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Key West Itineraries

Key West Itineraries

Key West Florida, USA Travel Guide

Time-Based Itineraries: 24-Hour Layover Highlights

Morning (Arrival to Midday): Arrive at Key West International Airport (EYW) and check into your accommodation, ideally in Old Town. Visit the Ernest Hemingway Home & Museum. For convenient booking, consider GetYourGuide.

Lunch: Try a classic Cuban sandwich and strong Cuban coffee at a local eatery like Five Brothers Grocery. Afternoon: Walk to the Southernmost Point Buoy for a photo. Relax and swim at Fort Zachary Taylor Historic State Park Beach.

Evening Activities & Farewell

  • Head to Mallory Square for the iconic Sunset Celebration, featuring street performers.
  • After sunset, enjoy dinner at a waterfront restaurant near the Historic Seaport.
  • End your day experiencing the lively atmosphere and live music on Duval Street.

Time-Based Itineraries Continued

From a weekend escape to a two-week deep dive, West offers diverse experiences.

Weekend Getaway 2-3 Days

Day 1: Old Town Immersion: Arrive, settle into your guesthouse. Spend the afternoon exploring Duval Street, the Hemingway Home, and climb the Key West Lighthouse. Attend Sunset Celebration at Mallory Square, followed by dinner.

Days 2 & 3 Activities

  • Day 2: Water and History: Morning snorkeling or dolphin watch tour. Afternoon choose between Fort Zachary Taylor Beach, Mel Fisher Maritime Museum, or Harry S. Truman Little White House. Enjoy fine dining.
  • Day 3: Leisure and Departure: Morning at Audubon House & Tropical Gardens or Key West Cemetery. Enjoy brunch.
  • Last-minute souvenir shopping or revisit a favorite spot before departing.
  • Travel planning Can be made easier with GetYourGuide.
This itinerary balances major attractions with leisure time.

One-Week Comprehensive Experience

Days 1-2: Old Town Immersion: Explore Duval Street, Hemingway House, Lighthouse, Truman Little White House, and Mel Fisher Maritime Museum. Enjoy nightlife and dining.

Mid to Late Week Adventures

  • Day 3: Water Adventures: Full day for snorkeling, diving, or deep-sea fishing.
  • Day 4: Island Exploration: Rent bicycles, visit Bahama Village, Key West Tropical Forest & Botanical Garden, Higgs Beach, White Street Pier.
  • Day 5: Dry Tortugas Excursion: Full-day trip by ferry or seaplane. Book well in advance.

One-Week Comprehensive Continued

Concluding days focus on relaxation and departure preparations.

Final Days in West

  • Day 6: Relaxation & Local Culture: Morning at Fort Zachary Taylor Beach. Afternoon for art galleries, a spa treatment, or a cooking class.
  • Evening enjoy a culinary tour or a special dinner.
  • Day 7: Departure: Enjoy a final Key West breakfast. Last-minute souvenir shopping before departing from EYW or driving north.
  • Full planning details for each day can be customized for your interests.

Two-Week In-Depth Exploration

Combine the one-week West itinerary with multi-day extensions to truly immerse yourself.

Expanded Itinerary

  • Spend 2-3 nights in Marathon or Islamorada for additional marine activities and state parks.
  • Consider a side trip to Everglades National Park on the mainland for 1-2 nights.
  • This allows for a deep dive into the natural and cultural history of the entire Florida Keys region.
  • Integrate this by driving up the Keys from West, giving great flexibility.

Long-Term Stay Recommendations

For stays of several weeks or months, a different approach to lodging and daily life makes sense.

Accommodation Choice

Consider booking a vacation rental with kitchen facilities for more space and cost savings on meals.

Local Immersion

Immerse yourself in the local pace of life. Explore community events and frequent local spots away from main tourist areas.

Daily Movement

Rely on bicycles or scooters for daily commuting, fully embracing the island lifestyle.

Flexibility is

These itineraries are suggestions; adapt them to your interests and pace. West's charm lies in its laid-back atmosphere.

Interest-Based Routes

Tailor your West experience based on your specific passions.

Historical and Heritage Focus

West is a rich past waiting to be uncovered through its many historical sites and museums.

Dive into History

  • Ernest Hemingway Home & Museum and Harry S. Truman Little White House.
  • West Lighthouse & Keeper's Quarters Museum, Custom House, and Oldest House Museum.
  • Walk through the West Cemetery, noting its unique epitaphs.
  • Explore Fort Zachary Taylor for both history and beach recreation.
A guided historical walking tour makes for insights.

Food and Culinary Experiences

West's food scene goes beyond just seafood, giving unique local flavors.

Taste of the Island

  • Embark on a Lime Pie tasting tour, sampling variations.
  • Enjoy fresh seafood at local fish shacks like Half Shell Raw Bar.
  • Experience authentic Cuban coffee and Cuban sandwiches.
  • Join a happy hour pub crawl on Duval Street.

Adventure and Outdoor Activities

For the active traveler, West is an outdoor playground with a focus on water-based fun.

