Unsurprisingly, traveling in a large group over the Christmas holidays has its challenges! These holiday travel tips for groups will help you navigate the highs and lows of planning a festive trip. You will avoid common travel mistakes to enjoy the most wonderful time of the year in a fun destination with your friends and extended family members.
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Best Holiday Travel Tips for Groups
Spending time with loved ones over the holiday season is non-negotiable for most people. It’s easy to celebrate together when you live close, but what about friends and family who live far away? Often, the burden lies on one household to host. A holiday trip is a great way to spend quality time and make memories with people you care about. Plus, it’s convenient. Young children will be on school break and many office workers have automatic paid time off. Use these holiday travel tips to plan a stress-free getaway.
1. Assign a Group Leader
Every group trip needs a leader. They need to be organized, flexible, and patient. As the person reading this, there’s a great chance that you’re up to the task! You will be the ‘go-to’ person for everyone’s questions and concerns. Yes, you will probably repeat yourself a lot! It’s a good idea to have a right-hand person to bounce things off before taking them to the group. Parents or best friends are best for this job.
Being the group leader doesn’t mean you are solely responsible for planning and booking everything. You’re the group holiday vacation project manager! Delegate jobs to the best people. Your brother might want to choose restaurants if his kid has an allergy. Your best friend might have a nose for sniffing out a good deal on accommodations.
Creating a group chat should be your first task. Whether it’s Facebook, WhatsApp, Slack… Choose the best travel apps for groups to help plan your vacation. List the roles and ask everyone to sign up for one. It’s better to do this in the group chat rather than face-to-face or in a private chat. Everyone will know who is responsible for what. You will have witnesses if someone isn’t helping!
2. Pick Travel Dates Wisely
You probably don’t need me to tell you that the Christmas travel season is an expensive and busy time of year. Airports and roads are packed from Thanksgiving until after New Year. The busiest-ever holiday travel season in the US was in 2019 and we’re on track to beat that record high soon!
These are statistically the busiest days to travel:
- Day before Thanksgiving
- Sunday after Thanksgiving
- Both days after Christmas Day
These peak travel days will also be the most expensive days to travel! Avoid them wherever possible.
These are statistically the cheapest days to travel:
- Christmas Eve
- Christmas Day
I understand why those with young kids might not want to travel on Christmas Day. However, your group might be open to the idea if there are really cheap flights. You still get to be together on the day. If you travel early enough, you can still eat dinner and celebrate together. Airports will have fewer crowds and roads will be almost empty! Just check you can still order airport transfers when traveling on Christmas Day.
3. Book Everything Early
The more organized you are, the better your options. This is especially true if you’re traveling as a large group or taking a long trip. Flights, rental cars, accommodation options, restaurants, and attractions book up months in advance around the holidays.
Book transportation and accommodation as soon as possible. Research when the attractions you want to book go on sale and set alerts. It will give you peace of mind later to know that you’ve reserved everything so no one is disappointed later. Plus, it should help your group budget if you’ve paid for everything (or know exactly how much you’re going to spend) in advance.
4. Manage Costs and Payments
Speaking of money, it’s a great idea to figure out how you will split the costs as soon as you start planning. It can get complicated! Unless someone is happy to do so, it’s usually better not to have one person pay for everything as it would soon rack up. A better option is to delegate everyone to pay for something so you are all sharing the burden.
If you’re paying upfront for the flights, someone else can pay for the accommodation. Be mindful of the group members who don’t have the means to pay large amounts upfront, even if they are being paid back. They might still be able to pay for a more affordable group activity like Santa’s Grotto tickets.
Use apps like SplitSave, Venmo, or CashApp so everyone can pay for their share. Again, put it all in the group chat so everyone is accountable!
You also need to figure out how to handle costs during the trip. These are items you can’t pay for in advance like food and gas. Some people will be happy to take it in turns and not squabble over a few dollars. Others will prefer to split everything to the penny and only pay for what they ordered. It doesn’t matter which you choose as long as everyone agrees. When in doubt, default to those who are on a tighter budget.
