What I Know Now About Solo Travel During the Holidays

What I Know Now About Solo Travel During the Holidays

“Ma’am, would you mind switching seats with my wife?” ‘Wait, what? I am a window- seat traveler through and through — was he talking to me?’ “Sir, I’m so sorry. No. I really enjoy the window seat.”

As I boarded a long flight to Hawaii from St. Paul, Minnesota, my second flight of the day, I had my first encounter with a fellow traveler. It wasn’t particularly a positive one. Yet it reminded me how fortunate I felt to be traveling solo during the holidays. I took a deep breath, put my earbuds in, and took a long glare out the window. 

Photo of the flight wing

Solo travel is a meaningful experience. It can be something different and more meaningful to those who do it. For those who travel more often, it becomes more natural. As of late, COVID variants, holidays, and other societal protocols have created some not so “normal” feelings for many travelers. During my recent trip to Hawaii, I noticed some solo travel peculiarities that left me feeling borderline awkward at times. This piece is written for those who travel solo and are single, married, straight, LGBTQ+, white, black, green, blue, and you get my point. Here is what I know now about solo travel during the holidays. 

Tips for Those Who Solo Travel During the Holidays

1. Speak Up

If you decided to solo travel during the holidays and have begun to feel uncomfortable, ask yourself why? Is this a situation that could be mitigated or made to be less awkward if the other party or company involved did better? Ask questions. Once you have your answer, then speak up. If this means waiting a few days to think it over, wait. If it means saying no to “Can I get a window seat?”, say no. 

In my situation, the airline moved my seat a few times and reticketed me. The airline staff who gave me a different ticket as I boarded told me she moved me to accommodate someone else. I asked her if it was a window because that was all I cared about. She said yes. Then I boarded and received the seat of someone who really wanted the seat, too, AND it was a married couple. If it had been a two-hour flight, I would have switched. 

Since this flight was about six hours, I wanted my window seat and should not have felt bad about saying no. But, in the end, it did feel mildly awkward during the flight as the husband was texting Delta (from what I could see and hear). His wife was sitting across the aisle instead of next to him at the window. They were talking about Delta for the first couple of hours. It didn’t feel good to be moved in the first place, and then fly and feel like a “solo traveler.” Do I regret saying no? No. Did I speak up and call Delta when I got home from the trip? Yes. Solo travel is personal, and these points can be modified if needed. This is based on my experience.

2. Be Comfortable

Seize the journey and all that comes with it. If you’ve decided to solo travel during a holiday outside of peak season, then it might not be the rush we all know and loathe. If the panic and chaos come crashing in on you at the airport as it did for me, remain calm. There are some things that are out of your control. Canceled and delayed flights are two of them. Remember that you are in control of yourself and what you say or don’t say. This is your chance to speak up and take control of YOU. Solo travel is easy because you control yourself. So, remember that, and don’t let naysayers get you down. 

Here are a few things I encountered after my arrival to Hawaii that made me feel slightly awkward. Looking back, hey, it’s about the journey and learning how to be more comfortable with yourself. It’s not about others — it’s about your experience. Sometimes eating as a party of one can get interesting — and awkward — if you let a naysayer make it that way.

Do your research and look up the place ahead of time. Book the table ahead through OpenTable or whatever reservation provider they have so you don’t have to wait. Make sure the restaurant knows you are a party of ONE (say it with confidence and pride). Booking in advance will guarantee you have a spot even if they are behind. You might have to wait just a bit but you will get a meal and a seat in a reasonable amount of time. Remember if it’s peak season, reservations are important. . Be prepared — be comfortable! 

Since it’s the holidays and families and couples are out everywhere, remain calm and stay centered. You are there for you and at the very least, remember your table conversation won’t be about any topic that you don’t want it to be. HIGH FIVE to YOU.

3. Talk to the Locals

Solo travel during the holidays can be great, but there are some caveats. When it comes to touring the town and going out during holiday and COVID-times, it’s important to remain safe. Locals know which areas are the best and quite frankly, solo travel means you have the day or night to do what you want when you want. Ask around about the safety guidelines and be sure to follow them. For example, before I realized how important reservations were for a party of ONE, my Uber driver Bradner gave me some local hangouts to try since I was striking out with some of the more popular places. 

