🇺🇸Weird America

Solo Travel Is Just Travelling Before Everyone Else Gets Organised

Tipple ToursTipple Tours
1 June 2026•4 min read
Solo Travel Is Just Travelling Before Everyone Else Gets Organised - wine travel guide from The Tipple Times
Destinations in this story

I love solo travel.

There, I've said it.

Not because I don't like people. Quite the opposite. Some of the best friends I've ever made started as complete strangers sitting beside me in a winery, brewery or roadside bar somewhere in the world.

The problem isn't people. The problem is organising them.

At some point we've all attempted it. You suggest a trip. Everyone says they're interested. A WhatsApp group is created. Excitement builds. Somebody suggests September. Somebody else can only do October. Another person wants Benidorm. Somebody else wants Thailand. One participant contributes nothing except thumbs-up emojis for three months.

Eventually the entire thing collapses under the weight of its own administration.

By this point I could already be on my second beer somewhere interesting.

That's one of the reasons I love travelling alone.

Freedom Is Addictive

The first thing you notice about solo travel is how wonderfully simple everything becomes.

Want to spend an extra hour in a winery?

Perfect.

Fancy taking a detour because you've spotted a bizarre Soviet monument beside the road?

Excellent.

Feel like changing plans entirely because somebody recommended a hidden brewery three towns away?

Nobody is stopping you.

Travelling with friends can be fantastic. Travelling alone gives you complete control over your own adventure. There are no committee meetings, no negotiations and no debates about whether everybody is happy with the itinerary.

The only person making decisions is you.

Which is surprisingly efficient.

The World Is Full Of Future Friends

One of the biggest myths about solo travel is that you'll spend the entire trip alone. I've never understood where this idea comes from.

In reality, travelling alone often makes you more social. You're more likely to start conversations, join activities and meet people because you aren't travelling inside your own little bubble.

Some of the best nights I've had travelling started completely by accident. A conversation at a bar. A winery tasting. A shared table in a restaurant. Before long you're discussing life stories with people you met forty-five minutes earlier.

Travel has a remarkable ability to speed up friendships. Possibly because everybody is slightly outside their comfort zone. Possibly because wine exists. The exact science remains unclear.

Why Solo Travellers Fit In Perfectly On Tipple Tours

This is one reason solo travellers tend to love Tipple Tours.

Nobody arrives already knowing everyone else. People come because they enjoy unusual destinations, good drinks and interesting stories. The result is that conversations start naturally and friendships form remarkably quickly.

I've seen it happen countless times.

Guests arrive looking slightly cautious. By the second evening they're sharing bottles of wine and discussing future adventures. By the end of the tour they're exchanging phone numbers and promising to meet again somewhere equally strange.

It happens so often now that I'm more surprised when it doesn't.

The Best Part? You Already Took The Hardest Step

The hardest part of any trip isn't crossing a border, boarding a plane or navigating a foreign city.

It's booking it.

That's the moment where most people hesitate.

They wait for friends.

They wait for partners.

They wait for the perfect moment.

Then six months disappear.

Then a year.

Then another year.

Meanwhile, the solo traveller has already visited Moldova, crossed into Transnistria, driven around in Boris the Soviet Lada and returned home with twenty new stories.

Waiting is underrated as a way of wasting time.

Why I Keep Travelling Solo

I've travelled through former Soviet republics, driven across strange corners of America and somehow ended up drinking wine in places most people couldn't point to on a map.

Much of it happened solo.

Not because I couldn't find people to come along.

But because I didn't want to wait.

The truth is that solo travel isn't really about being alone. It's about freedom. It's about curiosity. It's about deciding that life is happening now rather than whenever everyone finally agrees on dates.

And the funny thing is this:

The people who travel solo are often the ones who end up meeting the most people.

Which means solo travel isn't really solo at all.

It's just how the adventure starts.

Explore Related Tours

Turn This Story Into Your Adventure

Tipple Tours
Tipple Tours

Editorial Team

The Tipple Tours team writes about wine, beer, and travel based on firsthand experience running tours across Europe since 2018.

Learn more about us

Continue Exploring

More Stories You'll Love

Read more: How NOT to Swirl Wine (And Why Nobody Cares Anyway)🇺🇸 Weird America

How NOT to Swirl Wine (And Why Nobody Cares Anyway)

There's a fine line between 'experienced wine taster' and 'wizard having a moment'. Here's how to stay on the right side.

15 March 20266 min
Read more: Wine Snobs vs Wine Lovers: A Completely Unofficial Showdown🇺🇸 Weird America

Wine Snobs vs Wine Lovers: A Completely Unofficial Showdown

One will judge your choices. The other will share their glass. Here's how to spot the difference.

15 March 20266 min
Read more: Beer Flights: What They Are (And How Not to Accidentally Ruin Them)🇺🇸 Weird America

Beer Flights: What They Are (And How Not to Accidentally Ruin Them)

Everything you need to know about craft beer flights from selection strategy to drinking order. Spoiler: there is a wrong way to do it.

15 March 20266 min
Read more: Moldova: The Wine Country That Accidentally Stayed a Secret🇺🇸 Weird America

Moldova: The Wine Country That Accidentally Stayed a Secret

Moldova is what happens when 5,000 years of winemaking meets zero interest in moderation. Expect underground wine cities, unstoppable grandmothers and “just one glass” turning into a full-blown life event. 🍷

30 April 20266 min
Read more: Hops & Homicide: Why This Might Be the Strangest (and Best) Beer Tour in America🇺🇸 Weird America

Hops & Homicide: Why This Might Be the Strangest (and Best) Beer Tour in America

There are normal brewery tours. You know the type: “This is how hops work”, “This is our fermentation tank” or “Please enjoy this responsibly sized tasting”. Lovely. Educational. Calm. This tour is not that.

1 May 20266 min
Read more: Ale-ien Encounters: A Completely Rational Guide to UFOs & Beer🇺🇸 Weird America

Ale-ien Encounters: A Completely Rational Guide to UFOs & Beer

There are normal beer tours. Then there are beer tours where at some point in the evening someone says: “Wait…what was that in the sky?” Welcome to Ale-ien Encounters. Where the beers are real and the explanations are optional.

1 May 20266 min

Join the Tipple Family

Get early access to new tours, exclusive deals and wine tips that don't take themselves too seriously.

No spam, just wine wisdom. Unsubscribe anytime.

Tipple Tours

Possibly the most fun wine and beer tours in the world. We take wine seriously. Ourselves? Not so much.

Tipple Tours is a trading name of Tipple Tours Ltd, 4th Floor, Silverstream House, Fitzroy Street, London, W1T 6EB, United Kingdom.

Tours in Moldova and surrounding regions are operated by Smiling Grape Wine Tours SRL, str. Mihail Kogălniceanu 66, of. 4, Chișinău, Republic of Moldova.

Depending on the tour and booking location, payments may be processed by either Tipple Tours Ltd (UK) or Smiling Grape Wine Tours SRL (Moldova). The contracting entity will be specified at the time of booking.

Serious Wine & Beer. Not-So-Serious Atmosphere.

© 2026 Tipple Tours. All rights reserved. Drink responsibly, travel adventurously.

We use cookies — sadly not the chocolate chip kind — to keep things running smoothly. For the important but slightly dull details, see our Privacy Page.