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Got three days in Key West? We’ve mapped out the perfect way to spend them.
We’ve explored this island multiple times over the years, and each visit just gets better. From close-up wildlife encounters to unforgettable sunset sails and the best slice of key lime pie you’ll ever eat, we’ve packed this itinerary with our favorite finds and local-approved experiences.
Whether it’s your first time in Key West or your fifteenth, this guide will help you soak up the laid-back vibe, hit the can’t-miss spots, and avoid the tourist traps. With just three days, we’ll make sure you see (and taste) the very best of this sunny little slice of paradise. Let’s break it down day by day!
Don’t Miss Out On Our Top Choice!
The tour we loved the most and suggest booking ASAP is this one!
Our personal FAVORITE thing we did was this shark and wildlife encounter! We got up close to iconic Florida wildlife, including dolphins, turtles, stingrays, and sharks, while learning all about them from our expert guide.
Check out the 2,500+ 5-star reviews and book this tour here!
Day 1
Breakfast – Blue Haven
We started our first day with breakfast at Blue Heaven, a colorful, open-air spot that’s part tropical garden, part local legend. Roosters wandered between tables, music played softly in the background, and the vibe was pure island charm. We arrived right when they opened at 8 am to beat the crowds—by 8:30, the line was already snaking around the corner.
The food lived up to the hype. I ordered the lobster Benedict and a slice of their famous banana bread, while Dan went all in on the blueberry pancakes. The portions were big, the coffee strong, and everything came out fast. Even better, it’s just a 15-minute walk (or 4-minute drive) to the meeting point for the morning tour.
Morning – Shark and wildlife encounter
After breakfast, make your way to the marina by 10 am for one of the most unique wildlife experiences in Key West. Finding something that’s educational, family-friendly, and actually well-run can be a tall order, but this shark and wildlife boat tour nails it.
We boarded the Tiger Cat, a quiet, eco-friendly catamaran captained by local experts who clearly knew the area inside out. Cruising through the mangroves and into the Key West National Wildlife Refuge, we spotted dolphins, stingrays, and even a sea turtle gliding alongside the boat. Our first mate, Matt, kept things engaging with fun marine biology facts that had even the adults hooked.
Once we reached shark territory, the crew tossed out bait, and it didn’t take long for the action to begin. Lemon and nurse sharks swam in close while a few sleek blacktips darted just beneath the surface.
Everyone had space to get a good view, and the kids onboard were thrilled to help feed the sharks. At one point, a massive nurse shark glided right along the surface, giving us a perfect look at its sandpaper skin and wide, slow-moving fins. It felt like we were inches from a nature documentary!
We loved this tour for its mix of excitement, great storytelling, and up-close encounters with marine life, and we’re obviously not the only ones. Read THOUSANDS of five-star reviews here to see why travelers call this the highlight of their Key West trip!
See why travelers can’t stop raving—lock in your shark encounter here!
Afternoon – Check out Old Key West’s Historic Sights
After the morning on the water, we grabbed some iced drinks and set out to explore the historic streets of Old Town Key West. This part of the island is full of pastel homes, leafy side streets, and pockets of history that make wandering a real highlight.
You’ll have a few hours before the food tour starts at 3:30 pm, so it’s the perfect window to squeeze in a few landmarks, and maybe a light lunch. Just don’t fill up too much, because the good stuff’s coming later.
Here are a few of our favorite historic and laid-back stops, all within easy walking distance:
- Hemingway Home & Museum – You could easily spend an hour or two here soaking up stories of Hemingway’s life in Key West. The Hemingway Home & Museum is preserved with much of its original furniture, and the guided tours (which run every 30 minutes) are full of fascinating tidbits. Plus, the six-toed cats roaming the grounds are pretty unforgettable.
- Truman Little White House – About a 15-minute walk from Hemingway’s home, this quiet spot was once President Truman’s winter retreat, and you’ll get a glimpse into post-war history and presidential downtime in the tropics. Guided tours are available, but we opted to just check out the highlights and the grounds, and even learned that Truman spent 175 days of his presidency here—more than at Camp David!