Bradner, if you ever read this, thank you for the conversation and for mentioning LuLu’s Waikiki. It’s got such a great view and he was right — I didn’t have to wait. The food was casual, quick, and convenient for a solo traveler. Plus, the evening that I went online to look for LuLu’s I rediscovered OpenTable, and my dining experience quickly changed. I had used OpenTable before but didn’t realize how necessary this was over the holidays and for a party of one. In the US, OpenTable was a good option to book reservations.

Uber drivers, tour operators, concierges, and restaurant staff are gems. Talk to them!

4. Accomplish Your Goals

Who doesn’t like taking a walk on Waikiki Beach or going for a stroll in Waimea Valley to see the botanical gardens? Before you head to a location, you might hear lists and lists of things to do and see before you go. Since you are a solo traveler, some things will take a bit more time to do and some won’t. It depends on who you are and what you are doing. For example, I enjoy road trips and driving. Plus, I like seeing places from the sea and from the land. I made these my two top priorities and went from there. I went whale watching and toured Pearl Harbor which were both really important to me. 

Naysayers might get in your way while this is happening. Just let them say what they say and you do you. At the end of the day, a robust list of goals that is half accomplished is better than no list at all. If your plan is to lay out all day and become a golden Cleopatra, then do it. If you are staying at a place with a pool and/or are close to the beach make sure you get to that towel vendor early and get your spot, Cleo. The line starts super early over the holiday season and families of five or more are there super early. YOU have got this!

5. Be Confident

The holidays are special to everyone for different reasons. Christmas Eve was the last time I saw Tata so for me, the holiday means more to me than it ever did. Solo travel means more too. It’s not a sign of being alone but rather a symbol of strength.

This year I decided to solo travel during the holidays. I had arrived in Honolulu the evening before. Many places were closed on Christmas Eve, so I went to the Mai Tai Bar at the Royal Hawaiian Resort to have a meal. It wasn’t preplanned, and I did not have a reservation. It was on this evening where the very core of what I was celebrating was challenged (at first). I circled the bar and saw no seats available. Then, I went to the host and said “party of one.” I’m not sure if it’s the pandemic, the holiday, or if they were in the weeds (in over their heads), but I sat at the table without any interaction for about 10 minutes. 

I know I was on Hawaii time but… when you are a party of one on Christmas Eve and everyone else is either 1) with a group of kids, 2) holding up a pair of glasses to cheers, or 3) need I say more? My point is that confidence goes a long way even if you begin to feel lonely due to the nature of the day, moment, or all of the above times fifty (squared). 

How did this evening progress? I walked over to the bartender (a local) and asked him if he could find me a seat at the bar. As luck would have it, one became free and I ordered my Kir Royal and dinner at the bar with the locals. 

Wrap Up

Solo travel is rewarding, and not everyone does it. If you are a brave soul that ventures out over the holidays (any holiday) to celebrate — be confident. I had to write about this experience because I know the holidays can be hard on many of us and I sat there that evening thinking about how many other solo travelers or those who were at home felt like they didn’t belong. For those long 10 minutes that I waited, I felt that way too. 

I lived abroad, traveled while doing so, and have solo traveled since moving home. People can have opinions but you must make the experience yours. It’s about the journey, not the final destination. The world might be adjusting to new norms as far as the pandemic is concerned. This will be ever-changing for the travel industry. However, it’s a great opportunity for solo travelers during the holidays and all the time. There is less mental and physical baggage and more time for YOU! Bon Voyage!

Interested in learning more about other traveler’s experiences in solo travel around the holidays? Check out Leesa Truesdell’s Oahu itinerary and road trip to the north shore.

39 thoughts on “What I Know Now About Solo Travel During the Holidays

  1. I used to go solo to Oahu for the Honolulu marathon from 1995 to 2001. Left on Thursday and usually came back on Sunday or Monday. Short weekend get away. Glad you had a great time in Hawaii.

  2. I used to solo travel to Canada back in 2017 and it was a very good experience.
    Thanks for sharing your tips! I really want to do again.

  3. I totally love the article as I learn more about solo traveling and that’s what I’m gonna be doing in the near future. It gives me the confidence to do this stuff that I’m always wanting to do in the past.

