When a great sunset view meets drinks at a fun “Cheers”-like (remember “Cheers”?) atmosphere and good food, Dive Bar on the Bay, along with the food trailer Bites on the Bay, are places you don’t want to miss.
Bayfront space next to Mangrove Marina in Tavernier, MM 91.7 bayside, reopened a few months ago. They experienced storm surge from Hurricane Milton and used the opportunity to enhance the property.
“I originally thought I was just going to clean it (the food trailer) up to help the owner out, but I ended up talking to my friend and now business partner Demetrius ‘D’ (Powell) and asked him if he wanted to open up a food trailer,” said Bites on the Bay co-owner and general manager Brian James. “I showed him the trailer and said we have until tomorrow morning to decide, and ‘D’ said, ‘I’ll tell you right now we are going to do it.’”
“We took a few days, got our LLC, put a main menu together and gave out free food to get going,” James continued.
Originally from Boston, James moved to the Keys a little over two years ago with his wife. He has a background in operating pizza places and Italian restaurants in Massachusetts.
Originally from Miami, Powell was recruited to work for the Seafood Buffet at Whale Harbor in 2019. He lost his chef job during the COVID-19 pandemic, but then found a new chef job at the Moose lodge in Islamorada.
“When Brian (James) told me, I decided to take a leap of faith,” Powell says about the opportunity. They met at the Moose and still cook there and split the hours of Bites on the Bay.
They have paid particular attention to ensuring everything is simple, fresh and affordable. Some of the main menu items are Kickin’ Shrimp with Chef D’s secret special sauce, cheeseburger with fries, loaded nachos, beef quesadilla and blackened shrimp tacos. There is also a kid’s menu for $6 with items such as hot dogs, chicken fingers, or grilled cheese, all with fries.
Bites on the Bay recently added a delicious lobster roll weekend special that always sells out, stone crab claws for $5 each and occasional specials such as Chef D’s conch ceviche.
They also sell baked goods from Karen Buono’s Sweetie Pie Bakery, including cookies, cupcakes and other desserts.
Both businesses are committed to consistent hours, great food and drinks and fair prices. And right out of the gate, it’s been a huge hit.
The Dive Bar on the Bay’s manager, Emily Squilla, has concentrated on drawing traffic to the area with special offers and fun activities. Tuesday is “Yappy Hour” with special dog biscuits from Sweetie Pie Bakery, Wednesday is BOGO drink night and Sunday at 5 p.m. is a cornhole tournament. The cornhole tournament is only $10 to enter, and the winning pot has been from $100 to $150.
Having something fun to offer has already proven successful. The location is perfect for hosting private events such as small wedding receptions or birthday and anniversary celebrations.
“This was my first bartending job, and becoming the manager came about because I wanted to take on extra responsibility,” Squilla said. “I’m still learning, but it’s been really fun and super interesting, and everyone wants to see it succeed.”
“Chef D is also the bar manager at the Moose and knows all the reps, so he’s been super helpful to Emily,” James adds.
Fellow server Keri Lesko has also worked there since it opened, contributing to the location’s great energy. Lesko said one of the many reasons for the local draw is, “It’s a chill place with a beautiful sunset.”
The Dive Bar’s drink menu includes 12 draft beers from Florida Keys Brewing Company, Islamorada Brewery, and Waterfront Brewery in Key West. They also offer additional beer options, wine and canned drinks, such as the popular White Claw. Again, as with the food, they wish to have fair pricing, which is, on average, about $3 to $4 a drink, and recently added buckets of beer and mimosas.
In addition to cornhole, they offer live music on select nights, including Thursday nights with Too Tall Tom. The local community and liveaboards at the marina are a priority. The activities have been well received, and they plan to continue adding.
The backbone is the locals. The goal is for people to be happy, come back, and hope to be here a long time.
“I love working here; it’s fun, and the people are all great,” Squilla said.
Dive Bar hours are Monday through Thursday from 4 to 10 p.m. and Friday through Sunday from noon to 10 p.m. Bites on the Bay is open Wednesday and Thursday from 4 to 9 p.m. and Friday through Sunday from noon to 9 p.m.
