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Key West Travel Itinerary Guide
Travel guide: It’s all here in Key West — find out things to do, where to stay, when and where!`
Not Sure What To Do In Key West?
Don’t worry. Let us guide you.
Aerial View Of Key West In Florida
Key West, US is a captivating island city situated at the southernmost tip of the Florida Keys archipelago in the beautiful Florida Straits blue waters of the Atlantic Ocean. Featuring charming historic districts filled with pastel-colored conch architecture and towering palm trees, Key West entices visitors with its relaxing tropical ambience, stunning beaches, thrilling maritime activities, delectable seafood cuisine, and breathtaking sunsets over the Gulf of Mexico. Swaying coconut palms fringe the white coral sand beaches along the calm turquoise waters, perfect for swimming, snorkeling amidst coral reefs teeming with tropical fish, scuba diving around shipwrecks, kayaking through mangrove tunnels, or fishing for snapper, grouper, and marlin.
Paddle board across the clear shallow bays to secluded beaches, hop aboard a catamaran or glass-bottom boat to appreciate the marine life and golden sun dipping into the horizon. Let Journey Connected, your premier luxury travel agency, arrange the perfect Key West getaway, from booking you the ideal hotel to planning activities like snorkeling, sailing, and sunset cruises. With our expertise, your Key West vacation will be stress-free and incredible. Contact us today! Back on land, meander the palm-lined streets by foot, pedicab, or electric car, stopping into art galleries, quirky shops, coffee houses, and historic sites like the Little White House of President Harry S. Truman and Ernest Hemingway Home and Museum.
Catch a drag show on Duval Street, listen to live music at Sunset Pier, or watch buskers perform at the nightly Mallory Square sunset celebration. Indulge in the fresh catch of the day like Florida spiny lobster, crab, and shrimp or savor Key lime pie, the signature dessert of the islands. With its laid-back vibe, seaside activities, historic attractions, arts scene, dining, and stunning sunsets, Key West offers a one-of-a-kind tropical escape.
where to stay in Key West?
Discover our top picks for Key West hotels, a collection of our favorite hotels in Key West that we’re excited to share with you. Each hotel in Key West has been handpicked for a unique reason – whether it’s lavish amenities or unbeatable locations.
Ready to plan your Key West vacation? Connect with our Key West travel agency and get in touch with a travel artist who’s brimming with expert Key West advice on making your journey truly memorable. Your dream vacation in Key West awaits – let our savvy luxury travel advisors in Key West be your guide to a memorable Key West vacation.
If you’re looking for something different, use our exclusive partnership with booking.com to book hotels in Key West on your own, or get in touch with us to handle all of your hotel bookings in Key West for you! We are a full-service travel agency here to ensure your Key West vacation is memorable!
Looking For Top Budget Friendly Hotels in Key West?
Here are top 3 budget hotels as per Budget Traveler’s Choice.
Key West – This intimate adults-only boutique hotel is set in a beautifully restored circa 1800s Victorian-style Bahamian mansion right in the heart of historic Old Town Key West. Surrounded by swaying palms, hibiscus, and frangipani, it exudes tropical charm and offers an affordable island escape with complimentary gourmet continental breakfast served poolside daily. Unwind in the outdoor saltwater pool and jacuzzi tucked into lush gardens or enjoy a cocktail in the breezy veranda. Stylish rooms feature Caribbean-inspired décor, luxury linens, free Wi-Fi, and modern amenities. Walk to all major attractions like Ernest Hemingway Home, Key West Lighthouse Museum, Mallory Square, Duval Street bars and restaurants.
