Stock Island: Key West’s fishy, funky, promising neighbor

Just before you come to Key West on US 1, you cross an island that has long been its grittier, workaday partner, Stock Island.

In the last few years, some working boatyards and fishing-boat docks on Stock Island have given way to upscale marinas for yachts and pleasure boats. Two resort hotels opened in those marinas, as well as a handful of notable restaurants, led by the highly regarded Hogfish Grill. A few artists and artisans also have located there.

There’s even an I Love Stock Island Festival in June and I Love Stock Island website. While part of Key West, Stock Island has always had its own identity.

I visited recently to find out: Is Stock Island worth seeking out? Is it “like Key West used to be,” as it is sometimes depicted?

For me, the answer was yes and no, and I’ll explain a bit in this article.

Stock Island then and now

The standard wisdom is that Stock Island got its name because livestock was corralled here for use in Key West.

Whether true or not, Stock Island has long been a place where things that required more land were located – it has the only golf course in Key West; years ago, it had the drive-in theater; it’s still home to the fascinating Key West Botanical Garden (worth visiting) and where you’ll find the only campgrounds near Key West, Boyd’s and Leo’s.

Driving around Stock Island today, you see it plays a key role in providing housing for all the working-class folks who keep a place like Key West running. There are a lot of mobile homes, some deteriorating, some neatly maintained. Shiny new workforce housing is also here. Stock Island is where more industrial enterprises, workshops and businesses seeking lower rent have located.

More picturesquely, working fishing and shrimping boats have always been here, providing the source of fresh seafood you’ll find at Stock Island restaurants. There are a dozen murals around the island and some funky shops (example: Beards and Brews Barbershop and Bar).

Despite the occasional colorful marina, our bike ride around Stock Island wasn’t particularly scenic or interesting. Unlike Key West, it’s not a place to explore on foot and discover interesting buildings. It’s not built to be beautiful and it’s not particularly picturesque for tourists; it’s a utilitarian place.

Stock Island is worth visiting for lunch or dinner

While I don’t recommend it for a scenic stroll, I do recommend Stock Island for a visit and a meal.

While Stock Island is about 20 minutes from Old Town Key West, it’s even closer and more convenient if you’re staying in the eastern end of Key West, along either North or South Roosevelt Drive.

There are several restaurants that are worth seeking out here.

Hogfish Grill, 6810 Front St., Stock Island, FL 33040, 305-293-4041

hogfishbar.com(opens in a new tab)

Everyone wants to discover that funky inexpensive spot where locals go. In Key West, for several years, that was Hogfish Bar & Grill on Stock Island, which had excellent word-of-mouth for fresh off-the-boat seafood. Today, however, its fans extend far beyond locals and you won’t be “discovering” it. Travel  & Leisure magazine, for example, named Hogfish Grill one of the 30 best seafood spots in America. (When beloved one-time-local  Jimmy Buffett performed for the last time in Key West in February 2023, this is where he dined.)

A rustic spot located where fishing and shrimping boats dock, Hogfish Grill helped popularize the hogfish, a mild white fish caught with a spear. The other specialty here is fresh Key West pink shrimp, but all the food is very good. A Florida Rambler story on the Hogfish Grill.

The Docks Restaurant and Raw Bar, 6840 Front St., Stock Island, FL 33040, (305) 396-7049

The #2 restaurant on Stock Island (after Hogfish, which is just down the street), the Docks has a spectacular sunset view overlooking the water and the shrimp boats.

The Docks has that hidden-gem quality. To reach it, you drive down a road through an industrial-feeling working waterfront. From the exterior, you wonder if you’re at the right address. Around back, however, the waterfront tables and lovely view unfold.

Every review you’ll read uses the same words: Fresh fresh fresh. The Docks is known for its fresh seafood and craft cocktails. It’s a bit more expensive; you’re not getting any discount because it’s 20 minutes from Old Town. But you’ll find easy parking and a true working waterfront, where “dock to dinner” has meaning.

El Siboney, 5501 Fifth Ave., Stock Island, 33040, (305) 204-4725

This is the second of two El Siboney locations in Key West and both have long been popular with locals. It earns 4 ½ stars on Yelp and Trip Advisor. It’s family-owned, not fancy, known for large portions of traditional Cuban food, terrific fresh bread and moderate prices.

Some seek El Siboney’s Stock Island location because it’s easy to reach and there’s a big parking lot. It’s a large restaurant and it’s probably easier to get a table here. The crowd also skews more local. The lunch menu is a real bargain with a highly touted Cuban sandwich. Also: Try the homemade sangria.

