The Conch Republic isn’t just a nickname here. Key West floats at America’s southernmost point where the Atlantic meets the Gulf, historic Conch houses line narrow streets, and roosters roam freely like they own the place. 

This 2×4-mile island built its reputation on shipwreck salvaging and literary legends while evolving into a laid-back beach destination that surprises even frequent Florida visitors.

From Mallory Square’s nightly sunset celebration to the Hemingway Home’s six-toed cats, the island offers adventures without ever feeling overwhelming. 

If you’re snorkeling the coral reefs, bar-hopping down Duval Street, or simply watching Key West’s quirky characters pass by, this Florida Key delivers tropical paradise at an easy pace.

This guide breaks down the perfect Key West itinerary, whether for a quick weekend escape or a full week exploring the southernmost city.

Itinerary Summary

Planning your trip? Check out our guide on the best time to visit Key West for ideal weather and events before building your itinerary.

2 Days in Key West: 48 Hours Island Sprint

This fast-paced itinerary works for travelers driving through the Florida Keys or Miami visitors extending their trip. You’ll experience Key West’s most iconic moments without spreading yourself thin. Perfect for couples seeking romance or groups wanting maximum tropical vibes packed into one power weekend.

Day 1: Old Town and Duval Street

Morning: Start at the Southernmost Point buoy for photos marking just 90 miles to Cuba. Walk to the Hemingway Home and Museum for tours starting at 9 AM. The author’s former residence features six-toed cats, descendants of his original pets. The Spanish Colonial house and lush gardens capture old Key West character.

Lunch: Blue Heaven on Thomas Street serves Caribbean-inspired cuisine in a funky outdoor garden setting. Their shrimp and grits and lobster Benedict earn raves. Chickens and roosters wander the property freely.

Afternoon: Walk Duval Street exploring its mile of bars, shops, and galleries. Stop at the Key West Butterfly and Nature Conservatory for a climate-controlled butterfly habitat. Browse local galleries and grab Key lime pie at Kermit’s Key West Key Lime Shoppe. The tart-sweet pie represents authentic Florida Keys flavor.

Evening: Head to Mallory Square by 5:30 PM for the nightly sunset celebration. Street performers, artists, and crowds gather watching the sun sink into the Gulf. Dinner at Latitudes on Sunset Key requires a quick boat ride from the Westin dock. The island restaurant delivers upscale seafood with water views. Return to Duval for nightlife at Sloppy Joe’s or the Green Parrot.

Day 2: Water Adventures and History

Morning: Book a morning snorkel tour to the coral reefs. Multiple operators depart from the Historic Seaport, taking you to protected waters teeming with tropical fish and coral formations. The clear water and marine life create unforgettable underwater scenes. Tours typically run 3-4 hours, including equipment and instruction.

Lunch: Half Shell Raw Bar at the Historic Seaport serves fresh seafood in a casual waterfront setting. Their conch fritters and peel-and-eat shrimp represent classic Keys dining.

Afternoon: Visit Fort Zachary Taylor State Park for beach time and snorkeling right off the shore. The fort’s Civil War history interests history buffs, while the beach attracts swimmers and sunbathers. The underwater reef here rivals tour spots without the boat ride.

Evening: Final sunset from Smathers Beach, Key West’s longest stretch of sand. Dinner at Santiago’s Bodega for Spanish tapas, or El Meson de Pepe for Cuban cuisine. Toast your quick Key West escape with a mojito or rum runner.

Best Homes to Stay for a 2-Day Key West Trip:

3 Days in Key West: The Essential Island Weekend

Three days capture Key West’s essence perfectly for first-time visitors or groups celebrating special occasions. This itinerary balances water activities with cultural experiences, making it ideal for bachelorette parties, anniversaries, or friend reunions. You’ll experience the island’s unique character from historic sites to beach bars.