Marathon, Florida Keys – Nestled on 23 tropical acres in the Middle Keys, this laid-back resort features four swimming pools, hot tubs, shuffleboard, volleyball, free kayaks and paddle boards, on-site restaurant and bar, marina with fishing charters and water sports rentals, and free shuttle service to nearby beaches. Guest rooms offer private balconies, microwaves, mini-fridges, and a bright, island-inspired decor. Unwind under swaying palms at the large freeform outdoor pool and hot tub, get active with watersports at the private beach, or take the complimentary shuttle to beautiful Marathon beaches for swimming, seashell collecting, and memorable sunsets over the Gulf of Mexico. An affordable, family-friendly tropical escape.
Beachfront Hotel – Marathon, Florida Keys – Located directly on the pristine white sand beach in Marathon, this laid-back oceanfront hotel offers excellent value with spacious one and two bedroom suites featuring full kitchens, oceanview balconies, comfortable living rooms, and soothing tropical decor. Onsite amenities include a massive zero-entry lagoon pool, poolside tiki bar and restaurant, shaded beachfront cabanas, and complimentary use of bikes, kayaks, stand-up paddleboards, and fitness room. Start your day with a free continental breakfast then stroll the palm-fringed beach, snorkel the nearby coral reef, or watch a fiery sunset dip into the blue Gulf waters. An affordable, peaceful beachfront escape for couples and families.
Looking For Top Luxury Hotels in Key West?
Here are top 3 budget hotels as per Luxury Traveler’s Choice.
First opened in 1920, the iconic Casa Marina exudes historic elegance and romance. Situated oceanfront on over a mile of private beach, swaying palms fringe the enormous freeform pool shimmering in the Florida sunshine. Enjoy leisurely brunch on the sun-drenched terrace or cocktails in the lobby lounge under chandeliers and soaring arches. Rooms feature plush linens, white shutters, and marble-clad bathrooms, some with direct ocean views from the balcony. Indulge in coconut and honey-infused massages at the full-service spa set amidst lush gardens. Stroll the long stretches of sugar-white sand or bike to the nearby attractions of Old Town. With its grand architecture, indulgent amenities, pristine beach, and flawless service, Casa Marina envelops you in the most luxurious Key West escape.
Situated on a private island in the heart of vibrant Old Town Key West, this intimate adults-only boutique resort exudes romance and sophistication. Swaying palms fringe the outdoor saltwater pool while the full-service spa offers indulgent massages, facials, and body treatments. Enjoy sunset views over the Gulf of Mexico from the elegant seafood cuisine at Hot Tin Roof restaurant before retiring to modern yet cozy rooms featuring four-poster beds, private verandas, and jetted tubs. Stroll the resort’s lush gardens blooming with hibiscus and bougainvillea, then explore Key West’s top attractions like the Ernest Hemingway Home, Key West Lighthouse & Keeper’s Quarters Museum, and Mallory Square. Ocean Key provides couples with an intimate, luxurious island escape.
Built in 1875 as a private estate, this sophisticated adults-only historic hotel in Old Town Key West envelops guests in refined elegance and luxury. Lush tropical gardens blooming with orchids and bromeliads surround the intimate outdoor pool and veranda, while the on-site restaurant serves contemporary American cuisine with a Florida twist in a restored cigar factory. Luxurious rooms feature original artwork, plush linens, clawfoot soaking tubs, and four-poster beds draped in mosquito netting. Stroll the quiet tree-lined streets, relax poolside under the palms, then indulge in a rejuvenating spa treatment. With its historic architecture, lush gardens, and bespoke services, The Gardens Hotel offers a quintessential Key West luxury retreat.
where to eat in Key West?
Uncover the best restaurants in Key West. We have researched three of the best places to eat in Key West. These made our list for a number of reasons: they could have delicious food in Key West, be awesome Instagrammable restaurants in Key West, or be a high-end restaurant in Key West that can’t be missed!
Obviously, the culinary scene in Key West is second-to-none, and we can’t include all restaurants in this list so if you want other restaurant recommendations in Key West, contact one of our luxury travel artists (luxury travel advisors for Key West) to help plan your full vacation itinerary in Key West. We are a travel agency dedicated to providing memorable experiences in Key West.
