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Tash's Travel Tips: San Diego: What To Eat, Do and See and Staying at The Pearl Hotel in Point Loma

Updated: Oct 29, 2023

What a year it has been, right? Anyone else feel like we are living in a never-ending episode of "Groundhog's Day?" I love my home and my family and my life, BUT, heading into this last quarter of the year, I was starting to feel the weight of 2020.

COVID-19 and this global pandemic has really put a halt on the things that I feel make me ME and bring me joy: fellowshipping with others, connecting socially, traveling and exploring and as a mama who has been in the trenches, at home, dealing with remote learning, a toddler and pregnancy, I was desperate for a change of scenery.

I talked with my doctors about the risk of traveling and they reminded me that, right now, every decision we make comes with a risk, but it doesn't mean we should be prisoner to our circumstance. I left that appointment, called my sister and let her know that I needed time away and we went to work on planning our first #MomsAway getaway trip.

It was in my heart to travel internationally, to head on down to Mexico, but "wisdom" told me that staying in country, as a pregnant women in a pandemic was likely a smarter choice. So we chose what would become a short flight for each of us, to head down to Southern California, but with a twist. We both intentionally chose cities in the state that we hadn't had a chance to explore, but always wanted to, we checked on their COVID-19 procedures to make sure they were in alignment with our desires, and we leaped.

I think it's so important for women to listen to their bodies, to their mind, to their spirit and to prioritize themselves. I know that at times it can feel selfish, but like the old adage goes "you cannot pour from an empty cup," and I know that if I don't take care of myself, I am no good to anyone.

This trip was the perfect reset for me and my sister both. We work really hard, pour out to those around us, and have almost 7 kids between us, so taking this time to decompress, eat in peace, go to the bathroom with no one knocking on the door, and filling up our buckets was just what the doctor ordered.

It felt amazing to venture out with my best friend, take a "break" from motherhood (thank you to the family who jumped in so that we could jump out), fill our buckets, vision and plan for the future before this little one drops in the new year and The Pearl Hotel in Point Loma, San Diego was the perfect place to do just that. Special thanks for hosting us over the weekend and treating us so well. I felt cared for in a way that I so desperately needed, but more on that later.

Poolside at The Pearl Hotel

Traveling During Covid 19

Before I jump into our amazing weekend at The Pearl Hotel, I know many of you might be wondering how travel is working in this NEW COVID season of life. I felt that same way and wasn't sure if it was both safe or wise to travel. I watched my favorite travel bloggers launch out and there was a bit of me that was a little envious.

So, the question is, is it safe to travel during COVID-19?

My answer is "yes." But with the proper precautions.

Every place I encountered: at the airport, on the plane, in restaurants, at the hotel, in the convenience stores, COVID-19 was being observed and taken seriously. For me, it didn't feel much different from being in my own local neighborhood, except the location and the company had changed. I was impressed by how safe everything was and I feel in many ways that it is much safer now to travel then it has ever been, so go on out, stretch yourself and make it happen, but remember these few things below:

Is it safe to travel by airplane during the COVID-19 pandemic?

Although I am not a doctor, every place I read to prepare for this trip said most viruses and other germs do not spread easily on flights because of how air circulates and is filtered on the airplanes, but social distancing can be difficult on crowded flights, and sitting within 6 feet of others could increase your risk of getting COVID-19. So make sure you travel on an airline that is still taking COVID-19 precautions and breathe a sigh of relief.

I flew on Alaska Airlines and they are still holding the middle seat and sitting families together as often as possible.

Amenity box at The Pearl Hotel sanitized for our safety.

What steps should I take when traveling to reduce the chance of getting and spreading COVID-19?

Obviously, traveling is risky right now, so it's important that you acknowledge that and try to stay off planes, trains, automobiles and public places if you are sick or have been around someone with or exposed to COVID-19 in the last 14 days. If you choose to travel, it's important that you acknowledge the risk of travel and take good care of yourself. Drink plenty of liquids, and take the proper precautions.

  • Avoid close contact by staying at least 6 feet (about 2 arms’ length) from anyone who is not from your household.

  • Wear a mask to keep your nose and mouth covered when in public settings.

  • Wash your hands often or use hand sanitizer.

  • Avoid touching your eyes, nose, and mouth.

  • Do not travel with someone who is sick.

