Travel Tips

How to Travel Alone For the First Time Successfully

Posted on by Susan Portnoy
A young woman wearing a straw hat with a backpack over her shoulder about to travel for the first time alone.
Photo: Shutterstock

Congratulations! You’ve decided to start traveling alone for the first time. That’s awesome! You won’t regret it.

You’re probably thinking, now what? Where do I go? How do I go? No worries, I’ve got you covered.  I have a few suggestions to help get you started so that you’ll be sure to travel successfully.

First, to address the Covid-19 in the room. My guide below provides the basic strategies to consider when traveling alone for the first time. Be sure to check for Covid requirements and restrictions for your destination.

Solo Travel Tip # 1: The Most Important Question

When traveling alone for the first time, the key question you have to ask yourself is: How alone do you want to be? Do you want to travel completely solo, or, on your own but on a group tour?

Both are great options. Both have their pros and cons. I’ve listed a few of each below.

Traveling Alone

Pros

  • Freedom to be blissfully selfish. Your time is 100% yours to do with what you will. You can see what you want to see, change your itinerary at will, and spend hours in one place without feeling guilty. It’s all about you.
  • You’ll learn a lot about yourself. Good or bad, how you deal with the day-to-day of traveling alone will end up giving valuable insight into who you are, what you really enjoy, and what you’re capable of.  And that’s never a bad thing.
  • You’ll be totally present since you won’t have someone else to distract you or influence your perception. (This assumes you’re not spending all of your time staring at a device or bingeing on social media.)

Cons

  • You’re responsible for all the choices. It’s funny how even though you get to do whatever you want it can be challenging when you’re used to having others participate in the decision-making.
  • You might be a little lonely. I admit it. Now and then I get lonely. It rarely lasts long but it happens. That said, I’ve also felt lonely in a crowded room filled with friends and family.
  • From a security standpoint, you need to be extra conscious of your surroundings and the situations you put yourself in. Use common sense and don’t take chances. I’ve never had a problem but I’m also alert.
A man looking across a river with his back to the camera holding a duffle bag, and it's the first time he's traveling alone.
Photo: Shutterstock

Traveling Solo on a Tour

Pros

  • If you’re feeling a little shaky about your first trip alone, joining a tour is a great gate-way alternative that gives you a taste of independence without being completely by yourself.
  • Tours have set itineraries and staff to take the burden off you have to plan and manage logistics.
  • There’s a really good chance you’ll meet new friends you’ll keep in touch with long after you are home.

Cons

  • You’re subject to a set itinerary and a group consensus.
  • You may end up with a few people who rub you the wrong way.
  • It may cost more than traveling alone.
Susan Portnoy, The Insatiable Traveler at Machu Picchu. My first time traveling alone.
Me at Machu Picchu

Ok, you’ve thought about the pros and cons above and have decided how you want to go.

Next step…

If You Travel Solo

Are you going to plan your own trip or work with a travel advisor? That’s a good place to start. There’s no wrong answer, and I’ve done both. If my work/life schedule is insane, I’ll work with an advisor—someone who has expertise in the places I want to go and can narrow down the options, plus they usually have insight on deals I wouldn’t know about otherwise.

Food for thought: The onset of COVID-19 highlighted the weaknesses in online booking. When the crap hit the fan, those with travel specialists had someone behind the scenes working on all the particulars––changing flights, canceling/booking new hotels, etc.––whereas those who used Expedia et al, were left in a quagmire of inefficiencies.

For the short term, I’ll be using travel specialists for all my personal trips. With all the rapid changes in travel, agents are going to be in-the-know way before anyone else.

How to Find Great Advisors and Sound Advice

The obvious tactic: ask your friends who they use. You’re bound to get some great suggestions.

Try Consumeraffairs.com:  For a combination of travel websites and travel specialists that can assist you. The site has a nifty search engine that asks you a few questions about your travel needs and then spits out recommendations.

