The Deal Mommy

Lessons Learned from 20 Years of Solo Travel

solo female travel

Worshiping at the Pyramid of the Moon. Teotihuacan, Mexico.

I’m bemused, but no longer surprised, by the reaction to my solo travels from the Momosphere:  “That looks awesome but I could never do it” or some variation thereof.   Taking out those who are just being polite (IE those for whom it DOESN’T look awesome), the solo travel “I could never do it” usually comes down to one of three things: money, time, or fear of traveling alone.

Most of my blog is about the creative things I do to make the finances work and an entire trip can be completed in 48 hours, so today I’m going to talk about #3: facing the fear of solo travel and doing it anyway.

The case for Mom to get out of town

Moms, why am I so passionate about you traveling by yourself?  Because Girlfriend’s getaways are great, for what they are. But I don’t want you to be limited by others…and why should you be?  You have your own must-see list, don’t you? Also, it’s hard enough for YOU to get childcare, budget, and a plan.  If you wait around for a girlfriend, sister, or whoever else, you may never get off the ground!

Now I get it: fear is irrational.  Telling you, for example, that plane travel is statistically safer than driving to the airport does nothing for you if you’re afraid of flying.  And telling you that most hotels have wifi (and many cell plans include free international data and texting) so your family can skype you in real time does nothing to calm you if you’re afraid your kids will befall some calamity requiring Mommy at the exact moment you decide to leave the country for the 1st time. But you’re a good parent who chooses good proxies, right?

So now on to some real-life tips to help you rip off the band-aid for that first solo weekend. Readers who have traveled solo, please share your tips in the comments:

Tips for your first try at solo travel

  • When you’re keeping it short, destination choice is essential. Fly non-stop if at all possible.  Use this checklist to help you decide where to go.   I know many moms don’t have extended amounts of time either to plan or to take off so you need a workable idea.  For instance, I took a last minute weekend to Mexico City in the dead of winter. I needed sun and non-stop, and it fit the checklist.
  • Overschedule. Sleep when you get home. Go ahead and book two tours in one day.  It may look nuts on paper, but chances are at least one of them will not run (one of my 2 booked tours in Mexico City didn’t run and the other started an hour late). Worse comes to worse, you can cancel on them.  At least then you have the power. (By the way, this is NOT advice I give or take on longer trips, but when it’s an “ambush” type trip, ya gotta do what ya gotta do!)
  • Expect your body to fail you. Happens to me Every. Single. Trip. In Mexico City a cough and cold hit me and made my laughably border Mexican accent pretty much incomprehensible.  Just suck it up and take a shot of local medicine: it makes for a better story!
The most dangerous sign in all of Tenerife.

The most dangerous sign in all of Tenerife.

  •  Yes, Wine is cheaper than water.  Still stick to 2 glasses.  I abstained in Tenerife and reaped the rewards: the most amazing whale tour.   Half the boat missed the tour due to hangovers.
  • Same goes for shady cabs, after-clubs, handsome strangers.   Nuff Said.
  • Keep your wits about you even with “safe” forms of transportation. I let my guard down in a marked cab in Rome and almost paid dearly.
  • Beware GCS. Gilded Cage Syndrome, the dreaded disease that strikes every five star traveler at one point, will put the kibosh on all of your grand plans to explore unless you nip it in the bud.To fight it in Mexico City, I bypassed the Hyatt and St. Regis on purpose in favor of a Holiday Inn in a great location.  On the other hand, you NEED 48 hours locked in a hotel suite, ignore this advice, cancel the flight, and just drive yourself to the nearest FHR hotel.

Packing List

  • Sunscreen (I have missed this one and paid for it!)
  • Ankle wallet
  • Photocopy of passport (scan it into Google Drive as well)
  • Credit card and ATM Card (withdraw foreign currency at Bank ATM at airport, spend what’s left at duty free)
  • Carry-on (DO NOT check a bag!)
  • Cross-shoulder day bag
  • Kindle or i-pad loaded with city map and phrasebook,
  • Camera (if not on ipad).

You CAN do this! Where are you going to go first?

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solo travel

13 thoughts on “Lessons Learned from 20 Years of Solo Travel

  1. MickiSue

    I am grateful for the lessons learned from traveling alone for business for over a decade. I learned to pack light and predictably, so that my clothes could do double duty, and I didn’t have to pack toiletries each time I left; I could just make sure I had enough of everything I normally use.

    I learned to be assertive about the location of my hotel room. One time, I was at a Marriott that had two buildings. One was a walk across a poorly lit courtyard, and the room, just for bonus points, was at the end of a long and poorly lit hallway. I walked back to the desk and told them I required a room in the main building that was reasonably close to the elevator.