Day 1: Historic Key West

Morning: Breakfast at The Cafe for creative morning fare in a funky outdoor space. Tour the Harry S. Truman Little White House, where the president spent 175 days during his term. The guided tours reveal 1940s White House operations and Truman’s relaxed Key West visits.

Afternoon: Walk through the Key West Cemetery, where above-ground tombs and humorous epitaphs create quirky character. One famous marker reads “I Told You I Was Sick.” Continue to Fort East Martello Museum and Gardens, housing Robert the Doll, supposedly haunted. The Civil War fort’s towers provide elevated island views.

Lunch: Cuban Coffee Queen food truck serves authentic Cuban sandwiches and strong espresso. Multiple locations make it convenient for on-the-go eating.

Evening: Sunset from Mallory Square with street performers and artists. Dinner at Seven Fish, a tiny restaurant serving outstanding seafood with Asian influences. Their fish specials change daily based on fresh catches. Reservations are essential for this local favorite. End at Duval Street bars sampling Key West’s famous nightlife.

Day 2: Water World

Morning: Full-day sailing and snorkeling catamaran tour to the reef. These popular excursions include breakfast, lunch, unlimited drinks, and all snorkel gear. The calm morning seas make for comfortable sailing. Swimming with tropical fish and exploring coral formations creates highlight memories.

Afternoon: Your tour returns mid-afternoon. Relax at your rental’s pool or walk to the nearby beaches in Key West. The full day on the water delivers plenty of sun exposure and activity without additional planning.

Evening: Casual dinner at Garbo’s Grill food truck on Caroline Street. This tiny spot serves fish tacos and Cuban-Korean fusion dishes, earning a cult following. Simple picnic tables and friendly service capture Key West’s laid-back vibe. Walk Duval Street afterward for live music venues.

Day 3: Island Exploring

Morning: Rent bikes or scooters and explore the island independently. Key West’s compact 2×4-mile size makes biking perfect for getting around. Ride through residential neighborhoods, admiring Conch houses with their pastel colors and gingerbread trim. Stop at Higgs Beach for swimming.

Lunch: Grab lunch at B.O.’s Fish Wagon, another food truck institution serving grouper sandwiches and conch fritters since 1980.

Afternoon: Visit the Key West Aquarium, seeing local marine life including sharks, stingrays, and sea turtles. The touch tanks let you interact with sea creatures. Continue to the Shipwreck Museum, learning about Key West’s salvaging history through interactive exhibits and costumed guides.

Evening: Final sunset from Mallory Square, if you can’t get enough, or try Sunset Pier for bar atmosphere. Farewell dinner at Hot Tin Roof at Ocean Key Resort for waterfront fine dining. The rooftop views and fresh seafood menu suit celebration dinners. Toast three days in the Conch Republic.

Best Homes to Stay for a 3-Day Key West Weekend:

4 Days in Key West: The Balanced Island Explorer

Four days lets you dig deeper into Key West’s water activities while hitting cultural sites. This works perfectly for families with kids or groups wanting both adventure and beach relaxation. You’ll balance famous spots with local experiences that residents actually know.

Day 1: Downtown Deep Dive

Morning: Start at Blue Heaven for brunch in their famous garden setting. The fresh fruit pancakes and eggs Benedict fuel exploration. Walk to the Hemingway Home for morning tours before the heat intensifies. The house and gardens reveal the author’s Key West life from 1931-1939.

Afternoon: Explore Duval Street’s shops, galleries, and bars. Stop at the Key West Aloe factory store for locally-made skin products. Visit the Custom House Museum showcasing local art and history in a beautifully restored 1891 building.

Lunch: El Siboney serves authentic Cuban food in a no-frills setting off the tourist path. Their ropa vieja and moros y cristianos represent real Cuban home cooking.

Evening: Sunset sailboat cruise with Danger Charters or Fury Water Adventures. The two-hour sail includes champagne and snacks while watching the sunset from the water. Dinner afterward at Latitudes, requiring the Sunset Key ferry, or try the Cafe Sole for French-Caribbean fusion in an intimate setting.

