Traveling After Loss: When You Need to Get Away but Grief Comes With You

Traveling After Loss: When You Need to Get Away but Grief Comes With You

How do I even approach planning a vacation when my life has changed so much? Will I enjoy a vacation now that I'm alone? Will I spend most of my trip feeling lonely and depressed? What if I make mistakes? Is it too soon to even think about traveling after everything that has happened?

Will I still enjoy it?

I asked myself all of these questions when I took my first vacation after losing two of the most important people in my life. I was alone. I was grieving. I wanted to travel, but I wasn't sure I could make a success of a vacation when so much about my life had changed.

Before everything happened, my mother and I were doing well. We had purchased a home in a new town, and although her health was deteriorating, we were happy. One day, my mother was outside looking for a bunny rabbit in the greenbelt behind our home when somehow she hit the joystick on her electric wheelchair. The chair moved so quickly that neither one of us could control it.

That moment changed my life forever.

The heavy wheelchair fell onto my mother's leg and shattered her femur. After years of steroid use had weakened her body, doctors were unable to help her. Eleven days later, she was gone.

I didn't just lose my mother. I lost my best friend and the person I had cared for for most of my life. I had been my mother's primary caregiver since I was sixteen years old. Now I was forty-three, and suddenly that enormous part of my life—and the person at the center of it—was gone.

Nine months into trying to process that loss, my grandfather became ill. Without hesitation, Teddy, my mother's service dog, and I moved in to care for my granddad. I was still grieving my mother, but once again I had someone who needed me, so I focused on caring for him until he passed away.

Afterward, I was lost. Two of the most important people in my life had been taken from me so quickly that I honestly didn't know how I was supposed to continue with my own life. Teddy and my new puppy, Lola, became my anchors. Those two dogs helped me more during that time than I can probably ever explain.

There was also the practical side of loss that people don't always talk about. I suddenly had so many belongings from my grandparents, my mother, and my own household that I couldn't possibly keep everything. Eventually, I held a garage sale and earned a tidy sum of money.

And then I got an idea.

For years, I had wanted to go to a Star Wars convention.

Maybe I could actually go.

It sounded exciting when I thought about it—and terrifying when I started trying to plan it. This would be my first real vacation after everything that had happened, and I wasn't simply choosing a hotel and buying a plane ticket. In my mind, every decision seemed enormous. If I chose the wrong hotel, booked the wrong flight, rented the wrong car, or planned things badly, I worried that I would ruin the entire vacation.

And Orlando, Florida, wasn't exactly short on choices. There were hotels everywhere, Disney World and countless other attractions I wanted to see, transportation to figure out, flights to coordinate, and a convention center I needed to be able to get to easily. I spent days poring over hotel rooms and distances, trying to make every piece fit together perfectly.

Eventually, I realized I needed to stop trying to solve the entire vacation at once.

I took a deep breath and made an outline of what I wanted to see and, more importantly, what I actually needed. I fell back on techniques I remembered from my days working as a traveling auditor and started putting the trip together one decision at a time.

That vacation turned out to be one of the best gifts I could have given myself.

It didn't erase my grief. I didn't suddenly stop missing my mother or my grandfather because I got on an airplane and went to Orlando. But the trip reminded me that there were still things in the world I wanted to see, things I could look forward to, and parts of myself that existed outside of caregiving and loss.

That's something I want you to know, too.

Grief doesn't only come from the death of someone you love. You can grieve the end of a marriage and the life you thought you were going to have. Empty nesters can experience their own kind of loss when children grow up, move away, and build lives of their own. You can grieve a career, a friendship, your health, your independence, your financial security, or simply the version of your life you thought you would be living by now.

When life changes that dramatically, the thought of traveling can feel daunting. Even something you once loved can suddenly feel unfamiliar.

But you don't have to wait until you've completely finished grieving before you're allowed to experience something good again.

Whether you're considering your first solo vacation, finally taking that road trip you've talked about for years, or simply spending a weekend somewhere different, you can begin traveling again in a way that fits the life you have now.

I want that for you.

So let's talk about how to travel after loss and through grief—not by pretending everything is okay, but by making room for where you are right now and building a trip that works for you.

How Do You Know When You're Ready to Travel Again?

