Menu-hopping through historic downtown St. Augustine

St. Augustine, the nation's oldest city, offers too much to see and do – not to mention eat and drink – to spend all your time in one spot. So here's a top 10 of random, affordable menu items across the historic district that are worth a stop off the trolley.

1. Brownie Bourbon Milkshake from Prohibition Kitchen: Let's start with dessert, or your cocktail nightcap. However you want to view it, the spiked milkshakes from St. Auggie's best bar will most likely wrap up your evening – and it'll be worth it.

   

   Just FYI ... calories for the Brownie Bourbon Milkshake are not listed on the menu. Thankfully.

   
   

2. Buffalo Chicken Tender Sliders at Barley Republic: This seems simple enough. Chicken tenders on a King's Hawaiian roll topped with a pickle and coleslaw. But trust us, it's special. Perhaps it's the perfect proportions of buffalo sauce and coleslaw, or maybe it's the ranch dressing for dipping them that just seems better at Barley. Whatever the case, you'll be back for them again before your trip is over.

   
   

3. Grilled cheese at Sarbez: This 80s-themed joint is technically not inside the historic district, but it's still walkable just over the famed Bridge of Lions. Terrific beer selection, live music and an arcade probably make this worth a stop on the tour anyway, but the dozens of grilled cheese combinations push it over the top.

   
   

   The Tommy Pickles grilled cheese sandwich is remarkably simple and surprisingly addictive.

   

   The Philly Grilly from Sarbez is among the top three on the grilled cheese menu.

4. Smoked Old Fashioned at the Renaissance Historic Downtown Hotel: The hotel is somewhat new to the historic district, adding a cool look and vibe to the area. But pop into the Castillo Craft Bar + Kitchen inside and you'll see why locals are going there as much as the hotel guests. The "Smoked Elijah Craig Old Fashion" is the gem of an impressive drink menu. Plus, you'll be the center of attention for at least 30 seconds that night when they fire up the mini torch to smoke your glass.

   

   
   

5. Smoky Fish Dip at Meehan's: You can't go wrong with anything off the appetizer menu here – mac & cheese, wings, oysters, shrimp .... all delicious. But let's go with the smoky fish dip as the winner.

   
   

   Now, admittedly, part of this selection can be attributed to the setting. Don't get sucked into staying inside. It's fine in there and the upstairs balcony out front offers one of the best water views in the city and maybe even the state.

   
   

   But if you're looking to really have fun, head to "The Backyard" at Meehan's. The back patio is where it's at, and it's one of the most festive spots downtown, especially during weekend afternoons. This is supposed to be about menu items, though, so wherever you choose to eat Meehan's smoky fish dip, you'll be pleased.

   
   

   Entrees are probably good at Meehan's as well, but it's just tough to make it beyond so many tempting appetizers.

   

   The view from Meehan's upstairs balcony is among the best in the city, but for the more festive atmosphere, head to Meehan's "Backyard" ... and don't forget to order that smoky fish dip.

6. Maine Lobster Roll at Prohibition Kitchen: OK, the point of this guide is menu-hopping and not spending too much time at one spot. But if you're going to extend one of your stops somewhere, Prohibition (as the locals call it) is worth it. Prohibition offers the best vibe with nightly live music and the food is excellent, especially the lobster roll. The fries that come with it are surprisingly good, as well.

   
   

   Just don't plan on this and the spiked milkshake on the same visit. Do them on different days or your night will be over early.

   

7. Roadside IPA at Dog Rose Brewing Company: The beer scene in St. Augustine is actually good, with Dog Rose, the Bog Brewing Company and Old Coast Ales pretty much in the downtown area, or very close to it. Roadside gets our nod for best beer – or best IPA, at least – over a couple other strong challengers.

   
   

   Plus, Dog Rose is a cool downtown stop with frequent live music and permanent shuffleboard tables. Never underestimate the power of a shuffleboard table at a bar.

   

8. O.G. Sticky Rice Bowl at Funkadelic Food Shack: This used to be a permanent food truck (ok, ok, food trucks technically can't be permanent) at the Marina Munch, a fantastic collection of food truck dining not far from downtown with amazing views. Unfortunately, Funkadelic put the truck in drive and headed to Anastasia Island for a permanent restaurant location about 10-15 minutes from the historic district. Well, it's fortunate for the people in that neighborhood.

   
   

   But, anyway, the Funkadelic food truck still can be spotted close to downtown now and then so it counts for this.

   
   

   The sticky rice bowl comes with your choice of fresh catch of the day or shrimp (get it blackened) and a bunch of other healthy stuff. What's probably not as healthy is the extra extra extra Funk Sauce that is a must. Not sure what the Funk Sauce is, but whatever it is, damn it's good. Dump as much as possible into that rice bowl with blackened fish and it'll be the best part of your day.

   

   If you spot the Funkadelic Food Truck, don't walk but RUN to get a sticky rice bowl with blackened fish or shrimp. Or you can just drive south on A1A to Funk's new permanent location for it.

9. Smoked Salmon Flatbread at River & Fort Rooftop: There's a lot of "smoked" items on this top 10 list so if you don't like that particular flavor, apologies that you read this far. However if you do, even just sorta, you need to try the smoked salmon flatbread.

   
   

   This entry also was aided by the setting, as the rooftop at River & Fort is absolutely insane. Views of the fort, the bay, the boats, the bridges, the ocean. And the rooftop menu is really good, too.

   
   

   The lobster flatbread comes in a close second so if you're on a date or in a group (or just extremely hungry and not planning on hitting the gym anytime soon), try them both, enjoy a cocktail and savor that view.

   

   Views from the River and Fort Rooftop are crazy good. So are the flatbreads.

10. Breakfast Burrito at Juniper Market: The last spot on this coveted list is such a tough decision. So many other menu-hopping favorites in the historic district of one of the country's most beloved cities are being left off. But hey, a top 10 is a top 10 and difficult decisions are required.

    
    

    So this final spot goes to the St. Augustine staple of Juniper Market. This breakfast/coffee/lunch spot is a favorite among locals and it's situated perfectly along San Marco Avenue in the trendy, growing and somewhat eclectic Uptown District.

    
    

    The breakfast burrito (be sure to add in avocado and bacon) is a perfect way to get your St. Augustine tourist day started or simply shake off any cobwebs still lingering from those smoked old fashioneds the night before.