Last updated: February 3, 2026

Our complete 2026 travel guide hub for a perfect Key West vacation whether your itinerary is 3 days or 7 (or longer!), we’ve got your trip planning for an amazing Key West getaway covered!

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In this Key West hub guide we’ve gathered everything you need to plan your trip: where to stay, what to do, the best tours, where to eat, how to get here, 3, 5, and 7 day sample itineraries, and all the insider tips we’ve learned along the way.

☀️Check out the great Vacation Outfits on Amazon that are budget-friendly and Key West ready! 🌸 

Why Key West Is Such a Magical Getaway

The first time my husband and I ventured to Key West was on a quick one-day cruise port stop, but even in that short and totally filled day we knew something was special about this unique gem and we knew it would be our second home! Key West is one of those rare destinations that feels both wonderfully familiar and entirely new each time you visit.

It’s hard to put your finger on just why Key West is so special, but the turquoise water, pastel cottages, amazing food, laid-back vibes, live music drifting from Duval St., and sunsets so dramatic you really can’t believe they are real are all part of the “why”. The spirit of Key West gets inside of you and makes you want to come back again and again! (and we have so many times!)

In this Key West hub guide we’ve gathered everything you need to plan your trip: where to stay, what to do, the best tours, where to eat, how to get here, and all the insider tips we’ve learned along the way.

Along with this “hub” guide, we have some other helpful Key West guides to help you plan:
– One Day in Key West Itinerary
– Best Food Trucks & Quick Bites in Key West
– Key West Hotel Review & Comparison
– Best Restaurants in Key West
– Key West Top Sunset Cruises Guide
– Art Deco Landmarks in Old Town
– Key West Lighthouse Sunset Experience Review

These guides pair perfectly with your Key West trip planning and help you build a personalized itinerary and even your own walking tour.

Where Is Key West & How Do You Get There?

If you’re wondering how to get to Key West, you’re not alone, it was one our top trip-planning questions before we went back for the first time.

Key West sits at the very end of the Florida Keys, closer to Cuba than Miami, which gives it that tropical, Caribbean-style charm.

Fly into Key West International Airport (EYW)

The fastest and easiest option. The newly expanded airport (EYW) is still small, easy to navigate, and really convenient. This is the best option for a quick weekend trip so that you can maximize your time in Key West. (You can also fly in, rent a car and drive back to Miami/Ft.Lauderdale to fly home)

Drive From Miami to Key West (approx. 3.5 hours)

We think it’s one of America’s most scenic road trips and an experience that should be on everyone’s bucket-list. Seeing all of the Keys leading down to Key West and stopping at state parks (like our favorite stop, Bahia Honda) to snorkel and kayak along the way is such a different and special experience as opposed to flying in directly to Key West.

We love driving in and most of the time for us direct flights to Miami are cheap so we fly there and rent a car. If it’s your first time visiting Key West this is the most beautiful and scenic option and we definitely recommend adding a few days to stay in Key Largo or Islamorada along the way.

Ferry from Fort Myers or Marco Island

A unique way to arrive and often quicker than driving. We haven’t tried this option yet, but it is on the list to do a Tampa weekend trip and extend it into Key West using the Key West Express ferry! It’s also a great option if you are a Florida local and want a quick way to get to Key West without having to fly or drive.

Cruise Ship Port Stop: Arriving on a Cruise Ship

If you’re arriving by cruise, check out our One Day Key West Guide designed for walkability and hitting the highlights in a port stop or for a day trip. If you only have a day you’ll definitely want more of Key West! I think we started planning our next trip on the same day as our port stop day the first time we experienced it.

How Many Days Do You Need in Key West?

Honestly? Any amount of time in Key West is better than none and we’ve tried every trip length., but it will depend on your vacation time available. Ideally, we think 5-7 days is the perfect trip length (although I’d do any length) because it gives you enough time to slow down a little and also do a day trip like Bahia Honda State Park or take the Yankee Freedom ferry to Dry Tortugas to snorkel.

