Hey friend! Today I’m taking you to one of my absolute favorite hidden gems in Orlando — Otto’s High Dive. And no, it’s not a pool party (although the vibes are just as splashy). This neighborhood rum bar in Orlando’s Milk District is where tropical flavors meet classic Cuban comfort — all in a vibrant, welcoming space that’s earned a well-deserved spot on the Michelin Guide’s Orlando recommendations.
Where Is Otto’s High Dive?
Address: 2304 E. Robinson St. Orlando
MAP VIEW
Located in the heart of the Milk District, Otto’s High Dive is a Cuban-Floridian fusion restaurant and rum bar that transports you straight to the Caribbean. From its island-inspired cocktails to the bold, nostalgic dishes, everything here feels like a mini vacation — no passport required.
This spot has been on my Orlando foodie bucket list for a while, and I’m so glad I finally made it. We popped in for Happy Hour (weekdays from 4–6 PM) — but let me tell you, with an atmosphere this good, anytime feels like happy hour at Otto’s.
The Menu: Cuban-Inspired Comfort with a Florida Twist
Otto’s is all about Cuban cuisine with Floridian flair. Their Happy Hour menu is packed with tempting small bites and fresh cocktails, including:
- Shrimp Skewers – with mango sofrito and rice
- Half off oysters – super fresh and perfect with a mojito in hand
- Handcrafted cocktails – expertly mixed with rums from all over the Caribbean
Don’t miss their iconic Cubano sandwich — honestly, it was one of the best I’ve ever had. Pressed to perfection with tender pork, tangy pickles, and melty cheese.
Must-Try Dishes at Otto’s High Dive
We sampled a variety of items from the main dinner menu, and everything was delicious:
- Ropa Vieja (Braised Short Rib) – fall-apart tender and full of flavor, served with the best black beans and rice
- Lobster Escabeche – elevated takes on traditional dishes
- Fresh Salads with Caribbean zest – bright, balanced, and refreshing
Whether you’re dining light or diving into a full feast, there’s something for everyone here.
Craft Cocktails That Steal the Show
If you’re a cocktail lover (like me), you’ll be blown away by the bar program at Otto’s. These aren’t just drinks — they’re artfully crafted cocktails that make use of premium rums, fresh herbs, and house-made infusions. I could’ve stayed all night just sipping my way through the menu.
Why You Should Visit Otto’s High Dive Orlando
If you’re searching for:
- A fun and unique date night spot in Orlando
- A legit Cuban food experience without leaving Florida
- A lively but laid-back rum bar in the Milk District
- One of the best happy hours in Orlando
…then Otto’s High Dive needs to be on your radar. It’s warm, welcoming, and packed with flavor — just like Cuba itself.
Ready to go?! Click here for reservations.
This is a truly captivating and fun place for an evening out. With its fusion of Floridian and Cuban cuisine, tropical cocktails, and lively atmosphere, this neighborhood rum bar offers an unforgettable dining experience. So, gather your friends, bring your appetite, and dive into the flavors of Cuba at Otto’s High Dive. What’s better than good food, great company, and the spirit of the Caribbean?! Let’s go!!
Bonus Recommendation: Check Out Permanent Vacation
If you love themed bars (and who doesn’t?), make your next stop Permanent Vacation — a dreamy tiki bar tucked inside The Copper Rocket in Maitland. It’s got major enchanted island vibes and creative cocktails that will have you planning your return trip before you even finish your first drink.
Thanks for reading! If you’ve been to Otto’s High Dive — or have another favorite Orlando bar or restaurant I should check out — drop a comment or send me a message. I love hearing your recommendations!
Xx Autumn
MAP VIEW
