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Captain Gregory's

4.2 (314 reviews)
Closed • 5:00 pm - 11:30 PM

By appointment only

About Captain Gregory's

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CAPTAIN GREGORY'S ATMOSPHERE

What's the vibe?
Hipster
Intimate
Quiet

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Recommended Reviews - Captain Gregory's

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Inside
Sophie A.

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.

Puria D.

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!!

Kelsi G.

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!

Pork belly
Chandler D.

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.

Ash E.

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!

Mocktail
Nichole B.

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

Welcome sign
Brandi B.

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!

Brittney S.

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.

Chips and dip, drinks.
Lily D.

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

Marissa O.

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!

Gotta pull the flag to gain entry into the unknown
Evan B.

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!

Reservations donuts

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Brandon M.

Thank you for coming in!

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7 years ago

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2 years ago

Nice intimate spot! Drinks were great and such a creative theme! Make reservations will return!

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6 years ago

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2 years ago

Our favorite speakeasy in the DC area. Excellent cocktails and a very lovely staff. Very high quality drinks - worthy of a visit.

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6 years ago

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Brandon M.

Thank you so much for stopping by and sharing your review.

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3 years ago

Not too shabby, but by no means perfect. Vibe is cute, and drinks are good. Not sure if I would come back though.

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2 years ago

Great little speakeasy. The entrance was fun and the cocktails were custom made by the bar staff. Food was delicious.

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7 years ago

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Page 2 of 8

Ask the Community - Captain Gregory's

Do you need to make a reservation?

Thanks for asking. On weekends, reservations are highly encouraged. We have a wait list, but because we are small, it does not always get you in. Weekdays can be easier for walk ins, but you may have to wait a bit.

Do they allow you to bring kids?

I don't think they have a formal policy, but it's a pretty small bar. Most the tables only seat 2 and I wouldn't say the atmosphere is particularly kid-friendly.

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King’s Ransom - Sunset Park

King’s Ransom

4.3(134 reviews)
0.6 mi•Old Town Alexandria

I absolutely love King's Ransom! The atmosphere is really dope. It is definitely hard to find as it…read moreis in a pizza shop. I went there with one of my friends and we really enjoyed ourselves. It is a nice quiet, hidden speak easy with great vibes. The service was impeccable. The bartender was very friendly and attentive. She gave great suggestions for drinks. We decided on a sour. Which was whisky, lemon, and honey. It was perfectly mixed and served. I also tried the Toki Highball which was excellent. It was rich in flavor and not too strong. If you are really into Whisky King's Ransom needs to be on your list to visit. Unfortunately, we did not order food but the couple next to us ordered the pizza and fries and it looked delicious. The ambiance was great. Its a little upscale with dark lighting. The raised bar and lighting add to the unique experience. This bar is great for date night or just a night out with friends in Alexandria, Va. If you are in the area check it out...you won't be disappointed. Cheers!

My friend and I were looking for a quick bar to slip into around 10-11 PM and stumbled across this…read morespot. It's not too far from the waterfront, so it made for a nice walk after gelato. At first, you'll see what looks like just a pizza shop -- but if you head in and either use the side door or walk through and climb a set of stairs, you'll find the speakeasy upstairs. Very cool vibe: dark, cozy, and date-night ready. Drinks: 4/5 I ordered their take on an Old Fashioned, and it was definitely the highlight of the night but sweeter than I would have liked. They served it over a stamped solid block of ice (a small detail I ). My friend was abstaining from alcohol that night and asked for a non-alcoholic cocktail. To our surprise, they didn't just hand her a lemonade like most places -- they actually made her a crafted virgin drink, which she loved. Food: 3/5 We ordered fries and a slice of pepperoni pizza. The fries turned out to be waffle fries (not mentioned on the menu) and were overly crispy, so not really our favorite. The pizza was fine -- clearly sourced from the shop downstairs -- but it leaned oily and didn't really wow us. Service: 5/5 Pretty standard -- nothing over the top, but not neglectful either. Drinks came out reasonably fast, food followed, and we were checked on enough without it feeling pushy. Vibes: 4/5 The speakeasy itself is definitely the selling point. Dark, intimate, and stylish -- you feel like you've found a little hidden spot. All in all, the cocktails are the reason to come, especially if you're into whiskey. The food was forgettable, but it's convenient that you can order pizza upstairs. We spent about $30-40 for drinks and snacks, which isn't shocking for Old Town. Would I go back? Maybe if I was already in the area, but for a dedicated whiskey night, I'd probably head somewhere else.

