Updated: July 2026
A great Cuban sandwich is one of Florida’s most satisfying meals, and on Anna Maria Island, the local kitchens take it seriously. From the soft, buttery Cuban bread to the savory layers of roast pork, ham, Swiss cheese, pickles, and mustard, each bite delivers that perfect balance of flavor and crunch that makes the Cubano a Florida icon.
The Cuban sandwich has a rich history dating back to the late 1800s in Florida’s Cuban immigrant communities, from Ybor City in Tampa to Key West. Originally a simple, portable lunch for cigar factory workers, it grew into a beloved Florida staple with regional variations like Tampa’s salami-enhanced version and Miami’s classic no-salami take.
On Anna Maria Island, the Cuban is more than a meal. It is a fixture on menus across the island, showing up at waterfront dockside bars, cozy Pine Avenue cafes, and lively pubs alike. Here is your guide to the best spots, organized by experience and vibe.
For everything beyond the Cuban, my Dining on Anna Maria Island: My Insider Guide is your complete eating and drinking resource.
Beachfront & Waterfront Views
Bridge Tender Inn Dockside & Tiki Bar
- 135 Bridge Street · Bradenton Beach
- 941-778-4849
- Daily · 11:00 AM to 11:30 PM
- Live Music · Daily · afternoon & evening
Bridge Tender Inn serves a classic Cuban with ham, house-roasted pork, Swiss cheese, pickles, and mustard, best enjoyed alongside a bowl of black bean soup and a waterfront view. The dockside setting and live music make it one of the most atmospheric spots on the island for a midday sandwich. For more on what Bridge Street has to offer, my Bridge Street on Anna Maria Island: My Insider Guide covers the best spots, shops, and bites in the area.
Cortez Kitchen
- 4528 119th Street · Cortez
- 941-900-1506
- Sunday – Thursday · 12:00 PM to 9:00 PM
- Friday & Saturday · 12:00 PM to 10:00 PM
- Live Music · Friday through Sunday evenings
Cortez Kitchen serves Pete’s Pressed Cuban with slow-roasted pork, cherrywood ham, creamy mustard, and house-crafted dill pickles on La Segunda Cuban bread. Enjoy it with live music and bay views from indoor or outdoor seating, one of the most satisfying versions on the island. For more on the historic fishing village that is home to Cortez Kitchen, my The Historic Cortez Fishing Village: My Insider Guide is worth a read before you go.
Daiquiri Deck
- 107 Bridge Street · Bradenton Beach
- 941-253-3300
- Sunday – Thursday · 10:00 AM to 10:00 PM
- Friday & Saturday · 10:00 AM to 11:00 PM
- Happy Hour: Daily · 3:00 PM to 7:00 PM · 8:00 PM to close
- Live Music: Friday, Saturday, and Sunday · call for times
Daiquiri Deck serves the Mojo Cuban with house-roasted mojo pulled pork, Cotto salami, Black Forest ham, Swiss cheese, dill pickles, and yellow mustard aioli. Pair it with a frozen daiquiri and a waterfront view and it is hard to beat for a casual Bridge Street lunch. For more lively spots with great music nearby, my Live Music on Anna Maria Island: My Insider Guide has everything you need.
Casual & Cozy Cafés
Anna Maria General Store
- 503 Pine Avenue · Anna Maria
- 941-779-9200
- Monday – Saturday · 8:00 AM to 9:00 PM
- Sunday · 8:00 AM to 7:00 PM
The General Store serves a classic pressed Cuban with tender roast pork, smoky ham, Swiss cheese, zesty dill pickles, and mustard pressed between golden, crisp Cuban bread. A local favorite and a natural stop on any Pine Avenue morning. For everything the General Store has to offer your vacation, my Island Living Made Easy with Anna Maria General Store guide covers it all.
Ginny’s & Jane E’s Bakery Cafe
- 9807 Gulf Drive · Anna Maria
- 941-778-3170
- Daily · 7:00 AM to 3:00 PM
Ginny and Jane E’s serves a Cuban with roasted pork loin, ham, Swiss, Dijon mustard, mayo, and pickles on authentic Cuban bread. The charming cafe and gift shop atmosphere makes it one of the more memorable spots for a morning or midday sandwich on the north end of the island.
The Toasted Mango Cafe
- 3240 East Bay Drive · Holmes Beach
- 941-213-9948
- Daily · 7:30 AM to 2:30 PM
The Toasted Mango Cafe serves a Cuban piled high with slow-roasted pulled pork, ham, melted Swiss cheese, dill pickles, and mojo sauce on a fresh house baguette. The baguette swap is a standout twist on the classic and one of the more creative takes on the island.
