Updated: April 2026
Craving a Cuban sandwich on Anna Maria Island? You’re in luck! From the soft, buttery Cuban bread to the savory layers of roast pork, ham, Swiss cheese, pickles, and mustard, each bite is a perfect blend of flavor and crunch. On Anna Maria Island, local chefs and cafés put their own twist on this Florida classic—whether you’re enjoying it with a waterfront view, on a breezy rooftop, or right on the sand, it’s always a taste of island perfection.
The Cuban sandwich, or Cubano, 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’s grown into a beloved Florida staple—with variations like Tampa’s salami-enhanced version and Miami’s classic no-salami take.
Today, the Cuban sandwich on Anna Maria Island is more than a meal—it’s an experience. Here’s your guide to the best spots on the island, organized by experience and vibe.
Beachfront & Waterfront Views
Bridge Tender Inn Dockside & Tiki Bar
- Location: 135 Bridge Street · Bradenton Beach
- Hours: Daily 11:00 AM – 11:30 PM
- Highlights: Classic Cuban with ham, house-roasted pork, Swiss cheese, pickles, and mustard. Pair it with black bean soup, waterfront views, and live music for a true island experience.
Looking for more things to do along Bridge Street? Check out my guide 👉 Ultimate Guide to Bridge Street on Anna Maria Island for the best spots, shops, and bites nearby.
Cortez Kitchen
- Location: 4528 119th Street · Cortez
- Hours: Sunday–Thursday 12:00–9:00 PM, Friday–Saturday 12:00–10:00 PM
- Highlights: Pete’s Pressed Cuban with slow-roasted pork, cherrywood ham, creamy mustard, and house-crafted dill pickles on La Segunda Cuban bread. Enjoy live music and bay views from indoor or outdoor seating.
Daiquiri Deck
- Location: 107 Bridge Street · Bradenton Beach
- Hours: Sunday–Thursday 10:00 AM–10:00 PM, Friday–Saturday 10:00 AM–11:00 PM
- Highlights: Mojo Cuban with house-roasted mojo pulled pork, Cotto salami, Black Forest ham, Swiss cheese, dill pickles, and yellow mustard aioli. Perfect with frozen daiquiris and waterfront vibes.
Enjoy your Mojo Cuban with waterfront vibes and tunes—check out my guide 👉 Live Music Vibe on Anna Maria Island for more spots to catch great live music around the island.
Casual & Cozy Cafés
Anna Maria General Store
- Location: 503 Pine Avenue
- Hours: Monday–Saturday 8:00 AM–9:00 PM, Sunday 8:00 AM–7:00 PM
- Highlights: Tender roast pork, smoky ham, Swiss cheese, zesty dill pickles, and mustard pressed between golden, crisp Cuban bread. A local favorite for a classic Cuban experience.
Want to see what else Anna Maria General Store has for your vacation? 👉 Anna Maria General Store: A Quick One-Stop Shop for Your Vacation Needs
Ginny’s & Jane E’s Bakery Cafe
- Location: 9807 Gulf Drive · Anna Maria
- Hours: Daily 7:00 AM–3:00 PM
- Highlights: Cuban sandwich with roasted pork loin, ham, Swiss, Dijon mustard, mayo, and pickles on authentic Cuban bread. Enjoy it in a charming café/gift shop atmosphere.
The Toasted Mango Cafe
- Location: 3240 East Bay Drive · Holmes Beach
- Hours: Daily 7:30 AM–2:30 PM
- Highlights: Cuban piled high with slow-roasted pulled pork, ham, melted Swiss, crunchy dill pickles, and signature mojo sauce on a fresh house baguette. A standout twist on the classic.
Pub & Bar Style
Freckled Fin Irish Pub
- Location: 5337 Gulf Drive · Holmes Beach
- Hours: Sunday–Thursday 11:00 AM–11:00 PM, Friday–Saturday 11:00 AM–12:00 AM
- Highlights: Traditional Cuban with smoked pork, ham, salami, Swiss, pickles, and mustard in a pub-style setting. Enjoy live music and a casual midday or evening bite.
Looking for a great deal with your Cuban? Check out my guide 👉 Discover the Best Happy Hour Spots on Anna Maria Island for more spots to sip and savor around the island.
gRub Tropical BBQ
- Location: 415 Pine Avenue · Anna Maria
- Hours: Monday–Satueday 11:00 AM–8:30 PM
- Highlights: Creative “CuBen” with mojo pork, crispy pork belly, Swiss, pickles, and grain mustard on artisan bread. Served with a choice of sides on indoor or breezy outdoor seating.
Hurricane Hanks
- Location: 5346 Gulf Drive · Holmes Beach
- Hours: Food: Sunday–Thuesday 11:30 AM–9:00 PM, Friday–Satueday 11:30 AM–10:00 PM | Bar: Daily 11:30 AM–11:00 PM
- Highlights: Ybor Cuban with ham, seasoned pork, Genoa salami, Swiss, mayo, mustard, and pickles. Served with house potato chips and coleslaw for a hearty lunch or dinner.
Island Time Bar & Grill
- Location: 111 Gulf Drive South
- Hours: Wednesday–Saturday 11:00 AM–11:00 PM, Sunday–Tuesday 11:00 AM–10:00 PM
- Highlights: Warmly toasted Cuban with ham, slow-roasted pork, Swiss, dill pickles, and mustard aioli. Perfect for a breezy, casual lunch “on island time.”
Scott’s Deli
- Location: 6000 Marina Drive · Holmes Beach
- Hours: Monday–Saturday 9:00 AM–6:00 PM
- Highlights: Pressed Cuban with Black Forest ham, tender deli pork, herbed cream cheese, and pickles on toasted ciabatta. Free beach chair delivery brings it straight to the sand.
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
- Location: 9701 Gulf Drive · Anna Maria
- Hours: Tuesday–Sunday 11:30 AM–10:00 PM, Monday 3:00–10:00 PM
- Highlights: Pressed Cuban with roasted pork, ham, salami, Swiss, pickles, and mustard on authentic La Segunda Cuban bread. Relaxed sports bar atmosphere.
Catch the game while enjoying a Pressed Cuban—see my guide 👉 Guide to Watching Sports on Beautiful Anna Maria Island for the best spots to watch sports on the island.
Smoquhouse
- Location: 1701 Gulf Drive North · Bradenton Beach
- Hours: Monday–Saturday 11:00 AM–8:00 PM
- Highlights: House-smoked pulled pork, shaved ham, smoked Swiss, dill pickles, and mustard on artisan bread. Pressed fresh to order for a smoky, savory twist.
Wrap Up
Whether you’re craving a classic Cuban sandwich or a creative twist, Anna Maria Island has a spot for every taste and vibe. From waterfront views and beachside bites to cozy cafés and lively pubs, each sandwich is a taste of Florida tradition with an island flair. Grab one (or try them all!), soak up the sun, and discover why the Cuban sandwich is a beloved culinary icon on Anna Maria Island.
Want to explore even more delicious bites? 👉 Anna Maria Island Restaurant Guide has all the best spots to eat around the island.
Until next time…
· izzy