Check out the trusted and true: Many leading travel publications provide an annual list of their top travel advisors (some call them “specialists” or “designers,” they’ve got all kinds of names) grouped by destination or specialty or some other criteria that provides helpful direction.

Important: When you first reach out to a travel specialist, ask whether they charge a fee for their services. It’s pretty much 50/50 right now (some receive a commission from the vendors they work with instead) but the virus may alter their strategy.

Four people really happy in the Masai Mara including Susan Portnoy, The Insatiable Traveler
From L>R: Nancy, our guide Sammy, Yours truly and Lori .. two lovely ladies I still keep in touch with because of traveling.

Solo Travel Tip #2: If You Want to Plan the Trip Yourself

Keep it simple: Unless you really enjoy putting complicated itineraries together, keep it simple. Instead of going on a multi-city jaunt through France, choose a single city and really immerse yourself in it.

Decide on a daily activity anchor: When putting together your itinerary, choose one big thing that you want to accomplish each day. A museum visit, a day trip, a cooking class. Whatever. Figure out the timing requirements, transportation, costs, etc. Then fill in with other things around that such as meals, time to wander, smaller excursions. If you’re a person that likes to wing it, great, but if you need a little more structure this is the best way to start.

Research: To get some ideas of what you might like to see and do, you’ll need to do some research. Refer to travel guides you respect, ask friends, comb tourism websites, they typically provide lists of top tourist spots. Check out lux hotel websites and see what activities they suggest to their guests. Pull together lists of ideas that seem interesting and find your anchors.

Indulge in a private guide: Consider splurging on a private guide for some of your adventure. I suggest hiring someone when you’ve got a really special excursion in mind. Group sight-seeing tours can be good but the information is usually pretty general and often just scratches the surface. Printed travel guides are helpful but they can’t answer questions. A good private guide brings a destination to life.

I hired a guide when I explored Machu Picchu. It’s a vast and fascinating city and I wanted to know more about it. I wanted the details. We went at my pace and I didn’t have to compete with other travelers. Plus, I could ask questions to my heart’s content without feeling as if I was hogging his attention. The investment was worth every penny.

You Want to Travel Alone but on a Tour

Chances are, you have a dream destination in mind. Perfect. Now, how do you want to see it? Do you want a general introduction to your destination and hit the main tourist hotspots, or do you have a particular passion filter you want to apply to your decision?

Today, there are many companies that provide highly specialized tours that cater to all types of enthusiasts who love culinary trips, African safaris, polar bear tours, adventure activities to photography workshops, itineraries focused on history, and virtually everything else in between. I recommend these types of tours because focusing on something you love and traveling is a potent combination. You’ll also be with like-minded people, maximizing your chances of having a great time.

Susan Portnoy, The Insatiable Traveler on the edge of a sinkhole ready to repel down.
Me on a trip by myself to Belize repelling 300 ft into a sinkhole. Never did that before. You know what? It was awesome!

Solo Travel Tip # 3: How to Find the Right Tour For You

Use Google as a starting point: I love Google to get the creative juices flowing but there’s no quality filter there so use it as a tool, not as a definitive answer.

Try a Facebook Group: Ask people in a public Facebook group (or ask to join, they often are very welcoming) that share your particular passion for recommendations.

Go to the experts: If you want to indulge a passion, check reputable institutions in your field of interest. For example, if you’re into history or art, The Metropolitan Museum of Art in NYC offers trips. For photography, The Santa Fé Photographic Workshops leads tours in various locations such as Cuba and San Miguel de Allende. The Institute of Culinary Education offers periodic trips that include hands-on cooking and masterclasses.

Research your idols: If there is a professional you admire in a field you enjoy, check out their website. You may find they lead trips or guest host tours you can take.

A brand may have the answer: If your passion requires special equipment or garments, professional retailers may be affiliated with tours. Lovers of outdoor adventure who like the REI brand, REI Adventures, I’ve heard is a good resource.

