Had a ball learning about cigar making, the owner's family business, and rolling our own cigars…read more Andy was super knowledgeable and passionate about his art. Highly recommend!

Great lounge with even greater service and a wide selection of rolls. The ambiance was classy.read more

Amazing staff, amazing selection, and excellent prices! Super inviting atmosphere, the gold…read morestandard by which other cigar shops should be judged for a no frills, straight to the point experience!! 10/10!

If you're looking for a chill spot to smoke a cigar and avoiding something pretentious, Liberty is…read moreyour spot. The staff are super welcoming, all their regulars are cool and you'll make a lot of friends here. They got all the top rated cigars and their humidor is well stocked at all times. I find myself here more often these days, hey there's always an excuse to have a cigar right? Great prices, well aged cigars and ample seating. Come chill, light one up and chat away!

Love this place. The lounge is dark, cozy, and very comfortable. It has a great social atmosphere,…read morewith plenty of comfy couches and even a billiard table. Perfect spot to relax and spend time with friends.

Was looking for some cigars, heard about this spot and the photos on Yelp looked good. Here was my…read moreexperience. AMBIANCE Parking: Hillcrest area--street parking, might take a minute depending on the time. Seating: Multiple lounge-style areas--couches, chairs, even a pool table setup. Plenty of space to spread out and hang. Good for small groups Vibes: Welcome to the Hillcrest Gay-borhood. It's an eventful place from good eats to bars. This place leans heavy into that speakeasy / vintage lounge feel--dim lighting, moody atmosphere, and a slightly cinematic vibe. It almost feels like stepping into another era. DRINKS / EXPERIENCE They've got a solid selection of wine, beer, and cigars, and the humidor (cigar storage room) is stocked with a variety of options for different preferences. Even if you're not a cigar expert, the staff is known to help guide you toward something you'll actually enjoy--which makes it approachable for both beginners and regulars. CUSTOMER SERVICE Friendly and knowledgeable. Rocky was pretty helpful. TL;DR OVERALL 4 Stars. Solid selections and pleasant vibes. I'm not into the cigar culture but it looks like a unique spot in San Diego. Great for a chill night out, especially if you're looking for something different from the usual bar scene. TIPS: * Take your time--this isn't a rush-through spot * Ask for recommendations if you're new to cigar

I moved away from San Diego but enjoy hitting Churchill Cigar Lounge whenever I return for a visit…read more Central location in Old Town with a great selection of cigars (including a separate back room with OpusX and ST Dupont lighters) and an outdoor covered patio with televisions. Good beer selection--bottled and craft beer--as well as wine. Always worth a visit. Met up with friends to watch the NCAA Men's Basketball championship game.

Churchill's is a very clean shop with good service and a decent cigar selection. The staff was…read morefriendly and knowledgeable, and the overall atmosphere was nice. That said, I did feel there was a bit of pressure to purchase both a wine and a cigar, which made the experience feel more like a sales interaction than just enjoying the lounge. I also found the pricing a little higher compared to other cigar shops I've visited. The lounge area itself could use more of a community feel. There seemed to be more tables and not enough comfortable seating like couches where people can relax, socialize, and enjoy a cigar. Overall, it's a nice, clean place with good service, but based on my experience I probably wouldn't return.

Friday Smoke Show! Great draft selection. My fave tonite - Mother Earth Cali Creamin & a Fiddlehead…read moresmoke ‍

First time being here to try my first cigar with my friends. Had a decent selection of cigars, nice…read morepatio to hangout and smoke your cigars. Person working there was nice but not helpful and guiding us to the different types of cigars they had in stock especially since we've never done it before. If you're around the area, it's worth a look if you're looking for cigar to grab and go.

One of the better hookah lounges I've found in the area. The hookah is consistently good, the…read moreatmosphere is comfortable, and it's a place I actually enjoy coming back to. The service has always been friendly and attentive, and the staff does a great job making sure everything is set up properly. If you're looking for a relaxed evening with a quality hookah, this is definitely a place worth visiting.