1 Day

Perfect for cruise travelers or Miami weekenders: See our 1-Day Key West Itinerary for a walkable plan and free pdf Itinerary.

2–3 Days (Most Popular)

The ideal Key West long weekend: live music, great food, sunset cruises, and exploring Old Town. See our 3-day sample itinerary below.

4–5 Days

Enough time to slow down, explore Old Town deeper, enjoy tours, and do a day trip to a state park nearby. (See our free 5-day itinerary below)

7 Days

The dream trip! Plenty of time to relax, explore, and really get to know Key West as well as maybe a Dry Tortugas day trip. (Full downloadable 7-day itinerary included below.)

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Where to Stay in Key West

Key West hotels are famously limited and pricey, so choosing the right area matters for the best hotel experience. We prefer Old Town hotels for walkability and proximity to everything we love doing, but we also love staying a few days in New or Mid Town on some trips to save a little money or hotel points. The ability to walk to all of the great Old Town spots though is what you come for so look for a hotel in that area for at leas a few days of your trip.

Old Town vs. New Town

Old Town
✔ Walkable
✔ Historic charm
✔ Close to restaurants & bars
✔ Best for seeing it all and not having to drive

New Town
✔ More parking
✔ Slightly More affordable hotel options
✔ Quiet, spacious resorts

Our Best Key West Hotel Recommendations

We love so many of the hotel options in Key West, but there are a few that are at the top of our list when we plan a trip. Hotels in Old Town are generally a bit expensive, but there are also some great budget options that we’ve tried and using Hilton points or reward nights is the way to go for Casa Marina and The Reach resorts (see our Key West Hotel review guide for a comparison).

Hyatt Centric

Best for: couples, romantic escapes, being close to Mallory Square and the Historic Seaport. We use Hyatt points to stay at this amazing hotel when we can! We also always see lots of sea life there (and the resident turtles) and beautiful sunsets right off of the dock!
Charming grounds, amazing sunsets, great bar, snorkeling area right off dock, and boat/jet ski rentals right behind hotel. [Check Dates & Prices]

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Casa Marina Resort

Best for: beach lovers, spa experiences, amazing sunset views, updated luxurious rooms, 2 pools! This is our favorite hotel by far! We have always loved staying at this hotel. We usually use our yearly Hilton reward nights combined with points. They are one of the few Key West hotels that have a private beach too!
Private beach + incredible sunset views. [Check Dates & Prices]

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Blue Marlin

Best for: girls’ weekends, friends trips, easy parking spots, budget-friendly, amazing food truck right outside, free breakfast by the pool. We love booking here for a few nights even in high season because it is budget-friendly. It’s a great way to get a longer stay in Key West for less.
Great pool, great retro design, updated rooms, walkable location, updated rooms. [Check Dates & Prices]

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The Gardens Hotel

Best for: boutique luxury
Stunning tropical gardens with wine bar, garden cocktails, live music some nights, & attentive service. Even if you don’t stay here stop by to tour the gardens and enjoy some live music on the patio. [Check Dates & Prices]

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Orchid Key Inn

Best for: Art Deco charm and in the middle of the action, yet on the quiet side of Duval.
Lush tropical feel, free breakfast, parking. [Check Dates & Prices]

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Southernmost House Hotel

Best for: Historic Mansion with boutique feel on the quiet end of Duval next to the temporary location of the Southernmost Point buoy.
Luxe feel, great sunset views, free breakfast, parking, great pool. It’s also home to the best lobster pizza & mojito spot! [Check Dates & Prices]

* There are so many more great Old Town Key West hotels, but those are the ones we check first when we plan a trip.

Find more Details in our in-depth hotel reviews:
– Key West Hotel Review & Comparison
– Baker’s Cay Key Largo Review (for a Florida Keys road trip)

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Best Things to Do in Key West

This section targets our favorites list of the best things to do in key west, what to do in key west besides bars, and key west attractions and tours which are great for your first or any trip.

