Itinerary
Friday night to Sunday afternoon. Eight stops, properly sequenced for visiting drinkers.
Friday 17:00 — Arrival drink · Downtown · $$$ · Cocktail Bars
Orlando's most awarded cocktail bar. Drop bags. Find a hotel-adjacent bar within a five-minute walk. Order something simple to anchor yourself to the city.
Friday 19:30 — First proper cocktail room · Mills 50 · $$ · Date Night
Wine bar with one of Orlando's longest natural-wine lists. The polished room you'd take a first date to. Sit at the bar. Talk to the bartender. Stay one drink — you're scouting, not committing.
Saturday 20:00 — Dinner-with-drinks · Mills 50 · $ · Hidden Gems
Heritage live-music bar that has run since 1995. Eat somewhere with serious bartending built in. The right room is one you order both your dinner and your nightcap from.
Saturday 22:30 — The destination · Downtown · $$ · Craft Beer
Craft brewery taproom in Downtown pouring twelve house taps and the city's most adventurous local beers. The bar that made you book the trip. The pre-research one. Reservation-only ideally. Stay until last call.
Sunday 17:00 — Last quiet drink · Downtown · $$$ · Cocktail Bars
Cocktail bar with a tight rotating menu and a young dressed-up crowd. Find the hotel bar at your departure airport equivalent — somewhere quiet, low-volume, well-staffed. End the trip on a martini and a clean conversation.
The plan starts polished on Friday night and peaks Saturday late. We've left Sunday afternoon for recovery, a brunch cocktail, and a quiet last drink before you fly out. Every stop is editor-picked and walkable from at least one of the others.
Total spend across the weekend: roughly £200-£350 per person on drinks alone (not counting food). Reservations are essential at any room flagged 'destination'. Book those first; the rest you can walk to.
Each stop links to the full bar page if you want to dig deeper. Treat timings as guidance — adjust to your pace.