  • Eat places that have options for: drive-thru, delivery, take-out, and curbside pick-up.

  • Follow state and local recommendations or requirements after you return from travel.

One additional thing I did when returning, was boost my vitamins and minerals and got tested for COVID-19 a few days upon returning, just for additional peace of mine. One week after my first test, I re-tested and both tests were negative and that made me feel good about making sure I was protecting myself and my family.

photo credit: Melinda Watts

The Pearl San Diego, Point Loma

Now let's get into this recap of my NEW favorite hotel.

You guys, I love a good 'ole boutique hotel and The Pearl Hotel met my expectations and more. The reason I love boutique hotels so much is because they are usually owned by a smaller hotel group or a person you can touch and feel, who is is committed to excellence, but because of that they are usually under the radar and people aren't aware of them. Because they are boutique and smaller (usually 125 rooms are fewer), they put so much more detail into everything. The attention to the details and they put so much into their aesthetic, have worked to find the perfect staff that not only believe in what is happening from day to day, but also the heart of the mission and everything is done excellently. This is not to say that bigger hotel brands don't do things well, but as a small business owner myself, I understand what it means to the little guy every time a customer chooses them AND I am so happy we chose The Pearl.

The Pearl Hotel in Point Loma, is a retro-Americana style hotel fused with the coastal vibes that San Diego offers simply by its location. It's a perfect mix of retro modern, a motel re-done with the modern aesthetics, clean, minimalistic and dreamy vibes, that every mama who needs relaxation, every blogger/instagrammer is drawn to and with 23 rooms and 7 different room types to choose from, The Pearl got ALL of their details right.

This little boutique gem in the heart of San Diego hosts a beautiful inner courtyard, which is the focal point of the whole space - it's the social point of the hotel and all of the rooms and the restaurant and bar open up into that electric space.

Their very own globally inspired American restaurant and bar, Charles & Dinorrah, affectionately named after the visionaries of the original motel, is the place to be, and with a "dive-in" movie feature, there's no question why. You can feel the buzzing energy and eating there day to day was one of my very favorite parts of the trip.

The Pearl Hotel and Charles & Dinorah, offer weekly Wednesday dinner + movie nights, paired with a 3-course meals and drinks. Although I wasn't able to have this experience, I did get a taste of it and I cannot wait to go back during the week to have that epic experience in their heated salt-water pool. You can check out the weekly schedule of movies playing here.

One of my favorite parts of the hotel were all of the modern touches. I love walking into a space, seeing it from the outside and being transformed by the world I am whisked away to once inside, and I feel like The Pearl Hotel does this so well. From the outside looking in, you may easily pass it up and overlook it, but once you get inside and experience it, you can't easily forget.

Friends, the bed above, was INCREDIBLE. It was the softest and most cushy bed I have ever slept in. Melinda and I looked forward to every evening when we could plant ourselves in it with our snacks - as we watched the final season of "Greenleaf," all 10 episodes, and Beyonce's "Homecoming" on repeat, because the hotel has Netflix, Hulu and Disney+.

It was such a nice surprise, but with 22 rooms, you can be intentional about these little decisions that are sure to put a smile on your guest faces, especially us mamas who haven't had the chance to watch any season of anything in a while.

It's also incredibly reasonable in it's price point, with rooms starting in the low $100's per night and the distance to attractions makes it ideal as a lodging option when visiting the area.

In addition to being so absolutely gorgeous and photogenic and really the perfect all-inclusive getaway, the hotel has an incredible lounge area in the lobby that is perfect for morning coffee, reading or working with a cocktail OR mocktail.

The bar is absolutely gorgeous with plenty of indoor/outdoor seating and "The Happiest Hour," is daily Monday - Saturday from 4-6p. You can check out the menu here.

The staff is the most friendly and accommodating that I have ever experienced and I know that wasn't unique to just us, because as I was sharing our trip on social media, many of my followers who had stayed at The Pearl Hotel had raved about their own amazing experiences while staying there. It is their way and their reputation is known to those who are aware of this dynamic place.

They pay such amazing attention to detail, that every drink comes with a toothpick with A PEARL on it. (insert heart eyes emoji here).

If you are looking for a cute place for brunch, baby shower, girls weekend, bachelorette party, or a fun family vacation, look no further.