I wish there were an easy answer to this question. Wait six months. Wait a year. Wait until you can talk about what happened without crying. Wait until other people tell you it's time.

Grief doesn't work that way.

You might be ready to travel surprisingly soon after a loss, or it may take you years before the thought of packing a suitcase sounds remotely appealing. You may even find yourself wanting desperately to get away while simultaneously being terrified of leaving home. Those feelings can exist at the same time.

Being ready to travel also doesn't mean you're finished grieving. I think that's an important distinction because we sometimes treat grief as though it's a project we're supposed to complete. Once we've gone through the appropriate stages and enough time has passed, we're expected to emerge on the other side and resume normal life.

But what if normal life doesn't exist anymore?

After a major loss, sometimes the challenge isn't figuring out how to return to the person you were. It's learning how to live as the person you are now.

Travel can be part of discovering that, but it doesn't have to be a test. You don't have to prove you're independent. You don't have to demonstrate to your family that you're doing better. And you certainly don't need to book an expensive trip because somebody tells you that you “need to get away.”

Start with what feels manageable.

Maybe that means flying across the country. Maybe it means driving two hours away and spending one night somewhere you've always wanted to visit. Maybe you aren't ready to stay overnight anywhere yet, but a day trip sounds good.

Those all count.

Instead of asking yourself, “Should I be ready to travel by now?” try asking a different question:

“What kind of trip feels possible for me right now?”

That is a much kinder place to begin.

Travel May Feel Different Now—and That's Okay

One thing loss can change is the way you make decisions.

When I planned Orlando, I obsessed over details that normally wouldn't have frightened me so much. Which hotel? How far from the convention center? What airline? What time should I fly? Should I rent a car? How was I going to fit everything together?

I was afraid of making a mistake.

Looking back, I understand why. My life had already changed in ways I couldn't control. Planning the trip became something I could control, so I wanted to get every detail right.

You may recognize that feeling.

After experiencing a major loss, an ordinary travel decision can suddenly feel enormous. You aren't just choosing between two hotels. You're thinking, “What if I get there and realize I can't do this?” You're not simply deciding whether to take an early flight. You're wondering whether you'll be able to handle the airport alone.

Give yourself permission to make the trip easier.

Choose the nonstop flight if you can afford it. Stay somewhere that makes you feel comfortable rather than somewhere you think you “should” stay. Don't schedule six activities in a day because you're afraid of having too much time to think.

And build breathing room into your plans.

If you wake up one morning and don't want to go sightseeing, you haven't failed at vacation. You might need a slow breakfast, a walk, an afternoon by the hotel pool, or a few hours watching terrible television in your room. My article, How To Plan A Trip When Your Energy is Unpredictable will help you pace yourself when on vacation.

Your trip belongs to you. There is no vacation inspector waiting to see whether you used every hour correctly.

My article, Get there your way: Why there's no right or wrong way to travel will help you realize you can travel the way you wish now that your life is different now.

What If You're Traveling Alone Because You Didn't Choose to Be Alone?

Solo travel is often presented as an adventure.

Be independent. Find yourself. Meet new people. Enjoy the freedom of doing whatever you want.

And solo travel can absolutely be those things.

But there is another kind of solo traveler who doesn't get talked about nearly as much: the person traveling alone because life changed.

Maybe your spouse died.

Maybe your marriage ended.

Maybe the friend you always traveled with is no longer part of your life.

Maybe your children grew up and started families of their own.

Maybe illness changed what your partner can do, or what you can do together.

Suddenly, if you want to travel, you may have to do it alone.

That's different from deciding one morning that solo travel sounds exciting.

You can want to go somewhere and still wish someone were sitting in the airplane seat beside you. You can be proud of yourself for navigating a new city and still hate eating dinner alone that night.

Please don't judge the entire trip by those moments.

If you're new to solo travel, you can make it less intimidating. Choose a destination where transportation is straightforward. Stay somewhere that feels comfortable and central. Book a tour or activity if you want some built-in company. Eat lunch at a restaurant and bring dinner back to your hotel if evenings feel harder.

You aren't required to perform solo travel correctly.

You're learning what traveling looks like for you now.

When Grief Shows Up in the Middle of a Good Day

This is something I think people need to hear before they travel after a loss.

You can be having a genuinely wonderful day and suddenly feel terrible.