  4. Solo Travelling is something I have never done before. It’s a courageous thing to do and I envy people who can do it easily. This has been truly a wake up call for me. I hope I can travel alone this year

  5. Solo traveling during the Holidays sounds ideal to me. I visited France last Christmas and talked to the locals. Learning the best eating options from them was great.

  6. I love talking to the locals especially the tour guides and drivers. I always learn something new and get interesting facts from them.

  7. Talking to locals when you visit places is really useful. It helps keep you safer and you’ll discover some great places to see you might not have otherwise.

  8. I make it a point to travel too but just stopped when pandemic happened. I can relate to that airplane window situation. Haha! I haven’t been to any part of Hawaii but I am so looking forward to be visiting this place in the future!

  9. I had an amazing experience traveling solo for the first time. It somehow unleashed my adventurous spirit. I was kinda hesitant to travel alone before because I simply didn’t know what to expect. It gave me more confidence in traveling too.

  10. Great tips!!! It is very important to speak up. I used to travel solo a lot earlier on in my nursing career.

  11. This sounds great, I used to travel a bit around the UK solo but I have never been abroad, perhaps one day I will give it a try with these tips.

  12. I think it would be fun to travel alone. You can do what you want and when you want. Great suggestions for the lone traveler.

    1. Thank you, Tammy, yes, this can be so freeing. There are no timelines other than the one you have created.

  13. I love traveling solo. I know some people get scared to do that but it’s my absolute favorite because you can do whatever you want haha

  14. Being comfortable is the biggest goal to be scored on solo travel! Once it’s properly put into consideration every time, your travel bucket-list gets much easier to clear in no time!

  15. I once traveled alone to Bali for one month and it was an amazing experience. It’s different than traveling with someone. But I like traveling both solo travel and with others.

  16. Ahh I never thought about others minimizing your choices because of being a solo traveler. I can see that happening though.

  17. I have never traveled alone, not sure I would enjoy it. I do love to travel but with my side kick, my husband!

    1. Hi Kathy,

      Thanks for reading. Do you guys always want to go to the same places? When you travel, are you together for all of the trip? Do you split the time between places you like to see and he enjoys too? Have a wonderful day!

      Cheers,
      Leesa

  18. I have traveled alone to get from point A to point B but not for a trip like you mentioned. I do agree you have to speak up though. Thank you for your great tips for traveling solo.

  19. I enjoy solo travel and do not feel a bit guilty for not trading seats. For one, I usually pay an upgrade for the seat I want. My cynical brain says that the people asking me to trade didn’t pay for the upgrade and therefore getting a deal. So no. And I say, I paid for the upgrade. Second, my cynical brain says, plan better in the future. Now I realize that sometimes things happen that require last-minute planning. However, that’s not my issue. I’m not quite so cynical these days, so maybe I would approach it differently now.

  20. So glad you wrote a piece about solo travel during the holidays. I started traveling solo every year for Thanksgiving holiday in 2003. And besides during COVID, I haven’t stopped!

  21. I’ve never tried to travel alone. However, I am planning a solo trip this year. I hope it will be an exciting experience.

    1. Richelle, you’re going to have the time of your life. Trust me on this. I have been there and very much done that.

  22. My mother and I had this conversation lately. She is big into travel but has never went anywhere without my dad. But she’s considering taking her first solo trip next year and had no idea where to even begin. For context, my dad is still very much alive but he doesn’t want to go everywhere that she does – so this is her solution. I’ve sent this on to her!

    1. Hi Nyxie,

      Thanks for reading and for sharing this with your mom. I think it’s healthy that married couples are able to travel apart. I wish my parents did more of this. My dad wanted to do more traveling but didn’t. If she has questions, have her send in some questions about a location. Our contact information is on the front page. We’d be happy to help her begin an itinerary. Have a wonderful day.

      Cheers,
      Leesa

  23. It is good to plan ahead and also be a savvy traveler. I have never traveled alone and I give you credit for doing it!

    1. Thank you, Marysa! Planning a staycation is the best way to start your solo travels. Bon voyage.

      Cheers,
      Leesa

    1. Traveling with friends is great too, Catalina. But I really recommend taking the leap into the unknown. Try and you may very well like the experience.

  24. I only did two trips as a solo traveler in my whole life. I loved the experience, especially interacting with locals and having 100% of freedom what to do and where to go. It’s the great way to learn few things about ourselves too. Your trip looks fantastic.

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