There is always a strange little stretch of the year when summer has technically ended, but South Georgia has apparently missed the announcement.

The calendar says fall. The stores have pumpkins stacked beside Christmas decorations, school has been back in session long enough for everyone to settle into a routine, and somewhere there is probably a candle burning that promises to smell like crisp autumn leaves. Meanwhile, it is still warm enough outside to make you question every decision involving a sweater.

Still, there is a shift that happens around this time of year. Summer vacations have mostly wrapped up, the beach bags have been put away, and families begin looking toward the next big dates on the calendar: Thanksgiving and Christmas.

And those dates are coming quickly! 

Summer has always been treated like the main event of the travel year. Families plan months ahead for beach vacations, cruises, theme parks, and that one big trip everyone has been talking about since January. Then August comes, school starts back, and travel gets pushed to the side while everyone gets reacquainted with alarm clocks, homework, football schedules, church activities, and the hundred other things that somehow appear on a family calendar.

The funny thing is that some of the best opportunities to travel are still ahead.

Maybe the Holidays Could Look a Little Different This Year

There is something wonderful about traditions, especially around Thanksgiving and Christmas. Most families have those things that simply belong to the season. There is a particular dish that has to be on the Thanksgiving table, a Christmas movie everybody knows by heart, or a house where everyone somehow ends up gathering even though nobody remembers officially deciding that it would always be there. Those traditions become part of us.

Is it the written rule that those traditions have to happen at home? Of course not! Travel does not have to replace any of our favorite things, it can just give them a new backdrop.

Thanksgiving dinner can still be Thanksgiving dinner when there is an ocean outside the window. Christmas morning can still have all the excitement of Christmas morning when everyone wakes up in a cabin in the mountains. A family can exchange presents before walking onto a cruise ship, spend December wandering through Christmas markets in Europe, or take the kids somewhere warm and discover that palm trees look surprisingly good wrapped in Christmas lights. There is also something appealing about letting someone else handle Thanksgiving dinner for once. Don’t just talk about it this time, try it. 

Anyone who has hosted a large Thanksgiving gathering knows that “Thanksgiving Day” is often several days of grocery shopping, cleaning, cooking, rearranging furniture, washing dishes, and trying to remember which relative eats what and who is bringing it. A family trip can change it up completely. Instead of spending most of the holiday preparing for everyone to arrive, everyone gets to arrive somewhere together. That can become its own tradition.

Christmas Travel Has Its Own Kind of Magic

Some destinations simply know how to do Christmas, the first place most of us think of is New York. The vibe of New York during the holidays feels different from New York in July. Or how about Europe? European cities fill their squares with Christmas markets, lights, food, music, and traditions that have been around for generations. Or maybe the mountains? Mountain towns settle into that postcard version of Christmas with cabins, fireplaces, snow, and mornings that make you want another cup of coffee before doing anything productive.

Then there is the other version of Christmas travel, on board a cruise ship. A Caribbean cruise over Christmas break can be just as memorable as a snowy cabin. Or the all inclusive resort? Trading the snow for the sand. There is no rule saying Christmas memories require cold weather.

For some families, though, holiday travel really is about getting home. It has nothing to do with checking a destination off a list. It means finding flights that allow the grandchildren to spend Christmas with their grandparents or coordinating several households so everyone can be in the same place for a few days.

Sometimes the destination is somewhere completely new. Sometimes the destination is the same driveway you have pulled into every Christmas for twenty years. Nonetheless, travel is found in both. 

A Few Things Worth Knowing Before You Book Holiday Travel

Holiday travel rewards people who plan ahead. Thanksgiving week, Christmas week, and the days surrounding New Year’s are some of the most sought-after travel periods of the year, which means waiting for the perfect last-minute deal can sometimes leave you choosing from whatever is left rather than what you actually wanted.

A few things can make the process much easier:

Start looking earlier than you think you need to. If your travel dates are tied to school breaks or specific days off work, flexibility is already limited. Starting early gives you more options for flights, cabins, resorts, cruise categories, and room configurations, especially when several family members are traveling together. The best spots fill up the quickest. 

Give yourself some breathing room around flights. The Wednesday before Thanksgiving and the days immediately surrounding Christmas are popular travel days for obvious reasons. When schedules allow, shifting departure or return dates can sometimes make the experience considerably easier. For a cruise or international trip, arriving at least a day before the trip begins can also provide valuable protection against flight delays disrupting the entire vacation. I always recommend giving yourself plenty of time for the adventure. 