    I learned to negotiate for better things. Better rooms, better seats on planes when I was >< this close to elite status, and the flights that would take me over the top were already booked. I learned to push fun into a packed day, like driving through White Sands just before dusk on a travel day to a small city nearby.

    But most of all, given the issues that so many women seem to have with it, I learned to be comfortable traveling alone. It helped me to choose a flight, for example, to Milan, when a flight to Venice was overpriced in business, the year our grandson was born, and to be certain that could navigate the trip from the airport to Milano Centrale, and there, to buy a ticket to Daughter's city.

    And to share what I'd learned with Husband, when he came, a week and a half later. I echo everything you said, Dia. The benefits to be found in traveling with assurance far outweigh the fears to be overcome.

  2. Noway

    I guess I am a bit odd. I’ve been traveling solo (as well as with husband and family) since I was 21. I have been to the Amazon jungle and remote Cambodian villages as well as China shortly after it was opened for tourism.
    I have never thought about it, I just did it. I also fly in F globally and stay in St. Regis and Ritz properties (all on miles and points).

    I prefer traveling by myself as I do what I want, when I want and get to enjoy things my family do not enjoy. When I travel with husband and/or family I don’t do things I enjoy the most because they don’t like what I do and I don’t want to force them so it’s a compromise. I have the best of all worlds. I travel 8 – 10x a year solo, 4x a year as a couple and 1x a year with adult son and his GF. I retired early so I could do this. Some trips are a few days and some are three weeks,

    When I got a job that required travel it was such an easy thing as I had been traveling solo for 7 years previously. I would volunteer for Europe trips and couldn’t believe that others didn’t want them. Racked up the miles and points also,

    I love that you are following the same path I did and I encourage men (as some guys don’t like to travel solo) and women to just do it. BTW I always go into fine dining restaurants solo. That seems to be a stumbling block for some. If people do it once they will see it’s easy.

    You have a great blog,

    1. thedealmommy Post author


      One thing it’s taken me five years blogging to learn is that yes, people who prefer solo travel are odd ducks. Even on family trips (with adults, can’t do this with kids) I’m likely to say “I’m doing X, you’re welcome to join me or go do Y” which is NOT how others operate. Others tend to ask “do you want to do X or Y?” and go as a group. I don’t see the need for anyone in the group to do something they don’t want to do, but again, odd duck.

      Great point about solo dining. A book/kindle can be a good prop to get over the initial hurdle.

  3. Becky

    Great tips and I definitely agree that choosing the right destination is essential!

    My biggest piece of advise is not to push your comfort level too much. If you’re hesitant about going on your own, make it easy…group tours and day trips are okay, English speaking countries are okay, chain hotels are okay, and splurging for private transportation instead of subways is okay. You are traveling solo and not necessarily competing in an intrepid traveler competition!

    If you feel comfortable, you’ll be less stressed and more confident — very important for staying safe and alert. After you’ve traveled solo the first time, you’ll know if/how to push yourself further the next time in a way that makes sense for you.

  4. Pingback: Solo Travel, Avgeek Socks, Staples Rewards craziness, and AMEX Platinum changes - Tagging Miles

    1. Noway

      Just off the top of my head I know that Crystal Cruises is offering many sailings, including into mid 2017 for a 10% single supplement.

      Azamara Club Cruises also has a number of cruises with anywhere from 10-25% supplement. Seabourn also has some 25% single supplement sailings, though not as much as Crystal. The QM2 also added single cabins after their recent refit.

      NONE of these are listed on that site so it is lacking a LOT of data.

      I know about these single supplements because I have been booked or am booked for the future on them as a single.

      You state that the site lists cruises that you don’t pay a single supplement for but the page with the NCL listings (that seems to be all there is) shows single supplements.p except for one sailing.

      A good travel agent can find cruises with low single supplements. In general, and I am speaking from having done 100+ cruises, the sailings with a low SS are dogs. They are not selling well and in order to get BIB (butts in beds) they will offer a low SS.

      Also, book as far out as most cruise lines will increase the SS as the beds fill up.
      IF the SS gets decreased your TA can negotiate tomhave your price protected or get you a comp upgrade. Again, speaking from experience,

      I would never sail on NCL (been there done that before I knew there were way better products out there) but I applaud the single cabin initiative. has a very comprehensive listing of NO or low SS.

      Going on a cruise solo is a great way to start traveling solo.

      BTW, I never bring a book or an IPAD or a Kindle to a restaurant, I prefer to sit, sip wine, enjoy dinner and people watch.

      1. thedealmommy Post author

        Very helpful info. I agree reading material is a crutch, but it’s a useful one for many to get over he solo dining hurdle.

  5. Matt

    Withdraw foreign currency at airport is often a bad idea as many airport ATMs (especially any Travelex ones) have higher fees and poor conversion rates.

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