The Pearl is also known to host weddings so if modern retro is your thing, consider them - perfect wedding venue for these COVID-19 times and the special events in our lives.

Charles & Dinorah | at The Pearl Hotel

Charles & Dinorah is The Pearl Hotel's love letter to the original husband and wife owners of the The Pearl Hotel and their journey to create a sportsman's lodge in the 1960's.

After nearly 50 years, and a name change later, Charles & Dinorah is a the hidden gem of The Pearl that everyone NEEDS to know about. With seasonal, straightforward and globally inspired American dishes, anyone who visits will be profoundly impressed by their experience. Truly, my best dining experience of 2020.

Their menu can be enjoyed in the restaurant (social distanced, of course), over the bar, or relaxed at one of the many poolside tables OR in the pool itself.

Charles & Dinorah is open Mon-Saturday, 4p - 10p | Happy Hour from 4p-6p. You can make your reservation here

Melinda and I opted to dress up. It had been so long since we had been out somewhere fancy. I loved getting ready with her laughing and joking and just rejoicing for the opportunity to be together and to have this quality time with one another with no real responsibility. I am the silliest (besides with my kids) with her so I really needed this release. You can check out more of our BTS antics here.

When we arrived to dinner, there were mocktail recipes waiting for us. The staff knew I was pregnant but still gave me an experience with food and drinks that I could rave about. My mocktail was one of the best I ever had. I still think about it.

The food is out of this world. Melinda and I had the most incredible time at dinner, we had such a hard time deciding on what foods to try, we tried almost everything. Okay, maybe not true, but we tried to get in as much as possible. Be sure to check out the Shrimp Tacos, the JFC (Japanese fried chicken), The Grilled Prime New York Steak and the The Pearl Burger on the Sadie Rose Pretzel Bun (literally the best burger I ever had). The full menu for Charles + Dinorah is here. Don't forget to add on their famous "Date Cake" that isn't on the menu, I wouldn't want you to miss out on Heaven on a plate.

The food was exceptional, so much so Melinda and I are STILL talking about it. The vibes were VIBE-Y and the service was absolutely amazing. I struggled so much between having the burger (which New New wanted) and ordering the Chef's Charcuterie, that the chef came in on Sunday morning (when the restaurant was closed for the day) and made us a special grazing board we could eat for breakfast while we worked.

Isn't it stunning? That is what I call customer care.

My good sis even got in on the photography action and got her photo lesson in and I would be lying if I didn't tell you how proud of her I was. Check out that form below.

She even made this incredible picture of me and it is one of my faves from our trip.

photo credit: Melinda Watts

What To Do + See In San Diego

Nothing makes a trip, like the attractions around it, so I have taken the liberty of gathering a few cool places that you should consider visiting if you make it to San Diego. Honestly, The Pearl Hotel was so perfect, neither Melinda nor I wanted to leave to do anything, but we pushed ourselves to get up and get out and take in a few sights.

Below a list of amazing ones (and there are still so many that aren't listed). San Diego is loaded with incredible places to visit, check out and take in, so use this list as a starting place and make sure you do a little research to gather a list of ideas for yourself.

Sunset Cliffs Natural Park - as pictured above, rocky cliffs overlooking the ocean and the best place in San Diego to watch the sunset and also famously known for the location of the open ceiling sea cave - be careful when searching for it and make sure the tide is low before attempting to visit.

Coronado Island - a gorgeous island full of restaurants, cute shops and beautiful beaches. The world famous Coronado Hotel is also there - the inspiration for Roald Dahl's Emerald City in "The Wizard of Oz."

Old Town San Diego - Old Town San Diego is the oldest settled area of San Diego and the birthplace of California the state. It is the site of the first European settlement in present-day California and contains Old Town San Diego Park and Presidio Park, both of which are considered National Historic places and are protected by law.

La Jolla Cove - a small picturesque cove beach that is perfect for snorkeling, swimming, and scuba diving. The cove is protected as part of a marine reserve and is very rich in marine life. Make sure you're a strong swimmer before diving in!

Balboa Park - is a 1,200 acre historic urban cultural park filled with green belts, open spaces gardens, walking paths, museum, theatres and the world famous San Diego Zoo. The park is one of the oldest in the United States dedicated to public recreational use and its gorgeously photogenic - worth a stop by.

