Made a reservation for 6:15 and got here right when they opened at 6, they sat us right away. We had the whole place to ourselves which was very cool. Love the decor/design and vibes (music/theme). Service was great! Helpful, friendly, and accommodating. The bartenders are really serving up crafted cocktails. We ordered the following: -Start Me Up, my partner loved this. He is an espresso drinker and love the flavor profile -Like A Virgin, this is on the sweeter side but the prosecco side car really balances it out -So Fresh, So Clean: normally comes with tequila but I swapped for vodka and it was very refreshing -Davis In My Bones, partner loved this This place turns into a club at 9:30, so there are plenty of options depending on your mood! Come check it out! read more

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This is definitely not a happy hour or "let's grab a drink" place. It opens at 6pm, and on a Thursday at 6pm on the dot, I was offered only a bar seat without having a reservation. No big deal, as I wanted the bar anyway, but something others should keep in mind. The cocktail list is plentiful and intriguing. I tend to avoid tequila, so that eliminated a good chunk of the options. I went with Rose Colored Lenses, which was fantastic, and decently sized. Presentation was beautiful. My friend had All a Dream, also very good. The wine offerings are minimal, this is very much a cocktail or champagne type of place, with caviar being the primary food service. Speaking of service, the bartender was excellent, both in his mixology and demeanor. It took awhile to get the drinks, but I assume that was due to the complexity of the cocktails, paired with having just opened the doors a few min earlier. Two notes: 1. The barstools were a little too low, imo. I don't normally pay much attention to that detail, but these were uncomfortably low for me, even with my long torso, I was hyper aware of my posture. So maybe that's actually a good thing 2. Other patrons were rolling in shortly behind me, so there is probably an early crowd when they first open, then a late night group that appreciates the 2am closing time. Interior is beautiful, and you can use the steps up to the 2nd floor either from N Santa Cruz or the rear parking lot off W Main. More substantial food options are a mere few steps across the hall at Heritage. read more

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We had reservations for 9:15 PM and there seem to be some confusion as to our seating, which was quickly resolved. Once seated, our server was very pleasant and accommodating with giving us time to peruse the menu. I ordered the OG old-fashioned which was fine, but would not call it a craft cocktail. It was balanced, but very simple and basic. Something you'd make at home. I tried the dirty martini and it was a little better. Can see coming back for the martini cart experience. Other drinks I tried were the queen B, bidi bidi bom bom and Davis in my bones, sips only as I was the DD. I found Davis in my bones to be better than the old-fashioned, but wasn't wowed. Definitely not worth $30! It lacked the flavor tones listed; such as the nuttiness from the walnut, chocolate, demerara or banana. All of us found BIDI BIDI BOM BOM disappointing. As for the Queen B, thought it was well-made and balanced. One thing we liked about all the drinks was that they were not overly sweet. Inside was nicely decorated. I was debating between 3 and 4 stars and went with 3 as was had a nice time, but for a cocktail bar the drinks lacked the craft cocktail experience and listed notes in the menu. It was a mixed crowd of all ages and the scene changed right around 10 PM. Although there is no dance floor some began dancing in what was the walkway, and became more clubbish. One comment I would have is music was way too loud. That's not just an older person talking, lol, seemed a lot of people were struggling to have a conversation. read more

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Good Cocktails, Strict Closing The Drinks: Really good cocktails - they'll customize or switch liquors for you. One of the best espresso martinis I've had, served with a toasted marshmallow. Bartenders are usually in a good mood. The Vibe: DJ set starts after 9:30. Music is hit or miss and they don't take requests, but they try to read the room. Seating isn't the most comfortable - seems intentional for turnover. The Hard Cutoff: They enforce reservation times strictly and kick people out sharp at closing. After a birthday party, they literally told us to leave while we were in the restroom - didn't even let us finish half-drunk drinks. Another time, when at the bar, they immediately asked us to get up because they were taking all the bar chairs away at 9 pm. Just awkward. Pro tip: Wrap up 30 minutes before your time is up or closing time. The Reality: Only real lounge option in South Bay, so people flock here despite the rushed vibe. Bottom Line: Great drinks and decent atmosphere, but be ready to leave on their schedule and deal with some chaotic management moments. read more

Update: They now accept reservations for a party of 5 or less! (Was initially only allowed for parties of larger sizes.) They've had this change for about a year or so now if I remember correctly. Because of that, I keep coming back! Thank you for listening to customer feedback and implementing change! read more