Take a Key West Sunset Cruise

This is the #1 must-do activity. You can experience a Key West sunset on a historic schooner, a tiki boat cruise, a catamaran cruise with music, or many other options that put you on the water with those amazing sunsets! We’ve done them all and a sunset cruise is a must for at least one day of a Key West trip (we’ve still not seen the elusive “green flash” yet!). You will catch most of them from the Seaport/harbor walk marina.
→ See our Best Key West Sunset Cruises Guide

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Explore Old Town Landmarks & Neighborhoods

Colorful pastel cottages, historic buildings, quirky yard decor, long-standing uniqueness. We love just walking around and looking at the charming Old Town houses and buildings. Key West has a unique blend of Caribbean influences with historic architecture (even Art Deco) and you really get a feel for it just walking around (or riding around on a cart/scooter) and enjoying the different neighborhoods.
→ See our Art Deco Landmarks walking guide

Visit the Key West Lighthouse

Beautiful Key West views + history. Make sure to check out the Sunset Experience at the Lighthouse. We have climbed the lighthouse and explored the keepers quarters many times, but the exclusive sunset experience was so special and unique! We’ve done it twice and love having it to only our group at the most magical time of day!

Explore Hemingway House Museum & Grounds

Hemingway House is a must-do and you will even meet the famous six-toed cats! Even if you’ve never read an Earnest Hemingway novel, the grounds are beautiful and there are guided tours you can join to hear the history of his time in Key West. We still walk through on trips, but the guided tour is best for a first-time visit. We like exploring at our own pace and saying hi to the kitties!

Relax at Fort Zachary Taylor Beach

We think it’s the best beach in Key West. Hanging out, snorkeling, and exploring the fort are definitely worth a few hours or half a day at Zachary Taylor State Park! It’s a bit of a walk so if you rent a bike or electric cart it is easier to get to, especially in hot summer months. You can also explore the fort while you are there. There are some great views from the top of the fort too!

Experience the Sunset Celebration at Mallory Square

This is a great free way to enjoy the famous daily sunset ritual and explore all of the vendors and fun around the square.

Go Snorkeling or take a Sandbar Tour

If you have time, spend the day soaking up the sun’s rays and snorkeling (like off of the beach at Zachary Taylor Park) or take a  key west snorkeling, sandbar tour. It’s a great way to see some ocean life and enjoy the warm weather in Key West.

Wander through Key West Butterfly Conservancy

We loved walking through the Butterfly Conservancy and seeing all of the colorful variations as well as the famous flamingos! The gift shop also has some really cute jewelry and other artistic things. It doesn’t take too long to walk through the butterfly garden, but it’s a nice break.

Climb the tower and explore Key West Shipwreck Museum

The Key West Shipwreck Museum is a quirky, but interesting stop! There are many treasures displayed from different shipwreck expeditions and the tower climb has a dark past, but amazing views!

Visit Lower Keys Beaches & Memorial

A short drive up Roosevelt will bring you to Higg’s Beach (visit the African memorial and cemetery there) and keep on a little further for Smathers Beach to get an ocean view and different perspective than Old Town. We went parasailing from Smathers Beach and it was the highlight of that trip! There’s also the West Martello Tower Gardens (see below) and an amazing restaurant, Saluté, which is the sister restaurant to Blue Heaven that is definitely worth a stop.

Explore West Martello Tower Gardens

Home to the Key West Garden Club, this amazing garden paradise transformed a former Civil War fort and made it a must-visit spot. There’s a great ocean view from the back gazebo area and wonderful garden pathways and viewpoints throughout. It’s also totally free, though any donations help the garden club maintain this gem!

Explore Truman’s Little White House Museum

We were surprised how much we enjoyed visiting the Truman Little White House Museum and seeing the time capsule furnishings and history from that time-period.

Tour Papa’s Pilar Rum Distillery and sample Key West spirits

We really loved our tour of the Hemingway Papa’s Pilar distillery and learned the whole process, but the best part was our tour guide reading Old Man and the Sea in the Library bar while we sampled cocktails made with Papa’s Pilar rums. We’ve done it twice and will probably do it again! Even if you don’t do a tour visit the bar and have a cocktail with the bronze Hemingway statue!