It might be a song playing in a restaurant.

A smell.

A family walking past you.

A souvenir you instinctively think someone would have loved.

You might see something beautiful and your first thought is, “I wish they were here.”

Sometimes grief has absolutely no sense of timing.

You could be laughing one minute and crying in a bathroom stall twenty minutes later. That doesn't mean you were pretending to have fun. And it doesn't mean the trip was a mistake.

Both feelings can be real.

If that moment comes, give yourself somewhere to go with it. Sit down. Find somewhere quiet. Go back to your room if you need to. Call someone you trust. Write down what you're feeling. Cry.

Then decide what you need next.

Maybe you're done for the day. Maybe after an hour you want to go back out. Either choice is okay.

One painful afternoon does not cancel the wonderful morning you had before it.

Am I Allowed to Enjoy Myself?

This may be one of the hardest parts.

You finally laugh.

Really laugh.

Maybe it's the first time you've laughed like that in months.

And then guilt shows up.

How can I be having fun when they're gone?

How can I sit on this beach when my marriage just ended?

How can I enjoy being away when my children don't need me the way they once did?

How can I possibly be happy when my life isn't supposed to look like this?

Grief has a strange way of making happiness feel disloyal.

But enjoying something doesn't mean you've forgotten what you lost.

I didn't love my mother less because I enjoyed the Star Wars convention. I didn't stop loving my grandfather because I laughed, explored Orlando, and allowed myself to have a good time.

I was still grieving.

I was also living.

Those two things were allowed to happen at the same time.

You don't have to punish yourself by refusing every good experience that comes along. You don't have to remain miserable as proof that someone or something mattered to you.

What you lost can matter enormously.

And your life can still matter too.

Don't Make Your First Trip Carry the Weight of Your Entire Future

There is a lot of pressure surrounding the idea of “starting over.”

Take the trip.

Find yourself.

Begin your new chapter.

Come home transformed.

That's a lot to ask from a vacation.

Your first trip after a major loss doesn't have to change your life. It doesn't have to prove anything.

It can simply be a trip.

Maybe you discover that you love traveling alone. Maybe you discover you don't.

Maybe you realize five days is perfect and ten days is too long.

Maybe you learn that you enjoy group tours because you like having people around without having to coordinate an entire vacation with them.

Maybe you discover that you need more downtime than you used to.

Maybe the trip is wonderful.

Maybe parts of it are awful.

You can still learn from it.

Instead of asking whether your trip was a success or failure, ask yourself what you learned about traveling in the life you have now.

That information is valuable.

Your next trip can be different.

You Are Allowed to Change the Way You Travel

Loss changes us, and sometimes our travel style needs to change with us.

You might have once loved complicated itineraries and now find them exhausting. You may have always traveled internationally with your spouse and decide that domestic road trips feel better for a while.

Or the opposite might happen.

Maybe you spent years compromising about destinations and suddenly realize there are places you've always wanted to see.

Maybe you want to sit beside the ocean.

Maybe you want to visit museums.

Maybe you want to see every ridiculous roadside attraction between Washington and Florida.

Maybe you want to go to a Star Wars convention.

There isn't a correct version of your next chapter.

This is where I want you to be especially gentle with yourself. Don't try to recreate your old vacations exactly as they were. You may be setting yourself up for painful comparisons.

Instead, ask what would make traveling easier, safer, more comfortable, and more enjoyable for the person you are today.

You may be surprised by your answer.

You are allowed to travel at your own pace. Join the Single, Sick and Broke Traveler community and start traveling the way you want.

Give Yourself an Exit Door

There's one practical thing I think is particularly important when traveling through grief: don't trap yourself inside your itinerary.

You don't necessarily need to buy the cheapest, most restrictive version of everything if a little flexibility is within your budget. Know what can be changed or canceled before you book it. Understand your hotel's cancellation policy. Don't purchase tickets for every hour of every day before you know how you're going to feel.

And have a plan for the moments when you simply need out.

That might mean knowing how to get back to your hotel from an attraction. It might mean keeping enough money available for a rideshare instead of forcing yourself onto public transportation when you're emotionally exhausted. It might mean telling yourself before the trip, “If I need to leave early, I can.”

You may never use that exit door.

Sometimes simply knowing it's there makes it easier to stay.

