Last Updated on January 6, 2026 by Christine Kaaloa

Anthony Bourdain famously said, “I’m a big believer in improvising and getting lost.” While some travelers thrive on meticulously planned itineraries, I’ve found that embracing a level of spontaneity can lead to the most memorable and immersive travel experiences. Going into a trip with few plans to structure it can also lend to a fair amount of stress and anxiety…

In this post, I’ll share my tips for navigating the fine line between spontaneity and structure, and how to travel confidently without a plan.

This post contains affiliate links. I never leave home without travel insurance– I like to buy insurance that covers theft and adventure but here’s a trip insurance finder tool  to find a plan that matches your budget.

Spontaneity and improvisation: A unique safety net

Travel improvisation tests your adaptability on the road and while traversing unfamiliar territories, languages and customs. While the structure of a well-planned itinerary can provide a sense of security and stability, the art of winging it allows you to roll with the unexpected and respond to the moment with either, change or permission. Improvisation is an especially handy skill to have as a traveler and especially if you have long-term trip plans (and you need to stay on a budget).

There’s more to art of winging it than the fantasy of being a traveling hippie. Travel is unpredictable. The improvisation skill of being able to quickly re-route or change plans amidst obstacles, setbacks and potential dangers -while also planning an enjoyable trip- is a powerful safety net skill, when you are a solo traveler without a safety net of travel partners.

Being a fast improviser, troubleshooter, wing it traveler, gives you the flexibility and adaptability to roll-with-the-punches and think on your feet. This can come in handy when you’re getting scammed or when you arrive at your hotel at midnight only to find they gave your booking away.. my list of self-survival troubleshooting experiences grows longer each year.

When you can think fast on your feet and MacGyver plans from scratch, it makes you :

•  more confident navigating unfamiliar situations as a solo female traveler.
• better at gauging situations, your tolerance level for them
• confident at negotiating between risk and safety
•  resourceful in finding solutions.
• attuned to hearing and acting upon your intuition
• know your limitations and boundaries.

Finally,  it means you are capable of your own self-survival and landing on your feet despite the situation. That’s a powerful realization to carry in your daily life!

Why? No matter the situational fears I have about my own future, one thing my ability to improvise solo travel has made me absolutely confident of…  I know I’m capable of in surviving bad situations and I’ll always find a solution to get out of them if it is harmful to me.

Read Is solo travel safe for women?

Wing It Travel: 9 Ways to Travel without a Plan

Here’s some tools and mindset tricks I use when springing into last minute trips and traveling for longer periods with open-ended plans.

1. Not all plans are bad

After some time on the road, learning the rhythm and rules of it, long-term travelers and digital nomads eventually learn to travel without a plan through improvisation and winging it.   I used to be a hardcore “wing it” traveler, shunning guidebooks and embracing the unknown. However, I soon realized that this approach often led to chaos and unnecessary stress.

While I still believe in the importance of spontaneity, I’ve learned that a little bit of planning can go a long way. Researching basic information about your destination, such as transportation options, cultural etiquette and potential scams, can provide a valuable foundation for your travels.

2. Hit up the airport’s official city tourism desk

Most city tourism boards have a kiosk at the airport when you arrive. Look for the tourism board kiosk desk. They will have advice, city maps and help you find your way around. I use this a lot when I want to gain my bearings and quick overview of a city. I also use this resource when I have a long layover and I want to feel like my trip into the city has some guidance. I always ask for maps, inquire about public transportation operation hours and ask if they know about any travel discounts. In Tokyo, it led me to learning about Unlimited Metro day passes.

Travelers don’t think they can travel a city without researching it before hand. I have literally asked kiosk agents for their recommendations of top things to do in the city with my time frame and to circle them on the map and tell me the bus number if they know it.  Voila, you have a locally planned itinerary! Check out  free city sightseeing tours at the airport

Tip:  Please always be courteous and appreciative for their help. If there is a long line of travelers waiting for them and you know your query is going to be like mine, go grab a coffee and come back when there is no line.

3. Gain recommendations from other travelers and locals

I get tons of inspirations and tips from other travelers. I like to strike up conversations with travelers who are already in the destination I am traveling as they offer the most current information and recommendations about activities and places I have on my itinerary.  Often, I’ll get unfiltered opinions about whether a place fits my travel style and interest or not, and they warn me about scams and touts.

Meeting travelers, I also make new travel partners to share taxi ride, be a dinner date or be a sightseeing buddy the next day.  Read my post on How to Make Friends as a Solo Traveler

Local front desk agents offer a lot of tips and they can be highly informative and detailed information about navigating. I also like to ask them what neighborhoods I should avoid or safety tips they’d recommend to a traveler like myself.