Top three Restaurants in Key West: Journey Connected Expert’s Choice
Set right on Key West Bight Marina with views of sailboats bobbing in the turquoise waters, this lively seafood restaurant captures the funky, laid-back vibe of the islands. The outdoor deck strung with neon lights and dotted with palms is perfect for sunset drinks and photos. Inside, colorful vintage license plates and nautical décor create a cheery setting for feasting on fresh Florida stone crab, lobster rolls, and seafood platters. Try their famous conch fritters, Key lime pie, island cocktails, and local craft beers. As the pink and orange sunset reflects on the water, this is one of Key West’s best spots for kicking back, enjoying ocean views, and capturing Instagram-worthy moments.
For an unforgettable fine dining experience with majestic views, book a sunset table at Latitudes, located oceanfront at Sunset Key Cottages. As you dine on creative dishes like crab cake eggs benedict, whole fried Florida snapper, and tropical fruit crepes, floor-to-ceiling windows perfectly frame the sunset over the Gulf of Mexico. Enjoy a champagne toast as the sky ignites in dazzling hues of orange, pink, and purple, then linger to appreciate the blanket of stars in the night sky. With its refined ambiance, impeccable service, and breathtaking sunset views, Latitudes offers one of Key West’s most magical dining experiences. A bucket list moment.
Located on lively Duval Street, this cheeky adults-only restaurant serves outrageously-named decadent desserts in flamboyant style. From the provocative logo to the bordello-esque interior, it’s designed for Instagram and entertaining photos. Indulge in their famous “signature dish,” the Better Than Sex dessert – a cookie shell filled with rich chocolate ganache, caramel, and whipped cream. Other naughty-named treats like the “Trip to Heaven” cheesecake keep guests amused. With live music and risqué entertainment from vibrant drag queen waitstaff, it’s the perfect spot for bachelorette parties, date nights, and groups seeking sweet indulgence with a side of laughter.
what to see in Key West?
Discover our top picks for city attractions and activities, a curated selection of our favorite experiences in city that we’re excited to share with you. Each one has been carefully chosen for its unique charm and cultural significance.
Ready to plan your city adventure? Connect with our experienced travel experts who are brimming with insider knowledge on making your journey truly unforgettable. Your dream vacation in city awaits – let our savvy city travel advisors be your guide to a memorable city holiday. As a trusted city Travel Agency, we’re here for you!
If you’re seeking something different, take advantage of our exclusive partnerships to book attractions and activities in city independently, or simply get in touch with us, and we’ll handle all of your city itinerary planning for you! These are the top five things to do in City. Use our travel concierge Key West to book a custom Key West itinerary for your next trip to Key West!
top things to do in Key West
Here are top three recommended activities by our travel experts
Key West, Florida
Embark on an exciting watersports adventure in the beautiful surroundings of Key West with the “Watersports Adventure with Lunch.” This full-day experience offers a thrilling day on the water and a delicious meal to refuel. Your day begins with a variety of watersports activities, including snorkeling, jet skiing, and parasailing. Dive into the crystal-clear waters and explore the vibrant marine life, or enjoy the adrenaline rush of jet skiing and parasailing, all while taking in the stunning Key West coastline. After your aquatic adventures, you’ll be treated to a scrumptious lunch, where you can savor a selection of island-inspired dishes. Recharge and relax as you recount the thrilling moments from your watersports activities. This watersports adventure with lunch promises an action-packed and satisfying day for adventure seekers, families, and anyone looking to make the most of their time in Key West. Whether you’re an experienced watersports enthusiast or a first-time adventurer, this experience ensures a memorable and exhilarating day in the Florida Keys.
