Key West

Getting here is half the adventure. US-1, the Overseas Highway, threads through 42 bridges over 113 miles of sparkling water, with the ocean to your left and the Gulf to your right, until the road simply runs out. That's Key West!

Where to Stay	Beaches & water	Nature wildlife & snorkelling
Things to do for couples	Things to do for families	Eating & Drinking

Where to Stay: Hotels and B&Bs

Key West isn't cheap, but there's genuine range - from cute old-fashioned B&Bs and guesthouses to world-class resort properties right on the water. The most important thing especially at peak season is to book early, ideally up to a year in advance, and check on Trivago for possible bargains.

Mid-Range

Simonton Court is our go-to at Christmas time peak season when everything is quite expensive. It's a classic charming Key West Guest house, and generally quiet despite being in an excellent central location (short walk from Duval St). The selling point is that although there's not that many rooms (26 I think), it has several pools to choose from. We've only ever stayed in the Nanor house part, which is a charming old house in the Florida style, with a lovely wraparound porch. The drawback to it being an old house is old-house quirks such as slightly creaky plumbing!

Marquesa Hotel offers similar old-world charm with polished service and a gorgeous courtyard pool. For something a little more modern, The Marker Waterfront Resort is a newer property on the harbour with a lovely pool and great views, popular with families and couples alike.

Budget

Finding budget accommodation in Key West requires a bit of hunting, but it is possible. As well as checking Trivago well in advance, it's a good idea to check sites like Airbnb or Vrbo especially if you want a self-contained place for a family.

Truman Hotel looks like good value, reviews on TA are good, and the location is decent too only a 10-15 minute walk to the middle of Duval St.

Wicker Guesthouse looks to be cheap and the location is excellent, reviews are mixed though.

Key West Hostel & Seashell Motel is a perennial favourite among backpackers and solo travellers, with a fun social atmosphere and a genuinely central location.

Several small motels along North Roosevelt Boulevard offer basic, clean rooms at more accessible prices. Booking well in advance is essential, especially for stays between November and April.

Expensive

Ocean Key Resort & Spa sits right at the foot of Duval Street on the Gulf side, offering rooms with sweeping sunset views and a rooftop pool that feels like the edge of the world. The on-site Hot Tin Roof restaurant is excellent, and the location couldn't be better.

Margaritaville - big pools and beach access, but expensive and would need a short taxi/Uber ride into town, so not an ideal location

Southernmost Beach Resort - has access to a small-ish but nice beach, much better location than Margaitaville (15 min walk to centre of Duval St) but also expensive

Casa Marina Hilton Beach and The Reach Curio next door are both Hilton hotels with beach access, next to the Southernmost Beach Resort so also in a fairly good location for towna dn the small beach

Beaches & the Water

Key West isn't renowned for its beaches - if beaches are going to be a really important part of your trip then I'd recommend spending longer in beachside towns on the Gulf Coast, or at the gateway to the keys around Fort Lauderdale/Hollywood Beach area, or at stopoffs along the keys such as Bahia Honda and Sombrero Beach. The island is ringed by sea grass and shallow waters, which means the beaches are pleasant but modest. That said, there are some nice beaches here still:

Fort Zachary Taylor State Park is consistently rated the best beach on the island, and for good reason. The water is clearer here than anywhere else in Key West, the snorkelling just off the shore is genuinely good, and the park itself — centred on a Civil War-era brick fort — adds a fascinating layer to a beach day. Entrance fees are modest, parking is available, and it never gets quite as crowded as you might fear. Pack a picnic and make a full afternoon of it.

Smathers Beach is the longest stretch of sand on the island, running along South Roosevelt Boulevard. It's more of a locals' scene - volleyball nets, jet ski rentals, food trucks pulling up in the afternoon — and it has a lively, unpretentious energy. Sunrises here are spectacular. Higgs Beach (officially C.B. Harvey Rest Beach) is another good option, with calmer waters, picnic facilities, and the lovely White Street Pier stretching out into the Atlantic.

Nature, Wildlife & Snorkelling

This is where Key West truly earns its keep. The waters surrounding the Keys sit above the only living coral barrier reef in the continental United States, and the marine life is extraordinary.

Snorkelling & Diving

The reef lies roughly five to seven miles offshore and requires a boat to reach, but that journey is entirely worth making. John Pennekamp Coral Reef State Park is technically up the Keys in Key Largo, but it's the most famous reef access point in Florida — if you're spending time in the Keys more broadly, it's unmissable. Closer to Key West, numerous operators run daily snorkel trips to the reef, typically lasting three to four hours. Expect to see brain coral, elkhorn formations, sergeant major fish, parrotfish, moray eels, and if you're lucky, sea turtles drifting lazily between the coral heads. Fury Water Adventures and Sebago Watersports both run well-regarded snorkel excursions from Key West's Historic Seaport.

For divers, the SS Vandenberg is one of the largest intentionally sunk vessels in the world, resting about 140 feet down and now covered in a riot of coral and fish life. More accessible wrecks sit in shallower water and are reachable by boat from the harbour.

