Otto’s High Dive Milk District: Magical Dining Review & Orlando’s Best Tres Leches
Otto’s High Dive in Orlando’s Milk District is a Michelin Bib Gourmand Cuban restaurant that’s been on my radar for months. My wife brought home a slice of their tres leches cake a while back, and I was instantly hooked. That dessert alone ranks in my top 5 in Orlando, so I needed to know if their savory dishes could match up to what might be the best tres leches I’ve ever had.
When this Milk District gem joined this year’s Magical Dining lineup, we finally had our excuse to visit. For those unfamiliar, Magical Dining is a Visit Orlando sponsored charity event where restaurants offer a prix fixe three course menu at a set price. I’ll be honest, I rarely do Magical Dining because I prefer picking and choosing from a restaurant’s whole menu rather than being limited to a few options. Plus, it’s become less of a deal with each passing year.
But for Otto’s High Dive Milk District? I was willing to make an exception.
About Otto’s High Dive in the Milk District

Otto’s High Dive is an intimate Cuban restaurant perfect for date night. The moody lighting sets the vibe, and they have an extensive bar program if you’re into cocktails. Located in the Milk District, which has more of a hipster industrial vibe on the outskirts of downtown, Otto’s stands out as one of the more upscale dining options in the area.
I’ve never been to Otto’s High Dive for their regular menu, but from what I could tell, the Magical Dining portions were very generous. We definitely got our money’s worth.
What We Ordered at Otto’s High Dive Milk District

Watermelon Tuna Ceviche
The ceviche was decent. The watermelon provided a nice sweetness, but the tuna flavor wasn’t very strong. I honestly couldn’t tell all that well which pieces were actually tuna and which were watermelon in the dim lighting. Maybe it’s a restaurant illusion to make the dish seem like better value.
The one thing I did not like about this dish was the bitterness from the mustard seeds, which could be overpowering in some bites.

Smoked Fish Dip
This was better than the ceviche. The smoked fish dip had better overall flavor. The fish taste was pronounced but not fishy in a bad way. It was rich from what I assume is a mayonnaise based sauce and had a little bit of acidity from the pickled red onions. I’d recommend starting with this if you’re choosing between appetizers.

Lechon Asado (Roasted Pork)
By this point I was already pretty full, but the lechon asado was great. The lean pieces were still tender and juicy, and the fatty bits added some extra depth of flavor and richness.
Their chimichurri sauce was really good. It reminded me almost of Chinese ginger green onion oil with its strong oniony garlicky flavor. Not your typical chimichurri, but in a good way.

Ropa Vieja (Shredded Beef)
The ropa vieja was just okay. It’s one of my wife’s favorite Latin dishes, but it’s not Otto’s High Dive’s highlight. The shredded beef was a bit dry despite pooling in sauce. The flavor was also lacking a bit, felt one dimensional. It could have used more tang from the tomato based sauce.
If you’re visiting Otto’s High Dive in the Milk District and love ropa vieja, you might want to skip this one and try something else.
The Star of the Show: Tres Leches Cake

Dessert is the reason I wanted to come to Otto’s High Dive Milk District in the first place. I love a soggy rich dessert. Pudding, French toast, moist cakes, that’s my weakness. Tres leches is something I don’t get to eat a lot of, but Otto’s does it absolutely fantastic.
My wife and I both got a slice, and by this point it was borderline food coma time. We only managed a few bites before packing the entrees and desserts for the next day.
I love tres leches because it’s impossible to be dry. It’s drowning in milky goodness but has just enough texture so it doesn’t feel like you’re drinking a grainy milkshake, if that makes sense. The whipped cream on top just adds more decadence, and the orange zest ties it all together with some nice citrusy fragrance.
Highly recommend. Most of the time I’d suggest getting dessert somewhere else rather than at your dinner establishment, but not at Otto’s High Dive. This is worth the trip alone.
The Verdict: Is Otto’s High Dive Milk District Worth It?
Yes, especially for the tres leches cake. The savory dishes were hit or miss during our Magical Dining experience. The lechon asado and smoked fish dip were solid, but the ropa vieja didn’t impress, and the ceviche was just okay.
But here’s the thing: Otto’s High Dive in the Milk District earned its Michelin Bib Gourmand for a reason. I’d love to come back and try their regular menu where I can actually choose what sounds best rather than being limited to a prix fixe selection.
The intimate atmosphere makes it perfect for date night, and the Milk District location is convenient if you’re already in the area. Just make sure you save room for dessert, or better yet, come specifically for the tres leches and maybe a cocktail.
Tips for Visiting Otto’s High Dive Milk District
- Reserve ahead for dinner, especially on weekends
- Save room for dessert or you’ll regret it
- Order the lechon asado if it’s available
- Skip the ropa vieja unless you’re a die hard fan
- Parking can be tricky in the Milk District during peak times.
Have you been to Otto’s High Dive in the Milk District? What did you think of their tres leches? Let me know in the comments.
