Captain Gregory's
A hidden nautical speakeasy serving inventive cocktails and gourmet small plates. A truly unique and intimate bar experience.
Highlights
Must-see attractions
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Best Time
Blue hour photography, calmer galleries
Captain Gregory's
Highlights
Must-see attractions
A hidden nautical speakeasy serving inventive cocktails and gourmet small plates. A truly unique and intimate bar experience.
"The best speakeasy experience in the DC area! The drinks are fantastic and works of art."
Book Ahead for Seating
Reservations are highly recommended due to limited seating. Secure your spot in advance!
Ask for Drink Recommendations
The bartenders are skilled and can guide you to creative, custom drink creations.
Quick Facts
Cuisine
Bar / American
Price
$$$
Address
804 N Henry St, Alexandria, VA 22314, USA
Website
captaingregorys.com/Highlights
Discover the most iconic attractions and experiences
Secret Speakeasy Ambiance
Discover a hidden nautical-themed speakeasy with a funky, intimate atmosphere. A true adventure to find!
Artisanal Handcrafted Cocktails
Experience expertly crafted cocktails, both classic and creative, that are true works of art. Unique flavor combinations abound.
Complimentary Donuts
Delight in a surprise treat! Complimentary donuts are a sweet and unexpected ending to your Captain Gregory's experience.
Plans like a pro.
Thinks like you
Insider Tips
from TikTok, Instagram & Reddit
Book Ahead for Seating
Reservations are highly recommended due to limited seating. Secure your spot in advance!
Ask for Drink Recommendations
The bartenders are skilled and can guide you to creative, custom drink creations.
Consider Eating Before
While small plates are available, the food menu is limited. It's a great spot for drinks and lighter fare.
Tips
from all over the internet
Book Ahead for Seating
Reservations are highly recommended due to limited seating. Secure your spot in advance!
Ask for Drink Recommendations
The bartenders are skilled and can guide you to creative, custom drink creations.
Consider Eating Before
While small plates are available, the food menu is limited. It's a great spot for drinks and lighter fare.
What Travellers Say
Reviews Summary
Captain Gregory's is celebrated as a top-tier speakeasy with exceptional, artistic cocktails and a magical, intimate atmosphere. While the food is noted as good, it's the unique drinks and hidden gem experience that truly shine, making it a must-visit for a special night out. Some guests mention that staff can seem overwhelmed when at capacity.
"I’ve visited Captain Gregory’s three times over the past three years and it is by far the best speakeasy experience in the DC area! The drinks are fantastic - delicious and true works of art. The service is impeccable and the vibe is perfect for a romantic date night or nice relaxing chat with a friend. The quality far exceeds the speakeasies and cocktail bars I’ve visited in DC, which often charge a higher price. If I lived closer, I’d be here all the time. 100/10 would recommend!"
Katie
"Really cool speakeasy hidden in plain sight! Cocktails are incredibly unique, but an expertly balanced blend of flavors that you wouldn’t expect to work well together, but they hit the nail on the head! I stopped in traveling through on a slower Wednesday, but can definitely see how reservations would be recommended. Snack/food options are available too and looked delicious. Highly recommend and will be back!!"
Drew Augustyniak
"Some bars serve drinks and some are an experience. Captain Gregory's is definitely an experience. It has a fun speakeasy style entrance (don't want to give it away). Unique island/tropical decor and super stylish accents/glassware/details. We loved the drinks! Our bartender Jag did a wonderful job of making us feel comfortable on our 1st visit and made some guided us through the menu. We will definitely return."
Jared Ringel
What People Like
What People Dislike
Frequently Asked Questions
Captain Gregory's is a speakeasy hidden behind an inconspicuous wall. Revealing the exact entrance would spoil the fun, but look for hints within the description of a former donut shop.
Yes, reservations are highly recommended due to limited seating. Each seating is typically for 1 hour and 45 minutes.
Captain Gregory's offers gourmet small plates. While tasty, the menu is small, so many suggest eating a full meal beforehand and enjoying the drinks.
Yes, they offer unique mocktail options made to perfection upon request, ensuring a great experience for all.
The atmosphere is cozy, intimate, and funky, with a nautical theme and stylish Art Deco barware, creating a unique speakeasy vibe.
A small reservation fee (around $3) is typically charged, which often goes towards complimentary donuts at the end of your visit.
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It’s worth planning ahead to score a seat at one of the handful of tables at this speakeasy inside RailBird Kitchen (stop in for the buttery, crispy lobster fritters before or after your reservation). The petite, low-lit space combines Old Town’s nautical flavor—there’s a canoe hung from the ceiling—with elegant, thin-stemmed Art Deco barware. Their cocktail menu is firmly rooted in the classics, but more creative drinks like the brandy-based Pathological Playa Hater served in a tiki glass make seasonal appearances.
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There is something adventurous and exciting about hunting down a secret restaurant hidden in plain sight. Captain Gregory’s is one such speakeasy located behind an inconspicuous wall inside of a donut shop. Featuring crafted cocktails and creative small-plate dishes, this speakeasy is always busy so it is highly recommended that reservations are made in advance.
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Nestled inside the walls of a former doughnut-shop-turned-vegan-eatery, lies this subtle, yet verbose speakeasy. Revealing how to get in would be a journalistic travesty, since half the fun lies within searching for the treasures inside. Once you find it, though, it’s a dimly lit, sensory journey that feels like the inside of a boutique pirate ship.
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Captain Gregory’s—this place is a ten/fifteen minute walk away from the heart of Old Town, but I included it because it’s right on the border and such a cool concept. It’s a secret restaurant hidden behind a donut shop. They serve up small plates and hand crafted cocktails in a space that’s got a speakeasy vibe.
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Whenever I have friends in town, their ears perk up when I mention speakeasies. These hidden bars are always in unique locations and add a bit more magic to your day. The interior is cozy and the food is good.
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Captain Gregory’s - A secret spot serving innovative, award-winning handmade cocktails and tapas bites behind a secret sliding door in the Sugar Shack — in true speakeasy tradition.
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Back in Alexandria, blend sweets and spirits with delightful donuts alongside a handcrafted cocktail at Captain Gregory’s, Old Town’s nautical-themed speakeasy.
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from TikTok, Instagram & Reddit