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King’s Ransom - Plenty to choose from

Plenty to choose from

King’s Ransom - Great selections

Great selections

King’s Ransom - Old Fashion

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Alice Comfort Cocktail - Chive dumplings

Alice Comfort Cocktail

4.4(106 reviews)
0.6 mi•Old Town Alexandria

We stopped by for drinks and apps while exploring Old Town. They have two levels I think -…read moredownstairs is their restaurant for proper dining (Thai Signature, if I am not wrong) and upstairs is more like a cafe/lounge. The upstairs decor is very charming and whimsical and reminiscent of Alice in Wonderful. For drinks, we got the Mango Sticky Rice (Planteray 3 Star, Coconut Rum, Junmai Sake, Toasted coconut, Mango, Yuzu) and the Alice (Roku Gin, Elderflower Liqueur, Lychee Liqueur, Butterfly pea, Yuzu, Egg white). My first assumption on entering the bar was that "instagrammable" places like this are usually a gimmick - but I was so wrong. The drinks were very boozy, aesthetically pleasing and tasted fantastic. Their food menu also looked so good so we also decided to get a couple of apps to accompany our drinks. We got the Shrimp Dumpling (steamed shrimp and chicken dumplings served with homemade creamy ginger lemon soy sauce) and Curry Puff (chicken, sweet potato, shallot in the rice dough served with sweet chili peanut dipping sauce) and I am so mad at myself for not ordering more food here (we had lunch reservation elsewhere). The presentation was spot on, portions were generous and everything was super flavorful - the curry puffs tasted like Indian Samosas! The woman attending us was very sweet and pleasant. Would definitely return for more food and drinks, not too far from DC so maybe one of my next DC trips will drag me here!

Alice Comfort Cocktail is such a hidden gem in Old Town. If you're looking for a fun, slightly…read morewhimsical vibe with cute decor, solid food, and really well-made cocktails, this is definitely the spot. Just a heads up though the space is pretty small so I'd recommend making a reservation. The bar itself only has like 3-4 seats. I tried the shrimp dumplings, crab rangoon, and bang bang shrimp, and had the litchi cocktail with it--everything was honestly so good. Really glad I stumbled across this place and I'll definitely be back to try more of the menu.

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Alice Comfort Cocktail - Interior

Interior

Alice Comfort Cocktail
Alice Comfort Cocktail - Alice cocktail

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Alice cocktail

Joy on the Avenue - Rudolph's RNR Pretzel!

Joy on the Avenue

4.9(7 reviews)
1.0 mi

Ambiance: love the decorations. It wasn't too over the top. We sat by the 'fireplace' on the sofa…read morewhich was near the bar. It was comfortable and the patrons were all so kind and told us when our drinks were up. Love Del Rey neighborhood for the welcoming vibe as always!! Service: it was very busy but appreciated the bouncer outside that made sure it wasn't over capacity. We had a short wait outside then a longer line emerged. Inside, the bartenders were busy but it wasn't like a 20 mins wait or anything. Note that the kitchen closes at 10pm and they won't let anything slide in at 10pm... Food: no food but the drinks were on point! I would laminate the menus because it was pretty beaten up. I know it's a pop-up but with drinks and food - those paper menus get gross. Definitely a fun vibe and people had the best holiday cheer. Would recommend!

Transformed from the Nightmare on Mt. Vernon for Halloween, the pop-up space next to Pork Barrel…read moreBBQ is celebrating the season as Joy on the Avenue. Amazing decorations make the environment for imbibing or having some nibbles a wonderful holiday experience. Among the holiday named drinks the best are the Partridge in a Pear Tree, We Forgot Kevin!, and Baby It's Cold Outside. But for the best tasting holiday classic, the Cousin Eddie's Eggnog sports a reindeer cookie and a twist on seasonal nogg, and Jimmy Stewart's Sazerac is a delightful twist on an Old Fashioned. As sorry as I'll be to see January arrive and the Joy on the avenue disappear, I can't wait to see what holiday themed pop-up will arrive next!