Day 2: Reef and Beach Day

Morning: Book a morning dive or snorkel trip to Looe Key Reef, considered one of America’s best coral reefs. The pristine reef 7 miles offshore teems with tropical fish, sea turtles, and occasional dolphins. Dive shops offer both scuba and snorkel options for all experience levels.

Lunch: Pack lunch for the boat or grab food after returning to shore.

Afternoon: Spend the afternoon at Fort Zachary Taylor State Park. The beach here combines calm swimming with excellent snorkeling right off the sand. The Civil War fort provides historical interest when you need a beach break. Rent chairs and umbrellas or bring your own gear.

Evening: Dinner at Louie’s Backyard for upscale island dining on the water. The oceanfront deck and fresh seafood attract both tourists and locals celebrating special occasions. Their Key lime pie is legendary. End with drinks at the Green Parrot, Key West’s oldest bar with live music nightly.

Day 3: Day Trip to Dry Tortugas

Morning: Early ferry departure (typically 8 AM) to Dry Tortugas National Park. The 70-mile journey west takes 2.5 hours aboard a high-speed catamaran. The remote park encompasses Fort Jefferson, pristine beaches, and incredible snorkeling. The Civil War fort rises dramatically from the turquoise water.

Afternoon: Explore the fort’s hexagonal walls and chambers, snorkel the moat and nearby reefs, or simply relax on the beach. The park’s isolation means crystal-clear water and abundant marine life. Tours include breakfast, lunch, and all snorkel gear. The narrated boat ride provides Key’s history and marine life explanations.

Evening: Return to Key West around 5:30 PM, exhausted but amazed. A simple dinner near your rental or delivery lets you recover from the full day. The Dry Tortugas trip ranks as most visitors’ highlight despite requiring a full-day commitment.

Day 4: Local Life

Morning: Sleep in after yesterday’s early start. Leisurely breakfast at Harpoon Harry’s for waterfront casual dining. Rent kayaks or paddleboards, exploring the mangroves and backcountry waters. Several outfitters offer guided eco-tours explaining the ecosystem’s importance.

Lunch: Stock Island’s Matt’s Stock Island Kitchen serves creative New American cuisine at the Marina. The mahi-mahi and Key West pink shrimp showcase local seafood.

Afternoon: Visit the Key West Tropical Forest & Botanical Garden for native plants and butterflies in a quiet natural setting. Or tour the Key West Lighthouse, climbing 88 steps for panoramic island views. The keeper’s quarters museum explains lighthouse history.

Evening: Final sunset at Mallory Square, joining locals and tourists for the nightly ritual. Farewell dinner at Michaels Restaurant for an upscale American steakhouse, or Salute! on the Beach for Italian cuisine with sand-in-your-toes dining. Toast four days knowing you’ve experienced Key West beyond the Duval Street party scene.

Best Homes to Stay for a 4-Day Key West Trip:

5 Days in Key West: The Complete First-Timer’s Journey

Five days reveal Key West beyond the postcards and give time to appreciate why people move here for the lifestyle. Perfect for families planning vacations or couples wanting a thorough exploration without rushing. This pace lets you experience the island’s full range from water sports to lazy beach afternoons.

Day 1: Island Orientation

Morning: Conch Tour Train or Old Town Trolley provides narrated tours explaining Key West history and pointing out major sites. The 90-minute tours offer hop-on-hop-off convenience, making them perfect orientation tools. Learn about wreckers, Hemingway, and the Conch Republic’s quirky independence.

Lunch: Stop at DJ’s Clam Shack in the Historic Seaport for clam chowder and seafood baskets in a waterfront setting.

Afternoon: Walk Duval Street end-to-end, exploring its full mile. Browse galleries showing local artists’ work, including tropical paintings and photography. Stop at Fast Buck Freddie’s for Key West souvenirs and gifts. The historic building houses quirky merchandise across multiple themed rooms.

