Week In California – Bleisure Trip To San Diego And Los Angeles

in Travel

Disclaimer: The information contained in this post is provided for informational purposes only and is not intended to substitute for obtaining legal, financial or tax advice from a professional.

Having my own business gives me flexibility in my day-to-day schedule, my location and the projects I take. But my favorite type of flexibility that comes with self-employment is the flexibility to build out bleisure trips – traveling for work and mixing business with leisure. This year, I happen to have four business opportunities in the same place – Los Angeles. We can’t always tack on leisure segments, but for our first trip out, we combined four days of work/some fun in Los Angeles with four days of fun/some work in San Diego.

Flying JetBlue’s short-lived direct flight between Jacksonville and Los Angeles

View outside of airplane of a big city in the distance
Los Angeles in the distance on approach to LAX

Jacksonville International Airport is a dream to fly in and out of, especially coming from the overcrowded chaos of the New York City terminals – JFK, LaGuardia and Newark. With JIA, we can be from home to gate in less than an hour. Our travel credit card gives us lounge privileges at Club Jax, where we had a nice, leisurely breakfast of scrambled eggs, ham potato hash, mini bagel w/ cream cheese, mini muffins, fruit cup, OJ, cranberry juice and coffee.

Flying to Los Angeles from Florida instead of New York cuts down the flight time by over an hour – it was just 4 hrs 19 min. However, I still had a chance to see two movies – Blacklight with Liam Neeson (skip it); and Best Sellers with Michael Caine (skip that one too).

If it were up to me, I would fly all of my LA business trips in/out of JIA. However, JetBlue has sadly discontinued this route. We have flown in/out of Orlando (our July 2022 trip to Costa Rica), and that was surprisingly a smooth commute. However, Orlando is three hours away, not the under-an-hour zip to JIA.

Play first, work later

Sign over a street that says 'Encinitas'

We landed in LAX and did the leisure part of the trip first, driving from Los Angeles to San Diego on a beautiful, sunny Saturday. My best friend from college days has a condo in Encinitas that she normally uses as a vacation rental but kindly blocked off for Scott and I to use.

Encinitas reminded me so much of Tamarindo, with the postcard-perfect sunsets and the bustling shops and restaurants all clustered in a handful of blocks.

Sunset over a beach

I highly recommend a trip to the meditation garden at the Self-Realization Fellowship. There is a beautiful ocean view and many winding paths along succulents, flowers, even a koi pond.

Trail with a big cactus with the ocean in the far background

The Roxy offers good food (including chicken adobo, a Filipino dish!) and great live music. We saw a talented singer/ guitarist, Raynaldo Martine, who played a lightning round of excerpts across multiple decades and genres — Yacht Rock (Boz Scaggs, Steely Dan, Fleetwood Mac, Chicago), rock (Rolling Stones, John Cougar, ACDC), dance (Justin Timberlake, Drake), soul (Temptations, Al Green, Gladys Knight and the Pips), even country (Keith Urban). He interspersed trivia games with his performance and had a multi-generational crowd shouting answers and singing and dancing along.

Beaches, gardens, music and comfort food

japanese garden - rocks, lake, bridge
Japanese Friendship Garden at Balboa Park

The beach at Encinitas, meditation garden and The Roxy were just our first day highlights. During our short trip, we visited the beach at La Jolla and saw the seals.

Big rocks below with seals laying out
Seals sunning themselves at La Jolla

We visited two more gardens – the Japanese Friendship Garden at Balboa Park and the San Diego Botanical Garden. Bonus tip: we got into these gardens for free with reciprocal privileges from our membership at a Jacksonville garden, The Cummer Museum and Gardens. Reciprocal privileges can save you a lot of money when you travel and can make a membership to your local cultural site a no-brainer, even if you don’t visit that one particular site all that often.

Large group of bamboo on both sides of trail
Impressive bamboo forest at the San Diego Botanical Garden

The Japanese Friendship Garden was next to the Organ Pavillion which houses the largest outdoor pipe organ in the world. The Pavillion is a massive outdoor space where concerts are held. We visited during the day, so there was no performance at the time, but recorded organ music was playing continuously – quite the contrast from the previous night at The Roxy!

large crowd of people on a lawn outside

Our last night in San Diego was spent at an outdoor concert – by the beach, of course. Dinner was a potluck picnic, though by then we had more than eaten our share of San Diego.

Sandwich cookie made of ice cream and brownies
Brownie and ice cream sandwich cookie at Baked Bear

Scott and I lover our sweets, and San Diego has a lot to choose from. We went to VG Donuts twice, The Baked Bear twice for ice cream sandwiches made with cookies (or brownies!) and the local handmade ice cream shop, Cali Cream. Of course, we also sampled the tacos.

