Looking for a Caribbean escape right in Old Town? Captain Gregorie's is the spot. Step through the speakeasy entrance and you're met with fun, tropical vibes. We grabbed seats at the bar, where the bartenders were helpful in guiding us through both the drink and food menus. The cocktails were creative and distinctive, each one offering something different from their rotating list. We had the tasting menu to sample a bit of everything, and it did not disappoint. Every dish was flavorful, with the ahi tuna and the pork belly being my favorites. Whether you're looking for great cocktails, a cozy date night, or a fun evening out with friends, I recommend checking this place out. read more

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This is gonna be a short one because I was here about 3 wks ago.... I introduced my out-of-town friend to this gem. He loved all the cocktails we had and raved about the food. We had 4 dishes and the maple bacon donuts. It was a bit too sweet for me but he had two :) I loved all the cocktails. The bartenders always are right on with drink suggestions. We sat at the bar so we had great service. I should have an honorary badge for coming back and spending so much money within a month. Hahaha read more

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Speakeasy with a Caribbean/global traveler vibe and delicious cocktails In order to get in you have to pull the flag out front and wait for a host to open the door for you Inside has bar, table, and lounge seating. Making a reservation is reccomended I came here on a Friday night with my fiance and we tried a few different cocktails + small plates. Everything was delicious and the service was very fast The downsides are that the space is very dark and somewhat loud read more

A hidden gem speakeasy! As soon as we were seated, the bartender quickly tended to us. It was my birthday so we were given complimentary shot size. We ordered the Outcast Society drink, which was a light, refreshing drink similar to a pina colada and The Huntress drink, which was a smoky, bold drink. Both were great! I loved the vibe of the place and hope to come back again. read more

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The best speakeasy in the DMV!! Made a reso on a Thursday evening and quickly figured out the entry situation. Staff was super friendly, ambiance was top notch and the drinks were phenomenal!! Drew the bartender made the experience by recommending drinks and appetizers and was very thorough. Provided an explanation of the seasonal menu along with his favorites. The drinks he recommended were all delicious and strong. For appetizers we ordered the tempura cauliflower and duck fat chicken wings which were both delectable. Can't wait to return bc the drinks, food and service were top tier!! read more

Captain Gregory's - Cocktail Bars Near Me - Alexandria, Virginia

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This was a fun speakeasy! The bartenders were really friendly and fun to talk to. It was open enough to not feel cramped as well. The chips with pickle dip were sooo good! read more

Captain Gregory's - Cocktail Bars Near Me - Alexandria, Virginia

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My husband and I absolutely love this speakeasy!! Located in Old Town, Alexandria, reservations to Captain Gregory's is HIGHLY recommended as it is a small speakeasy. With a reservation you are guaranteed 2hrs! This place is a cozy little spot! They have a nice amount of small bites to choose from that you can share amongst your group and a nice seasonal selection of cocktails that are absolutely delicious! For food we ordered the deviled eggs, pork belly and the crab cake. To drink I ordered The Banana Stand, Purple Honeysuckle and Nectar of the Gods. read more

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Still the best cocktails in the area. Many other spots charge the same amount for regular ingredient cocktails, Captain Gregory's is infusing, washing, using a rotovapor to infuse flavors into their spirits. THAT'S creativity. Science! Always an adventure, with top notch service, and tasty snacks to boot. New drinks every few weeks as well. The Donut shop entrance may be gone, but the experience is better than ever. read more

Great speak easy. Great service. Drinks were top tier! We can't wait to come back. Decor is so cute and themed. We loved the Christmas decor they added too! read more