Evening: Sunset from Mallory Square, experiencing the nightly celebration. Dinner at Pier House Resort’s Chart Room Bar for casual waterfront dining, or Bagatelle for romantic fine dining in a Victorian house. End with a ghost tour learning about Key West’s haunted history and colorful characters.

Day 2: Hemingway and History

Morning: Start at the Hemingway Home before crowds arrive. The guided tours run continuously throughout the day, but mornings offer cooler temperatures and smaller groups. The house, writing studio, and gardens capture 1930s Key West when the author lived and worked here.

Lunch: Thirsty Mermaid on Caroline Street serves tacos and fresh seafood in a funky outdoor space with swings at the bar.

Afternoon: Visit the Harry S. Truman Little White House, learning about the president’s Key West retreats. The preserved 1890 home shows how Truman conducted government business while vacationing. Continue to the Custom House Museum for rotating art exhibitions and local history displays.

Evening: Dinner at Azur Restaurant for Mediterranean-inspired cuisine in an elegant setting. Their fresh fish and creative preparations earn consistent praise. End at Sunset Pier for drinks with live music and water views.

Day 3: Water Adventures

Morning: Book a full-day sailing and snorkel catamaran to the reef. Multiple companies offer similar trips, including Fury, Sebago, and Danger Charters. The tours provide breakfast, lunch, unlimited drinks, and all equipment. Swimming with tropical fish and exploring coral formations creates unforgettable experiences.

Afternoon: Your tour returns mid-afternoon. Relax poolside or at the beach, letting the sun and rum drinks wear off. The full day on the water delivers plenty of activity and exposure.

Evening: Casual dinner at Pepe’s Cafe, Key West’s oldest restaurant since 1909. Their steaks and seafood in a historic setting attract locals and visitors. The outdoor garden and indoor dining rooms maintain an old Key West atmosphere. Walk off dinner, strolling residential streets, admiring Conch architecture.

Day 4: Dry Tortugas Expedition

Morning: Early departure for Dry Tortugas National Park aboard Yankee Freedom ferry. The 2.5-hour journey west reaches this remote park accessible only by boat or seaplane. The massive Fort Jefferson rises from turquoise water, creating dramatic views. The hexagonal fort covers 16 acres on Garden Key.

Afternoon: Explore the fort’s dark passageways and gun emplacements, snorkel the moat and nearby reefs teeming with fish, or relax on the pristine beach. The park’s isolation, 70 miles from Key West, means crystal-clear water and minimal crowds. Tours include breakfast, lunch, and snorkel gear.

Evening: Return to Key West around 5:30 PM. Simple dinner and early bed after the long day. The Dry Tortugas trip requires a full-day commitment but delivers once-in-a-lifetime experiences.

Day 5: Beach and Chill

Morning: Sleep in after yesterday’s adventure. Brunch at Banana Cafe for French crepes and Key West atmosphere. Spend the morning at Smathers Beach, the island’s longest stretch of sand. Rent jet skis, paddleboards, or beach chairs. The wide beach rarely feels crowded.

Lunch: Picnic on the beach with takeout from nearby restaurants or food trucks.

Afternoon: Kayak tour through the mangroves with Blue Planet Kayak or similar outfitter. The guided eco-tours explain the ecosystem while paddling through narrow channels. Wildlife sightings might include herons, ibis, and occasional sharks in shallow water.

Evening: Final sunset at Mallory Square or from your favorite discovered spot. Farewell dinner at Cafe Marquesa for upscale New American cuisine in an intimate setting. The seasonal menu highlights local ingredients with creative preparations. Toast five days knowing you’ve experienced Key West comprehensively.

Best Homes to Stay for a 5-Day Key West Adventure:

7 Days in Key West: Island Living Like a Local

A full week lets you settle into Key West’s rhythm, discovering why artists and escapists choose this tiny island despite hurricane risks and high costs. This itinerary works for remote workers, extended families, or water enthusiasts wanting complete immersion. You’ll have time to revisit favorite spots and venture to other Keys.