Don’t be afraid to ask a tour operator a lot of questions: If an outfitter or leader seems at all hesitant or too busy to give you thoughtful answers, move on. That’s a big red flag in my book. Questions you might consider asking include:

  • How many solo travelers do they typically have on these trips? (You don’t want to find out after the fact that the tour is booked predominantly with couples, so you can decide if that works for you.)
  • Do they have any previous clients they can connect you with to give you a personal reference?
  • How flexible is the itinerary? (Schedules that are too rigid are less favorable because they don’t take advantage of serendipitous opportunities that often arise while traveling.)
  • How many solo travelers are booked thus far?
  • Are kids booked on this trip?
Susan Portnoy, The Insatiable Traveler learning to cook Thai food at the Amita Cooking School in Bangkok
Taking my own private Thai cooking class. Too much fun. And too much food. I was stuffed.


General Tour Advice

  • Smaller is better: Go with the smallest number of people your budget will allow. The smaller the group the easier it is to build camaraderie and receive personal attention. The larger the group, the less intimate the experience.
  • Consider the mix: Avoid tours that cater to couples. When you speak to the tour operator, ask them how many solo travelers they tend to have per trip.
  • Read the fine print: Be sure to look through all the information thoroughly, especially where it talks about what’s included in the tour and what additional costs you’ll be responsible for. For example, international flights are typically not included.

More travel tips you might find helpful 

Responsible Travel Made Easier: A Guide to Sustainable Hotels and Tours

24 of the Most Breathtaking Views in the World Worth Traveling For

I Travel for a Living. I Never Get Jet Lag. Here’s Why

Learn How to Travel Stress-Free – Use This Pre-Trip Checklist

The Best Podcasts to Listen to on Your Next Trip

Why You Should Apply for Global Entry

These 5 Great Tips Will Help You Enjoy A Long Coach Flight

Single Supplements

Be mindful of single supplements (the extra fee many companies charge to offset the cost of accommodations which are priced at double occupancy).

A number of tour companies — including Rick Steves’ Europe, Backroads, Intrepid Travel, and G Adventures — attempt to take the sting out of single supplements by offering a halfway measure, they will waive the supplement if solo travelers agree to be matched with a roommate. In some cases, if the travel company cannot find you a roommate, you get the room to yourself. Singles travel companies like AllSinglestravel.com offer roommate matching. No matter what, be sure to read the fine print. For instance, SinglesCruise.com notes that it “accepts no responsibility for roommate matching incompatibilities such as sleep patterns, snoring, noise or age differences.”

If you’re speaking to a company that charges a single supplement, don’t take it as a fait accompli, ask the representative if they’ll forgo the charge or at the very least reduce it. You may be pleasantly surprised. (Hint: tours looking to fill up their slots are more likely to be flexible closer to the departure date.)

Susan Portnoy, The Insatiable Traveler at the top of Wayna Picchu
Me after a climb up Wayna Picchu looking down over the lost city of Machu Picchu

A Great Resource

Solo Traveler is a wonderful resource for anyone interested in traveling on their own. Janice Waugh, author, public speaker, and one of the nicest women I’ve ever met, and her partner Tracey Nesbitt, have put together a comprehensive site that offers advice on trip planning, personal stories, and great travel deals, many with little to no single supplements.

She put together a wonderful handbook you may find useful.