Think about the whole cost rather than the advertised price. A cheap flight at an inconvenient time may require another hotel night, expensive airport parking, additional meals, or baggage fees. A resort price may look wonderful until transfers and other expenses are added. Comparing the complete trip usually gives a much clearer picture than comparing one number on a screen. You really do pay for what you get when it comes to the experience. 

Consider travel insurance carefully. Do not pass on adding travel insurance! The trip that you know you won’t need it, is the trip you will wish you had it. Winter weather, illness, flight interruptions, and unexpected family situations do not check your vacation calendar before appearing. Travel protection can be particularly worth discussing for holiday trips where the investment is significant or the itinerary includes cruises, international travel, multiple flights, or prepaid arrangements.

Build some margin into the itinerary. There is a temptation to squeeze everything possible into a holiday vacation because everyone has limited time off. A little open space can make the trip much more enjoyable. Nobody wants to return from Christmas vacation needing another vacation. 

If you are traveling as a family, talk about expectations before you leave. Communication with group travel is always a must. One person may picture everyone spending every waking hour together while somebody else is already dreaming about three uninterrupted hours beside the pool. Multigenerational trips work especially well when there is room for both togetherness and independence.

And This Is Where a Travel Advisor Becomes Especially Valuable

The internet has made it incredibly easy to search for travel. It has also given us approximately 47 tabs to open while trying to decide whether one hotel is actually better than another. There is a difference between being able to book a trip and having someone help you plan one.

Let Me Help Take the Stress Out of Holiday Travel

One of my favorite parts of being a travel advisor is taking that first little idea of “we should go somewhere for Christmas” and helping turn it into a trip your family can actually look forward to.

As part of a Signature Preferred Agency, I have access to travel resources, supplier relationships, destination knowledge, and professional support that allow me to help you sort through all the possibilities. Sometimes you already know exactly where you want to go. Other times, you just know that you want to get away together. Either way, we can start there.

I also want to know how your family actually travels because every family vacations differently. Maybe you want your days filled with excursions, reservations, and things to see. Maybe your perfect itinerary has plenty of white space and the biggest decision of the afternoon is where you are eating dinner. I can help you compare cruise lines, resorts, destinations, accommodations, transportation, and all those little logistical pieces that become especially important when you are coordinating holiday travel for several people. And when something changes, you have a real person to call who already knows your trip.

Travel is an adventure. Flights get delayed. Weather happens. Schedules change. Suppliers occasionally make adjustments. Travel sometimes comes with surprises. When I have helped you plan your vacation, I already know where you are going, how you are getting there, and what you have booked. You have someone in your corner who can help you navigate those moments. During the holidays, I think that kind of peace of mind matters even more.

Maybe Put a Memory Under the Tree This Year

Every Christmas, we spend so much time trying to figure out what to buy for people who often already have most of what they need. And listen, I love presents too. But there is something about giving an experience that lasts differently. Nobody sits around talking about the gift they received 10 years ago. Years from now, your family may have trouble remembering exactly what was wrapped under the tree in 2026. But you probably won’t have any trouble remembering the Christmas you spent on a ship. You will remember Dad getting hopelessly turned around in a city he insisted he could navigate without directions. You will remember the little restaurant you found by accident, the first time the kids saw snow, the view from the hotel balcony, or Grandma laughing harder than anyone had heard her laugh in years. Those are the moments that eventually become family stories.

That is one of the things I love most about travel. Of course, the destination matters. I want you to see beautiful places and experience things you have dreamed about for years. But when we look back on our favorite trips, so much of what we treasure comes back to the people who were standing beside us.

So as summer disappears into the rearview mirror and Thanksgiving and Christmas start looking much closer on the calendar, now is a wonderful time to start talking about what the holidays could look like for your family.

Maybe everyone comes home this year. Maybe everyone goes somewhere completely new. Maybe Thanksgiving happens in the mountains. Maybe Christmas morning begins at sea. Maybe the gift under the tree this year is an envelope announcing a trip you will take together a few months from now. I Whatever you are imagining, start the conversation now.

And if that conversation eventually turns into ten browser tabs, three cruise itineraries, four hotel options, conflicting flight schedules, and somebody finally asking, “Wait, I thought you were booking it?” then send all of that my way. That is exactly why I am here.

I would love to help you take all those possibilities and turn them into a trip that fits your family, your budget, and the memories you hope to make together.

Because the best holiday trips may begin with choosing a destination, but the stories we bring home are almost always about the people who went with us.

Sojourney Travel by Jessica Coen