Celebrate the Milestone, Take the Trip

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Birthdays have a funny way of making you reflect.

Maybe it’s because I’m celebrating another trip around the sun this week, but I’ve been thinking about the way we mark the important moments in our lives.

There’s usually a dinner. A cake. Cards. Maybe a gift or two.

And I love all of those things.

But you know what I remember most when I look back over the years?

The experiences.

The places I’ve been. The people I’ve shared them with. The meals that lasted for hours. The things we laughed about. The adventures that didn’t go exactly as planned. And those moments when you stop, look around, and think, I can’t believe I’m actually here.

That’s one of the reasons I love the idea of celebration travel.

Celebrations Have Always Been Part of My Travel Career

In some ways, celebration travel has been part of my career from the very beginning.

I started out planning destination weddings, helping couples take one of the biggest days of their lives and turn it into an experience they could share with the people they loved.

From there came the honeymoons—and perhaps surprisingly, New Zealand has become one of my top honeymoon destinations. Not every newlywed couple dreams about spending a week lying on a beach. Some want beautiful scenery, adventure, incredible food and wine, and experiences they’ll remember forever.

Over the years, the celebrations have expanded far beyond weddings and honeymoons.

I’ve planned trips for milestone birthdays, big anniversaries, family reunions, girls’ getaways, and multigenerational vacations where the entire family comes together to celebrate.

I’ve even been lucky enough to occasionally become part of the celebration myself.

While I was in Australia at the same time as clients celebrating a 60th birthday, I had the pleasure of taking them out and celebrating with them. I’ve also been part of a group of couples who gathered in St. Martin for a big birthday celebration.

Those are some pretty special memories from this career of mine.

One Milestone, One Very Special Trip

One of the things I love about celebration travel is that the destination can reflect the particular moment in your life.

I’ve had clients who have shown that beautifully.

One couple celebrated a 50th birthday in Hawaii.

Their honeymoon took them to Tahiti.

And when it was time to bring the family together for a family reunion, they chose the Maldives.

Three very different occasions. Three very different trips.

That’s exactly the point.

No single place is perfect for every celebration.

The right destination is the one that fits you, the people you’re traveling with, and what you’re celebrating.

Bring the Whole Family

Some of my favorite celebration trips have been the multigenerational ones.

A big anniversary is a wonderful reason to bring everyone together—not just the couple who reached the milestone, but their children and grandchildren too.

And these trips become about so much more than the anniversary itself.

Grandparents get uninterrupted time with grandchildren. Adult children get to reconnect. Everyone steps away from work, school, sports, appointments, and the million other things that make getting the entire family together increasingly difficult.

Instead of receiving another gift, the couple celebrating that big anniversary gets something much harder to wrap:

time with the people they love.

And everyone comes home sharing the same collection of memories.

Sometimes the Experience Is the Celebration

You don’t necessarily need balloons waiting in the room or a cake delivered after dinner to make a trip feel celebratory.

Sometimes the experience itself becomes the moment.

Watching the sun set somewhere you’ve always dreamed about visiting.

Sharing an incredible meal.

Seeing Australian wildlife you’ve dreamed about encountering.

Sipping wine among the vineyards.

Waking up over a turquoise lagoon.

Seeing a favorite sporting event in another country.

Getting the whole family together when everyone’s schedules finally align.

Or simply raising a glass somewhere beautiful and realizing how fortunate you are to be there together.

Those are the things we tend to talk about years later.

And unlike another sweater or gadget, you don’t eventually clean them out of a closet.

Tell Me What You’re Celebrating

This is something I always want my clients to tell me.

If you’re traveling for a birthday, anniversary, honeymoon, retirement, reunion, graduation, or another special occasion, don’t treat it like an insignificant detail.

Tell me.

It helps me understand what this particular trip means to you.

Maybe we should build an experience into the itinerary. Maybe one resort is a better fit for the occasion than another. We may find special options we wouldn’t otherwise consider.

