Explore Key West: Solo Cruisers, Couples and Families

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The motto of Key West is “One Human Family,” which underscores the laidback, come-as-you-are attitude of its locals. A melting pot of drifters and dreamers, artists and fishermen, restaurateurs and writers, there’s a poetry to its location as the southernmost point in the continental United States — the proverbial end of the road.

Key West is an exciting port to discover for friends, families, couples and solo travelers of all ages. While the island certainly has its beaches, they’re far from the main attraction; most of the excitement is found offshore by boat or throughout historic Old Town. The grid of palm-tree-lined streets flanked by charming conch cottages is easy to navigate by foot or bicycle, making it a dynamic port for exploration.

For Families

Conch Tour Train

Credit Conch Tour Train

The Conch Tour Train, located on Front Street, is an excellent way to gather your bunch and experience Key West in a fun and family-friendly manner. The Conch Tour Train traverses the island for an informative and entertaining introduction to Key West. This 90-minute tour includes three stops; you have the opportunity to hop on and hop off to explore sites like The Ernest Hemingway Home & Museum, the Key West Lighthouse and the Key West Butterfly & Nature Conservatory.

Glass Bottom Boat

Credit Fury Water Adventures

For those traveling with young children or older adults, the Pride of Key West glass bottom boat is a great way for a multi-generational family to experience the coral reef in comfort without getting in the water. Enjoy an informative harbor tour and nature talk while glimpsing the world’s third-largest barrier reef through the boat’s “windows to the sea.” This two-hour tour serves snacks and beverages and allows you to enjoy the sights from both outside decks and inside the air-conditioned cabin.

For Couples

Day Pass at Southernmost House

Credit Florida Keys News Bureau

Located just a block from the Southernmost Point Buoy, The Southernmost House (1400 Duval St.) is one of Key West’s most eye-catching Victorian mansions. Painted in sea foam green and conch shell pink, today the historic building is a boutique bed and breakfast with a zero-entry pool overlooking the Atlantic Ocean and hammocks strung between palm trees. Non-hotel guests can purchase a $10 guest pass to enjoy the pool, and the price includes one cocktail from the bar.

Lunch at Conch Republic Seafood Company

Credit Conch Republic Seafood Company

Share conch fritters and a blackened grouper sandwich at this open-air bar and restaurant overlooking the Historic Seaport. Conch Republic Seafood Company (631 Greene St.) is a laidback and idyllic spot to pause for a moment and take in the salty charm of Key West. There’s a large wraparound bar, a saltwater aquarium and, often, live music. Don’t forget to toast with margaritas or a rum punch.

For Friends

Key Lime Bike Tour

Credit Key Lime Bike Tour

Get the lay of the land on two wheels with the hilarious and wacky Key Lime Bike Tour. You’ll hit all the highlights on this entertaining guided tour, taking you past Jimmy Buffett’s old haunts, Mallory Square, the Hemingway Home and the Historic Seaport. Of course, you can’t leave the island without a photo op by the Southernmost Point Buoy. This tour is a great way to see a little more of the island than you would on foot.

Brewery Tour

Credit Waterfront Brewery

Day drinking is an art in Key West, and a great way to experience the island’s local offerings is on a self-guided brewery tour. Start with the newly opened The Waterfront Brewery (201 William St.) on the Historic Seaport and opt for a flight of their locally brewed beers, ranging from the light and refreshing Crazy Lady ale to the Fat Albert milk stout.

A few blocks away on Caroline Street, you’ll find Kelly’s Caribbean Bar/Grill & Brewery (301 Whitehead St.), where you can sip their Southern Clipper Wheat beer or Havana Red ale. Just down the block at The Porch (429 Caroline St.) is a craft beer bar loved by locals with 18 beers on tap and more than 50 by the bottle. Named for its spacious front porch, it’s a great place to waste the day away with some sudsy cold ones.

For Solo Cruisers

Key West Cemetery

Credit Key West Cemetery

We realize this sounds a bit creepy and odd, but we promise it’s well worth it. Located smack dab in the middle of Old Town, The Key West Cemetery is an intriguing attraction. The 19-acre cemetery was established in 1847 near Solares Hill, the highest elevation on the island, just slightly above sea level. Many of the 100,000 bodies buried here are interred in graves above ground because of the island’s low elevation and limestone bedrock. It characterizes the diversity of Key West’s population with historic Jewish and Catholic sections, as well as a memorial dedicated to the Cuban revolution. You’ll find a lot of hilarious headstones, with one headstone famously reading: “I told you I was sick.”

Explore Bahama Village

Credit Besame Mucho

For the cruiser in search of an off-the-beaten-path experience, head down to the historic Bahama Village on Petronia Street. Here, you’ll find Blue Heaven restaurant (729 Thomas St.), a sublime spot to enjoy lunch or a cocktail in its big backyard shaded by ships’ sails. There are also charming boutiques, such as Bésame Mucho (315 Petronia St.) and Wanderlust (310 Petronia St.), to pop into during your ramblings and pick out souvenirs from cute sundresses to luxe home goods.

For Older Adults

Hemingway House

Credit Florida Keys News Bureau

For history and literature buffs, the Hemingway Home (907 Whitehead St.) is a must. You can explore the home that Ernest Hemingway lived in during the 1930s with his second wife, Pauline. Check it out from the road or opt for a guided tour to glean all the juicy tidbits about this larger-than-life literary figure. You’ll explore his writing studio, lush gardens and meet descendants of his beloved six-toed cat, Snowball. There’s also a bookstore to purchase a copy of your favorite Hemingway novel — or a new one you’ve yet to tackle.

Historic Seaport


Enjoy a relaxing stroll along the Historic Seaport to get a taste of Old Key West. Take in the views of ship’s masts, mega yachts and fishing boats lining the marina. There are plenty of bars and restaurants (such as Schooner Wharf Bar, The Waterfront Brewery and Conch Republic Seafood) to choose from. So pick your favorite, then take a break with a cold beer, a fish sandwich or even a piece of Key lime pie while ships come and go.

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