Another option is to set up a small group fund. You can all pay the same amount every month in the lead-up to your trip. Even if it doesn’t cover all incidentals, it will help those with trouble saving. You can also use it to buy fun decorations for your rental apartment or outfits (more on this soon!).
5. Choose Your Destination
Unless you spent Christmas last year talking about the one place you’ve all wanted to visit, choosing a trip will be difficult! It may take a few weeks or even months to agree, so figure it out early. (I’ve already mentioned the group chat 100 times, but it’s useful for this…). The easiest way to choose is to post a poll using TypeForm or SurveyMonkey in the group chat.
Figure out if you want a typical winter wonderland or a winter sun escape first. Ask if everyone wants a winter sports adventure, relaxing cruise, city break, etc.
If you’re an American group, decide if you are staying in the United States early on. Here is some local holiday destination inspiration:
- New York City
- Ski town e.g. Park City UT or Aspen CO
- Bethlehem, PA
- Leavenworth, WA
- Charleston, SC
- Branson, MO
- Alexandria, VA
- New Orleans, LA
- Florida (for winter sun)
Choose somewhere that is easy to reach for the entire group. Smaller towns that go all out for Christmas are perfect for a road trip, but not if you’re flying. Larger cities with more direct flights are better if you’re based in different states.
You have even more options if your group is set on international travel. European Christmas markets, for example, are so fun. Here are some suggestions of the best places:
- Strasbourg, France
- Prague, Czech Republic
- Edinburgh, Scotland
- Lapland, Finland
- Oaxaca, Mexico
- Puerto Rico
- Quebec City, Canada
Again, check that the travel time and price are suitable for everyone. Don’t forget to keep those on a tighter budget and with mobility issues in mind. Booking a ski trip might not be fun for your octogenarian grandma. Even if that’s what the majority wants! Spending the holiday season together is more important.
6. Stay in Festive Accommodation
Decide whether to stay in a hotel or a short-term rental accommodation. Once you have, choose somewhere that goes all out for Christmas!
Airbnb or Vrbo hosts usually mention whether they decorate their accommodation for Christmas. Send a message if it’s not mentioned in the posting.
Hotels that decorate for Christmas usually have a page on the website. Decorations and festive events can turn a great time into the best time. It’ll make all the difference if you’re traveling with kids.
7. Plan a Flexible Itinerary
It can be tempting – especially as the group leader – to be responsible for everyone’s enjoyment. You might want to plan loads of activities so no one gets bored. This is such a common mistake! One of the best top tips anyone can give you is to allow a lot of extra time in your itinerary.
There are two main reasons. The first is that you want to allow plenty of time for flight disruptions or car trouble. Traveling in the winter months means bad weather is all but guaranteed! Don’t book a big family meal or an expensive show on your first evening. Organize the show-stopping group activity on your last day as a farewell celebration. Plan a low-key activity on the first day like a movie night or shopping. It’s a little bit of a buffer.
The second reason not to over plan is that everyone travels differently. Many love exploring non-stop while others need afternoon naps to function. You won’t change them for one trip!
If you’re traveling in a large group (seven or more), you can easily split into smaller groups. Agree to all meet up for one activity during the day (a show or tour) and one at night (dinner or show) at least. Plus, if you’re used to traveling in a couple, you might not realize how much longer everything takes with a big group.
8. Indulge in Festive Treats
If there’s one thing everyone can agree on it’s that people are happier with full bellies and cranky with empty bellies. Over Christmas, everyone wants to indulge in hot chocolate, cookies, eggnog, roast turkey, and everything else! Look into local markets and find restaurants with festive specials.
Make a big grocery trip when you arrive if you book short-term rental accommodation. This is essential if you are cooking Christmas dinner there, but it’s impossible to have too many snacks! Make a list with everyone’s input and use the money in the shared fund.