from $179.95
Key West, Florida
Explore the enchanting island of Key West at your own pace with the “Key West Hop-On Hop-Off Trolley Tour.” This flexible and convenient tour allows you to discover the island’s highlights while enjoying the freedom to hop on and off at your preferred locations. Board the trolley at any of the conveniently located stops and embark on a delightful journey through the island. The trolley’s informative narration provides insights into Key West’s history, culture, and attractions. With the flexibility to hop on and off as you please, you can explore iconic landmarks like Mallory Square, the Southernmost Point, and the Hemingway House. Stroll through charming neighborhoods and discover hidden gems on your terms. Whether you’re a history buff, a beach lover, or a culture enthusiast, the “Key West Hop-On Hop-Off Trolley Tour” offers a versatile and engaging way to experience the island’s unique charm. Whether you’re a first-time visitor or a returning traveler, this tour ensures an enjoyable and personalized exploration of Key West.
from $55.60
Key West, Florida
Savor the breathtaking beauty of a Key West sunset with the “Key West Sunset Champagne and Appetizers Cruise.” This magical experience combines the serenity of the open sea, the thrill of a sunset, and delightful culinary offerings. As you set sail on the tranquil waters off Key West, you’ll be greeted by the warm hues of the setting sun, casting a golden glow over the sea. Raise a glass of champagne and toast to the beauty of the moment. Indulge in a delectable selection of appetizers, perfectly paired with your champagne. As you enjoy the savory treats and the refreshing sea breeze, you’ll feel the stress of the day melt away. With the soothing rhythm of the waves and the stunning sunset as your backdrop, this cruise promises a serene and romantic experience, ideal for couples or anyone seeking an unforgettable evening on the waters of Key West. Whether you’re a first-time visitor or a returning traveler, the “Key West Sunset Champagne and Appetizers Cruise” ensures a memorable and captivating sunset adventure.
from $92.95
Key West, Florida
Embrace the romance and tranquility of Key West’s sunset with the “Small Group Sunset Sail with Wine.” This intimate sailing experience offers the perfect setting for a memorable evening on the water. As you set sail on the open sea, the sun begins its descent, casting a warm and golden glow over the ocean. The small group atmosphere ensures an intimate and peaceful voyage. Sip on a selection of fine wines as you enjoy the gentle swaying of the boat and the company of like-minded travelers. The soothing sound of the waves provides the soundtrack for this picturesque journey. With the beauty of the sunset and the calming ambiance, this small group sunset sail promises a serene and romantic experience, making it an ideal choice for couples or anyone seeking a peaceful and memorable evening on the waters of Key West. Whether you’re a first-time visitor or a returning traveler, the “Small Group Sunset Sail with Wine” ensures a cherished and captivating sunset adventure.
from $133.89
Key West, Florida
Embark on the ultimate adventure in Key West with the “Key West’s Ultimate Sandbar Adventure with Kayak Tour.” This thrilling experience combines the joys of kayaking with the pleasures of a sandbar party, complete with beer and wine. Your day begins with a guided kayak tour, where you’ll paddle through the clear waters, surrounded by the stunning Key West scenery. Explore the natural beauty and marine life of the area. The highlight of the adventure is the sandbar party. Anchor at a remote sandbar, where you can enjoy refreshing beer and wine, play games, and soak up the sun. Swim in the crystal-clear waters and engage in water activities. With a mix of adventure and relaxation, this ultimate sandbar adventure promises an action-packed and fun-filled day for adventure seekers, groups of friends, or anyone looking to make the most of their time in Key West. Whether you’re an experienced kayaker or a first-timer, this experience ensures a memorable and exhilarating day in the Florida Keys.
from $40.00
You can book these things to do in Key West from Journey Connected Travel Agency in Key West, browse all Viator Key West attractions, or let one of our travel planners take care of the booking for you!
Key West transportation
Key West Ground Transportation and Key West Airport Shuttle Service
Whether you need a ride to the Key West airport or transportation after your flight, these are our recommendations for Key West airport shuttle service and airport cars that provide convenient and reliable ground transportation in Key West.
