Weeknights in Gaslamp: Monday-Thursday Happenings in Downtown San Diego

Everybody’s working for the weekend, and many of us know (all too well) that ominous feeling that creeps in just as the weekend comes to a close. In San Diego, the land of surf, food, ambiance, and culture, your weeknights don’t have to be a total drag!

To help you make the most of your weeknights, we came up with a few easy ideas to make them seem more like, well, a Saturday. From San Diego tours to local hot spots, here are seven things you can do Monday through Thursday to amp up the hour of freedom you have after you get off of that long day of work.  Keep reading for some of our favorite things to do in Downtown San Diego.

#1 – Watch the Sunset from The Nolan Rooftop Bar

Photo: Passport to SD

This open-air rooftop bar and lounge is perched on the 14th floor of the Courtyard San Diego Gaslamp/Convention Center and offers an elevated escape from the rest of the city’s nightlife. With it’s breathtaking panoramic city view of San Diego and San Diego bay, this relaxing location features unique fireplaces and fire pits, architectural screens, and relaxing chairs and couches for you to let go of the stress from that long day at work.

The bar offers innovative drinks, from wine and classic cocktails to interesting takes on recipes from past and present, in a sophisticated social atmosphere. In fact, our favorite part of the Nolan Experience is the fun, open-air, feel-good environment. However, it is the menu that offers a variety of scrumptious and mouth-watering bites, for a flavorful culinary experience that is unmatched.

#2 – Indulge in a Late Night Snack at Ghiradelli’s

Photo: TripAdvisor

There are plenty of healthy, low-carb snacks late night in San Diego…and then there is Ghirardelli. Let us say, there is nothing like a customized sundae with hot fudge made from rich Ghirardelli chocolate, nuts, and at least one cherry, to get you going on a weekday evening.

Inspired by the original shop in San Francisco, CA, Ghirardelli is located in the heart of Gaslamp Quarter. This popular spot has been newly remodeled to feature additional indoor seating and an even bigger retail area. Visitors can create their own ice cream experience with many ice cream flavors, delicious toppings, and irresistible chocolate treats including chocolate chip cookie, decadent brownie, and dipped strawberries.

On top of it all, the old-fashioned soda-jerk waiters will serve you with a smile, and help you choose from a full menu of soda fountain classics such as real ice cream shakes, traditional malts, and hot cocoas. They will even help you pick out a chocolatey gift for a loved one, from the parlor’s Grab Shelf.

#3 – Listen to Live Music at House of Blues

Photo: Sandiego.com

House of Blues has four distinct areas, and all of them offer a good time.

There is one main entrance on the street at Fifth Avenue, and there is usually a crowd waiting to get in to see whoever is playing on any particular night. Once inside, there is a top and bottom level of the concert area, both offering a nice, intimate view of the performer. If you are going to see a concert, make sure that you either buy the tickets in advance, or from the box office until 5:30 pm weekdays.

House of Blues also has its own associated restaurant, Crossroads, which offers a variety of general American food and appetizers (burgers, sandwiches, salads, chicken wings). The restaurant is a great place to visit for happy hour which is from 4 pm to 7 pm nightly. This eatery is also notable for the fact that ticket holders who dine there on the day of show and spend at least $20 are allowed to bypass the line for that evening’s concert.

The inside bar at HoB has a standard selection of drinks. The bar area itself is not particularly well-lit during concerts, so bear that in mind when coming or going with food or drink in hand, and if you’re attending an all-ages show, you may be asked to stay at the bar, but don’t fret, you can still view the concert from the bar!

#4 – Have a Laugh at American Comedy Co.

Photo: American Comedy Co.

Have a blast at locally owned American Comedy Co. club and restaurant that hosts nationally acclaimed stand-up comedians. The cozy 200-seat loft-style club, with an old-fashioned speakeasy feel to it, features up-and coming comics and nationally celebrated comedians such as Bobby Lee, Joe Rogan and Kevin Nealon. A-list comic stars such as Drew Carey, Christopher Titus and Charlie Murphy have graced the stage as well. One day a week, the venue hosts open-mic night where anyone brave enough is welcome to try out their comedy routine.