Tip: If you get recommendations from other travelers, always get the address of the recommendation and/or a phone number or website. 

4. Hostels

Staying at hostels allow you to meet fellow adventurers. Doesn’t matter if you’re 20 years or 50 years old, hostels are hubs for real-time travel tips and budget-friendly options. Hostels are infamous for drawing a backpacking budget traveler crowd that is looking for cheap ways to get around and enjoy their explorations. Thus, local staff tends to point you at budget friendly options. Some have information on budget tour agencies or offer tours of their own.

Unpopular opinion- as a solo traveling woman in her 50’s I still enjoy staying at hostels.  I know many travelers my age feel they have outgrown the hostel experience. Personally, I think they’re approaching it with a different mindset that assumes with age, they should “upgrade” to a more costly adult choice.

This is the personal trade-off I feel between the two: I enjoy hostels because it is a community space with a friendly, open and inspired travel vibe; whereas, hotels can feel like isolation tanks for business, lovers and family travelers, who want to be left alone.  I’m not seeking to feel more alone than I already am.

Although I enjoy staying at my fair share of boutique hotels, I know my personality has a tendency to dip into lonely-ville and incubation mode and the task of motivating myself to explore the city feels more challenging. Hotel concierges often give “touristy advice” which advises you on how you can spend your money to get more convenience, comfort and assistance.

With hostels, I often get local insider advice that helps me make my dollar stretch, find more meaningful activities and I’m pointed at more authentic attractions and mom and pop businesses to enjoy.  Travelers entering hostels are more inspired to get out and experience things. Guests at hotels carry the opposite energy. If you ever get the chance, try both out. It’s a huge difference to how I enjoy and experience a place.

I might even pick up a companion to do things with if staying at a hostel. In a hotel- there’s no opportunity for me to find a travel buddy. If I want my own room at a hostel, I’ll simply request a single room option. I also prefer female only dorms where I might meet female travelers to do things with. In San Juan, I stayed at an all female dorm and found a travel buddies to spend dinner with to sightseeing Old San Juan’s top attractions.

Read how to budget for long term travel

5.  Using guidebooks and travel blogs

Guidebooks and travel blogs can be valuable resources, even for the most spontaneous travelers. I use them to get a general overview of a destination and identify potential points of interest or offer specific recommendations to alleviate my research time . However, always be prepared to deviate from physical and online guidebook information and embrace unexpected opportunities.

Once, a guidebook listed outdated hotel information in Phnom Penh. A tuk tuk driver warned me about it but I thought he was pulling a redirection scam one me.  When he dropped me at the vacant hotel, I realized he wasn’t lying. With quick on-the-fly decisions and checking my guidebook for alternative areas with accommodations, I was able to find my way to another neighborhood with hotels and found a hotel on foot. That improvisation cost me most of my day, but it also led me to a hidden gem.

6. Mobile apps

These days, having a smartphone with travel apps helps make last-minute decisions and bookings. I’ve had moments when I’ve booked hotels and train tickets from my mobile phone. I’ve used navigation apps like Google Maps and Waze app to find attractions and my way around the city. Metro maps help me navigate subway stations and these days, many cities have Uber or their own version of it.

Pro-Tip: Always have a data plan so you can make bookings and research information from your mobile phone. I use Airalo e-SIM that I can activate before arriving into a city and top off from my mobile app. It saves a world of stress!

7. Get lost & explore on foot

Embrace the “getting lost” experience. Sometimes, the most memorable travel moments happen when you step off the beaten path and explore the unknown. You might stumble upon a morning market or a shop selling odd but fun items; getting lost is wonderful for discovering hidden gems and interacting with locals. Unplanned moments are where a destination will occasionally reveal its magic and you’ll find your rhythm with a place.

However, when you wing it, you also have to be prepared for when things don’t work out smoothly.

8. Listen to your Intuition

Intuition plays a big part in solo travel because you don’t have another person to look out for you. Solo travel forces you to listen and trust your intuition more. Intuition becomes stronger not only because it plays a bigger part for you as a solo traveler, but because being alone allows you to better hear those firm but guided whispers.

Those “nudges” to “go to breakfast NOW”, which leads you to striking up a conversation with another traveler, who becomes your travel buddy for the day… to those whisper warnings to not trust a stranger, because he’s not who he says he is…  are all vital to your improvisations in travel. It’s your ESP safety guide through unfamiliar terrain.

9. Find balance

The key to successful “winging it” is finding the right balance between spontaneity and structure. Allow yourself the freedom to explore and discover, but also have a few key things planned, such as accommodation and transportation.

Travel is about embracing the unexpected and discovering the beauty of the unknown. By combining a sense of adventure with a touch of planning, you can create truly unforgettable travel experiences.