Captain Gregory's - Cocktail Bars Near Me - Alexandria, Virginia

One of the worst experiences at a so-called speaking of the I've ever had. They don't even have a phone number. They don't respond to emails and supposedly they have reservations. My ass. We came here hoping that walk-ins would be welcome as it says clearly on their website. Unfortunately the doors were bolted. The lights were off and there was no one in the house. We tried knocking on the door several times and didn't get any response If this place is in business, which is a big shock, if it is, they deserve to go out of business. I don't plan to come here again and I don't recommend that you do either plenty of other places to go to. We are currently enjoying killer cocktails at Kings Ransom. Come here instead. They're open and they have a cool entry bag. And phuck you Captain read more

Super dope space.. .they did a really great job with the remodel. Brandon and the rest of the bar staff know their s*&t so trust them to make you a proper cocktail. Plates were excellent as well. I dig a place that puts hospitality, product quality and atmosphere before ego. Kudos. read more

Everything! Friendly staff. Amazing food & beverage list. My sister and I enjoyed the secret door entry way too. read more

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I throughly enjoyed my experience at Captain Gregory's Christmas in the Keys! The speakeasy concept is very unique. Upon entering, you pull the flag, and you're greeted by one of the servers. We didn't make a reservation but were able to get seated on an early Saturday evening. The majority of the drinks were rum based with a few bourbon options on this rotating menu. The service was great and so were the drinks. I will definitely be back! Another Old Town Alexandria gem! read more

Captain Gregory's - Welcome sign - Cocktail Bars Near Me - Alexandria, Virginia

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If I could give zero stars, I would. The manager was rude and condescending, talking to me like I was clueless. We had a party of 7 with 6 seats ready, and he snapped: "You made a rez for 4 at 7 and 4 at 7:30. That's how rez works." Completely unprofessional. He needs a lesson in basic hospitality. They were not busy. They could have accommodated us. Reason and logic. I've waited tables, been a bartender and managed a high end steakhouse. Don't be a jerk. It wasn't like I asked for a complicated anything. #captainjerk read more

Very cool speakeasy bar, great for a date! Awesome cocktail menu. Our waiter, the bartenders, everyone seemed to be happy working here. We had other plans for dinner but we'll be back to try the food. We got a reservation on Resy, recommend that as it's pretty small inside. read more

Absolutely loved my experience at Captain Gregory's. My friend was visiting town and had never been to a speakeasy. When we pulled up to park outside she mentioned that the place looked closed. I love the fun of a hidden bar and would say Captain Gregory's knocked it out the park. When we entered, the signs and posters make it look like they're a tour company selling excursions. Once we followed the instructions to enter the bar, the space was beautiful with a nautical theme. Someone came over immediately to greet and seat us. We only ordered drinks, but they were both amazing! I'd love to visit again and explore more of the menu. read more

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Cool spot! Drinks are fun and strong. Cozy ambiance. Chips and dip were 10/10. We will be back! read more

Captain Gregory's - Chips and dip, drinks. - Cocktail Bars Near Me - Alexandria, Virginia

A fun speakeasy serving up delicious drinks in Alx. We've been several times and always enjoy the experience. From the entry (pulling a flag to reveal the doorway) to the finish, it's a must-try just a stones through from DC. You really can't go wrong with any of the cocktails. They use quality ingredients and have consistently had great service. Be prepared for quality prices--these cocktails aren't cheap. But they're worth it for a treat-yourself weekend or a date night any night. read more

Didn't eat here, but the drink menu is killer. The speakeasy vibe is so fun! Craft cocktails are the winner here! Bartenders were knowledgeable and efficient, if not super friendly. Definitely recommend. Make a reservation, you may still wait, but at least you'll get in. read more

What a great find in Alexandria! My husband and I really enjoyed ourselves at Captain Gregory's. Definitely recommend making a reservation especially Fri-Sun or you will be waiting a while .I over heard the host mention that there was a 2hr wait so I was glad we were able to walk right in! Ambiance is very intimate, dark, romantic. Great place to have a date night, catch up with a friend or a solo night. Bonus: The playlist was fire! The menu changes quite frequently but we had the Duck Fat Tots, Pork Belly & Wagyu Burger. Chef's kiss to them all! The Pork Belly was mainly fat but that's our favorite part so no complaints from us. Drink wise, I let the bartender pick for me each round and he didn't miss! My husband stuck with the Whiskey Old Fashion which he enjoyed. We will be back! read more