Unique and Off the Beaten Track things to see & do in Key West

• Garden of Eden (top of Bull & Whistle) – A clothing-optional rooftop bar on Duval 🫣
• Pirate’s Well – (411 Caroline St.) – Fun photo op if in the area.
• Key West Cemetery 9701 Passover Ln ) – Some unique grave markers and sayings on headstones.
• East Martello Tower (Robert the Doll) – 3501 S. Roosevelt. Art, and a haunted doll named, Robert. There are great views from the top of the tower!
• Find Horseshoe crabs in New Town Courtyard Marriott – There is a free boardwalk and you can see them come out at dusk! In warmer months we’ve seen bioluminescent plants under the shallow water too!
• Chart Room Bar – Tiny dive bar made famous by Jimmy Buffet’s musical start. It’s inside of Pier House Hotel at 1 Duval St.
• Vibrator Races for charity at Mary Ellen’s Bar 420 Applerouth Ln. This is a must-do if you are there on a Thursday! Bid on your favorite vibrator and if you win or donate over 100$ there’s a special task that you get to do! We loved this! Book early it fills up!
• Feed tarpon from Harbor Walk (outside of A & B Steakhouse) – You can buy food in the dispenser and feed them or just watch the fun, especially when fishermen are cleaning fish on the dock.
• Nancy Forrester’s Secret Garden – Parrot rescue and gardens that are worth a visit!

Where to Eat & Drink in Key West

Key West is a foodie haven with any type of food you crave! You can find the best Key Lime Pie at our favorite bakeries to amazing cortaditos at many Cuban cafés and waterfront seafood along the Historic Seaport. We have so many favorites that we broke it up into quick bites and food truck guides and the top restaurants in Old Town (links below).

Start with our Key West foodie guides:

– Best Restaurants in Key West
– Best Key West Food Trucks & Quick Bites

Where can you get the best Key Lime Pie in Key West?

We are a bit biased because our first taste of Key Lime Pie from Old Town Bakery was the best in our opinion! The gingersnaps in the crust make the difference for us. Other top places to find amazing Key Lime pie in Old Town are:

• Blue Heaven – Tall meringue and nice tart flavor/.
• Moondog Cafe & Bakery – Another tall and toasted meringue and milder flavor.
• Seaside Cafe at the Mansion – Unique piña colada take on Key Lime pie that we loved.
• Pepe’s Cafe – This is our second favorite and Pepe’s delivers on flavor!
• Kermit’s – We like the chocolate dipped key lime on a stick here.
• Two Friends Patio – Best Key Lime martinis (and great pie too).

Check out our YouTube video of some of the Key West highlights in Old Town:

Best Day Trips from Key West

• Ferry to Dry Tortugas National Park – We loved snorkeling in the beautiful waters there! You can also camp overnight if you have time.
• See the Key Deer (and keep your distance) in Big Pine Key then visit No Name Pub – We saw so many Key Deer on the way to the pub!
• Snorkel at Bahia Honda State Park – It’s a great place to snorkel, walk trails, and picnic.
• Visit Islamorada Bass Pro Shop – Climb aboard Hemingway’s boat inside the store then feed the tarpon behind it at Islamorada Fish Company or kayak at Robbie’s and feed more tarpons
• South Beach is only 3.5 hours away by car and definitely worth a day trip!

Best Time to Visit Key West (Weather, Crowds & Events)

Really, we think anytime is a great time to visit and we have visited in every season. Even during the most crowded times you can still find less crowded spots away from Duval Street.

Winter (Dec–Feb)

Perfect weather but highest prices (except first week of Dec). We love spending New Years in Key West though and have found it to be crowded, but fun.

Spring (Mar–May)

Balanced crowds, great temps, ideal for first-timers.

Summer (Jun–Aug)

Hot but fun, great water clarity, more affordable.

Fall (Sep–Nov)

Lower crowds (except Fantasy Fest week), sometimes best deals, but also sometimes hurricane season risk.