- Mel Fisher Maritime Museum – Located near Mallory Square, the Mel Fisher Maritime Museum tells the real-life story of Mel Fisher’s hunt for sunken Spanish treasure. Inside, you’ll find gold bars, shipwreck artifacts, and in-depth exhibits on the science of underwater archaeology. It’s ideal for anyone curious about the true adventure behind treasure hunting.
- Key West Shipwreck Museum – Right next door to the Mel Fisher Museum, Key West Shipwreck Museum is more theatrical, with costumed actors, dramatic storytelling, and a chance to climb a recreated 19th-century lookout tower. It’s fun and interactive—great if you’re in the mood for a livelier dive into maritime history. It’s right next to Mel Fisher, so opt to visit one or the other, depending on what kind of experience you’re after.
Late Afternoon – Food and walking tour
By late afternoon, we were ready to eat, but instead of getting stuck in one of Duval Street’s tourist traps, we joined this small-group food tour that showed us a whole different side of Key West. We booked the 3:30 to 6:30 pm time slot, which gave us the perfect mix of late lunch and early dinner while still leaving time for sunset plans later on.
Our guide, Kyle, was fun, knowledgeable, and very passionate about the island’s food culture. He blended local history, food lore, and fun stories into each stop, and by the end, it felt like we were walking the streets with a group of new friends.
We sampled jerk fish at a tucked-away backyard bistro, tried family-style Cuban dishes at a neighborhood favorite, and stopped for Cuban coffee and that iconic tart, creamy Key lime pie. The final tasting was a laid-back drink at a speakeasy-style bar that felt like a true local secret.
Every bite told a story, and each stop felt intentionally chosen with generous portions, bold flavors, and that easygoing island hospitality we’d come to love. Between tastings, we wandered banyan-shaded streets and pastel homes, learning not just what people eat here, but why they love it.
This tour gave us more than just great food—it offered a deeper connection to the island’s culture, one delicious bite at a time. If you want to skip the tourist traps and eat like a local, this is the best way to do it!
Book this award-winning food tour here and get FREE cancellation 24 hours before you go!
Evening – Mallory Square Sunset Celebration
After our food tour wrapped up, we took a leisurely 15-minute walk to Mallory Square for one of Key West’s best-known traditions—the Sunset Celebration. Not only is it a great sunset spot, but it’s also a nightly waterfront festival filled with energy and charm. It’s festive, a little quirky, and an iconic Key West experience that lives up to the name.
We watched fire jugglers and musicians, browsed local art, and grabbed drinks while the sky turned shades of gold and pink. One performer even balanced a unicycle on a ladder—no idea how he managed it. Locals and visitors gathered along the edge of the pier, clapping, laughing, and raising a toast to the end of a perfect day.
Related Read: Another one of our favorite Florida getaways is Fort Lauderdale! See our favorite things to do in Fort Lauderdale here and continue your travels.
Day 2
Breakfast – the breakfast club, too
We kicked off our second day in Key West at the breakfast club, too, a cozy and creative spot just off the main drag. The vibe was laid-back but fun, and the menu was packed with quirky twists on breakfast classics, including a pancake charcuterie platter that was both over-the-top and totally worth it.
They also serve 11 different kinds of Bloody Marys, which might just be the most Florida thing we’ve ever seen. We kept it light (ish), since our bike tour was just a 3-minute walk away and we didn’t want to start pedaling with a buzz. Whether you go savory or sweet, this place makes for a playful and filling start to the day.
Morning – See Old Key West on a bike tour
After breakfast, we walked just a few minutes to meet up at 10 am for this small-group bike tour—our favorite way to explore Key West without melting in the heat or fumbling with Google Maps. Wandering on foot sounds nice in theory, but once you see how much ground there is to cover, hopping on a bike makes way more sense.
The ride was easy and relaxed, with no steep hills or tricky terrain. Our guide, James, was a natural—friendly, funny, and full of quirky island stories that added flavor to every stop. He didn’t just rattle off facts – he brought the island’s past and present to life in a way that felt effortless.
We visited Mallory Square, Mile Marker Zero, White Street Pier, and, of course, the Southernmost Point for those must-have ocean view photos. But the best parts were the moments in between, like cruising shady backstreets, waving to locals on their porches, and watching roosters strut through the streets like they owned the place.
The tour ended with a slice of Key lime pie, which somehow tasted even better after a breezy ride around town. Even if you think you know Key West, this tour gives you a deeper look into the island’s charm.