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This place is such a vibe. We got there shortly after they opened without a reservation and were seated right away. Our waitress was incredibly sweet, she overheard it was my fiancé's birthday and surprised us with a little chocolate and candle to celebrate. We treated ourselves to caviar (always a good call), and I absolutely loved my Purple Haze mocktail, so delicious! read more

Second Story - Caviar with Crème fraîche and chips. Purple Haze Mocktail, and Queen Bee - Cocktail Bars Near Me - Los Gatos, California

The name of this bar immediately caught my attention -- Second Story, and yes, it's literally located on the second floor in downtown Los Gatos. The vibe is great from the moment you walk in. We were welcomed by a friendly waitress and seated at a cozy corner table. Even on a weekday, the bar was packed, which says a lot about its popularity. We ordered a few cocktails, and I highly recommend Queen B -- it's absolutely eye-catching, both in color and taste. Another favorite was Rose Colored Lens, a lighter and smoother option that's perfect if you prefer something more elegant. If you're into stronger drinks, Boys Club is the way to go. Overall, great atmosphere, solid cocktails, and definitely a place I'd recommend and revisit read more

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Cute bar in downtown los gatos, there is a stairway entrance as the bar is on the second floor. It has pretty interior and overall cute tasty drinks. We got the seasonal express yourself which was like a pumpkin espresso martini with a foam and was so good. The thug passion was fruity and sweet and good! We also got the Queen B which also was cute and good too! read more

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good experience at second story. we made a reservation so we could get a table. lots of people came in after and they had to stand. cute vibes and interior. we ordered: bidi bidi bom bom la bamba queen bee thug passion thug passion was probably my favorite. it was sweet and refreshing! the drinks were all really good. good flavors. pretty loud and dim/dark environment. would come back! nice service! the bouncer/security was really welcoming and happy. read more

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This is a fun and cute place. Go here for good quality drinks. They also have really good music. Not crazy loud but def a vibe. You must make a reservation bc they get busy but you walk in and stand at the bar. I recommend a reservation bc the seating is very cute and date nite/ girls night approved. The service is also good. Everyone is fun and sweet. read more

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This is my second time coming. Super vibing. Low key crowd. Great DJ music. Upscale and amazing decor. Moody lounge. Reserve your table in advance. Otherwise standing room only near the 2 bars. We have always found somewhere to linger. This past Saturday music was so good we started dancing. Cocktails are super good. I ordered nonsweet espresso martini. They included roasted marshmallow. Much tastier than some coffee beans. And it had a great kick. Husband ordered ranch water and we had a few tequila shots. It was a fun date night. read more

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Vibe: 5/5 Service: 5/5 Drinks: 4/5 Food:n/a Value: 3.5/5 Having been here twice now, I cannot relate to some of the negative experiences others posted. Maybe we just got lucky. We've always received nothing but friendly service from everyone working at this place. Yes, the music can get quite loud once the DJ starts spinning at 9 p.m. So come early if you want to chat and stick around to vibe to some 90s/2000s Hip Hop and R&B. The only gripe I have is with the consistency and price of the cocktails. The first time we came, Cassidy made our drinks, which were phenomenal. During our last visit, I got the same spicy cocktail, and it was super bland and tasted quite watered down. Also, compared to Soda Works, their cocktails are also more basic and less creative, yet the pricing is similar. So you're paying for the vibes. It's a fun place. If they can step up their cocktail game, I could see myself becoming a regular. read more

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Such a great spot for a date night with your partner or even a girls' night out. They had good music, a nice selection of drinks, and the service was super welcoming. The overall vibe was really fun. It does get pretty crowded after 9pm, so I'd recommend coming earlier or making a reservation if you want to grab a table. read more

Second Story - Cocktail Bars Near Me - Los Gatos, California

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Fancy cocktail bar. Love the indoor design, intimate and romantic. They have a DJ on site for music, but I wasn't a dance of the music selection. Also I thought the music could be a little quieter for conversatio We came on a Thursday night and got seated right away. The service was fast and friendly. We ordered the La Bamba, Gimme the Loot, Diamond Life. I do like sweet and refreshing taste, so I loved the La Bamba and Diamond Life. They have a lot of cocktails that look good, I do see myself going back for different drinks read more

