Key West

Your Guide to a Key West Weekend

A Warm-Weather Destination for a Winter Vacation

Thinking about planning a vacation for warmer weather this winter? Consider heading to south of Miami to relax in the Florida Keys. Get inspired with this comprehensive weekend itinerary on what you should see and do when visiting Key West.  Whether it’s a family vacation during the holidays, a group trip to ring in the New Year, or a fun getaway to thaw out from those frigid temps – you’ll want to add this popular travel destination to your travel bucket list. 

Day 1

Many people fly direct to Key West, but the 4-hour drive from Miami shouldn’t be missed. The verdant, limestone islands that make up the Florida Keys are connected by the Overseas Highway, which soars over the Florida Straits. Ocean views. Are interrupted only by tangled mangroves, chic resorts and strips of quirky shops. Marking the end of the road and the southernmost point of the continental USA, Key West’s red, yellow and black buoy is on a terrace jutting into the ocean – it’s the city’s most photographed spot.

Key West's black, red and yellow buoy to mark the southernmost tip of the continental U.S.
most photographed spot - Key West's black, red and yellow buoy to mark the southernmost point of the continental United States. 

Closer to Cuba than it is to Miami, Key West flaunts its difference with pride. Nowhere is this more evident than at Kermit’s Key West key Lime Shoppe on Elizabeth Street, a short stroll from the southernmost point. The shop’s eponymous owner guards the entrance dressed head-to-toe in neon green and brandishing one of his pies. Inside, everything is based on sweet, zingy limes; from a chocolate-dipped pie on a stick to piquant chutney. Then, head around the corner to Key West Butterfly and Nature Conservatory, where 60-plus species of butterflies flutter like wisps of colorful crepe paper. The path weaves past trees, tropical blooms and succulents, while a strutting pair of Caribbean flamingos adds to the bizarre beauty of this tranquil spot.

Chocolate-dipped key lime pie on a stick from Kermit's Key Lime Pie Shoppe
kermit's key lime pie shoppe - Don't miss out on trying a chocolate-dipped key lime pie on a stick from this popular spot among both locals and tourists. 

The city’s beaches are worth an afternoon of exploring. Many are rocky, while the sandy curl of South Beach is a favorite with locals who swim or snorkel in the clear, shallow waters. For something more active, head to Smathers Beach. This stretch of sand has volleyball nets, watersports rentals and access to a network of cycle paths.

Smathers Beach
smathers beach

Key West is the nightlife hub of the Florida Keys, with most of the action centered around lively Duval Street. Fill up on shrimp and grits or stone crab (a local favorite) at Ocean Grill & Bar, before jostling for space at the popular Willie T’s. The Smallest Bar in Key West is tinier than a shed (as its name suggests) with 3 stools, and shelves crammed with bottles of spirits. For a better chance of a seat, head to Caroline Street to The Porch, a quirky bar tucked inside a Victorian mansion. 

Duval Street Nightlife
duval street nightlife

Day 2

The inevitable hangover can be fended off with a spicy Bloody Mary and eggs Benedict with crab or lobster in Blue Heaven’s leafy courtyard, which is dotted with whimsical sculptures. At this local hangout, in the lively Bahama Village district, it’s perfectly acceptable – if not expected – to order a massive slice of Key lime pie at any time during the day. This restaurant serves it with huge peaks of whipped cream.

Small shops and vendors in Bahama Village District, Key West
 Small shops in Key west's Bahama Village district

Discover the island’s active side by kayaking through the mangroves, spotting sea stars, jellyfish and turtles around the submerged, tangled roots of trees. You can also rent a stand-up paddle (SUP) board, remembering to duck in spots where the foliage thickens.

Woman kayaking
key west activities - In addition to surfing and stand-up paddle boarding, vacationers can embark on a kayaking adventure through Key West's mangroves to get an up-close view of the local marine life.  

Back on dry land, it’s time for an iconic taste of the Keys: conch or sea snail. Briny and slightly rubbery at first bite, these mollusks are so synonymous with the city that Key West declared itself independent ‘Conch Republic’ in 1982. The tongue-in-cheek secession was never official, yet residents celebrate their ‘independence’ with a festival each April. Nibble the sea snails in fritter form from the Conch Shack on Duval Street. 

Conch Fritters
Local Cuisine - While visiting Key West, go ahead and indulge in delicious local foods such as conch fritters.

Day 3

Spend the morning browsing the boutiques, antique stores and curio shops dotted along the city’s easily walkable streets. Pause to take in the eclectic architecture reflecting Bahamian, Cuban and Floridian influences.

Mallory Square colorful vendor stalls
vendor stall at Mallory Square

Head to the Ernest Hemingway Home and Museum. His grand, traditional house is crammed with original mahogany furniture and watercolors in ornate frames. Most striking, however, are the 6-toed cats roaming the leafy grounds. More than 50 of these curious creatures have the run of the estate, each descended from a pet given to Hemingway by a ship’s captain. Free-roaming creatures are a reoccurring theme in Key West. At any turn, you might spot a mother hen herding her chicks along the pavement, or see a rooster sauntering across the road. These are the city’s ‘gypsy chickens’, which have been running free since cock fighting was outlawed in the 1970s, and they’re protected by law. End the day at Mallory Square Dock for the Sunset Celebration. 

Crowd gathers on Mallory Square at sunset
sunset celebration - The perfect way to end the day in Key West is to witness the beautiful sunset as crowds converge on Mallory Square.

Crowds gather nightly to watch the sky swirl with shades of pink and amber before the sun sets. Live music, tarot card readers and food stalls add to the festival spirit. Anywhere else, these scenes would be associated with ta fiesta or special occasion; in Key West, it’s just another evening – and another excuse for a celebration. 

Street performer during Sunset Celebration in Key West
sunset celebration - Before and after the sun sets, street performers join in on the fun as they try to capture the locals and tourists attention at Mallory Square.

When you book your Key West vacation, remember that you always get value-added perks when you consult one of Vacation’s expert travel advisors. Stay at the Casa Marina Resort or The Reach, A Waldorf Astoria Resort – part of our SELECT Hotel & Resorts program – where you get perks, including a $100 food and beverage credit, complimentary buffet breakfast for 2 daily, an upgrade upon availability at the time of check-in, and more!

Looking to spend a long weekend in Key West? Let one of Vacation’s on-call travel experts match you with a travel advisor, who can customize the dream itinerary that you deserve.

Casa Marina Resort, Key West
casa Marina Resort in key west