But don’t just take our word for it, check out THOUSANDS of glowing five-star reviews here and see for yourself why this bike tour is one of the most-loved experiences in Key West!
Don’t miss out – book this small-group bike ride here!
Lunch – Kaya Island Eats
After the bike tour, we weren’t quite ready to eat, so we spent some time exploring, taking photos, and soaking up the island vibe. When our appetites finally caught up, we made our way to Kaya Island Eats, a colorful little spot serving up bold Caribbean flavors with a seafood twist.
The menu leans tropical with dishes like coconut curry shrimp, grilled fish sandwiches, and house-made pineapple slaw. Everything felt super fresh, and the portions were just right for a mid-day refuel. Whether you stop here right after your ride or wait a bit like we did, Kaya hits the sweet spot between casual and seriously tasty.
Afternoon – Explore on your own
With the bike tour and lunch behind us, the rest of the afternoon was wide open, and that’s one of the best parts about Key West. There’s no rush here, just sunshine, salty air, and time to explore at your own pace. Whether you’re in the mood for history, marine life, or a beach break, here are a few standout spots to check out on your own:
Key West Lighthouse & Keeper’s Quarters
This historic lighthouse has stood watch over Old Town since the 1800s, and climbing the 88 narrow steps to the top rewards you with panoramic views of the island. The adjacent museum offers a glimpse into the life of the keepers who once lived here, complete with old photographs and nautical tools. Plan to spend about 1–2 hours here, and note that admission is $17 USD.
Key West Aquarium
Small but packed with charm, the Key West Aquarium is one of the island’s oldest attractions and is still worth a stop. You’ll find touch tanks, jellyfish, turtles, and local reef species, all housed in an open-air building just steps from Mallory Square. It’s a relaxed visit that’ll take around two hours, great for families or anyone wanting a break from the heat.
Fort Zachary Taylor State Park
Located at the western tip of the island, Fort Zachary Taylor State Park offers a mix of history and nature in one laid-back setting. You can walk through the Civil War–era fort, explore shaded trails, or just head straight to the best beach in Key West, complete with lounger rentals and calm, clear water. It’s a great spot to unplug for a while.
Relax on the beach
While Key West isn’t known for endless sandy stretches, it still delivers when it comes to scenic beach time. Fort Zachary’s beach is our top pick, but if you want something a bit more open and breezy, head to Smathers Beach on the southern shore. Bring a towel, some snacks, and give yourself permission to do absolutely nothing for a little while.
Evening – Relax on a sunset cruise
Instead of braving the crowds at Mallory Square again, we switched things up with this sunset cruise aboard a 60-foot catamaran. The boat departs right near Old Town at 6:30 pm, which made it super easy to reach after a relaxing afternoon at the beach or exploring nearby sights. We had just enough time to freshen up and stroll over without rushing.
We boarded just before sunset and grabbed a spot on the wide, open deck. A live musician played island tunes as we cruised past the harbor and caught views of Fort Zachary Taylor in the distance.
With a cold drink in hand and the breeze kicking up just enough to cool things off, the atmosphere was unbeatable. Sails flapped gently overhead, and the soft glow of golden hour made everything look postcard-perfect.
The crew was friendly and fun, always nearby with refills and snacks. We nibbled on mahi dip, fresh shrimp, and tomato-mozzarella skewers while the sky shifted from gold to fiery pink. As the sun sank below the horizon, it was one of those picture-perfect Key West scenes you don’t forget.
This sunset cruise was one of our favorite experiences of the whole trip. The views, the music, and the relaxed vibe made it feel like a little slice of island magic!
Secure this tour now and pay later when you book it here!
Why We Book Tours with Viator
Viator is a trusted online booking system for tours around the world! We almost always book our tours using Viator for a couple of reasons:
- Free cancellation on most tours – Most of the tours on Viator allow you to cancel and get a full refund up to 24 hours in advance. This is handy in case plans change, or if booking an outdoor activity, the weather forecast is looking grim.
- Reserve now and pay later – You can secure your spot on some of the most popular tours well in advance and not pay until closer to the day of the tour.
- Lowest price guarantee – If you happen to find the same tour at a lower price elsewhere, Viator will refund you the price difference.