And sometimes it’s the little touches that turn an already wonderful vacation into something you’ll remember forever.

That’s part of the fun of planning celebration travel.

Don’t Wait for the “Big Enough” Milestone

I think we sometimes convince ourselves an occasion has to be significant enough to justify a trip.

The 50th birthday.

The 25th anniversary.

Retirement.

But who decided the years in between don’t count?

You don’t necessarily need a zero at the end of the number to have something worth celebrating.

Life gives us plenty of reasons to put things off. There will always be another bill, another commitment, another project at work, or another reason that next year might be more convenient.

I’ve learned enough through my own travels—and through the lives of the people I’ve planned trips for—to know that we aren’t guaranteed the perfect time.

If the people you love can travel and there’s somewhere you’ve been dreaming about experiencing together, that’s worth considering now.

Another Trip Around the Sun

This birthday week has been filled with friends and family, laughter, dinners, surprises, and people I love.

And that’s really what celebrating is about for me.

It’s not so much about adding another candle to the cake.

It’s about recognizing that another year has given me more people, places, and experiences to be grateful for—and hopefully plenty more adventures still ahead.

So when your next milestone rolls around, you can certainly make the dinner reservation.

Buy the cake.

Open the presents.

But maybe you should also pack the suitcase.

Because sometimes the best way to celebrate another chapter of life is to go somewhere and live it.


Lisa Rossmeissl is the owner of Boomerang Escapes, a home-based agency located in Branchburg, New Jersey, and North Myrtle Beach, South Carolina, with agents in TN, MS, ID, and WI. 

She has been a professional travel consultant since 2008 and specializes in Australia and the South Pacific. Australia, New Zealand, Tahiti, Fiji, and Cook Islands are among the specialist certificates she holds.  Her agency’s focus is on creating custom itineraries with their client’s wants, desires, and budgets in mind.  She and her planners believe in getting to know the traveler to ensure they have a vacation to remember.  With each planner specializing in a different market area, Boomerang Escapes can offer a wide variety of leisure vacation planning.

Lisa RossmeisslCelebrate the Milestone, Take the Trip
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Why Every Woman Needs a Girls’ Trip

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We’ve all said it.

“We need to take a trip together!”

It sounds great in the moment. Everyone agrees. Someone throws out a destination. Maybe a group text gets started.

And then life happens.

Work schedules don’t line up. Someone has a family commitment. Someone else isn’t sure about the budget. Before you know it, another year has gone by, and you’re still saying, “We really need to do that trip.”

After a fun ladies’ night out with friends recently, I started thinking about just how important that time together can be—and how much better it gets when you take it on the road.

I’ve planned quite a few trips for groups of women over the years, and they’ve looked very different. Some have been big bucket-list adventures. Others have involved nothing more strenuous than deciding which cocktail to order next.

That’s the beauty of a girls’ trip.

There’s no right way to do one.

Time Together Without Everyday Life Getting in the Way

We can see our friends regularly and still not really have uninterrupted time together.

At home, there are jobs, spouses, children, grandchildren, appointments, errands, phones buzzing, and all the other things competing for our attention.

Travel changes that.

Suddenly you’re having breakfast together, exploring somewhere new, lingering over dinner, laughing about something that happened earlier in the day, and having conversations you might never have had during a quick dinner back home.

You get to simply enjoy each other’s company.

And sometimes that’s reason enough to go.

The Trip Can Be About Something You Already Love

One of my favorite examples was a group of ladies I sent to Australia who built their January trip around the Australian Open since they were big tennis fans.

Seeing their photos from the stands reminded me of something I love about planning these trips: sometimes the best vacation starts with something you already enjoy doing together.

They had something they loved and wanted to experience together. Australia became the bigger adventure surrounding it.

That’s something I love about planning group travel. You don’t necessarily have to start by asking, “Where should we go?”

Sometimes the better question is:

“What would we love to do together?”