While the performers will have you giggling to no end, the menu is nothing to laugh about. The venue offers a full restaurant–salads, sandwiches, wings and hamburgers are just a few of the delicious options, and a bar full of great cocktails, which guests are encouraged not to snort out of their noses, as the jokes here are known to catch audiences off guard.

#5 – Listen to Music (& Have a Laugh) at Shout House

Photo: The Shout House

The Shout House is a celebration of life at the top of one’s lungs. If you aren’t familiar with the term “Dueling Pianos,” it’s where two piano players (who are also singers) perform on face to face grand pianos, in front of two large mirrors playing classic rock ‘n roll hits from the 1950s to the present. It’s request driven by the audience and with the use of multiple teams, goes non-stop all night.

Watching the volunteers, birthday VIP’s, bachelor/bachelorette party guests, and even families get called to the stage, where they try to follow instructions, while everyone else in the room sings at the top of their lungs to great music hits of all time, with great showmanship and energy, all while inebriated, well, that alone is worth the price of admission! However, the ribs, fries, pizza, gourmet salads, and amazing drinks make the entire experience even more worthwhile!

#6 – Experience So Diego’s innovative Brothels, Bites and Booze Tour

Photo: So Diego Tours

So Diego’s Brothels, Bites, and Booze tour is an invigorating experience that allows you explore Gaslamp Quarter! You will discover the secrets behind the district’s historic buildings, some of which have scandalous pasts, all while indulging your taste buds at some of downtown’s best restaurants and learning what makes this city one of the top destinations for dining, shopping, and nightlife.

The food on this tour is well enough for a full meal, and you will make stops to four popular restaurants in the area, so bring your appetite! To wash it all down, the tour offers a taste of many unique craft cocktail bars and microbreweries in the neighborhood, with a sample-sized brew, cocktail, or other intoxicating treat for the full San Diego experience.

These tour guides are some of the best in the city. They’re fun, upbeat, and know San Diego like only local residents can. Your guide will provide you an in-depth look at the famous red light district of San Diego, the women who ruled the streets at the time, and will show you why San Diego is America’s Finest City!

#7 – Catch a Movie at Luxury Multiplex Theater Box

Photo: SD Union Tribune

This luxury cinema is a remake of the former Pacific and Reading cinema building. Like its predecessor, Theatre Box is a 73,000 square foot multiplex. However, unlike the latter, this new and improved theater is just oozing in luxuriousness.

There are eight auditoriums upstairs, each outfitted with leather recliners, and offering full food and drink service. The theaters also include “lily pads,” or open seating at the front where kiddos can sprawl out or squirm around. The adjacent concession stand is a full bar balcony for anyone who wants to peer over at the guests down below.

Downstairs is San Diego’s first Sugar Factory American Brasserie, an luxury dessert chain with restaurants all over the world! The restaurant showcases the brand’s over-the-top collection of Instagram-worthy confections, including expensive lollipops called “Couture Pops,” “insane” milkshakes, and even a Bacon Cheeseburger Milkshake (a burger atop an ice cream shake, served in a candy coated mug).

#8 – Watch a Play at Civic Theatreor Balboa Theatre

Photo: Civic Center San Diego (Aladdin Musical)

The Civic Theatre, located on 3rd and B Street, is this city’s largest and greatest attended performing arts venue. The theater has hosted the world’s finest talents in the fields of opera, classical music, dance, comedy, contemporary music, inaugurations, governmental addresses, religious services, and of course Broadway.

You can usually buy your tickets day-of, as long as there are tickets at the box office, but we recommend you buy well in advance, or even purchase year passes, to ensure you always have a good seat!

Balboa Theatre, at Horton Plaza, is a San Diego landmark. Built in 1924, the historic theater was an elegant vaudeville and movie palace in the heart of downtown. After remodeling, reconfigurations, housing U.S Navy sailors, housing single-occupants, and finally nominated to the National Register of Historic Places, the theater is one of San Diego’s main attractions and is now an integral part of the city! It’s home to many recurring shows, like Jingle” by the San Diego Gay Men’s Chorus, and Cult Classic movie showings such as Jurassic Park, Saturday Night Fever, Mad Max, and The Princess Bride!


Book our signature Brothels, Bites and Booze Gaslamp Tour Today!