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First, it's important to specify that our reservation was at 10:30 pm on a Saturday. My husband's cousin was visiting from Ireland and staying in Los Gatos and wanted to do a bar crawl. We visited a few places and then he mentioned Second Story - he had apparently stopped by on a Thursday early evening and said they had cocktails and jazz music. My husband's interest was piqued because he knew the location as the old Mountain Charley's and wanted to see the changes. We had NO IDEA this place turns into a club at night... we were like fish out of water. I'm normally an IDGAF what anyone thinks type of person but I was mortified to be there in jeans and a sweater and SNEAKERS. Despite this (and a posted dress code sign), we were seated, and ordered some drinks - everyone was polite and nice. The music was good but as others have said it was too loud to converse, but there were lots of people dancing. There isn't a dance floor, but people make do and it was packed full of people who were having a blast. If you're looking to dress up, get drunk with your friends, and dance - I imagine this would be the perfect spot!! After the first drinks, we were asked to move from our tables and honestly, that was our cue to leave and I was not mad at all. I've never felt more old or uncool in my life!! Age here seems to be about 30-40 year olds and everyone comes dressed to impress!! Come to dance and drink, but don't expect to have any deep conversations, you won't be able to hear. read more

Was eager to try this place bc it's been all over my instagram but idk if it's for me. It's decorated more upscale and intimate vibes. There's a dj playing loud music so not a place to catch up with friends but also not a place to dance either. Drinks are overpriced and mediocre in my opinion. Wouldn't be my first choice for a night out. If you are planning a visit I would make a reservation. There's some standing room around the bar but very limited table space. We were lucky to snag a table for 5 around 10pm on a Saturday. read more

Second Story - Cocktail Bars Near Me - Los Gatos, California

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Great ambiance. It has a romantic, low lighting, cereal and chandeliers vibe. Lots of cocktail options. Minimal food, but they do have a couple snacks. We knew this and went after dinner. We all had an espresso martini. One was regular and the rest of us had the pumpkin spice. It was SO GOOD! Pricing ran an average of $19-22 per drink. They were also very accommodating about moving my reservation slightly , even though all the times weee booked online. Book early for best options and call if you can't find something. read more

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The service here was very odd. We mentioned to the server that we were celebrating a birthday and ordered a bottle of wine and sparkling water for the table. The server poured our sparkling water and the bartender poured our wine, and everything seemed fine at first. However, when we wanted to order more, the server completely ignored us as if we were invisible. It was strange because she was actively talking and helping her other tables. Thankfully, the bartender was kind enough to help us order a couple more drinks and close out our tab. Overall, it was a pretty weird service experience. read more

I used to frequent Charley's and really miss it. I was excited that there is a new cocktail lounge that had taken its place and wanted to LOVE it. Unfortunately, it was a meh experience. It was packed on a Friday night as expected. Ambience was cool and you could see the remnants from Charley's which brought back memories. The staff from the hostess to the bartender to the other staff seemed overwhelmed and curt. The worst part was the super LOUD music. Loud music makes sense for a dance club but why would you have such loud music at a cocktail lounge where the expectation is that you have a nice ambiance where you can enjoy a drink with company and have a great conversation. Conversation as in can hear each other and don't have to yell. I lost my voice trying to keep a conversation going and the 4 of us ended up leaving 20 minutes in. Bummed because this is so close and was hoping to make it our go-to spot. read more

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I used to come here back when it was Mountain Charley Los Gatos Bar, so it was exciting to see how much this place has transformed. It's since had a complete facelift and is now a beautiful second-story nightclub and lounge--literally, as it's located on the second floor. The venue is ADA compliant, with an elevator conveniently located in the back by the parking lot, which is a huge plus. While it can definitely get packed, our group was well taken care of by Jamie, one of the owners, which made the night even better. The music selection was great, the energy was fun, and there was plenty of space to dance, even with a full crowd. Overall, we had an amazing time and loved seeing this spot reborn into such a lively and well-designed space. Definitely a place worth checking out for a fun night out. read more

This place serves a good martini! My sister has a dirty martini and I had a Manhattan. They were both delicious. They have a cart they bring around to make your martini in front of you (for this it has to be a classic martini). The ambiance is upscale, cocktail attire and fancy bar and sitting area. Service was impeccable. They don't serve food although I think they had some nuts. It wasn't super busy at 6 pm on a Friday which is great for us. They are sticklers on the dress code. We only had one drink before going over to dinner. If u want a great martini/drink you should stop here. read more

