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    Captain Gregory's

    4.2 (316 reviews)
    Closed Closed

    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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    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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    My favorite spot to have a tasty, interest cocktail with great service. Excellent place to relax with company.

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    Page 8 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.

    View All 3 Questions

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    King’s Ransom - Sunset Park

    King’s Ransom

    4.3(130 reviews)
    0.6 miOld Town Alexandria

    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.

    Photos
    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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    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!

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    The People's Drug - Truffle Fries

    The People's Drug

    3.9(394 reviews)
    0.6 miOld Town Alexandria
    $$

    It was a beautiful day, and we decided to check out a new spot for drinks and bites while soaking…read moreup some sun. We headed over to the People's Drug, where we found a cozy cafe table outside. We kicked off happy hour with some refreshing cocktails, the Bubble Buck and Gindependence Collin's, both were fantastic and refreshing. To snack on, we ordered again from the Happy Hour Specials and tried the HH Wings and Truffle Fries. No complaints, good service, drinks, tasty bites and a sunny spot made for a perfect afternoon.

    AMAZING impromptu date night find!…read more Happy Hour until 7pm with $10 cocktails and small bites ranging from $6-$8. Great indoor and outdoor seating Service was a bit slow but the staff were really friendly. I would recommend knowing what you want to eat upfront so that you can put in that order with your drinks. Happy Hour Drinks: Bubble Buck-Excellent balance of liquor, sweetness, and bitterness. Excellent drink Gindependence Collins- Perfect summer drink, recommended for anyone who doesn't want to drink heavy liquor and those monitoring their sugar intake. Excellent drink Rosie's Negroni- Perfect twist on a Negroni. Excellent drink Needless to say, all of the drinks were perfect. Happy Hour Bites Truffle Fries- this was SO good! Crispy, fresh, and bursting with truffle oil flavor. Crispy chicken wings- I'm not a wet wings lover but this sauce was undeniably delicious and the wings were beautifully prepared. Overall we loved this place and look forward to returning.

    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 - Rye Loaf with Spreads

    Matt and Tony's All Day Kitchen Bar

    4.5(1.1k reviews)
    0.6 miDel Ray
    $$

    Matt and Tony's was exceptional from start to finish! The food was a 10/10, the wait service was…read moreoutstanding, and the overall vibe was phenomenal. Definitely make reservations before you go because this place gets packed! We ordered the chicken biscuit gravy with chorizo, and it was absolutely delicious. We also had the MMT Breakfast, which gave us a little sample of everything. The homemade biscuits were amazing, and the bacon was not that cheap, flimsy kind -- it was thick, flavorful, and so good that we added extra bacon. The price was just right, the ambiance was great, and even though parking can be a challenge, the staff was super helpful in telling us where we could park. It's also not far from DCA airport and close to other great restaurants and scenery. I hate that I forgot to take pictures of our meal, but we were so hungry and the food was too good to stop! We will definitely be back for brunch, and this is officially becoming a regular brunch spot for us. Cheers to next time!

    I came here for Mother's Day brunch, and it did not disappoint. It was tough getting a reservation,…read morebut I was able to snag one last second. We were seated inside, which had a decent amount of seating. I thought the restaurant was cute, and it had a nice ambience. We ordered several dishes, starting with the cajun crawfish Mac & cheese, crab stuffed oysters, and charred spring vegetables. All 3 starters were delicious, with my favorite being the crab stuffed oysters. The Mac & cheese was a close second - it was nicely seasoned and perfectly au dente. The vegetables were also very good, and the pita it came with was great. On the breakfast menu, we ordered the chicken and waffles and shrimp and grits. Both were very good. I haven't had many chicken and waffles, but the chicken was tasty with the hot honey. The shrimp and grits was very flavorful. If I had to pick one though, I would probably pick the shrimp and grits. The service was solid, she was very friendly and came back a decent number of times. I would 100% come back again!

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

    Matt and Tony's

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

    Steak & Eggs

    Matt and Tony's All Day Kitchen Bar - TO-GO Chicken & Waffles

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    Captain Gregory's - cocktailbars - Updated May 2026

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