: Milestone birthdays, anniversaries, destination weddings, or a “just because” trip with your favorite people! Starting the conversation now gives everyone time to coordinate.
You don’t need to have every detail figured out before reaching out. Helping you figure it out is part of what I do!
💡 Travel Tip of the Month:
Less time in queue, more time for vacation.
With holiday travel coming up, let’s talk about a few ways to make the airport experience a little easier. You’ve probably heard of TSA PreCheck, Global Entry, and CLEAR, but do you know what parts of your travel day each will help with?!
🧳 TSA PreCheck: Easier security screening
If you frequently fly from U.S. airports, this is worth considering. Approved travelers can use a designated security lanes and generally keep shoes on and laptops & travel-size liquids in their bags. Just make sure your Known Traveler Number is added to your airline reservation.
🌎 Global Entry: Smoother arrivals after international trips
This program speeds up U.S. entry processing for approved travelers at participating airports and includes TSA PreCheck benefits. If international travel is on your calendar, consider Global Entry before applying for PreCheck separately.
We actually got the girls Global Entry for free this month! Children under 18 have their application fee waived when a parent or legal guardian is already enrolled or applying, although each child still needs their own application and approval. Such a great perk for traveling families!
📱 Mobile Passport Control: A free option worth knowing about
Don’t have Global Entry? The official CBP Mobile Passport Control app lets eligible travelers submit passport information and entry questions from their phones, helping streamline & expedite U.S. arrival processing at participating locations. Of course, you’ll still need your passport!
✨ CLEAR+: Help with the identity check step
CLEAR+ is a separate paid membership that speeds up identity verification at participating airports. It doesn’t replace security screening or automatically give you TSA PreCheck, but you can use the two together. Check whether it’s available at the airports you use most before signing up.
Also, some airports let you reserve a time to enter security through programs like CLEAR’s RESERVE. You still complete regular screening, but you don’t need a paid CLEAR+ membership.
🇨🇦 NEXUS: Easier travel between the U.S. and Canada
NEXUS is a paid trusted traveler program that offers expedited border processing when entering either country by air, land, or sea. It also includes Global Entry access and TSA PreCheck benefits for eligible members, making it worth considering if you frequently travel between the U.S. and Canada. Allow plenty of time for the application and required interviews before your trip.
My biggest advice? Get these pieces in place before your next trip. Check eligibility and participating locations, allow time for any required approvals, and still leave yourself plenty of time at the airport.
Before paying an application fee, check your credit card benefits, too! Some cards offer a statement credit that covers Global Entry or TSA PreCheck when you pay with that card. You may already have this perk without realizing it, just check your card’s terms before applying.
A little preparation can make travel day feel a lot less overwhelming.
⭐ This Month's Travel Favorite:
The gift of something to look forward to...
With holiday shopping around the corner, consider giving an adventure over a gift: a weekend away, a family adventure, or that trip you’ve been talking about for years.
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✈️ Where our Clients are Headed this Month:
October's trips are all about celebrating and spending time together.
My clients are heading to Walt Disney World for a multigenerational birthday and anniversary trip (plus their kid's first trip - their video of surprising them with the news is why I do this! 🥺), Nashville for a wedding weekend, Maui for a friends getaway, and London for a mom-and-daughters adventure. There’s also an epic Universal weekend, couples & friends off to Aruba, and a surprise fall foliage escape in the North Carolina mountains.
I’m especially excited for our SheWolf Wild Women Retreat in Massanutten (we still have two rooms available if anyone is interested in joining us!) and a group trip through Italy, with stops in Rome, Florence, Tuscany, Venice, Amalfi, and Pompeii.
🌍 Where Are You Dreaming of Going?
Consider this your October invitation to put something fun on the calendar. You don’t need a finished plan. A season, a rough budget, and a “we’ve always wanted to…” are enough to get the conversation started.
Reply to this email and tell me: What trip would you love to take in 2027?
You bring the wish list.
I’ll help with the details.
Travel should feel exciting, not overwhelming, and that’s where I come in. Whenever you’re ready to plan, we’ll take it from inspiration to itinerary. 🤍
Cheers & Bon Voyage,
Ashlee
