One of the most scenic strolls in Key West — and a top freebie — is the harborwalk along Key West Bight, also known as the Historic Key West Seaport.
From picturesque schooners to hungry tarpon to historic exhibits to the best happy hour specials in town, the Historic Key West Seaport has plenty to offer a visitor.
Key West Seaport is your entryway to dozens of nautical adventures, too, including at least 20 sunset cruises, kayak and boat rentals , snorkeling and scuba outings, fishing charters and the wonderful day trip to Dry Tortugas National Park.
History of Key West Seaport
The Key West Seaport’s original name was Key West Bight. (A bight is a curve or bend in a shoreline or a loop in a rope.)
It first became an attraction to tourists in the 1940s for what we now find to be a rather sad reason – ships came here to unload boatloads of sea turtles for delivery to canning factories and people gathered to watch the spectacle.
The turtles – usually the rarer green turtles — were stacked on their backs and kept alive until they were butchered for processing. Shallow pens in the water called turtle crawls or kraals lined the seaport and canning factories hugged the waterfront.
The sea turtle population dwindled and finally sea turtles were protected in 1971. (Green turtles are still endangered species here.) What’s left of the turtle trade is the historic Turtle Kraals Restaurant and Bar on the site of the former Granday Turtle Cannery.
The best thing about the Turtle Kraals Restaurant? Its Tower Bar. This open-air roof bar has a spectacular unobstructed view of the harbor. It’s a great place to watch the sunset and see all the sunset cruises head out. Because it’s on the second floor, it’s easy to miss and thus folks feel like it’s their secret spot.
Three other enterprises kept the Key West seaport bustling during the 19th and 20th centuries – sponge fishing in the late 1800s (there were once 119 sponging vessels employing a thousand people); shrimping during the last half of the 20th Century (there were 500 shrimp boats pursuing “pink gold”) and commercial fishing.
In all cases, however, the story was the same: over-fishing, over-shrimping, over-sponging until supplies were nearly exhausted.
By 1992, turtle fishing and sponging were done and the remaining shrimping and commercial fishing boats had moved to cheaper harborage elsewhere in the Florida Keys.
Rather than allow the scenic harbor to decline into seediness or be taken over by a hotel or resort, the citizens agreed to have the city acquire it. Since then, Key West has preserved the flavor of the seaport, added historical markers and enhanced the walkway.
Highlights of Key West Seaport
The best way to experience the seaport is to wander and linger. The harborwalk is about a mile along the water from Whiting Street to Front Street.
A few things to look for:
- The Dry Tortugas and Key West Bight Interpretive Center is located at 240 Margaret St. It’s built on a dock over the water and operated by Yankee Freedom, the ferry to the Dry Tortugas.
The free exhibit opened in 2013 and while it’s tiny, there are a few things worth seeing. First, there is a huge scale model of Fort Jefferson at Dry Tortugas National Park. Just seeing this fort makes you want to hop on the ferry. (It is well worth the trip.) One wall of this museum tells the story of the Key West Bight with fascinating historic photos and information. You can see the whole place in 10 or 15 minutes.
Slow down and peer into the water. Huge tarpon hang out looking for handouts and manatees bob up occasionally. In front of Alonzo’s Oyster House at the foot of Front Street, tarpon are fed every day at 4 p.m.
Late in the afternoon when the fishing charters come back, it’s fun to see what they caught, watch workers filet the fish and fend off the ever-present pelicans.
- Happy hour in the harbor is widely celebrated and is a great bargain. We recommend Alonzo’s Oyster House, which has outdoor seating on the harbor and offers half priced drinks and appetizers from 5 to 6:30 p.m. every day. Their appetizer page includes clams and oysters, peel-and-eat shrimp, fish fingers as well as sides such as coleslaw and conch chowder. It’s easy to make this dinner, and it may be the best restaurant buy in Key West. Other harbor restaurants also have happy hour specials. Alonzo’s is at 700 Front St.