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Joy on the Avenue
Joy on the Avenue - Scrooged Deviled Eggs!

Scrooged Deviled Eggs!

Joy on the Avenue - Rudolph 75!

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The People's Drug - Truffle Fries

The People's Drug

3.9(397 reviews)
0.6 mi•Old Town Alexandria, Braddock Road Metro
•$$

The People's Drug....a throwback to the 90s and decades before when this drugstore dominated the DC…read morelandscape. CVS bought them out. This was named in homage to the brand. Cool backstory huh? Anyhoo, met some friends for drinks here and it was fantastic. The People's Drug has been reimagined, with a general store, lunch counter style but a decidedly modern take on its offerings. Serving chef-driven gourmet sandwiches, locally-sourced bowls, and crafted cocktails, it's the perfect place for all manner of social indulgences. I spent $100 on drinks. I had a Negroni Incognito w/Italian Dill and a couple Old Fashioneds. We didn't order any food (although it looked good going by). Will definitely try some the next time. Limited street parking so I parked in the lot next door. Warning: the joint is kinda smallish with limited seating so beware depending on when you go! Good stuff.

Extremely small menu but hand crafted specialty cocktails. Although the cocktails are made by…read moretrained mixologist they were prettier than how they tasted. We stumbled upon this place and after looking at the menu must say it's bar food. Think burgers and wings. We ordered the wings and were told they are fried twice and double coated. They were wet and soggy in side. We ended up leaving g and after the waterfront we went to Bugsys to eat as they had more options.

Photos
The People's Drug
The People's Drug - Chicken skins--spicy!!

Chicken skins--spicy!!

The People's Drug - Oaxaca to Tokyo and a Shrute Farm Margarita

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Matt and Tony's All Day Kitchen Bar - Scotch Eggs

Matt and Tony's All Day Kitchen Bar

4.5(1.2k reviews)
0.6 mi•Del Ray
•$$

My sister and I came to Matt and Tony's for brunch with my toddler, and we had such a great…read moreexperience! We had reservations for 2 PM and were seated shortly after arriving. There was a little wait, but nothing long at all and definitely no complaints. My sister and I both ordered the steak and eggs, which came with potatoes and chimichurri sauce, and everything was absolutely delicious! The steak was flavorful, the entire meal was really good, and I would definitely order it again. For my toddler, we ordered the kids' waffle with fruit. My only small suggestion would be to offer a protein option with the kids' meal to make it a little more complete. It wasn't a big issue for us since I was able to share some of my food with him. The service was wonderful! Our server was quick, attentive, and made sure we had everything we needed. The restaurant itself is such a cute little spot with a nice atmosphere. Overall, great food, great service, and a really enjoyable brunch. I would definitely come back again!

I would start out by saying that I'm not sure if it is just that day or is it a constant…read moreoccurrence. We initially went to anther place but it was loud for Sunday brunch w dj music. This place was equally lively but we had already gotten there so we stayed. But the maître d' was super unorganized and chaotic. We don't have a reservation and was told to check the bar which was also full. The problem was because we had to wait first come first serve at the bar we were basically standing around the hallway and throuways where wait staff was delivering food. When we moved to be out of the way, someone else slipped into the spots. Another younger maître d' stepped in and finally took my name on the waitlist vs the first one didn't even ask if I would put my name down. Shortly after they seated us at a table right next to the door where people were coming in and waiting for the tables. Overall the wait and seating experience was chaotic and uncomfortar. When the food came, the delivery boy slipped my fiancée's has brown onto the table. He was apologetic and got us more from the kitchen. However when the bill came, they had charged us for a side. Which we had to correct if we had not looked at the bill and just blindly paid. In my mind, either the waiter should have asked us if we ordered something extra with someone else or check with his coworkers . The food wasn't bad but to be honest I was thinking about all that happened to enjoy the food. Might not come back

Photos
Matt and Tony's All Day Kitchen Bar - Matt and Tony's

Matt and Tony's

Matt and Tony's All Day Kitchen Bar - Rye Loaf with Spreads

Rye Loaf with Spreads

Matt and Tony's All Day Kitchen Bar - Steak & Eggs

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Steak & Eggs

Captain Gregory's - cocktailbars - Updated October 2026

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