Solo Travel Tip #4: General Travel Advice if You’re Traveling Alone

  • Provide a friend or family member with:
    • A copy of your itinerary and the contact information for the places you’ll be staying.
    • A copy of your travel insurance policy in case you can’t access your information.
  • Check-in periodically with people back home.
  • Take photos of your passport, credit cards, and insurance information for easy access. Be sure to keep print copy versions with you too should your device run out of juice.
  • Never keep all your money in the same place.
  • Don’t take stupid chances or drink heavily when out and about.
  • Write down the address and phone number of wherever you’re staying and keep it with you in case you need to find your way back and you don’t speak the language. If you’re at a hotel, grab a few business cards from the front desk.
  • Because dinners can sometimes feel more lonely than other meals, choose restaurants that cater to travelers and, if possible, have big bars you can eat at. It’s less solitary than sitting alone at a table, it’s easier to talk with strangers, and bartenders are good conversationalists if you feel like a chat. Plus, always have a good book on your phone (or in your luggage) that you can indulge in to keep yourself occupied if there’s no one around that you want to talk to.
Susan Portnoy, the Insatiable Traveler and fellow travelers on a photographic tour in South Africa
Me and some of the other guests on a photographic tour in South Africa.

Solo Travel Tip #5: Travel Insurance

I’m a big fan of travel insurance, especially if I am going someplace remote and want to be confident that I have proper medical care or flown out should I have an emergency.

My dad and stepmother canceled a trip to Russia at the last minute due to a close friend’s illness and received full reimbursement. It’s just a smart idea.

To find the right coverage, I recommend insuremytrip, a site that enables you to compare policies from multiple companies at once.

Medex is worth checking out too if medical and evacuation assistance to the hospital of your choice, including repatriation.

Medjet is insurance that is in addition to your standard travel insurance. Should you need medical care, Medjet will make sure you are taken to the hospital of your choice, in your home country. Unless your standard travel insurance is covered for repatriation, they will take you to the “nearest acceptable facility.” I don’t know about you, but I’d prefer to determine what is “acceptable,” especially if I am in a remote destination or third world.

(Note: In the age of Coronavirus, however, Medjet cannot evacuate travelers if borders are closed due to Covid or other reasons.)

Solo Travel Tip #6: Don’t Travel in a Bubble When Traveling Alone

While in your destination, Don’t be shy: Proactively engage in conversation with those around you, especially locals. Ask them what activities they love to do in the area. Where they like to eat. Are there any special festivals or events taking place you should know about?

Get an insider’s view. (Don’t let not speaking the language inhibit you. Ask those who are likely to speak your language: A concierge, a staff member at a museum or other popular tourist attractions, taxi drivers.

Connect with tradition: Try at least one new cultural something every day of your trip. It can be large or small: a new type of food, shop a unique store, try a traditional activity.

For more ideas, check out my piece Best Travel Advice: 10 Tips to Help You Break Out of Your Bubble.  

The Most Important Advice I can Impart for First Time Solo Travel.

Have fun. Embrace the adventure. Take things in stride. Yes, something will go wrong but whatever it is it doesn’t have to ruin your trip. Truth be told, some of my fondest memories are the result of getting lost, missing a flight, or my car breaking down.

It’s all part of the journey, both inside and out.

Cool Stuff Straight to Your Inbox

Receive inspiring travel stories, gear recommendations, and travel and photography advice.

Please wait...

Thank you for signing up!

109 thoughts on “How to Travel Alone For the First Time Successfully”

  1. ali ahmed says:

    its really awesome to hear about this experience of gathering the power to travel alone. its really inspiring and encouraging.

    Reply
  2. Roxy says:

    This article will help those to overcome their fear which is not getting confidence in a solo trip. Thanks for sharing this helpful article with us.

    Reply
  4. Susan Portnoy says:

    Absolutely. This article is focused more on the initial stages of determining how one wants to travel solo and the path toward determining a final destination. Once that destination is chosen, by all means, research is important. 🙂

    Reply
  5. Sujata says:

    Well summed up. I would like to add one thought of mine. If travelling solo, is it not better to research about the places one would like to visit and plan accordingly to save time and see what one really want to see? Bcoz each one has one’s own choices.

    Reply
  8. AHMED IJAZ says:

    Awesome post Susan. That’s a lot of good travel tips and advise. I have done many solo travels, but found many I could add to plan future travels from your post. Thank you!