Days 1-5: Follow the 5-Day Itinerary

Start with the comprehensive five-day plan covering history, water adventures, and beaches. This foundation ensures you experience Key West’s essential character before exploring deeper.

Day 6: Keys Road Trip

Morning: Drive north through the Florida Keys on Overseas Highway (US 1). Stop at Bahia Honda State Park (Mile Marker 37) for stunning beaches and the old Bahia Honda Rail Bridge ruins. The park’s Sandspur Beach ranks among Florida’s best with turquoise water and soft sand.

Lunch: Grab lunch at No Name Pub on Big Pine Key. This dive bar serves pizza and burgers in an authentic Keys atmosphere that locals love.

Afternoon: Continue to John Pennekamp Coral Reef State Park in Key Largo (Mile Marker 102). The first underwater park in the US offers glass-bottom boat tours, snorkeling, and diving. The Christ of the Abyss underwater statue creates unique photo opportunities. Return south, stopping at various Mile Markers, exploring small Keys communities.

Evening: Back in Key West, dinner at Tavern N Town for upscale casual dining off Duval Street. The neighborhood restaurant serves creative American fare that locals frequent regularly.

Day 7: Your Choice Day

Morning: Sleep in, enjoying a leisurely breakfast at a favorite spot discovered during the week. Final morning activity at your preferred beach or attraction. Maybe it’s one more snorkel trip, paddleboard rental, or simply beach lounging with a book.

Afternoon: Last-minute shopping for Key lime products, rum, and local art. The Truman Annex neighborhood offers quieter browsing than Duval Street. Or bike residential streets photographing colorful Conch houses and roosters.

Lunch: Final meal at Blue Heaven, B.O.’s Fish Wagon, or your personal favorite.

Evening: Sunset from Mallory Square one last time, appreciating the nightly ritual. Splurge on a farewell dinner at Latitudes on Sunset Key or Cafe Marquesa. Toast seven days knowing you’ve experienced the Conch Republic beyond tourism. End with drinks at the Green Parrot or wherever live music calls you.

Best Homes to Stay for a 7-Day Key West Experience:

10 Days in Key West: Total Florida Keys Immersion

Ten days transform Key West from a destination to a temporary home. This extended stay suits digital nomads, sabbatical travelers, or anyone craving complete island immersion. You’ll establish routines, discover secret beaches, and venture across the Florida Keys, exploring the island chain comprehensively. 

Days 1-7: Follow the 7-Day Itinerary

Complete the week-long plan, ensuring comprehensive Key West coverage from historic sites to water adventures. By day seven, you’ll know your favorite restaurants and bars.

Day 8: Islamorada and Upper Keys

Morning: Drive to Islamorada (Mile Marker 80), the sportfishing capital. Visit Robbie’s Marina to feed tarpon from the dock. These massive fish swarm in feeding frenzies, creating exciting wildlife encounters. Continue to Windley Key Fossil Reef Geological State Park, exploring ancient coral formations.

Lunch: Lazy Days Restaurant in Islamorada serves waterfront seafood and island atmosphere.

Afternoon: Snorkel or dive at Molasses Reef, one of the Keys’ best coral reefs. Several dive shops in Islamorada offer trips to multiple reef sites. The clear water and abundant marine life rival Key West’s spots. Return stopping at various viewpoints and beaches along Overseas Highway.

Evening: Back in Key West, casual dinner near the rental or simple takeout after a full driving day.

Day 9: Marathon and Middle Keys

Morning: Drive to Marathon (Mile Marker 50), visiting the Turtle Hospital. This rehabilitation facility rescues and treats injured sea turtles. Guided tours explain conservation efforts and let you see patients recovering. The educational tours run four times daily by reservation.

Afternoon: Continue to Sombrero Beach, Marathon’s beautiful public beach with palm trees and calm water. The reef offshore provides excellent snorkeling right from the beach. Or visit Crane Point Museum and Nature Center, exploring hardwood hammock trails and a butterfly garden.