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Deliciousness - 4/5 Happiness - 4.5/5 There's something so primally fun about an actual hidden bar. Whether it conjures up magical medieval castles, sordid speakeasies, or murder mystery mansions, it's just a great way to enter for your libations. And Gregory's commits fully to the bit. Once inside the hidden passage, you are very convincingly in the belly of a nautical ship. The drinks are also top notch. Fair warning, you have to be an adventurous drinker as they don't have a full menu - it's very limited to their specific cocktails. However, their drinks are pretty great and unique - replete with smoke and other cocktail goodies. The reason it's not 5 stars? The service was slow and relatively infrequent (i.e., you're sitting around awhile to wait to place your next order). And I wasn't at all impressed with the food. The devilled eggs we ordered tasted kind of sour (not the flavor profile I was looking forward) and the warm donuts were OK but too dry/crumbly. But you don't come for the food, you come for the ambiance and fantastic drinks. And you won't be disappointed! read more

Captain Gregory's - Gotta pull the flag to gain entry into the unknown - Cocktail Bars Near Me - Alexandria, Virginia

It's a vibe in here. From the entrance to the drinks to the snacks we had. We were sat at the bar and enjoyed our convo with the bartender. The cocktails are $20 and I had already been drinking so just opted for one and some scallops of all things. Idk, there was a marine theme. They were yummy, i am growing very fond of scallops. The donuts were also very good. They came from next door. I really like the ambiance here and glad we got to stop by. read more

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Tucked away just outside Old Town Alexandria, Captain Gregory's is a hidden gem for anyone who loves a good speakeasy vibe. The space is intimate, moody, and stylish--perfect for a date night or a chill evening with friends. Because it's so small, I definitely recommend making a reservation ahead of time--it fills up fast! The cocktails are where this place really shines. Creative, expertly crafted, and always balanced. The only downside? Food options are limited. What they do have is tasty, but I wish there were more variety or slightly heartier offerings, especially when you're sipping on stronger drinks. That said, if you're in the area and looking for a unique, high-quality cocktail experience with a cool, hidden-away feel, Captain Gregory's is absolutely worth a visit. read more

The hidden bar has (thankfully) been a long-obsolete necessity but speakeasy establishments seem to have become increasingly popular. Some are speakeasies more in name, given there's no real need for secrecy and deliberately hiding your bar is likely bad for business. Captain Gregory's does a good job of merging the "hidden bar" vibe with availability. Originally paired with a Sugar Shack donut shop, the bar really has a hidden entrance behind a false wall. The namesake ship's captain from Maine is credited with inventing the modern donut, cutting a hole in a ring to better cook the insides than the previously-traditional diamond and long shapes of fried cakes and twisters. Sugar Shack has now been replaced with a paired sister restaurant: Railbird Kitchen. As for the bar, Captain Gregory's offers top-end, craft cocktails. The menu regularly rotates and they keep it seasonal. When we went, we had a Pine Smoked Old Fashioned, Siren's Hymn, Jaws of the Python, and Royal Regatta. Walk-ins are available on a first-come, first-served basis. Be aware that Captain Gregory's is a small, intimate space with deserved popularity and a reservation is required if you want to be certain you'll get in. They do charge for it, however, it also includes their namesake donuts. read more

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This is a speakeasy so it is very hard to find. If you enter the restaurant that's marked on the map as Captain Gregory, you will find a flag on the wall. Pull down on that and they will let you in! It's very dark inside but they followed the pirate theme very well. It was a cool experience with strong alcoholic drinks. We ordered the Brussels sprouts which were really good. The server was also very nice. All in all, it was a cool experience! read more