- Pay in your chosen currency – Avoid costly international transaction fees by choosing to pay in your home currency.
- Peace of mind – When booking with tour operators you find in person on the street or in small booking offices, you are often promised one thing and given another. This online platform holds tour operators accountable with a written description of inclusions as well as the opportunity for customers to leave reviews.
Check out the Viator website here! Or, for more info, read our detailed review about Viator here.
Dinner – El Siboney Restaurant
Whether you eat before the sunset cruise or after, El Siboney is a must for dinner in Key West. Tucked away in a quiet corner of Old Town, this no-frills Cuban spot has been a local favorite for years, and once the food hits the table, it’s easy to see why.
We ordered the roast pork with plantains and the Siboney steak, both packed with flavor and served in generous portions. The black beans and rice were the kind you’d happily make a meal out of on their own, and the garlic bread disappeared fast. The atmosphere is casual, the service is fast, and everything tastes like it’s made with love. If you’re craving something hearty, authentic, and far from touristy, this is the spot!
Day 3
Morning – Go on a dolphin watching and snorkeling cruise
We kicked off Day 3 with this dolphin watching and snorkeling tour, and it turned out to be one of the most memorable mornings of our trip. We’ve done dolphin tours before that felt more like waiting games, but this one delivered from the moment we left the dock.
At 9 am, we boarded a roomy catamaran with a sunny upper deck, shaded seating, and plenty of space to stretch out. Even before the boat left the marina, it felt like a peaceful morning on the water.
Our guides, Stevie and Logan, were fun, knowledgeable, and passionate about marine life. Stevie knew just where to look, and sure enough, we soon spotted a pod of dolphins swimming and leaping right alongside us.
Next, we made our way to the Key West National Wildlife Refuge for a relaxed snorkeling session in calm, shallow water. Logan gave a quick but super helpful briefing, and all the gear we needed was included. We floated above colorful reef fish and gentle coral patches, with just the right amount of time to explore before climbing back aboard.
On the return cruise, we kicked back with cold drinks and soaked in the sunshine. If you’re looking for a stress-free, wildlife-filled adventure that’s equal parts fun and chill, this is a great way to start your day.
Reserve this top-rated tour here and get FREE cancellation options!
Lunch – Seaside Cafe at the Mansion
Our dolphin and snorkeling tour wrapped up around noon, and by then we were ready to dry off, cool down, and enjoy a long, easy lunch. Seaside Cafe at the Mansion was just the spot—elegant but not stuffy, with oceanfront views and a peaceful atmosphere that made us want to linger a little longer.
Set in a beautifully restored historic mansion, this spot offers more than just great food. We sat out on the terrace with ocean breezes drifting in and ordered from a menu filled with seafood, tropical flavors, and refreshing drinks. The blackened mahi sandwich and mango salad were perfect post-snorkel picks.
After lunch, you’ll have a few hours to do your own thing, whether that’s souvenir shopping, finishing up any last sightseeing stops, or just strolling along the waterfront. This is your final afternoon in paradise, so take it slow and enjoy every minute.
Afternoon – Kayaking or Cocktails
After lunch, you’ve got the afternoon wide open. For something active and off-the-beaten-path, head out on a guided kayak tour through the island’s mangroves. Or, if you’re ready to sip your way through Old Town, there’s a small-group cocktail crawl that skips the tourist traps and gets straight to the good stuff.
Here are two of our favorite ways to wrap up the afternoon—you really can’t go wrong either way.
Option 1: Go kayaking through mangroves
If you’re craving a peaceful escape from the crowds, this kayaking tour is the perfect way to trade the buzz of downtown for the calm of Key West’s mangroves.
We opted for the 2 to 4 pm tour and spent the afternoon paddling through the kind of scenery you’d never stumble into on your own. Key West’s mangrove creeks are quiet, maze-like, and brimming with life—an entirely different world compared to the busy streets and bars downtown.
The tour starts at Hurricane Hole Marina, where the vibe is relaxed and there’s free parking. After a quick intro from our guide, Courtney, we set off at an easy pace through shady tunnels of tangled roots and glassy water. She had a knack for pointing out tiny, camouflaged creatures, like sea cucumbers, jellyfish, and even sea stars hiding just below the surface.
