How to Plan a Solo Trip: 3 Apps I Use for Every Trip After 28 Countries
Most solo travel guides try to romance you into booking the trip. This one assumes you have already decided to go and want to know what to actually do next.
I have been to 28 countries, almost all of them solo. Over those trips I have stripped my planning workflow down to three apps. Everything else is noise. If you download these, learn the small set of tricks below, and stop overthinking the rest, you will plan a better solo trip than 90% of the people who spend three weekends agonizing on Reddit.
The three apps: Hostelworld, GetYourGuide, and Kayak. That is the whole stack.
1. Hostelworld — book the hostel, get the friends for free
The single biggest mistake first-time solo travelers make is booking a private hotel room. You will be alone. The whole point of a solo trip is the opposite of that.
Stay in hostels. It is the best way — and honestly the only reliable way — to meet new people in a new city. Hostels are designed around shared common spaces, shared kitchens, and shared rooms. You will end up in a conversation within an hour of dropping your bag.
Use Hostelworld to book them. Two reasons:
- The reviews are honest and dense. You can filter for “atmosphere” and “social” scores, which is what actually matters when you are picking a hostel solo. Cleanliness matters too, but a sterile, quiet hostel is just a worse hotel.
- You can connect with other travelers before you even land. Hostelworld has a chat feature that lets you talk to other guests who are booked at the same hostel during your stay. That means you can have plans for your first night before you have boarded the plane. This feature alone is worth the install.
The other thing hostels give you is built-in events. It is extremely common for hostels to run bar crawls, pub nights, beer pong tournaments, family dinners, walking tours — the staff knows their guests are mostly solo travelers and they actively engineer the environment for you to meet people. Just say yes to whatever is on the whiteboard at reception.
2. GetYourGuide — for the ideas, not always the bookings
GetYourGuide is the easiest way to find the top-rated activities in any city. Open the app, set your location, and you have an instant short list of what is worth doing — food tours, day trips, museum skips, snorkeling, paragliding, whatever the city is known for. The reviews are aggregated, the descriptions are clear, and you can purchase in two taps.
The catch: GetYourGuide can be pricey. They take a cut, and that cut is baked into the price.
Here is the move. Use GetYourGuide as your idea engine, not always as your booking platform:
- Browse the top activities in the city on GetYourGuide.
- Pick the ones that look interesting.
- Google the activity name plus the city. Nine times out of ten, you will find the local company that actually runs the tour. Book directly with them and you will pay less.
I still book through GetYourGuide when the convenience is worth a few extra dollars or when the local operator has no real website. But for big-ticket activities — multi-day trips, lessons, anything north of $100 — going direct adds up fast.
Always do at least one bar crawl
If you take one piece of advice from this entire post, take this one: book a bar crawl on your first or second night in a new city.
Bar crawls are the highest-ROI activity in solo travel. You are guaranteed to meet new people because everyone there came to meet new people. The whole social contract of the event is “talk to strangers.” I have never been on a bar crawl and not met fun people. Not once. Across 28 countries.
You will find them on GetYourGuide, on Hostelworld events boards, or just posted on the wall at your hostel. Pick one. Go.
3. Kayak — find the flight, then book it somewhere else
For flights, I always start on Kayak. The interface is fast, the filters are good, and it pulls from enough airlines and aggregators to surface the genuinely cheapest options.
But I never purchase my flight on Kayak. Here is the rule:
Use Kayak to find the airline with the cheapest flight. Then go to that airline’s own website and book directly.
Two reasons this matters:
- The price is almost always identical. Airlines price-match their own direct site against the aggregators they list on. You are not saving money by booking through the third party.
- You only get frequent flyer miles when you book direct. Most airlines either do not credit miles for third-party bookings, or credit a reduced amount. Over a year of travel, that is a free trip you are leaving on the table.
A third reason, which becomes obvious the first time it bites you: when something goes wrong — a cancellation, a missed connection, a schedule change — booking direct means you call the airline and they fix it. Booking through a third party means you call the third party, who calls the airline, who tells them to call you back.
Find the flight on Kayak. Book it on the airline’s site. Every time.
Honorable mentions
Two apps that fill in the gaps when the main three do not apply:
- Booking.com — for hotels when hostels are not available, or when you genuinely need a private room (long work trips, recovery days, partner is joining you for a leg of the trip). Big inventory, easy cancellation policies, and the loyalty program is generous if you travel often.
- Google Flights — a perfectly good alternative to Kayak. Same workflow: use it to find the cheapest airline, then book direct. I prefer Kayak’s filters, but Google Flights’ calendar view is better if your dates are flexible — it will show you the cheapest day to fly across a whole month.
The thread that ties it all together
Three apps. One philosophy.
- Hostelworld — stay where the people are. Book the hostel, and use the in-app chat to make friends before you land.
- GetYourGuide — let the experts pick the activities, then go direct to the operator to save money.
- Kayak — let the aggregator find the airline, then go direct to the airline to keep your miles.
The pattern is the same in all three: use the tool that is best at discovery, then route around it for the actual transaction whenever it is cheaper or earns you something. That is the whole skill of cheap, well-planned solo travel. Everything else is just showing up and saying yes.
Book the hostel. Show up to the bar crawl. Have a good trip.