The drinks here are so fun and inventive, and I totally love the speakeasy vibe here. It sort of feels like you're in a ship that's been infused with a tiki bar. Reservations are basically a must because the bar is really small. They have maybe 10 tables and a bar, so it never feels too crowded and the volume never feels too loud. Of the few times I've been here, every drink has been great. The menu rotates frequently, so it's unlikely you'll have the same offerings unless you visit in a really short timespan. While there are some food items available, it's by no means a full meal. That being said, their food is really tasty. We came here for restaurant week a few months back and were blown away by the food options for a more "traditional" meal. Servers are also super friendly and the service in general is great. read more

Drinks were out of this world good. Food from the adjacent Railbird Kitchen was incredible. Small space, but not crowded. Terrific music played in the background without ruining conversation. read more

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Once a Favorite, Now a Letdown Captain Gregory's used to be one of my favorite speakeasies in Northern Virginia. I'd brought countless friends here and recommended it widely. Sadly, my most recent visit was the worst experience I've had -- and it will be my last. The Walk-In Experience Everything now requires a reservation -- the bar, lounge, and dining area. In the past, I'd occasionally walked in without issue, but now it's a hassle. * Solo guests: Even if there are open bar seats, you'll be waitlisted. * Parties of two: You might get in without a reservation, but expect a short wait. * Parties of three or more: Prepare for a long wait, as only the small dining section can accommodate you. If you're in this category, make a reservation or go elsewhere. While waiting, I saw a major operational flaw: * A couple with a reservation left after waiting 20 minutes at the door because no one heard the entry chime. * Another guest waited over 30 minutes to be told they could sit at the bar but would still be waitlisted -- despite visible open seats. The current system for knowing someone is at the door is unreliable. Staff rely on hearing a chime or noticing a slightly raised flag -- both easy to miss in a noisy, dimly lit space. Calls to the restaurant went to a busy signal, knocking didn't help, and although there's a camera in the waiting area, it doesn't seem to be monitored. A simple fix, like a monitor at the bar, could prevent losing customers -- which happened twice while I was there. Food We ordered the wagyu "smash" burger -- "smash" in name only. It was average at best: slightly better than fast food, but worse than most burgers elsewhere. This was especially disappointing because it used to be a standout seasonal item that earned a permanent spot on the menu. Whether it's a change in chef or ingredients, it's not the same burger I've enjoyed many times before. Everyone at our table agreed it lacked the flavors it promised. Drinks The cocktails remain creative and well-made. If I lived nearby and could easily get a reservation, I might return for drinks alone. But for anyone traveling farther, there are other spots with equally good drinks and far better food. Service Staff were friendly but disorganized. It wasn't always clear who was responsible for our table, and even after the rush died down, it took far too long for anyone to check on us. Overall The expansion has stripped away much of the charm that made Captain Gregory's special. Between the frustrating entry process, declining food quality, and uneven service, it's no longer a place I can recommend. read more

super cool place. i surprised my two friends that have lived in the area and never been before. the place looked closed which made the surprise even better. when we entered a couple behind us almost ruined the surprise by trying to slide/force push the door open which was really odd. they also didn't have reservations so got turned away. they say you can try to get on the waitlist but it is a lot easier if you just book beforehand on resy! don't remember what drinks we got but the darker solid glass (middle) was the best, then the one to the left of it and in third the far right. donuts were fresh and delish as well. they sell small plates but we did not get any. however, the waiter was good and he also shared some facts about the place and captain gregory so extra points for him for being interesting. would love to come back and try some of their food. drinks are so fun and tasty! great ambiance, the only thing i would suggest would be a better playlist haha. they miss out on a great opportunity to place some good music here. read more

Captain Gregory's - a man sitting at a table with drinks - Cocktail Bars Near Me - Alexandria, Virginia