We learned about how the mangroves act as a natural barrier for the island and got a better sense of just how much biodiversity exists in these waters. The route changes depending on the tide and conditions, so each tour is unique. You can even bring your dog if they’re into kayaking.
For us, this was the perfect way to slow down and connect with a quieter, more natural side of Key West. Read through the reviews here and you’ll see we’re not alone. This tour has earned its praise for good reason!
Book this kayaking tour here and get free 24-hour cancellation!
Option 2: Cocktail crawl
If you’re leaning more toward “tropical buzz” than “nature escape,” this is the perfect way to drink your way through Old Town—minus the tourist traps. Key West has no shortage of bars, but finding the hidden gems takes some local insight, so we joined this small-group cocktail crawl that turned out to be one of the most fun (and flavorful) ways to explore the island.
We opted for the 3 to 6 pm tour, which gave us just the right amount of time to enjoy each stop without feeling rushed. Our guide, Mike, was laid-back, hilarious, and full of fun stories about Key West’s past and its drinking culture.
At each of the six stops, we tried unique drinks that went way beyond the usual rum punch, including a reimagined Hemingway Daiquiri and a tropical tiki creation we’re still thinking about.
What really made it special was the setting. We sipped cocktails inside a historic mansion, a quiet courtyard, and even a boutique hotel that used to be a hospital. Along the way, we also snacked on a few bites, like a taco from Garbo’s Grill, a legit local favorite featured on Diners, Drive-Ins and Dives.
If you want to experience the island’s cocktail culture without the chaos of a typical bar crawl, this one’s got you covered! It’s a laid-back, flavorful way to toast your time in Key West, and one we’d happily do again.
Check availability and grab your spot here before spots fill up!
Dinner – Sunset Pier
For dinner, we grabbed a table at Sunset Pier, a colorful, open-air spot perched right over the water—perfect for enjoying the ocean breeze with a plate of fresh seafood. The vibe is laid-back and festive, with live music playing in the background and boats drifting by as you dine.
We went with fish tacos and a round of mojitos, and both hit the spot. The setting really makes the experience here: bright umbrellas, tropical drinks, and front-row seats to that unmistakable Key West energy. Whether you’re coming from an afternoon of cocktails or a paddle through the mangroves, this spot strikes the right balance between lively and low-key.
It’s also just a short walk from the heart of Old Town, so once you’ve eaten your fill, it’s easy to head out for one last evening stroll.
Evening – Stroll through Old Town
To close out our last night in Key West, we took a leisurely walk through Old Town, soaking in the warm evening air and the charm of the island after dark. The streets were quieter by this point, lit by glowing porch lights and the soft hum of live music drifting out of tucked-away bars.
We wandered past pastel houses, peeked into shop windows, and eventually landed at Sloppy Joe’s Bar, a lively spot once frequented by Hemingway himself. Whether you’re in the mood for a nightcap or just want to say you’ve been, it’s a fun, historic stop worth ducking into.
Before calling it a night, we made one last detour to Kermit’s Key Lime Shop for a final slice of the island’s most famous dessert. Tart, creamy, and just the right amount of sweet, it was the perfect final bite to cap off a Key West trip full of flavor, sunshine, and laid-back charm.
Related Read: If you find yourself with more time, here are our favorite activities in Key West that you can add to this itinerary!
Where to Stay in Key West, Florida
Key West is a colorful, quirky island where laid-back vibes meet sun-soaked adventure, and finding the right place to stay can make all the difference. Whether you’re splurging on a luxury escape, planning a longer stay with all the comforts of home, or traveling on a budget, there’s something here for every kind of traveler.
To help you choose, we’ve rounded up some of the best places to stay in Key West, from upscale resorts to charming, affordable spots, so you can focus more on exploring and less on scrolling.
Luxury – $$$
Tucked along the Florida Bay, Parrot Key Hotel & Villas is a luxury escape just minutes from Old Town Key West. Surrounded by palm trees and tropical gardens, this resort offers spacious rooms and villas with private terraces, garden or water views, and crisp, coastal interiors. Relax in one of four pools, dine at The Grove Kitchen and Bar, or unwind on the sandy sun deck. Kayak adventures and a free Old Town shuttle add to the experience!