Duc is great! He is personable helpful, conversational and he works the cigar lounge, the coffee…read morebar and other areas. Must of their cigars are hand rolled and they are very good. They have dozens of seats throughout and a coffee bar with drinks, sweets and the vibe is very pleasant and relaxing. One of the best places I went to in Downtown San Diego area. Decent prices and many nice selections They have a hand roller on site.

Welcome traveler to Racine & Laramie Tobacconist…read more The oldest smoke shop in America's Finest City. The service is a yes. The prices are on the higher side, but you're getting a great experience from start to finish while supporting a small thriving business in Old Town San Diego. Stellar collection of cigars, pipes, lighters and various things. Not to mention old timey tunes on their speakers. Fun fixtures and displays. They have coffee, soft drinks and small lounge area for those who wish to partake in store, not to mention some match books with their logo, great souvenir. We had a couple of Nubs (short thick stick cigars), great flavors for a shorter smoke time (draw it in, don't inhale - like with any cigar). Jeffrey (aka Jeff) was a dapper class act and gentleman, the guy you'll most like encounter and the first face you'll see when you walk in as well as on their site. R & L T has some good bundle deals and sales throughout the year. We encounter lots of kind and interesting folks during our visit in. I've been curious about pipes and would definitely purchase with them. Great quality of all products, plus that top notch 1800s service in 2026, is a win cigar enthusiasts.

Such a charming historic location . Smoke selection is great and the employees are very…read moreknowledgeable. I enjoyed extensive conversation about pipes and tobacco blends Only down side is seating for enjoying your smoke if you purchase to have immediately . But if you lucky enough to grab the bench outside and people watch it's really a unique experience

Amazing!! We had 7pm reservations. We were shopping around and got some goodies for upstairs. We…read morewalked through this cute "farmers market" store towards the elevators. We went on "lovers night" so they had live do-woop music band inside which was really good. We were seated outside which was nice cuz it was humid hot! The breeze and sunset on the balcony was great. The bar downstairs also had live music so we were able to enjoy that. It seems that they are short staffed on the servers. It did take a minute to get some help but we got some great tasting drinks and started to pare take in our smoke sesh. Time was nowhere so who knows how long we waited for our food. the food was amazing!! Large portions!! Shareable! It was a great first time! Had so much fun! High-ly reconfirmed a chill spot.

Sessions on the Bay is such a vibe. From the moment you walk in, the experience feels unique. You…read moreactually enter through the dispensary first, where you can browse and pick up your favorites before making your way upstairs to the lounge. It almost feels like you're walking into a speakeasy as you pass through this cool market-style space, then down a hallway lined with awesome artwork and classic Hollywood movie posters with a stoner twist before arriving upstairs. Once you're in the lounge, the vibes are immaculate. The décor is trendy, the wall art is incredible, and when I went, the DJ was absolutely killing it. I was Shazaming song after song because the playlist was that good. The service was fantastic from start to finish. Our hostess seated us right away, everyone was attentive, and the staff made the whole experience feel welcoming. Word of advice, get a reservation! You won't have to wait. The food was honestly better than I expected. If you go, you HAVE to order the Ahi Tuna Crispy Waffle. It was incredibly fresh, and the sweetness of the mango tied everything together perfectly. I also ordered the Wake & Bake Espresso which was delicious. One thing I really appreciated is that although I don't smoke, I never felt out of place. My friends were able to enjoy smoking at the table, and you can even order products to be brought upstairs (the upstairs selection is a bit smaller than what's available in the dispensary below, but it's still super convenient). As someone who doesn't consume THC, I was a little nervous about ordering a cocktail since they're served with a THC additive. Thankfully, the additive comes separately on the side, so you have complete control over whether you use it. I simply handed mine to a friend, and it completely took the pressure off. There is a $10 lounge cover, which I think is totally reasonable for the experience. If I remember correctly, it's waived with a dispensary purchase of $50 or more. Overall, Sessions on the Bay does an amazing job creating a space that's welcoming for everyone. Whether you're a regular cannabis consumer or you're simply there for the atmosphere, great food, drinks, music, and company, it's an awesome place to spend an evening. I'll definitely be coming back and recommending it to both my friends who partake and the ones who don't.