The drinks were great. Super intimate setting, very personable service. Our bartender / mixologist, Drew, was fantastic. We ran the gamut on the drink menu and didn't find one that wasn't well made. Of course we liked some over others, but all were great. I highly recommend for what it is. If you are looking a woohoo bar night, this isn't it. If you are looking for well created drinks, a great environment, then this is it. Book a reservation. Lastly, it doesn't mean their drinks won't put you on your ass, just saying it isn't a "shots" or order whatever you want type drinks, type of place. We will definitely be back, for the great drinks and ambiance. read more

Captain Gregory's - Cocktail Bars Near Me - Alexandria, Virginia

We enjoyed our night out to Captain Gregory's. The drinks were good. Note: you really have to order drinks from the menu they don't have other options. Even something as simple as a rum and coke isn't an option. The secret entrance is cute and the space is intimate. I wouldn't go back but I'm glad I gave it a try. read more

Went to Captain Gregory's, a nautical themed speak easy on a Tuesday night. We arrived a little early for our reservation so we had to wait outside until the secret entrance would allow us in. This was my first time here and I found the inside very welcoming and cozy. The bartender was knowledgeable and explained the menu very well. We did not have any food but with the reservation came delicious donuts. Try to read the picture wall in this review for the story. I found the pricing a bit high for an old fashioned, but I am sure the rent is high in this location. Great for small, intimate parties only. Make that reservation. You need it. read more

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I've come to Captain Gregory's multiple times over the last few years. Similar to other recent reviewers, I am extremely disappointed in the recently added reservation fee of $6-7/per person. Attached is a picture of what is noted when you reserve via Resy "reservation cost covers a curated treat for the evening that arrives with the bill." The server had no idea what I was talking about and said she guessed that statement referred to small hard candies we were served with the bill I can understand charging a fee for no-shows, but a reservation fee with the impression that patrons will receive a treat worth ~$5 is a ripoff, especially at a place where drinks are already on the pricier side. Drinks are good for the most part but there are so many great cocktail bars in alexandria without reservation fees. If you happen to be in the area you could try, but if not there are many other options read more

Captain Gregory's - Resy noted the "reservation cost covers a curated treat for the evening that arrives with the bill." - Cocktail Bars Near Me - Alexandria, Virginia

I ordered the "tasting menu" which was $49. We have 2 people but there was nowhere in the menu that said both of us would have to have the same thing. The waiter also never asked or confirmed with us whether this would be for one or two. At the end of the night, the bill came out and they charged us $98 for two guests with the tasting menu. This came as a surprise and really ruined the experience. We would have appreciated if the waiter clarified, confirmed with us or said something before just taxing on another $49 charge. read more

We visited recently for a date night. This is a hip, intimate spot. The setting is dark and cozy with a few small tables up front, a bar area, and another seating section at the back. Intimate is the word - the space is quite small. We made reservations and were greeted after a short wait with complementary champagne, since I'd noted that we were celebrating Mr. G's bday. We each started with a cocktail (Goats for me and Banana for the Mr.) and ordered two small plates. The deviled eggs were good, but the pork belly was to die for. My only complaint of the evening was that the plates were cleared before I could finish scraping (read: licking) all the sauce from them. The drinks were quite flavorful and indulgent. The banana one was a spin on a gin fizz and really impressed. We finished off the evening with one more drink for the man and the complimentary donuts (make sure you read the wall by the bar). They were hot and delightful! I've recommended Captain Gregory's to several people already. If you want to tuck up close for a cozy date night, this is just right. The bill will reflect the indulgence of the evening, but it's an experience, not just a bar. Expert Tip: Be sure to make reservations! We saw a bunch of hopefuls turned away who hadn't. read more