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Awesome drinks, atmosphere, and service! I don't think you can go wrong with any of the drinks, but Phil makes the best margaritas, and the Drake martini. I don't think you can go wrong with any drink Phil prepares for you. Thank you Phil!!! read more

I came here with some girlfriends for a little G. N. O. It was exactly the vibe we were looking for. Classy, chic, and high end. We ordered delicious drinks (absolutely loved the kombucha mocktail) and caviar nachos, which were to die for. The DJ was playing the best rnb throwbacks after 9 and it was the perfect mix of upbeat and mellow. The place was busy but not overcrowded, and very light hearted and easy to socialize with those around us. Our server was super attentive as well. One of the owners Sammer check in on us as well. Overall, loved this spot and would highly recommend! Recommend you either arrive early to grab a table or reserve ahead of time to make sure you have a place to sit!! read more

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Nate is such a phenomenal bartender! He has the best personality and makes you feel comfortable: every order he aims to please and will make sure you're happy! Dakota is always smiles and wants to make the guests feel welcome! Overall such an awesome experience and so lucky these two were our bartenders! read more

Mannn, I went upstairs dancing with joy and was serviced rightfully and seated. Got a drink and was chillin but, it had been 25-30 minutes till I was not asked for another drink or if I need anything else... it's cool, but I wanted to walk out. And so I did. BUT... I had let the front 3, security, head of security and the front desk lady. And they were super friendly and very polite. They had invited me back and made sure I was serviced and talked to for another drink. And hey, then I made friends at the bar. Awesome night and awesome place. The music was just right, a whole vibe. I forgot the names of those people but I really appreciate all of you ! Drink safely and uber home if you have too. Second story will take care of you cause they also knew I had too many drinks hahaha and had let me know to go home, now I'm home in one piece. Thank you second story and thank you Victoria. read more

This was my first time here since it has opened. We had a great first experience. It is a high end lounge bar that has beautiful design and decor with the perfect ambiance and lighting. There was a DJ that was playing good music that allowed for a social vibe. The drinks were really strong which is a great plus. I would say a reservation is needed especially if you want a nice seating area. All the staff were incredibly nice and attentive to everyone around them. Definitely dress up when going here and it can make a cute vibe for a fancy night out on the town! read more

Second Story - Cocktail Bars Near Me - Los Gatos, California

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Everything was awesome Lovely place, great music and fantastic drinks... our server - ZICA was totally mind boggling, so courteous and friendly !! Difficult to find her sorts these days!! Will definitely be back often love the vibe of the place read more

Within first 45 minutes of entering this place and ordering a drink we finally got our vodka soda lime. You'd think it is a master class cocktail requiring hours of attention. Average run of the mill bar typically pours this up within 1 minute. The servers are great and friendly but there's something systematically wrong with this place where you can't just order and receive a drink within a reasonable time line. Nice ambiance but not worth going to a bar you can't even drink at especially when you're paying top dollar for cocktails/drinks. read more

If you're not ready to step into your villain era with a martini in one hand and caviar on the other--don't bother. This place? It's giving main character energy. Came here on a Saturday while in town for a quick trip, and it instantly became the highlight of the weekend. Low lighting, strong drinks, and just the right amount of attitude. The whole spot oozes cool without trying too hard. Sophie behind the bar? Iconic. Friendly, sharp, and pours like she knows your secrets. She made the place feel like our own private speakeasy. Also, let's talk about the caviar bump on the hand. Decadent. Dramatic. Delicious. I came for a cocktail and ended up living out a Bond villain fantasy. No regrets. Drinks were dangerously good, glassware was straight-up art, and every detail was dialed in. If you're looking to sip pretty and serve looks--this is your spot. read more

Second Story - Second Story Martini - Cocktail Bars Near Me - Los Gatos, California

Drinks were good. Decor was cool. Atmosphere was awful. They advertise a dress code they don't enforce. They pack the bar with as many people as they can without violating codes (or maybe they do, I wasn't counting). It's loud, overpacked and just not worth it. The drinks are expensive but good, but definitely not a place if you want to catch up with friends. read more

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Beautiful destination - classy and fun. There is an excellent selection of alcohol and a fantastic menu of cocktails imagined by Perry and Saul who you might recall from OCK. The ambience really shines and matches the quality of cocktails. Beautiful chandelier and wonderful staff. Highly recommend. read more

Second Story - Awesome decor with familiar faces down the hallway. I like the plants inside. - Cocktail Bars Near Me - Los Gatos, California