You Don't Have to Explain Your Grief to Everyone You Meet

People can be wonderful.

They can also ask questions without realizing how difficult those questions might be.

“Are you traveling alone?”

“Where's your husband?”

“Don't you have anyone to travel with?”

“Why did you come here by yourself?”

Most people probably aren't trying to hurt you. They're making conversation.

But you don't owe strangers your entire story.

You can say, “I'm taking some time for myself.”

You can say, “I'm trying something new.”

You can change the subject.

Or, if you want to tell your story, you can.

The important thing is that you get to decide.

Creating New Memories Doesn't Erase the Old Ones

This is another fear that can creep in quietly.

If I start making new traditions, what happens to the old ones?

If I visit somewhere without them, does that mean I'm moving on?

If I have a wonderful experience with new people, am I replacing someone?

No.

Your life isn't a room where something new can enter only after something old has been thrown away.

There is room for both.

You can return to a place you once visited with someone you loved and honor those memories.

You can also go somewhere completely new.

You can continue an old tradition.

You can start another one.

And you don't have to decide which kind of traveler you're going to be for the rest of your life based on what feels right today.

What If the Trip Isn't Wonderful?

Let's talk about this because I don't want to sell you a fantasy.

You could take the trip and have a difficult time.

You might feel lonelier than you expected.

You might become overwhelmed.

You may discover that you're not ready to travel as far or for as long as you planned.

You might come home early.

That doesn't mean you failed.

It means you learned something.

Maybe next time you'll go somewhere closer. Maybe you'll invite a friend. Maybe you'll take a group trip. Maybe you'll stay three nights instead of seven.

And maybe you'll wait awhile before trying again.

Travel doesn't have to become another standard you use to measure whether you're “recovering correctly.”

There is no correctly.

As you travel more, you learn how to travel better. Read, Make the trip work for your body, your budget and your life to plan your vacations better and make travel meaningful to you.

Making Room for the Life That's Still Yours

When I think back on that first trip to Orlando, what matters to me now isn't whether I chose the perfect hotel or found the cheapest rental car.

I remember that I went.

For years, so much of my identity had been connected to caring for the people I loved. I was a daughter. I was a granddaughter. I was a caregiver.

And then suddenly those roles were gone.

Underneath all of that, though, I was still me.

I was still the person who loved travel.

I was still the person who wanted to see things.

And apparently, I was still the person who really wanted to go to a Star Wars convention.

That mattered.

Your thing doesn't have to be Star Wars. It doesn't have to be Disney World, Paris, an Alaskan cruise, or some bucket-list destination.

Maybe it's a cabin two hours from home.

Maybe it's the beach.

Maybe it's getting into your car and finally taking that road trip you've talked about for ten years.

Maybe you don't even know what it is yet.

That's okay.

Grief doesn't disappear because we change locations. We can't pack a suitcase and leave the difficult parts of our lives sitting neatly at home until we return.

Sometimes grief comes with us.

It may sit beside us on the airplane. It may show up unexpectedly at dinner. It may walk along the beach with us or find us in a hotel room at two in the morning.

But something else can come with us too.

Curiosity.

Joy.

Laughter.

A little confidence.

And eventually, perhaps even excitement about what might come next.

You don't have to stop loving what you lost in order to love something that's still here.

You don't have to be completely healed before you're allowed to make another memory.

And you don't have to leave your grief at home in order to travel.

Sometimes grief gets a seat beside you.

You just don't have to let it choose every destination from here on out.

Get There Your Way

If you're thinking about traveling after loss, you don't need to start with the biggest trip you've ever taken.

Start with the trip that feels possible.

Give yourself room to change your plans. Give yourself permission to have good days and difficult ones. Give yourself permission to laugh without apologizing for it.

Most importantly, don't compare your timeline to anyone else's.

Your first trip after loss belongs to you.

Maybe you'll come home feeling stronger. Maybe you'll simply come home knowing that you did something you weren't sure you could do.

Sometimes that's more than enough.

Get there your way.

Learning how to travel when your life has changed isn't easy, but it's possible. Join the Single, Sick and Broke community by signing in with your email below.

The Single, Sick & Broke Traveler

Travel stories for the brave and budget-conscious.

Contact Me!

nessa@singlesickbroketraveler.com

© 2025. All rights reserved.