Looking for a fun and fabulous way to sidestep Valentine’s Day? At Date in the Diary, we’re all about skipping the clichés and diving into something way more exciting! Join us the night after for a cocktail trail adventure through Windsor’s best cocktail bars.

Whether you’re a fan of Margaritas or Pornstar Martinis, we’ve lined up four incredible cocktail spots, each with its own unique vibe—from chilled and chic to immersive and lively, plus a few hidden gems. All within walking distance, this is your chance to explore Windsor’s finest.

Who will you crown the best cocktail bar? And, more importantly, who’ll still be standing by the end? Don’t worry, we’ve got mocktails at every stop, so drivers are totally welcome.

Grab your Date in the Diary buddies and let’s make it a night to remember! Will you be joining us?