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Captain Gregory's

4.2 (316 reviews)
Closed 5:00 pm - 11:30 PM

By appointment only

Captain Gregory's Photos

Business Info

CAPTAIN GREGORY'S ATMOSPHERE

What's the vibe?
Hipster
Intimate
Quiet

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Recommended Reviews - Captain Gregory's

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Reviews With Photos

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.

Wings
Ha N.

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

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!!

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.

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!

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!

Reservations donuts
Melinda N.

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.

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

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Brandon M.

Thanks! We hope to see you again soon for the new menu.

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10 months ago

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Brandon M.

Thanks for the kind words :)

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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.

View All 3 Questions

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I've been here many times in the evenings to enjoy a cigar and live music. The lounge is upstairs…read moreand has a cozy, old rustic feel with wooden bar tops and tables close to the musicians. The bartenders can be busy but are always friendly. I ordered the Rocky Patel 15th Anniversary, which was a little on the dry side possibly their humidor was a bit off. It also gets fairly loud when the music is playing, so it's not ideal for conversation. Overall, it's still a great spot to relax, enjoy a cigar, and listen to live music.

Came here for a good night of drinks and music. Made reservations for the restaurant then…read moreafterwards the plan was to slide upstairs for the band. Well the plans changed. Given the size of the upstairs I'm glad we came right upstairs first. As it is very very small and tight. It's first come and first serve. Ordered wings fries and crab soup. The wings were okay from what my friend said. The soup could be better. It needed old bay seasoning and more crab. It was very bland. Too much scallions in it. It was like eating scallion cream soup. For $15 it could have been better. The drinks. They put too too much ice in them. My whiskey sour turned into water sour. My friend's old fashioned was old ice with orange and cherry bitters. Very disappointing. Even with the food and drinks not being the best the music was on point. The band was awesome. The space is very very tight and limited so you will need to arrive early if you want to sit by the band. But there is also seating at the bar down the hall. And the balcony seating does not do any justice as you can't see band only hear them. They could expand if possible. I gave it 2 stars due to the food and drinks. The music pushed it to 3. I may go back but do things different depending on the time we go. And bring our own cigars is a must. It's definitely a jewel in the Old Town neighborhood. Stop by to see the band and bring your cigars. And order drinks with light to mo ice.

The 219 Restaurant - Chocolate mousse dome

The 219 Restaurant

(389 reviews)

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WHAT A ONE-STOP SHOP!!!!!…read more 219 is a VA gem, that I personally don't want too many people knowing about. The bottom floor - the Bayou Bar. The middle floor - dining within 219. And the top floor? - the performance space and the side cigar lounge! When I say there is something for everyone at this location, you could not miss going here. My friend and I made reservations via Open Table and had no issue making our allotted time, neither did 219 with having our table ready upon our arrival. Our server was super attentive, giving all of his best recommendations, including the jambalaya, and wings! (Both pictured). We were also seated by the window which was surprisingly not cold (the fireplace was also not lit this night), and was able to have a nice view of the street! She and I love people watching, and this was nice! Loved this place, and took our drinks right upstairs to the jazz performance where we spent another hour or so. Greaaaat performers come, along with great sounds! It's set up as a first come, first serve basis so please come early! 219 is a great place to come for a cozy. comfortable night!

Came here for a good night of drinks and music. Made reservations for the restaurant then…read moreafterwards the plan was to slide upstairs for the band. Well the plans changed. Given the size of the upstairs I'm glad we came right upstairs first. As it is very very small and tight. It's first come and first serve. Ordered wings fries and crab soup. The wings were okay from what my friend said. The soup could be better. It needed old bay seasoning and more crab. It was very bland. Too much scallions in it. It was like eating scallion cream soup. For $15 it could have been better. The drinks. They put too too much ice in them. My whiskey sour turned into water sour. My friend's old fashioned was old ice with orange and cherry bitters. Very disappointing. Even with the food and drinks not being the best the music was on point. The band was awesome. The space is very very tight and limited so you will need to arrive early if you want to sit by the band. But there is also seating at the bar down the hall. And the balcony seating does not do any justice as you can't see band only hear them. They could expand if possible. I gave it 2 stars due to the food and drinks. The music pushed it to 3. I may go back but do things different depending on the time we go. And bring our own cigars is a must. It's definitely a jewel in the Old Town neighborhood. Stop by to see the band and bring your cigars. And order drinks with light to mo ice.

King’s Ransom - Sunset Park

King’s Ransom

(130 reviews)

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The service was great as usual and the drinks were great. I had two of them which were the Modena…read moreSpritz and the Toki Highball. Both were excellent! The atmosphere was bar appropriate with minimal noise, so I didn't need to raise my voice at all since I was in the tabled area in the back. Would I go back? Yes, absolutely.

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.

Captain Gregory's - cocktailbars - Updated May 2026

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