Cocktail Bars Wynwood

The Sylvester

$$ · Wynwood, Miami
Address
3456 N Miami Ave, Wynwood
Best For
late dates, pool table sessions, Wynwood crawls
Opening Hours
Tue-Thu17:00-02:00Fri-Sat17:00-03:00Sun-MonClosed
Reservations
Walk in; groups can book through the website
Dress Code
Casual
Price Range
$$
Wynwood Pool Table Late Night Florida Kitsch
Plan Your Visit
Reserve a Table Get Weekly Picks

The pool table and back couches go early on Friday and Saturday; arrive before 10pm.

Our Take
Published · Reviewed by Marcus Webb, barsforKings editorial

Florida Kitsch with a Serious Bar Underneath

The Sylvester runs the corner of 3456 N Miami Ave in Wynwood, dressed in flamingo wallpaper and grandma's Florida room furniture. The team behind Beaker and Gray built it, which is why The Infatuation rates the cocktails as the real draw underneath the kitsch: locally sourced ingredients, sharp technique, fair prices.

It suits drinkers who want a proper cocktail without a speakeasy password, and anyone who judges a bar by whether it owns a pool table. Skip it if you came to Wynwood for a club night; the room is a bar that stays a bar.

The Room

Retro Florida from front to back: patterned wallpaper, comfortable mismatched seating, and a pool table that anchors the rear. Reviewers on Restaurantji rate the ambiance 4.7 out of 5 for retro chic with modern touches, which is the most accurate scorecard the room could ask for.

The Drinks

The cocktail list changes with what the team can source, and In Wynwood's spotlight calls the program cutting edge for the neighborhood. Order off the current menu rather than asking for classics; the kitchen backs it with grilled cheese and a pastrami medianoche that soaks up a third round honestly.

Current menu cocktail
The seasonal list is the program; trust the page, not the classics.
Pastrami medianoche
The bar snack The Infatuation flags as worth the order.
Grilled cheese
Late night insurance, available until close.
A cold Florida lager
The pool table pacing drink.

The Crowd

Locals who work in Wynwood and drinkers escaping the strip's tourist crush. Tuesday through Thursday runs mellow; Friday and Saturday fill by 11pm and hold until the 3am close.

The Neighborhood

Wynwood's bar circuit sits within a ten minute walk. Gramps Miami covers the backyard beer and pizza brief, J Wakefield Brewing Miami handles the craft beer stop, and Sweet Liberty Miami is the award circuit cocktail room across the causeway.

When to Go

Weeknights for the full grandma's parlor effect with room to move. Friday after midnight if you want Wynwood's least chaotic late night option.

What Regulars Say

  • Drinks rate 4.8 out of 5 for quality ingredients, per Restaurantji's review aggregate.
  • It works as a date spot and a group night equally, per Yelp reviewers.
  • The pool table is the room's social engine; claim it early.

Who It Is For

  • A date that wants good drinks without ceremony
  • Industry drinkers finishing a Wynwood shift
  • Avoid if you want bottle service energy; the room refuses it

Wynwood keeps inventing louder rooms, and The Sylvester keeps outlasting them by being the one you actually return to.

Explore the full Miami cocktail bars guide, or see everything in the Miami bar guide.

Sources: The Infatuation; In Wynwood; thesylvesterbar.com (2026-06); Restaurantji review aggregate; Yelp reviews (n=199).

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Photos via Google Places. The Sylvester · Vincent Mulgrew · Angela Galantucci · Facundo Chomczyk · Chandon Sanders · Jens Aumueller