These Key West car services have drivers that will pick you and drive you directly to the airport terminal or hotel. These are the best Key West airport taxi and Uber services to get you to the airport in Key West on time with no stress. These Key West shuttle services and ‘transportation near me’ help avoid the hassle of parking and expensive parking fees; book these Key West airport shuttle service in advance.
Contact us today to schedule Key West airport shuttle near you and relax on your next trip or click the links below to book on your Key West airport transfers on your own.
plan a Key West vacation
Help Planning A Vacation to Key West With A Top Key West Travel Agency
Journey Connected proudly presents a free three-day Key West travel guide, meticulously curated to showcase the finest attractions in Key West and the best Key West experiences. Unveil the magic of one of the world’s most visited cities, exploring top landmarks in Key West and delving into hidden gems. Indulge in the Key West culinary scene with recommendations for the best restaurants in Key West, enhancing your journey through this enchanting destination.
From Key West in the summer to the festive allure of Key West in the winter, this guide captures Key West seasonal delights. Embark on a seamless adventure in one of the best cities to visit in the world, leaving no top things to see and do in Key West unexplored. Your vacation to Key West awaits – an epitome of the best places to visit in the world.
Use our Key West travel guide or contact our luxury travel agency Key West, and let us plan your next Key West vacation! If you’re looking for a great weekend trip, visitors can drive Atlanta to Key West or from many other nearby cities for a fantastic weekend in Key West!
Download our travel guide for planning a trip to Key West.
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Elevate your next journey with expert vacation planning that turns every trip into an unforgettable adventure! Stop wasting time and money—trust our professionals to book your travel and create the perfect, personalized itinerary just for you.
Tired of travel plans that fall short?
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Key West travel blogs
Enjoy our Key West Travel Blogs Full of Key West Travel Information
Our Key West travel blogs offer insider tips, inspiring stories, and helpful Key West advice to make your next vacation in Key West the best one yet. Written by our team of passionate Key West travel experts, our blogs cover a range of information about traveling in Key West and must-do activities in Key West. You’ll discover new places to explore in Key West and learn insider secrets about old favorites.
Our travel writers and Key West travel advisors provide detailed Key West guides with Key West recommendations on where to stay, what to do, where to eat, and how to get around in Key West. Whether you are an expert on Key West or just starting to plan your vacation to Key West, let our travel guides and blogs be a partner to you. You’ll find engaging articles, beautiful Key West photos, and practical information in our collection of fun and informative travel blogs. Reading our Key West blogs is the next best thing to being there yourself!
When you’re ready to plan your Key West vacation, contact one of our expert Key West travel advisors and let Journey Connected travel agency provide you a custom Key West travel itinerary for your vacation!
Key West FAQs
Frequently Asked Questions about Key West
The best month to visit Key West is typically March, as it offers the perfect balance of pleasant weather, fewer crowds, and vibrant events. However, the ideal time depends on your preferences. Here’s a seasonal guide:
Why March Stands Out
- Weather: Temperatures average in the comfortable mid-70s to 80s°F, with low humidity and minimal rain.
- Crowds: It’s post-peak season, so it’s less crowded compared to January and February.
- Events: March often features lively festivals like the Conch Republic Independence Celebration or spring break activities without being overwhelming.
Other Great Months to Visit
- December to April (Peak Season): Enjoy perfect weather and Key West’s vibrant social scene. It’s a great time for outdoor activities like snorkeling and kayaking, but expect higher prices and more crowds.
- May (Shoulder Season): Warm and less crowded, with temperatures climbing but before the humid summer months hit.
- October (Fantasy Fest): Key West’s iconic festival, with cooler weather returning and a lively, colorful atmosphere.
When to Avoid
- June to November: This is hurricane season, with the highest risk in September. While travel deals are enticing, it’s also the rainiest and most humid time of year.
Journey Connected can help you plan the perfect Key West getaway, whether you’re visiting in March for ideal weather or during one of its many festivals. As a full-service travel agency, we handle your travel bookings and create customized itineraries tailored to your interests, ensuring a seamless and unforgettable trip!