Thrills and Nature

  • Rent a kayak or paddleboard to explore the serene mangrove channels.
  • Try parasailing or jet skiing for an adrenaline rush.
  • Explore Fort Zachary Taylor's beach and nature trails.
  • A full-day trip to Dry Tortugas National Park grants unparalleled snorkeling.
Remember sunscreen and hydration for all outdoor adventures!

Family-Friendly Itinerary

West is a destination for all ages, with many activities suited for families.

Fun for Everyone

  • Enjoy active beach days at Smathers Beach for swimming or Fort Zachary Taylor.
  • Visit the Mel Fisher Maritime Museum and West Aquarium.
  • Explore the West Butterfly and Nature Conservatory.
  • Take a fun ride on the Conch Tour Train or Old Town Trolley for an island overview.

Art and Architecture Emphasis

West's visual appeal lies in its unique buildings and art scene.

Visual Wonders

  • Take leisurely strolls through Old Town's side streets.
  • Visit the numerous art galleries scattered throughout the island.
  • Pay special attention to those featuring local artists like Harrison Gallery.
  • Check out local artists displaying work at Mallory Square during Sunset Celebration.

Spiritual and Wellness Journey

For those seeking peace and well-being, West offers tranquil spaces.

Finding Inner Calm

  • Participate in yoga classes offered at local studios.
  • Find peaceful moments for meditation at the West Tropical Forest.
  • Indulge in spa treatments for relaxation and rejuvenation.
  • Visit the AIDS Memorial at Higgs Beach for a solemn and moving experience.

Budget-Based Plans

Backpacker's Guide

Stay in hostels. Cook meals from groceries. Use buses, walk, or bike. Focus on free attractions like Mallory Square and public beaches.

Mid-Range Traveler's Itinerary

Guesthouse in Old Town. Mix casual with mid-range dining. Rent a scooter or bicycle. Enjoy one or two paid excursions like a snorkeling tour or museum visit.

Luxury Experience Plan

Luxury resort or private villa. Fine dining nightly. Private charters for fishing or sailing. High-end tours and a seaplane trip to Dry Tortugas.

Value-Focused Recommendations

Travel during the low season (summer/fall) for lower accommodation rates. Pack a Cooler with drinks and snacks. Look for combo tickets or passes for attractions.

Seasonal Specialties

West grants different experiences depending on the time of year, often tied to weather and events.

Summer/Winter Highlights

Each season in West holds unique benefits for visitors, from fewer crowds to ideal weather.

Seasonal Overview

  • Summer (June-August): Fewer crowds and lower prices. Very hot and humid, ideal for water activities.
  • Lobsterfest occurs in August, a popular local event for seafood lovers.
  • Winter (December-February): Ideal weather – cooler, drier, and less humid.
  • Perfect for outdoor exploration and enjoying the bustling streets.
Summer is generally the off-peak season, while winter draws the largest crowds.

Festival or Event-Centered Visits

West's calendar bursts with unique festivals and events throughout the year, drawing special interest.

Popular Annual Events

  • Fantasy Fest (October): A 10-day costuming and parade festival. Book accommodation months in advance.
  • Hemingway Days (July): Literary events, look-alike contests, and fishing tournaments celebrate Ernest Hemingway.
  • Lime Festival (July): Indulge in all things Key Lime, from pie-eating contests to culinary demonstrations.
  • Check the local events calendar for other smaller festivals and activities.

Off-Season Exploration Strategies

Traveling during the quieter months can yield benefits like fewer crowds and better rates.

Embracing Summer's Heat

  • Embrace the heat and humidity; focus activities around water to stay cool.
  • Grab lower prices and fewer crowds at attractions and restaurants.
  • Be ready for afternoon thunderstorms and track hurricane forecasts closely.

Local Specials and Quiet Charm

  • Many local businesses grant "locals' rates" or summer specials.
  • Enjoy a more relaxed, less crowded West.
  • Service staff might have more time for personalized interactions.

Maximizing Seasonal Fun

Aligning your trip with West's seasonal patterns makes for a more tailored and joyful visit.

Optimized Experiences

  • Check event calendars far in advance for major festivals to plan accordingly.
  • Pack according to the season's typical temperatures and humidity.
  • Factor in higher prices for accommodations and flights during peak winter season.
  • Off-season travel often comes with the added benefit of quieter beaches.

Weather-Specific Activities

Certain activities are best enjoyed when the weather cooperates, enhancing your overall experience.

Best Times for What

  • Windy conditions in spring are ideal for sailing and windsurfing.
  • Fishing charters have different target species depending on the month.
  • Beach days are possible year-round, but summer heat makes ocean dips more refreshing.
  • Birdwatching is especially rewarding during spring and fall migrations.

Hurricane Season Alert

Peak Period for Storms

Hurricane season runs from June 1 to November 30. September and October are typically the most active months. Travelers during this time should monitor weather forecasts closely.

Travel Insurance Advisable

Purchasing comprehensive travel insurance that includes coverage for weather-related disruptions or evacuations is very important during hurricane season.