Juggie's Place — The World's Smallest Bar, Biggest Personality
Iconic tiny bar in a Front Street alley with rum milkshakes, cigars, and legendary hospitality from Juggie himself.
Why Go
Juggie's Place, tucked in an alley off Front Street, claims the title of the world's smallest bar—and packs more personality into its few square feet than most full-sized establishments manage in an entire building. Run by the legendary Juggie himself, this tiny institution serves rum-infused chocolate milkshakes (no actual milk), cold beers, creative cocktails, and cigars alongside conversations and hospitality that have made it a must-visit for travelers who discover it.
The Experience
Finding Juggie's is half the fun—the bar hides in an alley off Voorstraat, and its tiny footprint means you might walk past it twice before spotting it. Inside (if you can call it inside), Juggie holds court with the warmth and wit of someone who has been making strangers feel like friends for years. The rum-infused chocolate milkshake is the signature—it contains zero milk but delivers a rum punch disguised as dessert. Cold beers and cocktails flow from a space that seems physically incapable of containing a bar. The bras hanging from the ceiling are not decoration for decoration's sake—they support Juggie's breast cancer awareness donation drive. This place runs on personality, generosity, and really good rum.
What to Try
The rum-infused chocolate milkshake is non-negotiable—this is the drink that built the legend. Follow with a cold beer and a cigar if you smoke. Strike up a conversation with Juggie—his stories are worth the visit alone. Bring a bra to donate if you want to contribute to his breast cancer awareness initiative.
Insider Tip
Juggie's is the kind of place travelers tell friends about for years. It is open daytime hours (10 AM to 5 PM, Saturday until 4 PM, closed Sunday), so plan accordingly—this is not a nightlife stop. The alley location near Penha and Infinity Jewelers is easy to miss, so keep your eyes open. Tell Juggie where you are from and he will probably have a story about someone from there.
The Practical Stuff
Located in an alley off 53/3 Voorstraat (Front Street), Philipsburg. Open Monday through Friday 10 AM to 5 PM, Saturday 10 AM to 4 PM. Closed Sundays. Moderate pricing. Cash preferred. The world's smallest bar—literally.
Pair It With
- Penha Duty Free St. Maarten at Frontstreet Guide — Historic duty-free shop right nearby on Front Street
- Dirty Sanchez Crew Bar — Continue the Philipsburg bar experience on the Boardwalk