The Dry Tortugas

About 70 miles west of Key West, accessible only by seaplane or high-speed ferry, the Dry Tortugas National Park is one of the most remote and remarkable places in the entire national park system. The centrepiece is the massive 19th-century Fort Jefferson, rising improbably from a tiny coral island. The surrounding waters are pristine and teeming with life - snorkelling directly off the beach here is among the best you'll find in North America, with visibility sometimes exceeding 100 feet. The Yankee Freedom III ferry departs Key West's harbour each morning and makes a full day of it; the seaplane option is quicker and even more dramatic, landing on the water beside the fort. Book either well in advance.

Wildlife Watching

Key West is prime territory for wildlife encounters beyond the reef. Kayaking through the backcountry mangroves on the Gulf side is a serene, almost otherworldly experience — the water is glassy and shallow, herons stalk the shallows, and manatees occasionally surface beside your boat. Several outfitters offer guided mangrove tours that double as ecology lessons.

The Key West Butterfly & Nature Conservatory is a lovely indoor garden filled with hundreds of free-flying butterflies and tropical birds - small but genuinely enchanting, and a welcome cool break on a hot afternoon. Meanwhile, the wild chickens that roam freely through every neighbourhood of Key West are as much a part of the wildlife as anything offshore. Nobody knows quite how they got here. Nobody seems to mind.

Things to Do for Couples

Key West has always been a romantic destination, and it earns that reputation honestly.

Start with sunset at Mallory Square. Every evening, the waterfront square transforms into a carnival of street performers, musicians, and vendors, and a crowd gathers to collectively watch the sun drop into the Gulf. It sounds touristy because it is — but it's also genuinely magical, and the shared ritual of it has a warmth that surprises you every time.

Rent a scooter or a bicycle and explore the back streets of Old Town. Away from Duval Street's bars and souvenir shops, the neighbourhood unfolds into quiet lanes lined with conch houses painted in pastel yellows, blues, and pinks, their porches draped in jasmine. This is the real Key West, and it rewards slow, aimless wandering.

For a romantic dinner, Louie's Backyard serves excellent modern American cuisine on a terrace literally built over the Atlantic. Cafe Marquesa in the hotel of the same name is intimate and beautifully executed. And for something more low-key, grab stone crab claws from Half Shell Raw Bar on the waterfront and eat them at a picnic table with cold beer — sometimes that's all romance needs to be.

A sunset sail is essentially mandatory. Fury Water Adventures and Sebago both offer booze cruises and quieter sailing options aboard traditional schooners. The schooner Western Union is a restored 1939 vessel that runs an evening sail with live music that ranks among the loveliest experiences in the Keys.

Things to Do for Families

Key West is more family-friendly than its party reputation might suggest, and children tend to love it.

The Key West Aquarium on Mallory Square is small but well done, and offers shark feeding demonstrations and touch tanks. It's been operating since 1934 and has a pleasingly old-fashioned charm alongside its solid educational content. Nearby, the Mel Fisher Maritime Museum tells the remarkable story of the treasure hunter who spent 16 years searching for a sunken Spanish galleon and eventually found $450 million in gold and silver. The actual artefacts are on display and genuinely stunning — kids find it captivating.

The Conch Tour Train and the similar Old Town Trolley offer narrated tours of the island that cover a huge amount of ground efficiently — a good way to orient the family on arrival. The Hemingway House is charming (and home to 50-odd polydactyl cats that children are obsessed with), though the literary significance is more for the adults.

For active families, the backcountry kayaking trips mentioned above are excellent with older children, and a snorkel trip to the reef is a formative experience for kids who've never encountered coral before. Glass-bottom boat tours are a lower-commitment option for younger children or nervous swimmers — you get the reef views without getting wet.

Eating & Drinking (Briefly)

DJs Clam Shack on Duval Street is one of our favourite places to get a Lobster Roll, it's quite expensive for a casual lunch, but the lobster roll is amazing!

For a romantic (albeit really expensive!) dinner, we love the Cafe Marquesa for a special treat-dinner night. Another really nice restaurant we've had good lunch/brunches at is

No guide to Key West is complete without mentioning Key lime pie, which is the island's signature dish — it should be yellow, not green, dense and tangy rather than sweet and fluffy. Try it at Kermit's Key West Key Lime Shoppe or the Blond Giraffe. Stone crab claws, in season from October to May, are the other unmissable local speciality. And on Duval Street, the legendary Sloppy Joe's Bar served Hemingway and still serves everyone else over 21 - it's loud, fun, and unapologetically touristy in the best possible way. They have a big stage and dance floor so seeing a band here is a good way to round off a Key West bar crawl.

Getting Around & Practical Tips

Key West's Old Town is small enough to walk almost everywhere, and the flat terrain makes cycling a genuine pleasure. Rent a cruiser bike for the week — you'll use it constantly. If you're driving in, be aware that parking is scarce and expensive; staying somewhere central and leaving the car is almost always the better strategy.

The best time to visit is November through April, when the humidity drops, the skies clear, and the temperature sits at a perfect 75–80°F. Summer is hot and humid, hurricane season runs June through November, and July through September sees the fewest visitors and some of the lowest hotel rates of the year.

One final thing: Key West operates on what locals call "island time." Clocks are technically present, but nobody pays them much attention. Things start late, end later, and the line between lunch and afternoon and evening blurs pleasantly. The best way to experience the place is to abandon your schedule and let the island set the pace. It knows what it's doing.