The solo traveler starter kit

The first trip is the hard one. Here's everything you need to book it anyway.

Somewhere in your camera roll there's a screenshot of a trip you didn't take. The Portuguese one, maybe. The Santa Fe one. You saved it, did the math on going alone, and let it expire quietly, like a coupon. This particle is the anti-aversion plan: where to go, how to stay for free, what to pack, how to get there. Consider it your starter kit.

Where to go first

Pick an easy win for trip one. Veteran solo travelers consistently point to the same shortlist: Portugal is wonderful for its welcoming atmosphere and vibrant cities like Lisbon; Tokyo is known for its safety, while Italy offers a blend of rich culture and relatively safe urban environments for solo travelers; and Europe is packed with traveler-friendly spots such as Vienna or Dublin. Domestic counts too. Savannah, Sedona, Santa Fe: places where dinner alone at the bar is a local sport, not a spectacle.

First, permission from the experts

Because the industry is finally built for us. Travel coach Deb from Wanderlust Solo Women Tours, who runs trips specifically for this demographic, puts it plainly: the beauty of solo travel is doing exactly what YOU want, but preparation helps. And the writer behind Bald Girl Will Travel, a solo traveler over 50, draws the distinction that should be pinned above every packing list: being prepared is not the same thing as being fearful. "I am not interested in traveling scared."

One boundary worth packing

From the Bald Girl Will Travel playbook: you do not owe strangers your itinerary, your hotel information, your relationship status, or confirmation that you are alone. You can be friendly without being overly revealing. "My friend is meeting me later" is a complete sentence.

The free accommodation trick: house sitting

Here's the part that changes the math on everything: you can stay in real homes, all over the world, for free, by watching someone's pets while they travel. TrustedHousesitters is the big player. It's an international platform that connects pet owners with verified house sitters; sitters care for pets and homes while owners travel, without any exchange of money between the two parties. Founded in the UK in 2010, it has grown into a global marketplace listing up to 10,000 house sits at any given time across the UK, Europe, the USA, Canada, Australia, New Zealand, and beyond.

You pay an annual membership instead of nightly rates, and the numbers get silly fast. One longtime sitter reports: "I basically get my money back for my membership in a day. I've done housesits in homes where I've stayed for weeks at a time."

•
It's safer than hotels. You're in a residential neighborhood, not a tourist district. You have a local's address. You know someone (the homeowner) is expecting you.
•
You get companionship without commitment. A dog to walk means morning routine. A cat to feed means coming home to something alive. Perfect for women who want company but not conversation.
•
It forces you to slow down. House sits are usually 1-4 weeks. You're not rushing through a checklist. You're living somewhere. That's a different kind of travel — the kind that changes you.

The packing list nobody gives you

Beyond clothes (which you already know how to pack), here's what solo women swear by:

•
A door wedge. Hotel doors don't always lock well. A rubber wedge costs $3 and buys peace of mind.
•
A portable charger + international adapter. Your phone is your map, your translator, your emergency contact. Keep it alive.
•
Copies of everything. Passport page, insurance card, reservation confirmations — printed AND digital. Email copies to yourself.
•
A scarf. It's a blanket on cold planes, a modesty cover for religious sites, a beach cover-up, a pillow, and something to hide behind when you're eating alone and want privacy.
•
A book. Not your phone. An actual book. For dinners alone. For waiting in line. For the moments when being alone with your thoughts feels too loud.

"The first trip is always the hardest. Every trip after that is proof: you can do this."

Making friends on the road

Solo travel doesn't mean lonely travel. Some of the deepest friendships form between strangers who happened to choose the same café table. Join a walking tour (everyone there is also alone). Take a cooking class. Say yes to the couple who invites you to their table. Women are remarkably good at finding each other — trust that instinct.

Book the trip. Pack the bag. Go.

The screenshot in your camera roll isn't a fantasy. It's a preview. And we'd love to hear about it at Girl Dinner — bring photos.

Vicky Townsend

Founder & Fellow Bear