Long story short, Second Story was one of the best cocktail bar's I've ever been to. We went there last night for our friend's birthday party, and we were just ordering drinks from the bar. The bartender (manager?), Filippos, recognized we had a lot of people, and proactively got us a comfortable seating area for all of us. Thank you Filippos for being so thoughtful and hospitable! And once we got seated, we had a server named Tikka, who was amazing. She made our whole night smooth and memorable. The service was above and beyond. Also, shout out to Dakota, one of the best bartenders. He was super friendly (even though it was very busy) and wanted to make sure everyone was taken care of. In terms of drinks, I recommend the Vesper and So Fresh So Clean. All their drinks are exceptional. The ambiance was the most impressive part. It's very spacious and you don't feel cramped like other cocktail bars. And they have two bars that are both well-staffed, so no one is annoyed trying to order a drink. Even when it's crowded, you don't have to wait. Thank you, for all the hard work behind the scenes to create best-in-class customer service and cocktails. read more

What a wonderful night it was! A huge Thank you to Melissa and her team who executed the perfect Happily ever after party for my son and daughter in law. The night was exactly what they wanted; Great friends, incredible cocktails, yummy food, music and a whole lot of Love and Laughter!!! Do not hesitate to book a party at SS, read more

Such a cool spot. Had a great time there with my boyfriend our server Adela was great! She recommend us great cocktails. Definitely coming back soon! read more

TALK ABOUT SWANKY! WOW! This bar was a feast for the eyes and the tongue. We came here after dinner to get a few drinks. We ordered a martini, All a dream, and some wine. When you order a martini, they come out in a cart to explain how they make one and the types of gin they use. The person serving the martini was VERY knowledgeable and could tell us where to find certain liquors. The saxophonist got there around 9:30pm and was interactive, moving through the tables to play for patrons. I loved how unique that was. The bathroom was also gorgeous and interesting. We took a selfie in the restroom due to the size and the full length mirrors. We will definitely come back for more drinks and live music. read more

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Omg such a fun spot! I didn't know places like this existed in the South Bay! Came here post-dinner on a girls night and had a fun time. Music was all throwback R&B. Great vibe, great crowd, and great drinks. My girlfriend and the foresight to reserve a table in advance. I don't even think they took payment for it - but I'm so glad we had the spot cuz it allowed us to sit down, chat, and enjoy our time. Would defs recommend! read more

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

I've been to Second Story a handful of times now, and it's easily one of my favorite lounges! Every visit has been such a great experience. On my most recent trip, our reservation unexpectedly grew by a few people, and the staff went above and beyond to accommodate us. We really appreciated how hard they worked to make it happen! The cocktails are next level creative, delicious, and unlike anything you'll find at your average bar. My absolute favorite is the Bidi Bidi Bom Bom shot! And of course, we always order the caviar because... why not? The vibe here is everything. Whether it's girls' night, date night, or a celebration, there's always an amazing crowd. The DJ knows exactly how to read the room and keeps everyone singing along/ dancing with banger after banger. One night there was even a live saxophonist who absolutely stole the show, it made the whole experience feel so special! I also love the Renaissance inspired artwork by the entrance featuring icons like Drake, 2Pac, Sade, and more. It's such a cool touch and adds to the atmosphere. Second Story never misses, and I already can't wait for my next night out here! read more

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It was my first time here and fortunately we reserved a table because it was crowded on a Thursday night. Drinks were delicious. Music was good. Service was amazing. Thank you Dakota for the delicious/surprise cocktails and thank you Mackenzie for the service. You both were amazing! read more

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Excellent spot if you are looking for a great date night spot in the area. It was nice for a late nightcap, offering an intimate and stylish environment that makes it perfect for wrapping up your night. The service was decent throughout our visit. Drinks were good and there were some snacks which looked good. 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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Overall good experience. Went here after dinner for a drink. And they make nice drinks. Had the old fashioned. And a non alcoholic drink both were good and I will come back be more adventurous. The only negative was I saw later they charged my card for someone else's drink then credited it. No foul but I would have liked to be told. read more

My colleagues and I had a really awesome time at the Second Story. Classiest joint in the desert of nerd land. Solid. I never give reviews, I ain't doing your job for free, what am I, chat gtp ? Lol. Seriously, McKenzie is Da Bomb. If you are gen x, you know. ​ read more

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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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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Haven't had food from here but this spot is definitely a vibe. They have lots of cocktails to choose from, but your wallet will pay for it... they are fun drinks, good music, and love a good lounge bar vibe. read more

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

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Great drinks, great bartenders! The vibe is nice too, high ceilings and beautiful decor. Lots of drink options to choose from, I got la bamba, it's a version of their espresso martini. I really liked it! They had a bartender come around 8ish and he started around 8:30pm for a party. There were lots of seats and tables that were reserved and also the back lounge, but we were able to walk into the bar to sit at bar seating. They also have a martini cart service you can get and they also offer bottle service. I think it also turns into a club after hours! read more

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

This is such a cute, moody, and ambient bar. The drinks and service were great. My friends and I overall had a wonderful experience. I will say, besides the salty bites and caviar, I wish they offered some other small bites. If you want a table to enjoy with a group, reserve ahead of time. The reservation's good for two and a half hours. 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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Always 5 stars taking good care of us at SS everytime we are here. Adela is always a vibe . Love her! read more

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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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

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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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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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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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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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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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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Tarah was so amazing! She made sure my group was well entertained and made some amazing drinks. I'm usually iffy about new bars I addend but she made sure I felt right at home. I can't wait to come back! read more

Thought the drinks were great. For a first timer it was a little surprising it was a very lively bar instead of a quiet cocktail lounge but definitely a great space if you're looking for a little night out. Giving it a 3/5 for being charged an extra bottle of water that was never received and mind you the water is $8 a bottle. Left my phone number twice for someone to get back to me and never heard back. read more

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

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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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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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

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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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

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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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 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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Music is always off the hook. The vibes are good. server is Adela!! We love her!! She always makes sure our drinks are filled!

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