Planning A Girls or Group Trip? Easy Tips for Success

Some friendships span lifetimes, and then some. My high school girlfriends and I have been friends since kindergarten, but like many of us, life pulled us in different directions after graduating high school.

• Best Cruise Options for Seniors: Relaxing Vacations on the Water

Then, for our 50th birthdays, someone tossed out a feeler: Who wants to go to New York at Christmas? Seven of us, the “Hog-Eye girls” reconnected, and it was the trip of a lifetime. We actually did our school cheer, “H-O-G-E-Y-E, Hogeye, Hogeye, T-N-T!” on The Today Show!

Since then, we’ve made memories all over the map: Nashville, Atlanta, Savannah, Martha’s Vineyard, the Dominican Republic, New York at Christmas, a houseboat adventure, Rosemary Beach, and even a cruise.

Traveling with a large group isn’t always easy, but we’ve discovered that a few simple habits make it fun, flexible, and full of joy.

If you’re planning group travel with friends, family, or multiple generations, here are habits that help you enjoy the trip without losing your mind.

First: It’s Not About Everyone Doing Everything Together

Group travel only works when everyone feels free to be themselves.

Most of our group loves shopping. Me, not so much. Some of us prefer sitting with a coffee. Some want to get up early. Others like late mornings. Trying to make everyone do the same thing at the same time usually leads to frustration.

The rule that changed everything:

Set expectations with clear time limits, not pressure.

For example: “We’re shopping at TJ Maxx. Everyone met at the front of the store in 45 minutes.”

This simple time boundary gives everyone:

• Structure
• Choice
• Freedom

When people know they’ll return to the group, they shop with confidence. And when the timer goes off, the reunion is easy.

One “Captain” Keeps the Group Grounded

Even the most harmonious group benefits from one person taking the lead.

We always choose a team leader, someone who:

• Does the research
• Books hotels
• Maps routes
• Suggests restaurants
• Keeps the itinerary flowing

This doesn’t mean one person makes all the decisions. It means:

• Plans exist
• There is a starting place
• Everyone else can choose to opt in or out

On our trip to Savannah, this strategy worked beautifully. Even if we separated for our own adventures, we knew where and when to regroup.

It kept the rhythm easy, and that’s the heart of group travel that feels good at any age.

Give Permission to Be Independent Within the Group

One of the biggest lessons I’ve learned over many trips is this:

Being together doesn’t mean doing everything together.

Group travel is richer when:

• Some people take a morning walk
• Others linger over breakfast
• A few explore a local market
• A couple rest and chat

On our cruise, some went on the excursions, and some stayed by the pool. Some were early birds and enjoyed the exercise classes, while others sat watching the waves and drinking coffee. We were all happy.

Allowing space doesn’t diminish connection. It enhances it.

Choose Accommodations That Support Flow, Not Fuss

Where you stay matters.

Group trips are smoother when your home base:

• Has multiple common spaces
• Offers privacy as well as gathering spots
• Feels like living together, not hotel roulette

We prefer houses over hotel rooms because:

• Everyone has their own bed
• There are shared meals
• People spread out naturally

Nobody feels boxed in. And that creates a much happier energy. To choose rooms, we simply put everyone’s name in a bowl and pull them out one at a time. If you get chosen first, you get your pick of the beds. We do bend the rules every now and then. If someone previously got a bad room or the couch, we let them choose first this time.

Staying In Hotels

Occasionally, we don’t have another option than a hotel stay. If you’re with good friends or family and don’t mind sharing a bed, it certainly saves money. We don’t draw names for those, but tend to go by volume. The louder ladies get put together, and the quieter, in-bed-by-nine folks usually wind up together. We also take into consideration the amount of belongings each person has. The girls with four bags each won’t all fit into one room!

• Longer stays require more personal space
• Ask for connecting rooms to keep the noise inside, not the hallway
• Let the person with points book the room for savings

Balance Flexibility With Gentle Structure

Structure doesn’t have to be strict. It just needs to communicate:

• What’s happening
• When it happens
• When it ends

Sample language we love:

• We’re shopping before lunch; join us if you like.
• Good morning stretches at 8:30 – optional!

When everyone knows the parameters, they relax, and relaxation improves everything.

Humor Is Required. Grace Is Optional… But Recommended.

We laugh a lot on our trips. At ourselves, the weird moments, the unexpected detours.

In New York, Tami fell asleep during the Broadway play. We still give her grief about that. And I got hangry at the Nashville Flea Market. They now always make sure I have a candy bar if we’re eating late.

Humor lubricates group travel. But what really keeps the peace is grace; giving people space to be human, to change moods, to slow down, to rest.

Traveling with friends isn’t about perfection. It’s about presence.

Lean Into Fun

At 60+, we’re allowed to live life our way. We bought matching shirts for our cruise, and matching pajamas for our Christmas trek to a fancy hotel. And we encourage each other to try new things.

Life is too short to worry about what the other tourists think about our crew.

Items I Always Carry Along

First and foremost – a good walking shoe! The initial trip to New York taught me that lesson.

I’ve never regretted wearing Sketchers. I walked for miles in India in a pair. These are cute and easy to slip on and off. Plus, they’re light, which helps with luggage weight.

Most rental places provide a hair dryer, so I leave mine at home. We are all happy to share our curling and flat irons, but since we’re getting ready at the same time, I include mine in the luggage. My friend, Jan, suggested this BaByliss curling iron, and I’ve used it ever since.

Luggage and Bags

I bought new luggage last year for the cruise. I like a soft side, and I love the external zipper pockets. I can grab my laptop, etc. as needed on the flight without opening the whole thing.

A crossbody bag is a must on trips! This one is inexpensive (it’s Clucci, not Gucci lol) but it did the job nicely. Having my hands free for shopping bags, my phone, etc. was very helpful.

I did a ton of research before I purchased packing cubes. I didn’t find that they gave me a significant amount of room, but they were super helpful for keeping my things organized. I threw them in the drawers and didn’t even unpack them.

I’m not naming names, but we have some folks who snore. These earplugs come in handy when you have noisy roomies, street traffic, proximity to the elevator, etc.

Speaking of snoring, have any of you tried mouth tape? I’ve been considering it for my husband, lol. Let me know in the comments if you’ve ever used these!

There’s nothing worse than being on a great trip and having your phone die; no great pictures, no texting your travel companions if you’re lost, etc.

Bon Voyage

Travel after 60 is different from travel in earlier years. It’s not about checking boxes or conquering schedules.

It’s about:

• Making memories
• Laughing without restraint
• Honoring differences
• Supporting each other
• And returning home closer than we left

That’s why seven girls who grew up together will still travel together decades later.

Quick question:
When you travel with friends, which one are you?

• The planner • The wanderer • The relaxer • A mix of all three

Tell me in the comments. I love hearing how others travel.

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