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Popular Key West Annual Events:

• Fantasy Fest – (October) You just have to experience it once to love it!
• Hemingway Days (July) – It’s fun to see all of the “Hemingways” in town and see the festivities.
• Sunset Festival (daily) – Mallory Square, Key West Lighthouse, Zachary Taylor Park Beach, or by boat!
• Key West Songwriters Fest (April/May) – Huge festival celebrating amazing songwriters.

Cheapest Time to Visit Key West (With Estimated Prices)

One of the biggest questions people ask us is: When is Key West the cheapest?

Here’s the breakdown:

⭐ Cheapest Months: August, September, early October (and first week of Dec)

Warm water, fewer crowds, and significantly lower hotel prices.

Average Nightly Price Ranges:

• Winter: $450–$650+
• Spring: $300–$500
• Early summer: $250–$400+
• Late summer: $180–$300 (best prices)
• Fall: $250–$400+
• Pre-holiday Nov–mid Dec: $300–$500 (except the sweet spot of the first week of December)

Best Budget Tips:

– Visit during shoulder or summer seasons for the best hotel prices
– Stay in New Town or nearby Keys (like Marathon) to save money
– Leverage hotel points or reward nights to save money on hotel stays.

⭐ Cheapest Months:

August, September, and early October (or first week of December)
– Lowest hotel prices of the year (except Fantasy Fest week)
– Warm water + good snorkeling
– Fewer crowds

3-Day Key West Sample Itinerary (Perfect for Long Weekends)

Old Town Classics + Sunset – Day 1

• Coffee (or our favorite cortadito) + breakfast at Cuban Coffee Queen or Ana’s Cuban Cafe
• Explore Old Town architecture and take a walk down Duval Street when it’s not too crazy.
• Visit the Key West Lighthouse and climb to the top
• Lunch at Sandy’s Original Cafe walk-up (get their famous Cuban sandwich)
• Swim or hang out at the beach in Fort Zachary Taylor State Park
• Sunset boat cruise on a schooner
• Dinner at First Flight or Garbo’s Grill + enjoy live music

Water Adventures + Walkable Exploring – Day 2

• Breakfast at Koffie House on Greene then early Snorkeling or sandbar tiki tour
• Lunch at B.O. Fish Wagon (best grouper sandwich) near the Historic Seaport then watch Tarpon feeding from the Harbor Walk (near A&B Restaurant)
• Walk toward south end via Duval or Simonton to Southernmost Point (Have a mojito at Southernmost Mansion)
• Visit Butterfly Conservatory
• Hemingway House Museum, have a drink at Papa’s Pilar Rum Distillery, then on to the Mallory Square Sunset Celebration
• Dinner at Two Friends Patio in Old Town near Mallory Square

Relax + Local Favorites – Day 3

• Slow breakfast at Four Marlins Cafe overlooking The Reach Resort beach and pier.
• Bike ride through Truman Annex and visit Truman Little White House Museum
• Visit Key West Garden Club at West Martello Tower and explore Higg’s Beach and memorial
• Lunch at The Key West Lobster Shack for the best lobster rolls ever!
• More exploring at your own pace and discovering your own hidden gems
• Dinner at Blue Heaven in Bahama Village with live music and amazing Key Lime pie
• Another amazing Key West Sunset then head home

Free: 5 and 7-Day Key West Sample Itineraries

If you have a bit longer to explore Key West, feel free to use these sample itineraries to help you plan your trip. No email signup required!

PDF

Download the 5-Day Key West Itinerary

Perfect for a longer weekend or relaxed Key West getaway: beaches, food, Old Town highlights, and sunset moments.

Tap the itinerary preview to open • Printable & mobile-friendly

PDF

Download the 7-Day Key West Itinerary

The full Key West conch experience: Dry Tortugas Day trip, snorkeling or sandbar tours, food tours, and unforgettable sunsets.