Rates range from $300–$900 USD per night, depending on the season and room type. Book this hotel on Booking.com.
Mid-range – $$
The Laureate Key West is a great mid-range hotel located on North Roosevelt Boulevard, just a short drive from Duval Street and the airport. The spacious suites feel more like mini-apartments, with separate living areas, kitchenettes, and balconies—some offering ocean views. Guests love the year-round outdoor pool, on-site parking, and the friendly, helpful staff. It’s also pet-friendly and ideal for families or longer stays, thanks to the extra space and amenities.
Prices range from around $250–$400 USD per night. Check availability for your stay on Booking.com.
Budget – $
For a budget-friendly stay in Key West, The Palms Hotel is a great pick! Located just a mile from Duval Street, it’s close to the action but tucked in a quiet, tropical neighborhood. Rooms are clean and comfortable with flat-screen TVs, ceiling fans, and coffee makers—some even have kitchenettes. Guests love the heated pool, daily continental breakfast served poolside, and the friendly staff. There’s also free Wi-Fi, bike rentals, and a laid-back vibe throughout.
Rooms start at $230 USD per night with breakfast. Book now on Booking.com!
For more options, see all of Key West’s hotels listed here!
Renting a Car in the USA
The United States is a vast country with diverse landscapes, from bustling cities to scenic national parks. While public transportation exists in major cities, renting a car is often the best way to explore the country’s wide-open spaces and hidden gems.
We always book with Discover Cars and can’t recommend them enough. It’s super easy to compare prices, check company ratings, find the right vehicle for your needs, and add affordable full coverage insurance. If you want a full breakdown, check out our Discover Cars review here.
Tips for Renting a Car in the USA
- Drive on the right: In the U.S., vehicles drive on the right-hand side of the road, and the driver’s seat is on the left. If this is different than your home country, take some time to adjust before hitting busy streets!
- Know the local rules: Speed limits, road signs, and driving laws can differ between states. For example, turning right on red is generally allowed after a complete stop, unless a sign indicates otherwise. Always check the specific rules for the states you’ll be driving in.
- Add full insurance: We always recommend full coverage rental insurance, especially in the U.S., where long distances, varying road conditions, and unpredictable weather can lead to unexpected situations. Discover Cars makes it easy (and affordable!) to add this peace of mind when you book.
- Choose the right car: Consider the nature of your trip. For city driving, a compact car is convenient, while for road trips or national park visits, an SUV might be more comfortable. With Discover Cars, it’s easy to filter by vehicle type, transmission, fuel efficiency, and more to find the perfect fit.
What You Need to Rent a Car in the USA
- A valid driver’s license from your home country.
- An International Driving Permit (IDP) is recommended if your license is not in English or uses a non-Roman alphabet. Some rental companies may require it, so it’s best to check in advance.
- A credit card in the driver’s name is typically required for the security deposit.
- Most rental companies require drivers to be at least 21 years old, with a young driver surcharge applicable for those under 25. Some companies may have higher age requirements, so make sure you double-check.
Ready to hit the road? Book your car with Discover Cars here and discover the freedom of exploring the USA on your own terms!
Don’t Forget Travel Insurance!
If you’re looking to save money on travel insurance, we currently use and recommend SafetyWing. We’ve been using their coverage since 2018 and they’ve had our backs when we needed emergency flights and got sick overseas.
SafetyWing is one of the cheapest providers out there and covers everything from medical costs to lost luggage, travel delays, and emergency flights. A huge difference we’ve found between them and other companies is that they let you take out a policy AFTER leaving your home country. We’ve also found it handy that it’s a monthly payment rather than a lump sum, and you can get a refund for unused time.
SafetyWing has helped us out in some scary situations before and their affordable coverage has given us peace of mind. You can read our honest review of SafetyWing for all the pros and cons.
Thanks for reading!
Key West was such a lovely getaway, with historic charm, stunning sunsets, and so much Key lime pie! We followed this exact itinerary and thought it gave a good balance of exploring and slow beach vibes. Stick to our recommendations and I know you’ll have a fabulous time!
If you need help planning more of your travels, check out our other USA blogs. We have traveled all over the country and put together where to stay guides, top things to do, and multi-day itineraries. Here are a few related blogs to help you plan and inspire your travels – cheers!
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