Newly Widowed? Tips for Women Traveling Together

by | Oct 14, 2020

Mature woman wears sun hat on catamaran on the ocean
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Last updated on December 13th, 2023

Feature Image: A life well lived, loved and travelled deserves some R&R in the sun / Photo provided by Diana Eden

A Seasoned Traveller Tells All

by Diana Eden

In 2015, I lost my husband, my lifelong travel partner. We had been a perfect match travelling together, enjoying the same destinations, pace, and activities. I thought I would never travel again — who would go with me? Apparently, this is a common fear among the newly single.

After some time had passed, I was indulging one of my favourite pastimes – checking out gorgeous villas in faraway places on VRBO  when I came across one in Antigua that I just HAD to stay in. I went out on a limb and put a deposit on it, wondering if I would be there alone. Amazingly enough, once my friends and neighbours heard about it, they were begging to be included.

That started a lovely tradition of renting houses or apartments in all sorts of exotic locations. I have been with my friends to villas in Antigua and St Croix, an apartment in the heart of Paris, a chalet at Lake Arrowhead, California, and a villa on the south coast of Spain – with more to come I hope!

The friendship of women, especially those over age 65, is invaluable. They have seen both the joys and sorrows of life and are so ready to be in the moment. And while every experience planning our travel has been excellent, I did learn a few things along the way.

Older women enjoy the pool at a villa

Diana’s friends enjoy the pool at their villa in St. Croix / Photo provided by Diana Eden

How to assign the rooms fairly

The assignment of bedrooms has the potential to be a complicated minefield. But there is a fair way and a smart way. The fair way might be to do it by lottery – whatever number you pull, that’s your ranking on choosing your bedroom. The smart way is to assess everyone’s needs and hope there are the right bedrooms and mix of people to accommodate. Not all bedrooms in a villa are created equal. Someone will get the master suite with a balcony, others the kids’ room.

Most of the large villas I have rented have four bedrooms, one of which usually has twin beds. (Pro Tip: Be sure to research how many BEDS a rental has, not just bedrooms and bathrooms.)

There are two groups of travellers: Those who cannot go to sleep without the TV on, and those who cannot sleep WITH a TV on. I belong in the latter group. Some people like to chatter and are high energy at night; others, like myself, are introverts and prefer quiet at bedtime and in the morning.

Amazingly though, it all seems to work out. One person will get the bedroom on the main floor with no stairs involved, two friends will agree to have a girls’ dorm experience and share a room, and somehow it becomes clear who gets what.

A note on bathrooms: Not all old houses in Europe have a bathroom for every bedroom. They just aren’t built that way. And while modern women may throw their hands up in horror at the thought of not having their own bathroom, that too has a way of working itself out. How did we manage to grow up in houses built with one bathroom for a family of five? Timing is everything. And a bottle of Poopourri is a necessity.

Tracking shared expenses

The rented house will have been paid for before we arrive, and that gets divided up evenly between occupants. But upon arrival, there are supplies to be purchased – wine, diet colas, produce and sundries. And then there are tours and dinners out.

There is nothing more embarrassing than the withering stare of a professional waiter after you’ve eaten a four-course meal with several bottles of wine, and someone asks: “Can we have separate checks?”

Luckily, there’s an app (or several) for that. I use one called Trip Splitter, which has saved me from hours of advanced calculus and is so easy to use. I enter the names of all the guests (each gets a color and an avatar), and then for each expense, I enter the amount, what it was for, who paid, and who is splitting. It allows me to split the costs evenly among everyone or manually if one person has had a salad and a Perrier and others have eaten more robustly. At the end of the trip, you ask the app to please “EVEN UP,’ and magically, it figures it all out and tells you who owes whom how much. Clever little app.

Charcuterie board in Paris

A beautiful charcuterie board in Paris / Photo provided by Diana Eden

A menu board in paris

The happy hour menu is priced just right / Photo provided by Diana Eden

Honouring group rhythms

If I have one other rule, it is this: If we say we are leaving for dinner at 6 pm, that doesn’t mean four of us are ready at 6 pm and sitting in the car, and one is still fooling around in the bathroom with her mascara. Consideration is everything.

I think the main thing is to honour everyone’s rhythms. Some are early risers, some late. Some like to hang out and go slow; others can’t wait to get going and see things. There are so many ways to make sure everyone gets to do what they like, and at the pace they enjoy. Sometimes I encourage everyone to make a list of the top two to three things they want to do, and between all of us and six or seven days to do those things, everyone goes home satisfied.

It’s also smart to play to individual strengths. One of our group we call “The Captain,” whose job it is to advance party and scout. As the rest of us are all still extricating ourselves from the car, limb by limb, she sprints ahead, becomes best friends with the maitre d’, and secures us the best table in the house. Another loves to cook breakfast. The whole deal. Eggs, bacon, English muffins. She’s also really good at grocery shopping and loves the beach. Another friend loves to do the pre-travel research and will condense the guidebooks of all the places we are to see into a truncated version, printed out in pamphlet form for each of us. She has never met a museum she didn’t like, be it the Rijksmuseum in Amsterdam or the Museum of Cooking Utensils of Prehistoric Tribes in St Croix. Another of us likes maps and loves to plot out our route. (OK, that’s me.)

Two cars are better than one for groups

I always rent one or two cars. Two is better if you can do it. You can have two groups doing different things. If there is only one car, it can get squishy in the back seat, and the driver may feel like the tour guide, the alcohol-deprived designated driver, and the Mom. Better to have two cars, two drivers.

Following these tried-and-true tips for group travel with seasoned women travellers can make the difference between returning home with a rift in the group or a suitcase full of wonderful memories.

Read More Stories on Traveling After Loss

Diana Eden is a Contributing Writer for JourneyWoman magazine, focused on travel for women over 80. She was born in England, raised in Toronto, lived and worked in New York, Los Angeles, and now Las Vegas. She is a former dancer, actress, Emmy-nominated costume designer, and now author. She recently published her memoir, "Stars in Their Underwear: My Unpredictable journey from Broadway dancer to costume designer for some of Hollywood’s biggest stars."


  1. joyce poole

    Thank you. This is a great way to keep traveling in the spring! Great ideas for how to make this happen with less aggravation all around!

  2. Janice Griffin

    I love the suggestions in this article. Very good tips on traveling with others.

  3. Patricia Stephenson

    What a wonderful article. Sounds like the ladies all have strengths and they end up with a great holiday. Journey Woman is an excellent website. I am so glad I found it a few years ago. Keep up the good work!


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