Tap the itinerary preview to open • Great for trip planning

Key West Packing List – This is what we bring on each trip

• Reef-safe sunscreen – [Amazon] travel size
• Breathable clothing – We love wearing outfits like this cute v-neck dress on Amazon!
• Sandals + walking shoes – Our favorites are Birkenstock Gizeh sandals.
• Water shoes – These are our favorites because they pack well and are budget-friendly [Amazon]
• Snorkel gear – You can rent or bring your own, but I wouldn’t pack fins unless you have a ton of room.
• Sun hat – We love this one on Amazon because it packs well and keeps our hair off of our shoulders.
• Waterproof phone case – [Amazon] Keeps your phone with you in the water.
• Portable fan – Key West is so hot in summer you need something to keep cool!

Neighborhoods in Key West (Where to Stay & What it’s Known For)

Key West may be small, but where you stay can really shape your trip. Old Town is the most popular area for visitors because it’s walkable and packed with attractions, while nearby neighborhoods like Midtown and The Meadows offer quieter and more budget-friendly alternatives. 

Duval Street Corridor (Central Old Town)

Best for: nightlife, restaurants, first-time visitors

This is the most famous stretch in Key West and where much of the action happens. Staying near Duval puts you steps from bars, live music, shopping, and great restaurants. However, it can be loud during crowded times. 

Old Town Historic Seaport Area

Best for: waterfront views, sunset cruises, boat tours

Located near Mallory Square and the marina, the Seaport area is ideal if you plan to take sunset cruises, snorkeling tours, or ferry excursions.

Truman Annex

Best for: quiet luxury, some waterfront stays, walkable convenience

Truman Annex is a gated waterfront neighborhood with upscale condos and boutique-style accommodations. It’s peaceful, yet still walkable to Mallory Square, Fort Zachary Taylor Beach, and Duval Street.

Bahama Village

Best for: local culture, food lovers, budget-friendly stays

This colorful neighborhood near the Southernmost Point is rich in Bahamian and Caribbean heritage. It’s home to iconic restaurants like Blue Heaven and has a more local, laid-back vibe. 

South Beach / Casa Marina Area

Located at the southern end of Old Town and in the Casa Marina neighborhood, this area is home to the famous Southernmost Point buoy and South Beach. It’s slightly quieter than the center of Duval and our favorite area to stay on a trip!

The Meadows 

Best for: charm, boutique guesthouses, peaceful stays

The Meadows is one of the prettiest residential neighborhoods in Old Town, filled with pastel conch houses, shady streets, and small boutique inns. 

Midtown Key West

Best for: slightly more affordable hotels, airport access, parking convenience

Midtown is located between Old Town and New Town and offers more budget-friendly hotel options with easier parking. Practical area if driving in.

New Town Key West

Best for: affordable hotels & rentals, airport access, usually free parking

New Town offers some solid options and can be less expensive, but you’ll have to drive in or take a ride share to Old Town.

❓ Frequently Asked Questions About Key West

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Final Thoughts on Planning the Perfect Key West Trip

Key West is one of those rare places that feels both vibrant and laid-back, lively yet deeply peaceful for us. It’s a destination where you can pack your days with adventures or simply wander Old Town with no schedule at all. That’s part of the magic here: no matter what kind of traveler you are, Key West meets you exactly where you are and we love it.

Whether you’re coming for one day, a long weekend, or a full week of island time, I hope this guide helps you plan a trip that feels effortless, fun, and authentically you. Key West has a way of settling into your heart long after your trip is over.

If you’re exploring more of the Florida Keys, diving deeper into Old Town, or dreaming of the Dry Tortugas, this guide is your home base. And as always, I’ll keep this post updated with new tips, restaurant finds, hotel recommendations, and itinerary ideas from every visit. Until then… I hope your next Key West getaway is filled with sunshine, slow mornings, cortaditos, and your own unforgettable stories.

Author’s Note

Key West has become one of our favorite destinations to revisit year after year (sometimes multiple times a year), and this guide is built from all those experiences. I hope it helps you discover not just the famous Old Town landmarks, but also the local gems, small moments, unforgettable sunsets, and Conch vibes that make Key West so special. ~KJ