Three to four days is typically enough to enjoy the highlights of Key West while soaking in its laid-back island vibes. Here’s how you can structure your trip:
Day 1: Explore Old Town and Historic Sites
- Walk along Duval Street and visit the Ernest Hemingway Home and Museum.
- Snap a photo at the Southernmost Point marker.
- End the day with a sunset celebration at Mallory Square.
Day 2: Outdoor Adventures
- Spend the morning snorkeling or kayaking with a guided eco-tour.
- Visit Fort Zachary Taylor Historic State Park for a blend of history and beach time.
- Enjoy fresh seafood and live music at a local restaurant.
Day 3: Day Trips and Unique Experiences
- Take a day trip to Dry Tortugas National Park for snorkeling and exploring the historic Fort Jefferson.
- Alternatively, relax on Smathers Beach or go on a dolphin-watching tour.
Optional Day 4: Relax and Discover More
- Explore Key West Butterfly and Nature Conservatory or visit Harry S. Truman’s Little White House.
- Stroll through local art galleries and boutique shops in Old Town.
Journey Connected can craft a customized Key West itinerary to make the most of your time, whether you’re planning a quick weekend getaway or a longer island retreat. We handle all travel bookings, from accommodations and activities to transportation, ensuring your Key West adventure is seamless and unforgettable!
Miami is generally cheaper to stay in compared to Key West, though costs can vary depending on the season and type of accommodations you choose. Here’s a breakdown to help you decide:
Why Miami is Cheaper
Accommodation Options:
- Miami has a broader range of accommodations, from budget-friendly hotels and hostels to luxury resorts, allowing for more flexibility in pricing.
- Key West primarily offers mid-range to luxury hotels, boutique inns, and vacation rentals, which can be pricier due to limited availability.
Competition:
- Miami’s larger size and higher number of hotels create more competition, often leading to lower prices compared to Key West.
Accessibility:
- Miami is easier to reach by car, train, or flight, while Key West’s remoteness can add travel expenses, especially if flying directly into the island.
Key West Pricing
While Key West tends to be more expensive overall, it offers a unique charm with its island vibe, historic inns, and proximity to water activities. Prices are especially high during peak seasons like winter or during festivals such as Fantasy Fest.
When Each is Better
- Choose Miami: If you’re looking for a budget-friendly city with vibrant nightlife, beaches, and diverse attractions.
- Choose Key West: If you’re seeking a relaxed, tropical getaway with an intimate, small-town feel and unique island experiences.
Journey Connected can help you compare accommodations and create a customized itinerary for either destination. We handle all your travel bookings, ensuring you get the best value for your trip while enjoying a seamless and unforgettable experience in Miami, Key West, or both!
The cheapest months to visit Key West are typically September and October. During this off-peak season, accommodation rates and airfare are generally lower due to decreased tourist traffic. While you’ll benefit from fewer crowds and better deals, it’s important to note that these months fall within the Atlantic hurricane season (June to November), so there’s a higher chance of rain and potential storms.
If you’re willing to embrace the unpredictable weather, visiting during these months can offer significant savings and a more relaxed experience of the island’s attractions.
Journey Connected is here to help you make the most of your Key West getaway. As a full-service travel agency, we handle all your travel bookings and specialize in creating customized itineraries crafted by experts. We’ll help you find the best deals and ensure you’re well-prepared for your trip, so you can enjoy a seamless and memorable Key West experience!
Are you tired of travel plans that don’t live up to your dreams?
Elevate your next journey with expert vacation planning that turns every trip into an unforgettable adventure! Stop wasting time and money—trust our professionals to book your travel and create the perfect, personalized itinerary just for you.
Tired of travel plans that fall short?
Elevate your journey with expert, personalized vacation planning for an unforgettable adventure.
Download Free Key West Travel Guide
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