    Reply
    • Susan Portnoy says:

      I’m so glad to hear it! What a wonderful compliment. Thank you for checking it out and for letting me know. 🙂

      Reply
  9. Doctor with Needles says:

    Thank you for the post. It’s very useful. I do find that taking photo is difficult if I want myself in it : P

    Reply
  10. Adventurous Kate says:

    Lots of great advice for first-timers here! I love your tip of planning one big activity for each day. That’s something that I should have done more often, to be honest, and I’ve planned some trips way too long (a full week in Medellin, WHY?!) and way too short (two weeks in Macedonia, Kosovo, AND Bulgaria? No). Now that I’m based in NY and traveling less often, I try to plan my trips with a scalpel — no endless days of free time, but plenty of cool activities packed.

    Reply
  12. Paolo says:

    So far, I’ve only had two trips alone. Both lasted 3 days: the first in Venice and the last in Tuscany.
    I will definitely follow these tips because I want to make a longer travel.

    Reply
  17. louresa says:

    Oh wow! One day I will travel solo! But for now I love traveling with my twin sister. But when the time comes this post will be very very helpful so thank you!

    Reply
  20. carlamcgill says:

    So much valuable information here, Susan. How nice of you! Thanks for the suggestions and perspective! I am not currently traveling much, but I enjoy vicariously traveling through your photos.

    Reply
  21. thewanderingdiabetic says:

    Solo travel is the scariest, most liberating thing I have ever done. You have just inspired me to book another trip away!
    Thank you for the inspiration 🙂
    Looking forward to following your journeys.
    Aislinn

    Reply
  23. spreefirit says:

    Hey Susan,

    Great deal of writing on the things you need to be aware while you are solo travelling. Keep up the good work. Looking forward for more works from you.

    Regards,
    Ramjith

    Reply
  25. sapphirestone315 says:

    Hello! This is such a great post!
    I’ve recently started travelling solo (alone with a tour), and I’m loving it! And your post just opened up a whole new set of things for me to think about and experience!
    Can’t wait to read all your other posts! 😀
    Cheers!

    Reply
  26. mirang12 says:

    yy On Mar 10, 2017 9:56 PM, “The Insatiable Traveler” wrote:

    > Susan Portnoy posted: ” Congratulations! You’ve thought about traveling > solo for a while now and you’re finally going to take the leap. That’s > awesome! You won’t regret it. You’re probably thinking, now what? Where do > I go? How do I go? No worries, I’ve got you covered. Fi” >

    Reply
  27. marieryan says:

    Hi Susan…Great post.
    I’m a bit of a ‘solo’ traveller too and can agree with absolutely with all of your tips.
    I’ve found that a big friendly smile goes along way and that often other ‘solo’ travellers are always happy to team up.
    Regards. Marie.

    Reply
  28. jazminej11 says:

    This is super helpful, thank you for sharing your knowledge! I have been contemplating traveling solo and this guide gave me the push to take the plunge.

    Reply
  33. Vinz Eusala says:

    Thanks for these great and useful tips. Now, I feel like more confident and excited for my next solo travel. The large photos are completely fine I guess.^^

    Reply
  36. Jolien says:

    I’d love to travel solo with my dog (so I guess it’s not totally solo). With an animal by my side, I have more courage to visit remote places.
    I don’t know if you have experience with that, but thanks for the tips anyway!

    Reply
  37. vadettevanderhaar says:

    Thanks great article. While I love the idea of travelling solo, my head automatically goes to everything that can go wrong (I’m a little obsessed with crime shows). I have a holiday club and almost every year have to forgo hiking.

    Reply
    • Susan Portnoy says:

      Ok.. I totally get that you have concerns about safety in general and you’re probably exacerbating that perspective by watching crime shows. Try going on a tour by yourself. You’ll feel safer and it’s a great way to start and then maybe the next time you’ll feel better about doing it by yourself. You don’t have to go to a third world country, by the way. Try baby steps. Go on a long weekend somewhere in your home country (not sure where you live) and make it easy on yourself.

      All that said: Why do you have to forgo hiking?