You can never research enough cafes, coffee shops, delis, and cool restaurants. It’s always good to have a backup plan if you show up and a restaurant can’t find your reservation. Consider everyone’s preferences and dietary requirements. It is easier to order takeout from different restaurants and eat together if you’re staying in rental accommodation.
9. Check Weather Forecasts
Winter weather can be so unpredictable. Even if you are flying to the Caribbean, the weather where you live might still be volatile. Check and double-check air travel updates on your airline’s app and weather forecasts. The last thing you want are flight delays, but you’ll be better equipped to handle it if you know about it ASAP.
You’ll also need to check the weather forecast a couple of weeks before you pack. If there’s an unexpected snowstorm, you might need to buy new gear!
Some of your group members might not be used to cold weather. If they live in somewhere like Arizona, for example, they might not comprehend Canada’s frigid temperatures. They may not even own gloves! Share your packing list in your group chat so others can see what you’re bringing. Research a few inexpensive retail stores where you’re traveling to in case anyone needs to buy clothes last minute.
10. Prepare for a Successful Flight or Drive
Do you know those people who seem to attract disaster and misadventure? You probably have one of those people traveling in your group. Whether you are flying or driving, do everything within your power to have a smooth journey.
For flights, persuade everyone to only bring carry-on bags and a personal item. Luggage is more likely to be lost in a busy travel season. There will always be someone who wants to check a bag and there’s little you can do to stop them. No one likes early morning flights, but no one likes long lines and a busy airport. Usually, check-in lines are shorter, airport lounges are quieter, and you’re less likely to have canceled flights.
For road trips, get your car serviced and cleaned. Plan frequent stops even if it’s not a long drive. Always expect journeys to take longer than you expect. You may want to plan alternate routes in case there is a road closure. This is a common occurrence in snowier places!
If you’re all piling in one vehicle, the single most important thing is to ensure you have the correct car seats for every kid. They’re easy to forget!
11. Pack Smaller Gifts or Do Secret Santa
Packing a Christmas present for every person in your group can quickly take up space in your suitcase. Pack smaller gifts or arrange a Secret Santa/White Elephant/Yankee Swap. This is the best way as you’ll only have to pack one present.
If you’re traveling with lots of young kids, you could agree to buy them small, extra presents. Just make sure all kids have the same number! Put a cost limit on the present so they’re all of a similar value.
12. Co-ordinate Festive Outfits
You don’t have to coordinate festive outfits, but think of the photos! You’ll have a super cute picture for next year’s holiday card.
Arrange to wear red and green on Christmas Day, holiday pajamas, or sparkly clothes on New Year’s Eve. Wear “ugly” Christmas sweaters for one meal and vote on whose is the ugliest. There should be a prize for the winner which you can buy your pre-arranged group fund.
13. Offer Help to Infrequent Travelers
Some of your group might be frequent travelers, but some won’t. Without being patronizing, offer help and advice to those who don’t travel as frequently. It will save them and the rest of you lots of headaches!
Send a reminder in the group chat about travel insurance. It may be one of the benefits of their credit cards. This is a must if you are traveling overseas! It is less of an issue if you are traveling domestically. Mention currency, travel debit cards, and phone eSIMs if your holiday trip is international.
There’s still a lot to consider even if you are flying domestically. Starting in May 2025, Americans must travel with REAL ID-compliant identification. It will apply to Christmas 2025 trips. Remind your less-traveled family and friends about not packing necessary medications and electronics in their checked bags.
Holiday Travel Tips for a Relaxing Christmas Break
Planning a big trip around the holidays can be stressful. The more people you travel with, the more opinions and needs you have to consider. But you will always remember the incredible holiday vacation you spent together. Hopefully, these Christmas travel tips for groups will help you be more organized and enjoy a smooth planning process.