Solo Trip to San Diego for Twenty Days

I grew up hearing about how amazing San Diego was from my dad. He was stationed there when he returned from Vietnam in the 60’s. Every once in a while he would throw around the idea about moving with my mom but, that was not happening. When he passed away in June 2017, I had my first trip to San Diego planned just one month later for work. It didn’t take long for me to realize my dad was 100% accurate as to how breathtaking and fun it really was. In 2018 I had another trip, February 2019 another and eventually in early March I decided to get an Airbnb (check out how I selected my short term home) for 20 days to really immerse myself in all things SoCal had to offer.

March 30, 2019: I boarded my plane from cold and snowy Buffalo, NY to warm and sunny San Diego, CA. This would be the start of my 20 day solo travel trip to “America’s Finest City”.

I want to start off by saying this was not a vacation. I was living, working and going to the gym like a local. I found a gym in Hillcrest where I was staying and after a few days really started getting into a comfortable routine. An important thing I want to share about solo travel is that you have to be disciplined when doing a trip like this. It can be really hard to get into the mindset that you are not on vacation while traveling solo for extended periods of time and keep motivated when it comes to work. With the sun shine and warm weather – far different than how it was back home – it was a constant struggle. Discipline and the fact I enjoy my job really helped. However, that doesn’t mean I didn’t find my self bringing my laptop and my hot-spot to the beach or an outdoor patio to work on days where I just had to get into the sun.

Weekend One: Before I checked into my Airbnb I mostly explored the area of La Jolla. It was overwhelming how happy I already was to be there. My dear friend and I biked along the coast, explored a sea cave that was 145 steps down the cliff, laid out on Windansea beach and saw sea lions. It was beautiful and the perfect way to start out my next few weeks of solo travel.

After a couple days, I checked into my new home in Hillcrest. When I arrived I was greeted by two of the kindest people Christina and Curtis plus their adorable dog Chewie. I immediately felt comfortable and like I had always lived there. Going into an Airbnb, especially solo, you always get a bit nervous because you never really know who your hosts are. Boy did I luck out. The place was so cute and quaint. 

The first couple days I spent time exploring Hillcrest. I wanted to really focus on getting acquainted with the neighborhood and the people. Along the way I found the cutest little restaurant Chocolat. It became a regular stop during the week when I would go to different locations and work remote.

During the work week I pretty much stuck to a routine of getting up at 6 am for remote work, taking a mid-day break to venture to the gym and find a spot to post up at for the remainder of the workday followed by an occasional dinner on the town with my friends. Some of my favorite restaurants are: Rustic Root, Bankers Hill Bar & Restaurant, Rockin’ Baja Lobster, Sear Sucker, Cold Beers and Cheeseburgers, Henry’s Pub. 

Over the next couple weeks I was able to see so much of San Diego. I didn’t hit everything on my bucket list but, hey – there is always next time (check out my San Diego bucket list).

Weekend Two: The main thing I wanted to do was see dolphins and I did it. I have loved dolphins my whole life. I have a ton of figurines and even a tattoo. On a gorgeous Saturday afternoon my friend and I took a whale watching cruise with Flagship Cruises . Although we didn’t see any whales, we saw so many dolphins (video at the bottom of this post).

Weekend Three: The finale.

Stop 1: Historic Old Town is one of my favorite parts of the city so, on Saturday my friend and I made the most of our day exploring the shops and street vendors, eating delicious Mexican food at el Antojo and visiting La Casa de Estudillo. We also stumbled upon Semper Fry a Veteran owned, family run business making and creating unique and delicious hot sauce. I got their Spicy Avocado and Kalamata Olive flavors.

Stop 2: Drinks and lunch at Hotel Del Coronado’s Sheerwater and Babcock & Story Bar

Stop 3: Petco Park for a Padres vs. Reds game

Stop 4: Out on the town visiting Trailer Park After Dark , Craft and Commerce, Noble Experiment 

My time in San Diego was one of the best experiences in my life and seeing it come to an end was bittersweet. Not only did I explore as much of the city as I could and find more to love but, I was also inspired to start the Solo Travel Woman tribe and invest more into my world of travel.

I want to thank all my friends, old and new who live in San Diego and were a part of my journey. The love I have for each of you is deep.

I know in my heart that leaving San Diego was not forever. It was just a see you later.

Until next time…happy exploring.





One Thought to “Solo Trip to San Diego for Twenty Days”

  1. […] Living in San Diego was an amazing experience. Event short term. I hope my story inspires you to do the same. No one ever knows how life is going to go or when it is going to end. So, live it. Enjoy it. Explore it. […]

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