USS Midway Museum- is a historical naval aircraft carrier, commissioned to be built for its maiden voyage WWII, but was completed one week too late and never was used in the war. The museum is perfect for history buffs, those interested in war ships and has tons of old planes and flight simulators to try.

Annie's Canyon Trail (Solana Beach) - a great short trail for hiking with family and kids, full of rocks to climb and a canyon with fantastic views, in an ecological reserve.

Where to Eat in San Diego

Food, food, food is one of my favorite things about visiting a new place and I take my restaurant research VERY seriously. Ask anyone who's ever traveled with me. I am going to look for the "hole-in-the-wall," the uncanny, the luxurious - but no matter how many stars are after the restaurants name, we always, always eat well. Our trip to San Diego was no different. There are so many amazing restaurants, I couldn't check them all off of my list, but my top recommendations for breakfast, brunch, lunch and dinner, on your weekend trip to San Diego are below and you WILL NOT be disappointed. Not only will the food taste good, but it will look good too! ;)

pictured above my amazing smoothie bowl from Northside Shack


Snooze, an A.M. Eatery - traditional breakfast with a modern flair, fresh ingredients, very large portions and amazing service. Try the corn beef hash and their yummy seasonal pancakes.

Northside Shack - a community-oriented breakfast bar specializing in custom blends and creative bowls. Health conscious concoctions including juice and vegan bowls and they are so yummy.

Donut Bar- if you LOVE donuts, you will love donut bar. Creative and fun donuts created for the donut lover in you! :)


Lucha Libra Gourmet Taco Shop - the yummiest taco shop, with fresh ingredients, top quality meats and really fun and funky menu items: tacos, burritos, cali burritos, cauliflower ceviche, corn, burrito bowls and so much more. On this menu, there is truly something for everyone.

Le Parfait Paris - award winning cafe for dessert, coffee, croissants and so much more. They also offer Macaron Baking class, so while you are grabbing brunch, sign up for a class, after COVID-19 passes of course.

Atypical Waffle - COVID aware and friendly restaurant bringing you waffles in sweet, simple and savory offerings and it tastes so good. If you love waffles, you will love Atypical.


Trailer Park After Dark - a subterranean dive bar with American comfort faire served up in a funky trailer park-themed restaurant and on tv dinner trays and is fun to the max. Make sure to check out the the Truck Stop Frito Pie, Sloppy Joe Sliders, The Kitchen Sink Tater Tots. If you can't decide you can go with the Nightly TV Dinner Special and finish it up with a Cotton Candy Ball.

Charles & Dinorah - my very favorite restaurant I ate at in San Diego. Charles & Dinorah offers guests the opportunity to experience "familiar dishes prepared through a global lens" and as mentioned above, that is exactly what we got. It as IMPOSSIBLE to choose what to eat because I wanted the whole menu. My only regret? We weren't there long enough to experience it all.

Louisiana Purchase - a Louisiana flair with a San Diego hipster vibe. Louisiana Purchase is an intimate cocktail restaurant inspired by the charm of Louisiana. Make sure to try the Alligator Andouille Cheesecake, the Sriracha lime butter Crab Fingers and all of the desserts.

Dinner faire from Louisiana Purchase SD

Kid-Friendly San Diego

Although Melinda and I left the family and our kiddos at home, that isn't normally how we travel. In fact, we love traveling with our families and that is a huge part of what makes my platform unique is my particular passion for Black family travel - so I took the liberty of listing some top attractions for families traveling to San Diego with their little ones. These are places, had my family come with me, that I would have put on the itinerary.

This list isn't as spelled out as the one above, but provides links to the sites and the info you need to enjoy these special kid-friendly places. I hope that it is helpful in helping YOU create the perfect itinerary for your family.

This trip to San Diego with my sister and best friend was JUST the medicine I needed to get past the monotony of day-to-day life and having such an incredible host as the staff at The Pearl Hotel, I felt taken care of and showed up for the way that every mama dreams. When you are planning your trip to San Diego, I hope that you will consider making The Pearl Hotel your home for the time. I know it is my home away from home any time I go to San Diego and I am counting down the days until I can get back.

Have you ever been to San Diego? What is your favorite part? Is there anything else I should add to my list? Drop them in the comments below and let's build the perfect itinerary together!

With strength, courage and wisdom,



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