- Another popular half-price happy hour is at the Half Shell Raw Bar, 231 Margaret St. The Half Shell is iconic: worn-out bar stools, license-plate decor, a taxidermy sailfish on the wall. It’s such a clasics that country music’s Kenny Chesney used a photo of it for the cover art to the single, “When I See This Bar,” off the album, “Life on a Rock.” Yelpers rave about the seafood quality and happy hour prices.
- There are always beautiful and historic boats in the harbor, starting with Florida’s official flagship, the 1939 Schooner Western Union. The 130-foot Western Union was the last tall ship built in Key West, constructed to lay Western Union cable lines in the Caribbean. It’s gorgeous. It also takes visitors out on a variety of sunset sails and other cruises. It’s docked at William Street.
Another beauty is the schooner Hindu, a 79-foot sailboat built in 1925. Hindu has had four names and as many roles over the years, including serving in World War II cruising for U-boats. After coming to Key West, its owner lost the boat to bank foreclosure and it fell into disrepair. In 2011, William Rowan bought “Hindu” from the bank and began restoration work. Hindu offers sunset and daytime sails in the winter in Key West and heads to Provincetown in the summer.
Other tall ships include the two-masted Appledore Schooners II and V, which specialize in sunset cruises. Also, from November to April, you’ll see, America 2.0, which looks like an 1850s schooner, but is actually a recently built boat with an electric engine and carbon-fiber (not wooden) masts.
Key West sunset cruises
If you are interested in a sunset cruise (and it’s a great way to enjoy a sunset), shop around. There are many variations on the theme.
Some are “all you can drink” cruises . The pirate-themed Jolly II Rover schooner with its jaunty red sails is $35 and is BYOB. Some cruises are on historic sailboats with champagne. Others are on catamaran party boats that critics say look like giant toaster ovens. Some are party boats with DJs and dancing; others are small and quiet.
We were invited by Classic Harbor Line to take a sunset cruise on the Beacon, which looks like an antique 1920s rum runner but is actually a replica built in 2002. There’s a cash bar with cheap drinks (a big glass of wine in a plastic cup for $3 or beer for $1) and a singer/guitarist entertaining. The crew is friendly and works hard to find dolphin to view. Tickets are $39 each, which is on the lower price range for Key West sunset cruises.
Watch for promotions and discounts, though, as it is a competitive business.
Resources for a visit to Historic Key West Seaport:
- Official site of seaport
- Alonzo’s Oyster House
- Half Shell Raw Bar
- Dry Tortugas and Key West Bight Interpretive Center
Sunset cruises and other boat outings:
- Classic Harbor Line for Beacon and America 2.0
- Jolly II Rover schooner
- Sunset Watersports
FTC Disclosure of Material Connections: While there was no requirement of a positive review, the Beacon sunset cruise was arranged by Classic Harbor Line at no charge to me.
More things to do in Key West:
- Print out this mile marker guide to enhance your road trip to the Florida Keys.
- Key West is less crowded (and more enjoyable) when cruise ships are not in town. Check the cruise ship calendar when making your plans.
- Eight Key West restaurants for authentic local flavor (including some bargains!)
- Hogfish Grill: Where Key West residents go for fresh fish
- Free beaches in the Florida Keys
- Fort Zachary Taylor Historic State Park
- All about those Key West chickens
- Find peace at Key West Butterfly Conservatory
- Audubon House, a lovely refuge in Key West
- Historic Key West Cemetery is full of stories
- Dry Tortugas: Day trip and camping
Things to do in the Florida Keys:
- Florida Keys wildlife: Places to see animals
- Florida Rambler guide to the Lower Keys
- Feed the tarpon at Robbie’s Marina
- Tiki bars: Soak up the Keys atmosphere
- Biking or walking the Old Seven Mile Bridge
- Visit historic Pigeon Key in Marathon
- Kayak or canoe to historic Indian Key
- No Name Pub worth finding on Big Pine Key
Camping and lodging