Women's Group Travel: Friends, Milestones, and Trips That Restore You

Start With What Everyone Wants From the Trip

Before choosing the destination, talk about what everyone actually wants the trip to feel like.

Do you want to relax? Explore somewhere new? Eat your way through a destination? Spend time on the beach? Shop? See shows? Try new experiences? Stay up talking until midnight and then refuse to get out of bed before 10 the next morning?

There is no right answer. The important thing is making sure everyone isn't imagining a completely different vacation.

One person may be picturing excursions every day while someone else is picturing a pool chair and a book. Figure that out before you book, not after you arrive.

Talk About the Budget Early

Money can become uncomfortable when you're planning with friends, but avoiding the conversation doesn't make it disappear.

Everyone may love the idea of the same trip and still have very different ideas about what they are comfortable spending.

Talk about a realistic budget before falling in love with a resort, cruise, or destination. And remember that the trip cost isn't only the hotel or cruise fare.

Depending on the vacation, travelers may also need to budget for airfare, transportation, excursions, meals, gratuities, travel protection, and spending money.

Nobody should feel pressured to spend more than they're comfortable with just to be part of the group. A great girls' trip shouldn't come home on the credit card with you.

Roommates Are Worth Talking About

Sharing a room can make a trip more affordable—and it can be a lot of fun. But being great friends does not automatically mean you are great roommates.

Who snores? Who needs complete darkness? Who needs the television on to sleep? Who takes an hour in the bathroom? Who is up at 6:00 a.m. ready to conquer the world while everyone else would prefer not to speak before breakfast?

These things sound small until you're sharing a room for seven nights. Have the roommate conversation before the trip. And if someone would rather pay more for her own room? That's okay too.

Don't Schedule Every Minute

You don't have to fill every morning, afternoon, and evening with an activity just because you're somewhere new.

Plan the things everyone is excited about. Then leave some space.

Maybe half the group goes shopping while the others stay at the resort. Maybe someone books a spa appointment. Maybe everyone sleeps late. Maybe lunch lasts three hours because nobody stops talking.

Some of the best memories from a trip are the things nobody scheduled.

Everyone Doesn't Have to Do Everything Together

This is one of the easiest ways to make group travel more enjoyable.

You're traveling together. That doesn't mean you need to be attached to each other from breakfast until bedtime.

If four people want to zip-line and three would rather spend the afternoon at the spa, wonderful. Meet back up for dinner and tell each other about it.

If someone wants a quiet morning alone, let her have it. A good group trip gives you plenty of opportunities to spend time together without making anyone feel guilty for occasionally doing her own thing.

Feeling Safe Matters

Feeling comfortable in a destination matters. That doesn't mean choosing only places that feel familiar or avoiding adventure. It means doing a little homework before everyone arrives.

When I'm helping plan a women's group trip, I want to look at things like: How easy is it to get around? Is the hotel or resort in an area where the group will feel comfortable walking or going out? What transportation options are available after dark? Are excursions being booked through reputable providers? How far is the group from the main areas they want to visit? Will anyone be going off on her own during the trip? Does everyone know how to reach the hotel, tour provider, or emergency contacts if plans change?

A group can also make a few simple plans before traveling. Share the itinerary. Keep each other's contact information. Let someone know if you're heading somewhere on your own. Use reputable transportation. Pay attention to your surroundings. Know how everyone is getting back to the hotel if the group splits up.

And if something or somewhere doesn't feel right? You don't have to talk yourself into it just because it was on the itinerary.

Safety isn't about being afraid to travel. It's about being prepared enough that everyone can relax and enjoy where they are.

Choose a Destination That Fits Your Group

The best destination isn't necessarily the one everyone is talking about online. Think about your particular group.

How comfortable is everyone navigating somewhere unfamiliar? How much walking does the destination require? Does everyone want nightlife, or would they rather have quiet evenings?

Would a cruise make things easier because everyone can choose their own activities? Would an all-inclusive resort take the pressure off deciding where to eat and what to do every day? Would a guided tour make everyone more comfortable exploring a destination they've never visited?

Transportation, accessibility, comfort, activities, and how easy it is to get around all matter. The right destination is the one that works for the women actually taking the trip.

Celebrate the Reason You're Going

Maybe someone is turning 50, 60, or 70. Maybe someone retired. Maybe you've been friends since high school and suddenly realized high school was a lot longer ago than any of you care to discuss. Maybe your children are grown and you finally have a little more freedom to travel. Or maybe there isn't a milestone at all.

You don't need a major life event to justify getting away with people you love spending time with. Sometimes the trip is the occasion.

Take the Trip You've Been Talking About

There will always be another reason to wait. Someone will always have a busy schedule. There will always be something happening at home. And getting several women to agree on dates may occasionally feel like negotiating an international peace treaty.

But eventually, somebody has to say:

"Okay. We're actually doing this."

Because ten years from now, you probably won't be talking about how difficult it was to coordinate everyone's calendars. You'll be talking about what happened when you finally went.