Lunch: Keys Fisheries in Marathon serves dockside seafood, including their famous lobster reuben.

Evening: Return to Key West for the final night. Dinner at your absolute favorite spot discovered during ten days, or splurge at Seven Fish or Cafe Sole one more time. Reflect on ten days knowing you’ve experienced the Keys beyond typical tourism.

Day 10: Favorite Spots and Farewell

Morning: Return to favorite breakfast spot for final Key West morning. Maybe it’s Blue Heaven’s chickens, Cuban Coffee Queen’s espresso, or somewhere you discovered independently. Final beach time at Fort Zachary Taylor or Smathers Beach, soaking in the tropical atmosphere.

Lunch: Last Key lime pie at Kermit’s or your preferred shop. You’ve earned strong opinions about Key West’s signature dessert.

Afternoon: Last-minute exploring or souvenir shopping. Duval Street shops offer everything from tacky t-shirts to fine art. Or simply sit at Mallory Square watching the world pass by, appreciating the laid-back island pace.

Evening: Sunset from Mallory Square or your personal favorite spot. Farewell dinner at Louie’s Backyard, Latitudes, or Cafe Marquesa, depending on celebration level and budget. Toast ten days knowing you’ve truly experienced the Conch Republic beyond the party reputation.

Best Homes to Stay for a 10-Day Key West Immersion:

If You Have Extra Time

If you have extra time or are looking for other things to do in Key West, consider exploring these places to make your trip even more memorable.

Day Trips Beyond Key West

Everglades National Park: Two hours north, this UNESCO World Heritage Site protects sawgrass marshes and mangrove forests. Airboat tours show alligators and wading birds in their natural habitat. The park’s unique ecosystem contrasts dramatically with the Keys’ island character.

Miami: Three hours north via Overseas Highway, Miami offers an urban contrast to Key West’s small-town vibe. South Beach’s Art Deco district, Wynwood’s street art, and Little Havana’s Cuban culture make for worthy day trips.

Key Largo: One hour north (Mile Marker 100), this largest Florida Key features John Pennekamp Coral Reef State Park. The underwater preserve offers outstanding snorkeling and diving with glass-bottom boat tours for non-swimmers.

Hidden Key West Gems

Key West Cemetery: The above-ground tombs and humorous epitaphs create quirky character. Self-guided walking reveals interesting residents and funny markers like “I Told You I Was Sick.” Free to explore daily.

Fort East Martello: This Civil War fort houses museums, gardens, and Robert the Haunted Doll. The towers provide elevated island views that tourists miss. Admission benefits the Key West Art & Historical Society.

The Key West Butterfly and Nature Conservatory: Climate-controlled habitat houses hundreds of butterflies from around the world. The peaceful garden with a waterfall provides an escape from Duval Street energy. Birds and flowers add to the tropical atmosphere.

Not sure where to stay? Check out our curated lists of top Airbnbs in Key West for neighborhood-specific recommendations.

Getting Around Key West

Key West’s compact 2×4-mile size makes getting around easy compared to mainland cities. Most visitors walk, bike, or use scooters to explore the island. Understanding transportation options helps maximize beach time while minimizing hassle.

Biking and Scooters: The flat terrain and short distances make biking perfect for Key West exploring. Dozens of rental shops offer beach cruisers, electric bikes, and scooters. Expect $15-25 daily for bikes, $35-60 for scooters. Bike lanes on major streets provide some protection from cars. Lock bikes securely as theft occurs.

Walking: Old Town’s compact layout makes walking viable for most attractions. Duval Street stretches one mile from the Gulf to the Atlantic side. However, August heat and afternoon thunderstorms make walking challenging. Distances to outlying areas like Smathers Beach or Fort Zachary Taylor require wheels or rides.

Rental Cars: Not necessary for Key West proper, but useful for Keys road trips. Limited parking and one-way streets make cars more hassle than help on the island. If driving from Miami, consider returning the rental at Key West Airport and exploring the island car-free.