Matt’s Stock Island Kitchen and Bar, 7001 Shrimp Road, Stock Island,  33040,  (305) 294-3939

One of two restaurants in the excellent resort hotel The Perry, Matt’s has a gorgeous waterfront view overlooking an expansive marina full of yachts. It serves breakfast, lunch, dinner and a popular Sunday brunch.

We dined here while staying at the Perry. We had outstanding cocktails (I recommend the Pineapple Mojito) and dinner while we watched the full moon rise over the yacht harbor. There is a small menu with entrees in the $30 to $50 range and our dinners were superb. I followed the advice from reviews and ordered the Key West Shrimp Linguini. My husband had the Grilled Pork Chop over sweet corn and asparagus risotto after we heard a woman at a neighboring table rave about it.

In the winter, you’ll enjoy the fire pits.

Roostica, 5620 MacDonald Ave., Stock Island, FL 33040, (305) 296-4999

Sometimes, you just need good pizza. Roostica makes hand-formed wood-fired pizzas, and this fills half the menu. But they also offer other choices, including a catch of the day and Italian favorites such as lasagna, shrimp penne ala vodka and veal marsala. Nightly specials sound special too, like Key West pink shrimp scampi on Tuesdays.

Cayo Hueso Brewing, 5635 1st Ave., Stock Island, FL,  305-209-0599

This new craft brewery held a grand opening for its new tap room at the end of October 2023. It’s tucked in a complex adjacent to Roostica, whose food is offered here. The brewery’s beers are served in many local restaurants.

Staying on Stock Island

There are only a few choices for accommodations on Stock Island.

We stayed at The Perry, a resort hotel that was built at the same time as the adjoining marina, from which it gets considerable business from visitors who dock their boats here.

It’s a wonderful hotel, with two large pools, a scenic setting on the marina and comfortable spacious rooms with perfectly appropriate contemporary furnishings and artwork. Customer service is excellent.

In the dead of August, The Perry seems like a deal — $180 a night, which is about as cheap as Key West hotels get at any time of year. But once you add taxes, a $50 daily resort fee and a $25 a night parking fee, the off-off season price is more what you’d expect for a luxe resort. Like all of Key West, prices here are very seasonal, edging up month by month until they peak at $500+ in February and March. Like many hotels in Key West, there is no beach.

Why stay on Stock Island if it’s comparable in price to Key West?

I love staying in the historic center of Key West and walking or biking everywhere. But The Perry is different. It’s a resort experience. The rooms are bigger and more modern than many Key West hotels. The pools are expansive with more space around them. It provides a more relaxing off-the-beaten path experience without traffic or street noise. It’s easy to hang out here, have a meal at the excellent restaurant and try other Stock Island restaurants. And there are still chickens strutting around the pool.

The Perry offers a free hourly shuttle that drops you off and picks you up at a central location in the historic district, so you can stay here and still have your Key West experience. A concierge desk in the lobby will help you book snorkeling, jet ski tours, sunset cruises and more. Some of those services are provided from Stock Island in fact.

On the other end of the scale in terms of accommodations, the only campgrounds in Key West are also located on Stock Island: Boyd’s and Leo’s. We’ve heard good things about Boyd’s, which has a large waterfront property. (Like everything else Key West; camping here is not cheap.)

Is Stock Island the authentic Key West we’ve lost to tourism?

Nah. I was prepared to write that version of the story, but, while cool, Stock Island doesn’t compare to Key West.

It’s a fun place to discover an out-of-the way restaurant. It offers an appealing resort experience in accommodations. I hope Stock Island continues to host artists and entrepreneurs (without forcing out the working class residents, if that’s even possible). It is on track to continue developing into a destination.

But Key West, with its architecture, history and quirks? It took 200 years to develop, and though it’s at risk of outpricing itself and squeezing out its unique character with overdevelopment, it’s still an incomparable place.

Resources for planning a trip to Stock Island and Key West:

• When you head home from Stock Island, consider picking up fresh fish at an outstanding fish market, Fishbusterz. Fishbusterz Fisheries, 6406 Maloney Ave., Stock Island, is the largest wholesale fishery in Florida.
• Key West is less crowded (and more enjoyable) when cruise ships are not in town. Check the cruise ship calendar when making your plans. (In general, cruise ships seem to skip Wednesdays more than most other days.)
• Here’s a Florida Rambler guide to finding hotels and restaurants in Key West for the budget-minded.
• Free things to do in Key West
• Overseas Highway Mile marker guide with dozens of stops to help make the most of your drive south.
• A great bike path if you’re staying in Stock Island or Key West
• Florida Keys wildlife: Places to see animals
• Tiki bars: Soak up the Keys atmosphere
• Top 10 restaurant stops on a roadtrip on the Overseas Highway
• Best beaches in the Florida Keys
• Shopping for authentic souvenirs in Key West