Work and some play in Los Angeles –more beaches, gardens and comfort food

Lots of red roses in a field
Rose Garden at USC

While I had a couple of meetings in San Diego, it was more leisure than business. Los Angeles was the business leg, with just a little bit of leisure. However, my conference presentations were on the USC campus, which has the beautiful and free-to-the-public Exposition Park Rose Garden near by– a perfect way to cap off a hard day’s work.

View from mountain top of city in the background
View of downtown LA from Mulholland Drive – Hollywood Bowl in the foreground

Because of the timing of our return flight, we had the equivalent of more than a full day after the conference ended to squeeze in more sites. We did some scenic driving on Mulholland Drive and along the Malibu and Santa Monica coastline.

We stopped at Manhattan Beach and caught another sunset while walking along the beach.

View up the coastline of a beach
Manhattan Beach

We hit another iconic California university, UCLA, and visited their gardens, as well as Manhattan Beach Polliwog Park.

Small brook amid trees and greenery
UCLA Botanical Garden

The UCLA and Manhattan Beach gardens were free to the public, but our reciprocal privileges came in handy once again with free entrance to the Museum of Neon Art. This is a museum we wouldn’t even have known about except we saw it on our reciprocal list. That is also true of the Bata Shoe Museum, which we stumbled on during our Toronto trip – check your reciprocal privileges from other memberships!

Room of neon signs - a car, building, signs
Museum of Neon Art

The Museum of Neon Art is small but mighty. You can walk through it in less than an hour, but it has some beautiful art – and an interactive room where you can learn more about neon than you probably care to!

View of old dining room, complete with a bank of pay phones
Philippe’s is definitely a throwback

Of course, we never go anywhere – business or leisure – without sampling the comfort food. Scott went to In ‘N’ Out twice while in California. Together, we also hit some independent diners, including Philippe, a 110-year old restaurant that is the oldest operating restaurant in Los Angeles and home to the original French Dip sandwich. We also discovered Green Apple China Bistro, a Chinese restaurant so good that we returned there during our second trip to LA a month later.

We returned to LA just over a month later

Large sign from behind that says Hollywood backwards and a hilltop view beyond

As I’m writing this, we actually completed two trips to LA in a span of five weeks. The second trip to LA was a quick three days that was all business for me. Scott, however, squeezed in some leisure, including a hike up to the famous Hollywood sign.

Desert mountain trail - very steep
The trail up to the Hollywood sign was very steep and rugged
Single tree in a clearing
Also on the top of the Hollywood Hills is the Wisdom Tree

On our first trip we took a drive on Mulholland Drive and stopped to take a few pictures at the scenic overlooks. One of those pictures included the hotel we would stay at on our 2nd visit!

View from a hilltop - city in the distance
From Mulholland Drive on our first visit: Hilton Universal is the black building on the right
View of a highway and small hill in the distance
From Hilton Universal on our 2nd visit: nice view of the hills which contains Mulholland Drive

We stayed at the Hilton Universal City, which is near one of the LA train lines, and Scott spent an afternoon exploring the city by train. A full day pass was only $5.00 (half price in these post-Covid times), and he was able to get on and off at several different areas of the city.

View of city from airplane with horizon turning orange from sunrise
New York City, with Manhattan on the lower left side

On this second trip, we needed to fly in and out from New York City, due to committments there, and on the redeye flight back to JFK we were treated to the most beautiful pre-sunrise view of New York City.

I guess that is a benefit of flying in and out of New York City – a view that is way more spectacular than flying from Jacksonville.

two people sitting at table with dinner foodWe are Scott and Caroline, 50-somethings who spent the first 20+ years of our adult lives in New York City, working traditional careers and raising 2 kids. We left full-time work in our mid-40’s for location-independent, part-time consulting projects and real estate investing, in order to create a more flexible and travel-centric lifestyle. Read more about our journey.

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Jim September 16, 2022, 10:45 am

I hadn’t been to LA or San Diego in 15 years, i’m sure a lot has changed. Looks beautiful though, especially the gardens. Thanks for sharing this!

Caroline September 16, 2022, 3:14 pm

We hadn’t been in many years as well, but it was just as beautiful as I remember — weather-wise and activity-wise. We definitely plan to be back and not let as much time pass in-between visits.

Eric Bowlin December 14, 2022, 4:24 pm

Truly nothing better than taking a trip and being able to write it off for tax purposes.

Caroline December 18, 2022, 8:47 am

Yes, bleisure travel is expected to increase in the next years.

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