Pub & Bar Style
Freckled Fin Irish Pub
- 5337 Gulf Drive · Holmes Beach
- 941-251-3930
- Sunday – Thursday · 11:00 AM to 11:00 PM
- Friday & Saturday · 11:00 AM to 12:00 AM
- Happy Hour · 3:00 PM to 6:00 PM
- Live Music · Tuesday and Thursday through Sunday · 7:00 PM to 11:00 PM
- Live Music · some Saturdays · 3:00 PM to 6:00 PM
Freckled Fin serves a traditional Cuban with smoked pork, ham, salami, Swiss, pickles, and mustard in a casual pub setting with live music. A solid midday or evening option with a cold beer alongside. For the best happy hour deals near your Cuban, my Best Happy Hour Spots on Anna Maria Island: My Insider Guide has the full rundown.
gRub Tropical BBQ
- 415 Pine Avenue · Anna Maria
- 941-900-2874
- Monday – Saturday · 11:00 AM to 8:30 PM
- Happy Hour · Monday – Saturday · 3:00 PM to 5:00 PM
gRub puts its own spin on the Cubano with the CuBen, featuring mojo pork, crispy pork belly, Swiss cheese, pickles, and grain mustard on artisan bread. It is one of the most creative versions on the island and very much worth trying. Served with a choice of sides on indoor or breezy outdoor seating. For more on what gRub does with slow-smoked meats and bold flavors, my Best Barbecue on Anna Maria Island: My Insider Guide has the full story.
Hurricane Hanks
- 5346 Gulf Drive · Holmes Beach
- 941-778-5788
- Food · Sunday – Thursday · 11:30 AM to 9:00 PM
- Food · Friday & Saturday · 11:30 AM to 10:00 PM
- Bar · Daily · 11:30 AM to 11:00 PM
Hurricane Hanks serves the Ybor Cuban with ham, seasoned pork, Genoa salami, Swiss, mayo, mustard, and pickles. Served with house potato chips and coleslaw, it is a hearty, satisfying version that leans into the Tampa tradition.
Island Time Bar & Grill
- 111 Gulf Drive South · Bradenton Beach
- 941-782-1122
- Wednesday – Saturday · 11:00 AM to 11:00 PM
- Sunday – Tuesday · 11:00 AM to 10:00 PM
- Happy Hour · Monday – Friday · 11:00 AM to 5:00 PM
- Live Music · Daily · 7:00 PM to 10:00 PM
Island Time Bar and Grill serves a warmly toasted Cuban with ham, slow-roasted pork, Swiss, dill pickles, and mustard aioli. A breezy, casual lunch option with that easygoing island pace built right into the name.
Scott’s Deli
- 6000 Marina Drive · Holmes Beach
- 941-778-3000
- Monday – Saturday 9:00 AM to 6:00 PM
Scott’s Deli serves a pressed Cuban with Black Forest ham, tender deli pork, herbed cream cheese, and pickles on toasted ciabatta. The herbed cream cheese is an unexpected twist that works beautifully. They also offer beach chair delivery, bringing your sandwich straight to the sand. For more on that experience, my Beach Chair Dining on Anna Maria Island: My Insider Guide covers all the best ways to eat by the water.
Enjoy your Cuban right from your beach chair—check out my guide The Ultimate Guide to Beach Chair Dining on Anna Maria Island for more ways to savor island eats by the sand.
Slim’s Place
- 9701 Gulf Drive · Anna Maria
- 941-567-4056
- Tuesday – Sunday · 11:30 AM to 10:00 PM
- Monday · 3:00 PM to 10:00 PM
- Happy Hour · Monday – Friday · 3:00 PM to 5:00 PM
Slim’s Place serves a pressed Cuban with roasted pork, ham, salami, Swiss, pickles, and mustard on authentic La Segunda Cuban bread in a relaxed sports bar atmosphere. For the best spots to catch a game alongside your lunch, my Best Spots to Watch Sports on Anna Maria Island: My Insider Guide has you covered.
Smoqehouse
- 1701 Gulf Drive · Bradenton Beach
- 941-242-5340
- Monday – Saturday · 11:00 AM to 8:00 PM
SmoqeHouse serves a Cuban built around house-smoked pulled pork, shaved ham, smoked Swiss, dill pickles, and mustard on artisan bread, pressed fresh to order. The smokehouse treatment gives it a depth that sets it apart from a standard pressed Cuban and makes it one of the more distinctive versions on the island.
Coastal Close
Whether you are after a classic pressed Cubano or a creative island twist, Anna Maria Island has a version worth trying at every turn. From dockside bars and Pine Avenue cafes to lively pubs and casual grills, the Cuban sandwich is woven into the fabric of the local dining scene in a way that makes complete sense for a community this close to Tampa.
For the complete picture of where to eat on the island, start with my Dining on Anna Maria Island: My Insider Guide or pick up my downloadable Anna Maria Island Restaurant Guide on Etsy.
— izzy