Updated June 2020
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.
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. Obviously, with the impact the virus has had on the industry, once you determine how you want to proceed, you’ll need to research the virus-related restrictions and policies unique to your destination or activity. Unfortunately, it’s so early in the game, there are no blanket suggestions I can offer.
The real question: How “alone” do you want to be?
What I mean is, there are two ways to approach your first solo trip: Going completely on your own, or, on your own but with a tour. Both have their pros and cons. I’ve listed a few of each below.
How To Travel Alone For the First Time
- 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.)
- 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.
Traveling Solo on a Tour
- 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.
- 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’s likely to cost more than a traveling solely by yourself.
Ok, you’ve thought about the pros and cons above and have decided how you want to travel. 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.
- Condé Nast Traveler – Travel Specialists
- Travel & Leisure: The A-List
- Wendy Perrin: “The WOW List: Wendy’s Trusted Travel Experts.”
- If you’re not sure how a travel specialist works, how they get paid, or what they offer, this is one of the better overviews I’ve read from Sally Black, founder of Vacation Kids.
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.
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 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 a great 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 a part 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. I wanted the details. We went as fast or slow as I wanted 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.
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 shares 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 seem 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 predominantly 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.)
- If you’re interested in a photography tour specifically (I’ve gone on more than a few), I wrote a couple of posts you may find helpful.
- “Seven Questions to Ask Yourself Before Choosing A Travel Photography Tour.”
- Photography Workshop or Tour: Which is Right for You?
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
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.)
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.
General Travel Tips 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 chat with strangers you think are interesting, 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.
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 you only want medical and evacuation assistance. Note: Medex does not provide policies to recoup trip expenses.
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 Corona virus, however, Medjet cannot evacuate travelers if a country’s borders have been closed.)
Don’t Travel in a Bubble
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.
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