Latitudes - Sunset Key Cottages — Restaurant in Key West

We booked an 8:45pm dinner reservation here for our 10-year wedding anniversary. We wanted to see the sunset during dinner, but you have to reserve farrrrrr in advance of your trip for that. Months, not weeks.

First, I'll say that the free 5-minute ferry ride over was really nice. The captain of the ferry is funny yet polite, and his driving/docking abilities are incredible.

The ambience of the restaurant itself was beautiful, both inside and outside. Like an upscale Bonefish. We sat outside during our 8:45pm reservation, and it was a comfortable temperature with an occasional slight breeze that felt amazing. We did notice several large cockroaches scurrying towards tables, which would eventually crawl down into the cracks of the wooden platforms each table is on. Somehow we sat at the only table without armrests on its chairs.

We ordered French Onion soup to start. This was absolutely the best I've ever had. Perfectly cooked cheese with slightly burnt edges (in a good way!) and an unbelievable broth. Not the wisest choice when you're sitting outside trying to stay cool but it was worth it!

My wife ordered the chicken, which came with mashed potatoes and Brussels sprouts. The chicken was very tender and flavorful, though it was cooked on the bone, which is not for everyone. The mashed potatoes were extremely smooth and silky with an excellent flavor. The Brussels sprouts were soft but not mushy, and had a nice vinegar taste but not overpowering.

I ordered the center cut tenderloin, which came with cauliflower gratin and large steak fries. I ordered the steak medium rare. It had a good flavor, however it was relatively dry and slightly overcooked. To be perfectly honest, Costco steaks cooked in the air fryer are far thicker and more juicy if you salt them properly and let them come down to room temperature before cooking. The cauliflower gratin threw me off a bit because it tasted very sweet - almost like creamed corn. I wasn't a fan. The steak fries were very thick pieces of hand cut potato, and were seasoned and cooked very nicely. For $72 though, this is not the way.

The service was good. Food runners and bussers were extremely polite and watched the tables like hawks, waiting to clear empty plates. Our multilingual waiter was attentive, friendly and funny. I was honest when he asked me about the steak, and he seemed somewhat taken back, presumably because he'd recommended the dish to me in the first place. No effort was made to accommodate or make up for it though.

As others have said, when making your reservation they ask if there's a special occasion, and we selected "Anniversary". However none of the staff acknowledged this at all, so it seems strange to ask in the first place. We did notice several other tables who'd ordered desserts had them delivered with sparklers tucked inside, which I can only assume was because they'd indicated an anniversary or birthday as well. So it seems your occasion is only important if you order dessert.

Overall, it was a very memorable experience, and the food was, for the most part, top notch. We had a $150 bill for 2, which seems very fair, all things considered. We would definitely go back, but next time we'd like to try sitting inside, and I'll stay away...

Disappointing Experience at Latitude’s – A Beautiful Setting Undone by Poor Management

Latitude’s in Key West is undeniably beautiful—the boat ride over was lovely, and the setting is picture-perfect. Unfortunately, the experience that followed was anything but enjoyable, thanks entirely to the appalling behavior of the manager, Jerry.

When we arrived, the heat was intense—something you’d think a restaurant of this caliber would be prepared for. No one asked whether we preferred indoor or outdoor seating; we were simply led outside and seated in full sun. When we politely asked to move to a nearby table with partial shade, the staff had to “ask for permission”—a process that took several uncomfortable minutes. Even after we were allowed to move, only half our table was shaded. My husband had to sit on the same side as me to avoid baking in the sun.

But the absurdity didn’t stop there. We weren’t asked if we’d prefer the last table in the row, and when my husband sat down momentarily to escape the heat, Jerry, the manager, actually came over to tell him he couldn’t sit there. No flexibility. No customer consideration.

Sensing our discomfort, our kind and empathetic waitress offered to move us inside. She led us to a room with several open tables—only one of which was occupied. She told us to choose any table, and we selected a four-top that allowed us to enjoy the view together. Moments later, Jerry stormed over and told her she couldn’t seat us at that table. That was the final straw. After just 15 minutes, we’d had enough and decided to leave. On our way out, Jerry—clearly aware of our dissatisfaction—said nothing. No apology. No acknowledgment. Just indifference.

In all my years of dining out, I’ve never been treated with such disregard. What’s worse, it was obvious that Jerry’s attitude is not just an isolated problem. Staff morale was visibly low, and several employees made subtle comments suggesting that his toxic management style affects them too.

Latitude’s has all the ingredients for a five-star experience—gorgeous atmosphere, great reputation, and kind frontline staff. But until the ownership takes a hard look at who’s running the show, particularly Jerry, I can’t recommend this restaurant. Beautiful views don’t make up for being treated like a nuisance...

This restaurant is certainly not the same post-pandemic, and unfortunately it's no longer the best dining experience in Key West.

You used to be able to make a reservation within the week, but now they are reserving tables 2 months out, and this never used to be the case. It's because they are limiting their seating. Where once the entire restaurant would be full, now both indoor rooms are entirely empty and only the outdoor seating is occupied. This is more obvious on the ferry ride to get to sunset key, where we were denied entry to the ferry even though it left only half full. This never used to happen.

As for the food, it's the exact same menu options that it was 5 years ago. In fact, I ordered the same waygu beef meal that I had back then and have been talking about ever since. Unfortunately, the quality of last nights meal couldn't hold a candle to the meal from 5 years ago, and I sadly wouldn't be bragging to anyone about it.

There were no specials, and no catch of the day. They were out of ingredients for some of the appetizers and entrees we wanted to order. The atmosphere wasn't as lively, and the food, unfortunately, wasn't as memorable. Most likely we won't be coming back, which is too bad because they have the best location for outdoor seating of any restaurant.

As for our ferry debacle, we attempted to get on the ferry at 7:15pm for our 7:45pm reservation but were denied (we had been there since 6:50), even though half the ferry was not seated. The hostess pam tried explaining that we couldn't board because 7:45pm was our FERRY reservation, not our table reservation, except two groups ahead of us had the same time reservation of 7:45. When we brought that fact up to her she then said it was because there were 5 in our party, and they didn't have enough room for us on the ferry, even though she let a group of four on in front of us that only 2 people had a reservation. Pam even told the 2 extra people in that party that the restaurant may not accommodate them because they were not apart of the couples reservation. To have the hostsess deny us ferry boarding after all those facts was unprofessional. Like I said, it never used to be like that, and it just added extra stress and frustration to a dining process that should be...