Family recommended we stop in here for drinks before dinner and it was AWESOME! I love a good speakeasy. There's a little flag hanging on the wall that you pull down to alert the staff to open the door. I definitely recommend making a reservation because they were getting busy quickly and we were only there on a Thursday at 5, so weekends are probably even busier. Our server was so great. He knew the drinks really well. I loved the selection of cocktails and ended up ordering American Werewolf in London. So good. The cacao nibs were the perfect touch on top. We were met with little champagne shooters immediately upon sitting down at our table and then key lime coconut donuts came out halfway through our time there. Those donuts were insanely delicious. I loved the whole vibe inside- the lighting was perfect and it was cool temperature wise. Super comfortable seating. I wish I lived closer to be able to come back more often! read more

Captain Gregory's - Selection of drinks! - Cocktail Bars Near Me - Alexandria, Virginia

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I need to set the context that this place charges a $15 cancellation fee for reservations. Excited to try a new, local establishment, so we made reservations. Arrived at our designated time of 7:15 and pulled the flag. We waited 10 minutes before I started jingling the flag to avoid a late charge. After I asked the host how he was doing, he responded with "Great, until you rang the flag 17 times" which really set the mood for the evening. By the grace of god, host turned out to be our waiter. Fine enough service, cocktails are good but overpriced. Food options are charitably limited (and overpriced). Ambiance was made by someone who hasn't spent a night underway on a ship but read a couple books about 1950s Tiki Bar culture. Speakeasy combined with a Tiki Bar doesn't logically flow, but I'll give them the benefit of the doubt. Might have been back if not for the terrible introduction. Their system of entry is a flag with bells they don't monitor, so be prepared to wait if you pull it, or risk the displeasure of the staff if you announce yourself again to avoid their cancellation fee. It was clear their host and our future waiter did not appreciate me double tapping of the bell, and I likewise did not appreciate the attitude ensuring we avoided the cancellation fee associated with an overpriced faux Tiki Bar. Won't return, excited for what occupied this space next. read more

Captain Gregory's is one of the most fun speakeasies/cocktail bars I've been to anywhere and definitely ranks highly among NoVA/DC area speakeasies. They really sell the speakeasy aspect. There's no street level signage, you pull a flag to get in and then they open up a wall. They have excellent drinks. The service is great. And, the decor is pretty fun, with a mix of quirky ocean-themed decorations, tools hung on walls, maps as wallpaper (and, having once been a little boy, I love a good map), etc. They also do a great job at writing their menus. Drinks are well categorized... the menu changes seasonally, but it's currently divided among shaken drinks (generally less boozy), stirred drinks (generally more boozy), and infusions. The drink names give you a sense of the flavor profile. It's all spelled out so that the thing you think you want is likely to be something you actually particularly enjoy. The service is also very good. Captain Gregory's delivers the full experience. Highly recommend. read more

Captain Gregory's - "Chocolate" Cocktail. - Cocktail Bars Near Me - Alexandria, Virginia

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The concept behind Captain Gregory's is a good one- a speakeasy inside a plant-based donut shop. Genius. Here's what's to love: 1) Concept: It's one that attracts all types of people. The inside is dark and feels like a true speakeasy with candles lit and a lone bartender making craft cocktails. During the pandemic, they have outdoor seating and limit inside seating to help keep everything safe. 2) Food: There's a small menu of small plates like brussels sprouts and even seasonal donuts. When I went, they have 7-8 donut flavors available. 3) Service: It's stellar. The person who greeted us once we raised the flag to open the wall to get in was very friendly, helpful and attentive. The only thing to note is the cocktail list is unique, but skews a more sweet palate. I have a sweet tooth and found my drink a bit too sweet. My housemate likes stiff drinks and thought he ordered one, but it ended up very sweet. Also, the prices are $15 per cocktail, a little expensive. read more

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Just some tourists dropping by on a random week night during the summer. I'm glad that we checked this fierce little speakeasy out. We almost didn't go in at all because the restaurant the speakeasy was in was dark and empty. We had some unique cocktails (pricey but not surprising) and chatted with a very friendly bartender who engaged in conversation and answered our questions about the neighborhood. The best part about this venue is the charming decor and sexy date night vibes. read more