How to Eat Your Way Through A Long Weekend in San Diego and More

In the second of the never been so wanderlust ‘long weekend’ series, we head to San Diego. The city of San Diego is the land known for being ‘sunny and 75’ year round. It’s the place of the happiest souls. Which is the main reason we chose to escape Baltimore’s winter and head to the west coast in February. Mother Nature had other plans. It was actually 70 and sunny in Baltimore, while it remained mid-50s, windy AF and rainy for most of our visit. At one point, we were on a rooftop in the pouring rain (because San Diegans live for their rooftops) and every person was recording the storm, assuring us it hadn’t rained like this since the 90s.

We tried our best to stay outside for as many pockets as we could, but due to the weather, we were forced to restaurant/bar hop for the full four days (there are worse things) and lucky for you, I’ve listed out my hits and misses and should-haves. Even with bad weather, I’ve never been so in love with this city and we are already planning our trip back.


Of all the neighborhoods in San Diego, we decided to stay in the Gaslamp Quarter and I don’t think I would have done it differently. It’s centrally located and easy to get to various neighborhoods via uber/lyft. We stayed at the Gaslamp Marriott, nothing special by any means, but fit our budget and location. There are plenty of other swanky hotels in the area, if that’s more your style.

We caught a flight getting us into San Diego 4PM, giving us enough time to check in and still explore for the afternoon and evening!

Rustic Root
535 5th Avenue, Downtown
This quickly became one of my favorite places. We had no problem finding a seat on their covered roof top during happy hour, which had 1/2 priced apps and discounted drinks. The rooftop has a limited menu compared to the dining room downstairs, but the rooftop is so worth it. If you do dine downstairs, there’s currently a yelp offer for 1/2 off a glass of wine at check-in!
TIP: The brie toast and firecracker shrimp are must-haves.

The Quartyard
1102 Market Street, Downtown
This 22,000 square foot downtown San Diego outdoor setting is worth checking out the calendar of events. They normally have live music and food trucks, as well as a full kitchen and bar within the venue.
TIP: There’s a shrimp taco truck that is UH-mazing, we didn’t catch the name of it, but if you see it, you order those tacos ASAP.



Donut Bar
631 B Street, Downtown
The Donut Bar has a vast assortment of donuts and craft beer! And when they say #bestdonutsintheworld, they are not lying. Will isn’t a fan of donuts, he can take them or leave them, but these donuts…he couldn’t get enough.
TIP: They sell until their sold out, so get there early. Don’t be turned off by the line, it goes quick and sometimes they even bring out samples!

7 Café
1152 7th Avenue, Downtown
Right around the corner from Donut Bar, is this family-owned café that will satisfy any savory breakfast craving. We ordered the chorizo con tots wrap to share and it was more than enough. It even came in the shape of a heart.

Ocean Beach
We drove out to ‘OB’ and we both instantly loved the energy of the place. It has a bohemian small town vibe and definitely worth checking out. One of my favorite shops in NJ, Often Wander at Noon, has it’s original location in OB – check it out. It sits right next to the cutest coffee shop tied to a flower studio, so you can imagine the smells are to die for.

5010 Newport Avenue, OB
The original location in OB is a must-see. There will be a line, so get there when it opens at 11am or prepare to wait. They get people in and out quick so the line moves fast. The place is full of character and the burger will be messy.
TIP: Get the double and be happy with the side of onion rings. Do not get an extra side, you will pop.

Mike’s Taco Club
5060 Newport Avenue, OB
We had no intention of stopping by this place, but a local raved about it, and I’m ever so happy we did. The surf and turf taco is a must. The steak is incredible.
TIP: Make sure to load up on the sauces!

Juniper & Ivy
2228 Kettner Blvd, Little Italy
This was sort of a happy mistake. It was pouring and we needed to kill time until a comedy show, so we uber’d up here based on yelp reviews, and come to find out, head chef is Richard Blais. The décor is well thought-out and the menu is interesting.
TIP: The pork belly is the best I’ve had. The biscuit has a smoky flavor you won’t forget. And the meatball toast, well you can’t go wrong with a meatball toast.

Vin De Syrah
901 5th Avenue, Downtown
I don’t want to give too much away on this one because this bar is very special and I think you’ll appreciate it more finding out the details on your own. I will tell you it’s inspired by ‘Alice in Wonderland’ and their cheese plate is phenomenal.
TIP: Look carefully.