      Reply
      • vadettevanderhaar says:

        I live in a 3rd world country 🙂 South Africa. My group prefer spa’s and 5 star hotels etc, we have a majority rules policy. I love outdoors and don’t really care if there is someone to wash my dishes and clean my room. As long as I get to leave in the morning and return at night. So exhausted but knowing that I experienced or saw something that I will not again. I think that luxury accommodation is so well refined in terms of their offerings that you get the same experience as everyone else. Will try baby steps. Thanks

  38. wallaceadventure says:

    Great tips, even for me travelling with my hubby. We’re going for a 2 week trip to Ireland for our anniversary in August. I’m doing all the planning and have decided to combine group tours, one private tour and time to explore on our own. Hopefully will achieve a balanced & memorable experience! Thanks for sharing the insurance website…definitely gonna check that out!

    Reply
  42. Simply Splendid Food says:

    I jumped in to read your blog. I am thinking about traveling alone. The main thing I worry about is the feeling lonely. You want to see the faces of your friends and loved ones and talk to them about your days experience. Thank goodness for the internet. Skype may be my new friend! 🍀

    Reply
    • Susan Portnoy says:

      I won’t lie, every now and then I get lonely, but it’s brief. Really brief. Sure, social media is a great way to feel a connection as well as Skype. There’s so much to get out of going alone. Consider it a gift to yourself. If you feel like it would be difficult to go totally on your own, definitely find a great tour that’s connected to a passion. Looking at your website address, you might adore a culinary trip of some kind. You’ll make new friends who “get” your passion for food. You won’t regret it.

      Reply
  44. mybookinggreatblog says:

    I loved travelling on my own. I travelled around Thailand it was truly liberating! You’re safer than what you fear!

    Reply
  45. backalleyorchids says:

    Great post! Thanks for the summary 🙂 I`ve been travelling solo for years now and it has it´s challenges and blessings 🙂

    Reply
  48. francetaste says:

    Don’t limit yourself to English-speaking tours, especially if you speak a foreign language. I did two weeks of trekking in Morocco with Nouvelles Frontières. It was wonderful. Well-organized, plus intensive French practice (I was the only non-French person).
    When traveling alone, especially solo women, consider hiring a guide just to have peace. I would be beseiged the instant I set foot outside my hotel (in any country). I would pick the youngest candidate, explain that I was calling the shots, and as soon as the other guides saw me with this child, we would be left alone. The price was very low, even though I never haggled. And every time, the kid turned out to be great company.
    I also made many friends, both other travelers and locals, whom I never would have met had I been traveling with companions.

    Reply
      • ColorMeLocal says:

        Sorry for the very late reply – I was about to travel when I commented on your post. I traveled through Scotland and Wales, staying mostly with friends of friends. It was so wonderful. =) In many ways I enjoy traveling alone and meeting people along the way. I do wish I would have been able to have joined a group hike or something like you suggested, but I did get to meet some locals in addition to the friends of friends. =)

  51. lilisar says:

    Great advice, thank you! I’ve been travelling solo for years now and quite like it. Also, I like to make a “menu” for sightseeing, divided into “dry weather options” and “rainy day options” with, like you’ve written, all the opening hours. That saves a lot of precious travel time!

    Reply
    • travelwithclem says:

      Lilisar, I agree. I have been traveling solo for a few years now. At first, it was a burden, but now I am enjoying it and in fact,I feel like I prefer traveling solo. I have been independent for so long that it feels difficult to revert back to traveling in groups! Of course, an occasional travel partner would be great here and there, but I do love traveling solo.

      Reply
  57. Dacian says:

    Awesome article! Thank you for the tips and lists!
    I always find myself wondering if I want to travel somewhere alone or not. How would I enjoy and experience that location best? Nice to find someone else who also thinks about these things, and organizes them so neatly haha
    Great photos as well! Thanks

    Reply

I would love to hear from you! What did you think of the post?