Maybe it’s tennis in Australia.

Maybe it’s food and wine.

Maybe it’s live music.

Maybe it’s beaches and sunshine.

Maybe it’s seeing a destination that’s been sitting on everyone’s bucket list.

Start there, and the destination often follows.

Sometimes You Just Need a Beach

I’ve also sent plenty of groups of women to the Caribbean, with the Dominican Republic being a particular favorite.

And I completely understand why.

An all-inclusive resort can make a girls’ getaway wonderfully easy. Once everyone arrives, there’s very little to think about beyond where you’re having dinner, whether you’re going to the beach or pool, and who’s ordering the next round.

For a group coming from different places, that simplicity can be a huge advantage.

Nobody has to cook. Nobody has to entertain. Nobody has to coordinate restaurant checks every night.

You can actually relax and enjoy being together.

You Don’t Have to Go Halfway Around the World

Girls’ trips don’t have to involve passports or long flights, either.

I’ve planned U.S. getaways for women celebrating birthdays, bachelorette weekends, and other special occasions.

Sometimes a few nights away is all you need.

That’s another reason I don’t think there’s a formula for the perfect girls’ trip. A weekend away with your best friends can be every bit as memorable as a two-week international adventure.

It’s about the people you’re traveling with and how you want that time together to feel.

Milestones Are Better With Friends

Birthdays. Bachelorettes. Retirement. A big anniversary of a friendship. A new chapter in life.

Sometimes there’s a reason for the trip.

And sometimes the reason is simply, “We’ve been talking about doing this forever.”

I think that counts, too.

As we get older, schedules don’t necessarily become easier. Children grow up, grandchildren arrive, careers change, people move, and suddenly getting five or six women in the same place at the same time requires the logistical skills of an air traffic controller.

Which brings me to something I’ve learned from planning these trips.

Getting Everyone to Commit May Be the Hardest Part

Picking a beautiful destination is usually easy.

Getting six people to agree on dates, budget, trip length, and what they actually want to do?

That’s where things can get interesting.

My biggest advice is to settle a few things before anyone starts searching online.

Agree on a realistic budget. Find dates that actually work. Decide how long everyone can be away. Talk about what kind of vacation you’re imagining.

And designate one person as the group’s main point of contact.

Otherwise, one person is looking at a luxury resort, another has found an Airbnb, somebody else wants a cruise, and your relaxing girls’ getaway has turned into a full-time job before anyone has left home.

That’s also one reason having a travel advisor coordinate the trip can be especially helpful. I can be the person keeping track of the moving pieces without one member of the group having to spend her entire vacation playing travel agent.

Because she deserves to enjoy the trip, too.

So, Send the Group Text

Maybe your girls’ trip is a long weekend in the U.S.

Maybe it’s an all-inclusive in the Caribbean.

Maybe you’re finally going big and heading to Australia.

The destination isn’t really the point.

It’s getting away from everyday life for a little while, reconnecting with women who matter to you, experiencing something together, laughing—a lot—and coming home with another collection of stories that belong to all of you.

So send the group text.

Pick some dates.

Start the conversation.

Because “We should take a girls’ trip someday” can be said for years.

Maybe it’s time to turn someday into an actual departure date.


Lisa Rossmeissl is the owner of Boomerang Escapes, a home-based agency located in Old Bridge, New Jersey with agents in TN, MS, and WI. 

She has been a professional travel consultant since 2008 and specializes in Australia and the South Pacific. Australia, New Zealand, Tahiti, Fiji, and Cook Islands are among the specialist certificates she holds.  Her agency’s focus is on creating custom itineraries with their client’s wants, desires, and budgets in mind.  She and her planners believe in getting to know the traveler to ensure they have a vacation to remember.  With each planner specializing in a different market area, Boomerang Escapes can offer a wide variety of leisure vacation planning.

Lisa RossmeisslWhy Every Woman Needs a Girls’ Trip
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