The American Comedy Club
818 B 6th Avenue, Downtown
We lucked out here because we got to see one of my favorite comedians, Whitney Cummings, without having any idea she was going to be there until the day before we left. She was hysterical. Google the calendar before your trip, the club is right downtown, they have some pretty good comedians and the tickets are relatively cheap.
TIP:  Get in line early and you’ll likely get front row.
*excuse the horrific lighting


Breakfast Republic
707 G Street, Downtown
This is a new spot that has all the necessities you’d ever want in a brunch spot. They have flights of lattes, flights of antioxidant shots, flights of pancakes and flights of French toast. Need I say more?? We ordered the Kalua Pig Sushi Bowl because it was a special, but next time I need to order the smore’s French toast.

North Park
I loved the North Park neighborhood. I liked the shops, more than the food selection. Had it not been crap weather, we probably would have stayed longer.
Noteworthy shops:
3801 30th Street, North Park
Mimi & Red
3041 University Avenue, North Park
*Don’t waste your time on City Tacos, gets good reviews, but you can do better.

Hammond’s Ice Cream
3077 University Avenue, North Park
These mini cones are the best idea since avocado toast. Being able to have a mini scoop of several flavors to share is the best.
TIP: Tahitian Vanilla is BOMB.

Liberty Public Market
2820 Historic Decatur Road
This is a cool spot to stop by if you have time or are in the area. TONS of artisan food vendors, we just weren’t hungry, so I can’t comment.

Coronado Island
We honestly weren’t too impressed with Coronado. Maybe in better weather, it would have been more exciting. But we were just kind of bored. We stopped in one wine shop and it was a little too uppity for us.

Café Sevilla
353 5th Avenue, Downtown
You’d miss this place if you weren’t looking for it, but it is one of the best meals we had. The paella was full of flavor. The music was on point. Some nights they have live Spanish music and dancing.
TIP: Order the sangria.


Oscar’s Mexican Food
703 Turquoise Street, N. Pacific Beach
Any place that opens at 8am and serves me (non-breakfast) tacos is ok in my book. And even better, the tacos were soo good.
TIP: Order the smoked fish.

La Jolla
We took a drive out to La Jolla in hopes the weather would get better and it did! This area is known for it’s seals and it’s swanky homes. I zillow’d a few, $14.1M is nothing to scoff at.

Murals of La Jolla is a pretty cool art project throughout La Jolla. Try to see how many you can spot!

La Jolla is also a great spot to rooftop hop.
Noteworthy rooftops:
George’s Terrace
1250 Prospect Street, La Jolla

Duke’s La Jolla
1216 Prospect Street
TIP: Order the Lavender Colada

Herringbone La Jolla
7387 Herschel Avenue
My absolute favorite place during the whole trip. The décor inside is the most thought out I’ve ever seen in a restaurant. From the seating to the glassware to the trees. Everything was eye catching. Not to mention the food and drinks were great too.
TIP: Live acoustic music during brunch hours on Sunday. AND bottomless rose. Hello.


Before heading back to the airport, stop somewhere in Little Italy and grab a sandwich or a donut to take with you to the airport, we grabbed both ha. But the Smore’s donut from Devil’s Dozen Donut Shop was insane. Everyone at the airport gate was salivating in jealousy.

There were at least several other places in Little Italy I wish we could have squeezed in and will definitely make it to next time:

Queenstown Public House, Prep Kitchen, Ironside Fish & Oyster, Kettner Exchange, Ballast Point Brewery, and Pali Wine Co.

Phew. I’m exhausted and 10 lbs heavier, but it was all so worth it. Tell me your favorites!



  1. Lisa N.
    February 26, 2017 / 1:25 pm

    Did you check out the roof top bar at the Gaslamp Marriott? It’s called Altitude. Great views, even in the rain. Thanks for all the ideas! I’ve saved this article to check out a few of the places I haven’t been to, but you were pretty spot on! I live in OB and Mikes surf and turf is amazing! When you come back, try the lamb burger at Raglan and the Peanut butter Jameson shots next door at OB Noodle Bar 1502.

  2. March 6, 2017 / 3:12 pm

    Loved San Diego when we visited in September last year. It was so beautiful. We also had great food & at some of the same spots. We went to Breakfast Republic and Hammond’s which was the best! We also got tacos at Taco Perla in North Park, pizza at Pizza Port in Ocean Beach, Indigo Grill in Little Italy, drinks at Modern Times in NP, Bird Rock Coffee in La Jolla. I’d recommend them all. Biggest food regrets were definitely Hodad’s & Donut Bar – will have to go to them next time!

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