Taxis and Rideshare: Taxis wait at major hotels and can be hailed on Duval Street. Uber and Lyft operate with decent availability. Expect $8-15 for cross-island trips. However, short distances often make walking or biking faster during high traffic times.

Pedicabs: Bicycle taxis cruise Duval Street, offering rides. Negotiate prices before riding, as no meters exist. These work well for short trips when feet hurt from walking.

Where to Stay in Key West

Choosing the right home base shapes your entire Key West experience. AvantStay offers premium vacation rentals across the island’s best locations. From Old Town historic homes to beachside condos, our curated collection positions you perfectly for exploring the Conch Republic.

Why Choose AvantStay

Unlike traditional vacation rentals, AvantStay properties are professionally managed with consistent quality standards. Every home features thoughtful design, high-end furnishings, and modern amenities, making your stay comfortable and memorable. 

Our Key West homes span from central Old Town to quieter residential neighborhoods, ensuring you’re positioned for whatever Key West experience you’re seeking.

Concierge Services and Upgrades

AvantStay’s personal concierge service elevates your vacation beyond simple accommodation. We handle the details so you can focus on experiencing Key West’s tropical magic.

  • Mid-Stay Cleaning: Keep your space fresh during extended stays, so you can relax without worrying about upkeep during your island adventure.
  • Bring Your Pets: AvantStay encourages time spent with loved ones, and pets are no exception. We offer pet-friendly properties where your furry family members are welcome.
  • Private Chef: Elevate your dining experience with a personal chef creating island-inspired cuisine featuring fresh seafood without restaurant waits.
  • Stocked Fridge: Skip the grocery store hassle and let us handle the shopping. Send us your list or select from our curated packages featuring tropical fruits and local products.
  • Transportation: Need a ride to the airport, Dry Tortugas ferry, or Keys road trips? We arrange reliable transportation throughout your stay, exploring Key West stress-free.
  • Find Local Child Care: Traveling with kids, but want adults-only sunset sails? We help you find and hire local sitters with detailed profiles, references, and reviews.
  • In-Home Massage: Perfect after snorkeling and beach days, indulge in ultimate relaxation without leaving your rental with spa-quality treatments.
  • Rent Baby Gear: Traveling with a baby doesn’t mean packing your entire nursery. Rent cribs, strollers, car seats, beach toys, and more.

For other requests, rentals, or special occasion setups, our concierge team handles whatever makes your Key West vacation exceptional.

Book Through the AvantStay App

Download the AvantStay app to browse properties, manage bookings, and access concierge services all in one place. The app provides 24/7 support, check-in details, local recommendations, and direct messaging with our team.

Download via: AvantStay iOS Application

Download via: AvantStay Android Application

Essential Travel Tips

Before you dive into turquoise waters and explore Duval Street, a little preparation goes a long way to avoid mistakes for your Key West trip. These essential travel tips will help you feel at ease while having the best Key West experience.

Getting To and From Key West

Key West International Airport (EYW) sits on the island’s east side with direct flights from major cities, including Miami, Fort Lauderdale, Atlanta, and Charlotte. The small airport makes arrivals easy compared to mainland hubs. Most visitors either fly directly or drive the Overseas Highway from Miami or Fort Lauderdale.

Airport Transportation: The tiny airport sits 4 miles from Old Town. Taxis wait outside baggage claim, charging a flat $15-20 to downtown hotels. Uber and Lyft pick up outside arrivals with similar pricing. Several hotels offer free shuttle service. Rental cars are available, but unnecessary for island exploring unless planning Keys road trips.

Driving from Miami: The scenic 3.5-4 hour drive along Overseas Highway (US 1) crosses 42 bridges connecting the island chain. Stop at various Mile Markers, exploring different Keys. Book accommodation with parking, as street parking is limited downtown. Consider a one-way rental returning the car upon Key West arrival.

