There are so many great spots for drinks! Firstly, you can't beat a sunset cocktail at Caps on the Water. Caps is right on the Intracoastal so you'll get great views of the boats going past and the bartenders know how to make great cocktails!
For wine lovers, your first stop will need to be Carrera Wine Cellar on San Marco. Carrera is a wine store that also sells wines by the glass and there are some cute seating areas. They also have an outdoor patio which is a fun place to be. If you are interested in wine classes they offer classes on many nights during the week.
If you like martinis, you can't miss the Tini Martini Bar! This is a popular spot and is in downtown St Augustine right on the waterfront.
Other favorites include the Ice Plant Bar which is walking distance from Casa Lovett. For an island vibe, you may also like to try Odd Birds or the Conch House on Anastasia Island. The Kingfish Grill bar is another fun place for a mariner vibe.
Further afield, you might like to try Valley Smoke, for an excellent selection of wines, bourbon and Scotch.