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Was not expecting to find a spot like this in Los Gatos. Second Story has a welcoming, modern, and chill aura that completely caught me off guard--in the best way possible. It's upscale in aesthetic while remaining relatable to varied crowds. They have a lot of nice portraits of music icons as soon as you walk in which was nice (Shout out to whoever chose the Sade pic) The bar staff was top tier. Moose and Dakota were the best; friendly, knowledgeable, and clearly passionate about the craft. The whole team helped set a tone that felt inclusive and easygoing, like you could go solo or roll in with friends and still feel right at home. The drink menu was approachable price-wise, especially for a place with such an impressive liquor selection. And the music? Also top tier. Curated in a way that added to the energy without overpowering the vibe. I'd love to see them host a daytime function, as it would be the perfect venue for something like that . Adding a dedicated outdoor space would be the finishing touch. Second Story is a fresh breath of air in the South Bay nightlife scene. Highly recommend. read more

The cocktails we had were tasty. The decor was fancy. The music and noise level inside was WAY too loud. This is more like a bar than a cocktail lounge. They blast the music so you can't talk. I do not like that they allow people to stand at the bar because it makes it feel more like a bar than a fancy cocktail lounge. I was really looking forward to trying this place with my wife on our 10 year wedding anniversary but we couldn't even hear ourselves think. read more

Great location delicious drinks awesome music the perfect place for a night out with friends . read more

Second Story - Cocktail Bars Near Me - Los Gatos, California

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The listing for Monte Serrano is incorrect as it is in Los Gatos. What used to be Mojntain Charlie's is now a higher end craft cocktail bar. The space was dead for a good long while so glad to see the revival of another choice of drinking that is open past 11pm had a good scotch/amaro drink at the bar with some of the friendly bartenders. Find Ben and he will take care of you! It maybe a bit loud for sone people as it has the music and space but if you're at the bar it's a nice vibe read more

Shout out to Moose and Nate! The best bartenders in the game! Made first our experience amazing and over the top! Where super helpful and answered all our questions to make sure we had the right cocktails that were out of this world! They were both so energetic and mesmerizing making each specialty cocktail, couldn't recommend them plus second story more! A+ cocktails, experience, and vibe! LG must try! Ask for Moose and Nate, they will elevate your experience on top of a top tier bar already! read more

Second Story - Bar vibes - Cocktail Bars Near Me - Los Gatos, California

Second Story is a whole VIBE! The decor is on point (very IG friendly) and the live DJ was playing those R&B hits we all loved in the 90's. When you walk in, you don't feel like you're in Los Gatos/ South Bay anymore. We did the full martini experience + other cocktails. Very refreshing. The highlight was definitely the ambiance- very posh. Great spot for a first date because the music is not super loud, so you can actually hear... PRO TIP: You can park in the lot on the other side of the street AND look for the black "SS" carpet to go upstairs to the bar (lack of signage up front). read more

Vibe+ Drinks are unmatched! Dakota took care of us all night, ask for him when you come

Let's talk about a glow-up; the space that once housed Mountain Charlie's has completely transformed. Second Story is the new go-to for luxe nights in Los Gatos. Whether you're planning a date night or just feel like dressing up for cocktails and caviar (as you should), this place delivers. The ambiance? Moody, elegant, and intimate with a hint of mystery. The music had me vibing all night, and the whole experience felt like a mini escape. The staff? Absolute stunners. Caviar nachos were an instant yes ;I can never say no to caviar, and they did it right. The cocktail selection was so tempting, but I had to go with their decadent espresso martini topped with a toasted marshmallow... I mean, come on. Obsessed. I went around 7-8pm, and the vibe was perfect not too crowded yet, but you could feel the energy picking up. Definitely want to come back with my dancing shoes on next time. And can we talk about the full-wall mirror in the bathroom? A whole moment. Las Gatos is having its moment, and I'm so here for it. Second Story, I'll be back ASAP. "A world of flavor, elegance & indulgence one decadent bite and sip at a time." @indulgewithenaa read more

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Martinis and a cool atmosphere?! What else could you want. The service, ambiance, and drinks are all A++. Highly recommend for a date night (the 7-9pm martini cart is awesome!) or grab a group of friends and enjoy! read more

Second Story - Table side martini service with a smile (and some cool history on the martini!) Try the No3 London gin! - Cocktail Bars Near Me - Los Gatos, California