Ferry Service: Key West Express operates high-speed ferry from Fort Myers and Marco Island (seasonal). The boats carry passengers only, no vehicles. The scenic cruise takes 3.5 hours each way, making day trips possible, though overnight stays work better.

Packing for Key West

Year-Round Essentials: Reef-safe sunscreen (Key West bans harmful chemicals), swimsuits (bring multiple), flip-flops and water shoes, light breathable clothing, sun hat and sunglasses, and a light rain jacket for afternoon showers. Casual dress prevails even at nicer restaurants. Bring your own snorkel gear if you plan frequent reef trips.

Winter (December-March): Peak season brings perfect weather with 70-80°F days and minimal rain. Pack light layers for occasional cooler evenings. This is the driest season and the prime tourist time, meaning higher prices and crowded attractions. Book everything well ahead.

Summer (June-September): Hot and humid with 85-90°F temperatures and afternoon thunderstorms. Hurricane season runs from June through November, though direct hits are rare. Pack rain gear and prepare for sudden downpours. Rates drop significantly, making summer attractive for budget travelers who can handle the heat.

Spring/Fall (April-May, October-November): Shoulder seasons offer warm weather with fewer crowds. Occasional rain possible, but generally pleasant conditions. Spring brings spring breakers in March, while fall sees fewer tourists. These seasons balance good weather with reasonable prices.

Practical Key West Preparation

Island Time: Key West operates on a relaxed island schedule. Restaurants open late for breakfast, close between lunch and dinner, and stay open late for nightlife. Service can be slow but rarely rude. Embrace the pace rather than fighting it.

Roosters and Chickens: Feral chickens roam freely throughout Key West, protected by ordinance. They crow at all hours, not just dawn. Light sleepers should pack earplugs. Feeding chickens is illegal as it attracts them to areas and makes them aggressive.

Costs: Key West is expensive. Expect $20-35 for casual meals, $50-100 for nice dinners, $8-12 for beers, and $12-18 for cocktails. Attractions range from free beaches to $200 for Dry Tortugas trips. Groceries at local markets cost 30-50% more than mainland prices.

Reservations: Book popular restaurants like Blue Heaven, Latitudes, and Louie’s Backyard days or weeks ahead, especially for sunset times. Dry Tortugas ferry sells out during peak season. Snorkel tours and water activities book up quickly from November through April.

Hurricane Season: June through November brings hurricane risk, though Key West rarely receives direct hits. Monitor weather forecasts if visiting during this period. Most hotels and rentals offer hurricane evacuation policies. Mandatory evacuations happen occasionally when storms approach.

Reef Protection: Key West’s coral reefs are protected by law. Don’t touch, stand on, or remove coral or marine life. Use reef-safe sunscreen only, as harmful chemicals damage these fragile ecosystems. Violations result in hefty fines. Follow the snorkel and dive guides’ instructions carefully.

Water Safety: Strong currents exist at some beaches and snorkel sites. Always check conditions before entering water. Jellyfish appear seasonally. Watch for red flags indicating dangerous conditions. Never snorkel alone and stay aware of boat traffic when swimming.

More Questions About Your Key West Trip?

Planning a Florida Keys adventure involves countless details, and we’re here to help. Whether you need recommendations for family-friendly properties, locations near beaches, or homes with specific amenities, our team can answer questions and guide your booking process.

Contact us via:

  • Email: experience@avantstay.com
  • Phone: (833) 442-8268

Let the Conch Republic Welcome You

Turquoise water stretching to the horizon, roosters crowing at sunrise, that first bite of authentic Key lime pie. The sunset applause at Mallory Square, six-toed cats lounging at Hemingway’s, tropical fish darting through coral reefs like living rainbows.

The memories you create here will absolutely become the stories you’ll tell for years. Key West is the perfect place for beach lovers, snorkelers, history buffs, and adventurers seeking a tropical escape without leaving the United States.

Ready to book your stay? Browse our top vacation rentals in Key West today.

Leave a comment

Your email address will not be published. Required fields are marked *