How to Date Yourself: 4 Beginner’s Rules to Vacationing Alone

Four Beginner’s Rules to Vacationing Alone

RULE NUMBER 1. KNOW THYSELF

One of the best things about traveling alone is that you get to make it all about you. No sharing a room with a friend who can’t sleep unless the thermostat is at 70 degrees leaving you scrounging around for extra blankets.  You can happily pop that sucker up to 80 (which I absolutely did) and sleep naked.  No having to collectively decide on a restaurant that everyone likes and can afford, you can be as miserly or extravagant as you desire. You can let the TV play all night, or keep it off your entire trip, and if you do choose to have it on, you can watch as much Real Housewives as you want.  

Friends may also push you into experiences you may have otherwise passed on.  For instance, I really like to go with the flow on vacations, but my friend Star likes guided tours and the like, so when vacationing in Europe with her, I ended up on guided excursion after guided excursion.  Guess what, they were awesome. They enriched the experience so much more. Now, I prefer to be guided when I am visiting historical sites.

See, those are two great examples of things to know about yourself when you are planning a trip, that you are a lazy bee in the mornings likely to sleep the day away if you don’t have a plan, and that you like guided excursions. Fix: plan that guided excursion at the crack of dawn!  Okay, if not the crack of dawn, early enough to force you out of bed at a reasonable time.

When traveling, I can be a bit of a kind and lovely diva. Kind and lovely because I do my best to be polite, I truly enjoy making things easier on people, I fully understand when a mistake is my fault and I don’t mind paying for it (for instance, I don’t do dairy, so if the menu says there is dairy on a salad, and I forget to ask for it with no cheese, I will still send it back, but I am completely okay with paying for two salads, and if it is taken off of my bill, I will often leave the cost of that salad included in the waiter’s tip). But the diva part is that I want what I want, and I don’t want to feel bad about it. I love to be persnickety on vacation and I prefer to stay in locations that consider customer service their strong suit (and love to deal with lovely divas like me).

When going on vacation alone, knowing these things about yourself is essential to guaranteeing a decent time. And what can make a decent time wonderful is planning.

RULE NUMBER 2. KNOW THY PLAN

So, here is where my own weekend began to crumble before it even started. Three months ago, when I concocted my Palm Springs vacation, I started out so strong. I Googled the best Palm Spring Hotels, then canvassed my friends on the best places to stay. I googled and canvassed “things to do in Palm Springs”, I checked the Palm Springs weather for the weeks I intended to go. I planned my outfits. Three months out I was gangbusters.

One week out, not so much. After several starts and stops, the week leading up to “Me Day” were packed and hectic.  I didn’t even have my hotel. Of my hotel search, two kept recurring. One was very pricey, and though it looked amazing, I wasn’t sure if I wanted to spend that amount, especially my first time out the block and with my planning falling apart the way it did.  The other was the Ace Hotel and Swim Club.

I didn’t even book until 30 hours before, and those 30 hours were so relentless of my time, that if it wasn’t for the hotel’s one-night charge cancelation policy, I would have changed my mind.  I hadn’t planned my days, hadn’t shopped for my solo gal weekend wardrobe, left four hours late, and arrived at the hotel around 9pm, to *gasps*, no valet or baggage service!…   

Once there, the loneliness deepened. I found it hard to settle into my safari a la single girl surrounded by girl groups enjoying holiday Friendsgiving vacays. My heart kept leaping to the fun my girlfriends and I would be having.  When I found myself eavesdropping on two women, vacationing from the fam, chatting it up with a lone guy there to finish writing some songs, I realized I was experiencing a weird kind of FOMO — I was at the event, but feeling like I was missing out on the experience I assumed those around me were having. Feeling awkward and alone, I resisted the urge to hide inside my phone and talked myself out of fleeing back to my room.  

Once my Malbec and fish tacos (absolutely divine, perfectly fried, ordered without the shell) arrived, I remembered my promise to myself in How to Date Yourself — stay out of the hotel room. I headed out to the patio. There, flanked by a couple playing ping pong and guy group playing corn hole, I drank my wine and ate my tacos, second-guessing if I was the type to travel alone the entire time.

In hindsight, I totally get why Ace Hotel doesn’t have baggage service. It’s one of those places where you get to disappear into your experience, none the wiser — not even the front desk staff.  But you definitely want to know this ahead of time, so as not to start your experience in a salty mood. Especially if you are by yourself. Bad mood plus loneliness is no way to begin your vacay.

But, despite inauspicious beginnings, I’d arrived, and by golly I was going to make the best of it. And the good thing was Ace Hotel was going to be with me the entire way. I had chosen the perfect location, and if you are traveling alone, you should do your best to, too.  

RULE NUMBER 3. KNOW THY LOCATION

The Ace is a boho glam oasis parked in the middle of the desert. The restored two-story mid-century building sports an organic spa (a necessity for me), organic roadside diner (organic food, also a necessity), vintage photobooths, hidden speakeasy-esque bar, open for service ice cream truck, commune, two heated salt water pools and a hot tub, bike and scooter rentals and more — all which make it very easy to, as the website encourages…

Well, early Saturday morning this free wandering, freethinking, artistic, mystic was up, fed, and on her way to her pre-planned mellow yoga class, and from there, straight to the pool. I had figured out my Saturday much better than my Friday, and I gotta say, it made all the wonderful difference. And because I did manage to choose a hotel with my top amenities in mind, my solo vacation turned around quick, fast, and in a hurry.    

Noon found me luxuriating poolside in my bikini sipping a hot toddy next to trucker hats and tattoos, animal print one-pieces and tortoiseshell glasses (rocked in the truly fabulous way that only a sensational woman of a certain age can rock), silver haired foxes, silk robed fashionistas, momma and poppa millennials, and the rest of the beatniks lounging in their Ace issued robes as Stevie Wonder tunes spoke directly to our sun soaked souls.  

Scared of the “fish out of water” feeling I’d had the night before, I’d come to the pool loaded with work and podcasts.  Finally, I abandoned fear.  With the snow-covered mountains smiling upon me on a 72-degree day that under the desert sun easily clocked in at 85, being serenaded by Ace Hotel’s very gifted DJ, I had one simple thought… f*ck yeah, Palm Springs.  

As day slow-faded into evening, and the playlist relaxed into a fantastic fete of old-school R&B, I was happy that I’d committed to this plan. The weekend had turned for the better. My choice for my solo vacay was a wonderful idea.

RULE NUMBER 4. GIVE THYSELF A CHANCE

This leads me to my final lesson: Give it a chance, and a little time. Vacationing by yourself can be a bit wobbly at first, especially if you are used to out of town excursions with others, as I am, but give it a chance, even if it starts out a little rocky.  

I could have turned around that first night with promises of Marvelous Mrs. Maisel singing me all the way back to Los Angeles.  Unsure about the hotel, the success of this trip, and spending so much money on myself so close to Christmas, that would have been the easiest and most comfortable way out.  But I persevered, and half way into day two, I was living my best life.  

If you have to modify your plan a bit, modify it. I had planned to have my spa time at Ace Hotel, but then found out they didn’t do nails (clearly, I didn’t make this appointment ahead of time), so I changed to the Avalon Hotel and Estrella Spa. Heading off the Ace property gave me an opportunity to see some of Palm Springs that I’d missed since I arrived so late and let me check out another stunning hotel. My experience was fantastic and included a super fun conversation about boys, skincare, and overall bad behavior with my pedicurist. It was just the girl talk I’d been craving.

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