There’s something magical about Key West that draws people back over and over again.
Maybe it’s the cute little historic homes with wraparound porches, the salty breeze and palm trees, the locals, or the island time.
If you’re planning a quick getaway to the southernmost point of the U.S., this 3-day Key West itinerary will help you soak up the best of the island — whether you’re here for the food, the views, or the quirky charm.
Let’s dive in!
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Day 1: Welcome to Key West (AKA The Conch Republic!)
The first day is a full day. So if your plane doesn’t land until later in the day or evening, I recommend getting settled, grabbing a drink and/or dinner, then starting this itinerary on your first full day.
Morning:
- Brunch at Blue Heaven – Blue Heaven is one of the most popular and best places for breakfast on the island. And for good reason! It has a vibrant, laid back vibe. They are famous for their lobster Benedict and mile-high key lime pie.
- I also have a blog post on the best breakfast spots in Key West if you want more options!
Afternoon:
- Stroll Duval Street – After breakfast, wander around Duval Street. Pop into shops, galleries, and local boutiques. Or bar hop, it’s always acceptable to bar hop in Key West no matter the time! Basically, Duval Street is a great place to just explore and wander.
- There are tons of great spots to eat for lunch in Key West. Try BO’s Fish Wagon for seafood, Amigos for good tacos and people watching, or Lagerhead’s for incredible views and laid-back food (don’t forget your swimsuit if you choose this option!)
- Tour the Ernest Hemingway Home & Museum – Even if you weren’t a Hemingway fan, you’ll appreciate the lush grounds and cats. The cats are descendants of Hemingway’s polydactyl cat, which means that it had an extra toe. Most of the cats on the grounds today have an extra toe on at least one of their paws!
- Snap a photo at the Southernmost Point Buoy – It’s touristy, yes, but it’s iconic for a reason. The line can get long but it moves fast because it doesn’t take too much time to snap a quick picture (but you can also go early in the morning to beat the line!)
Evening:
- Dinner at Latitudes on Sunset Key – Latitude’s is only accessible by a short ferry ride. It is an upscale dinner spot. You will need a reservation (you are only allowed on the ferry ride if you have a reservation) and they do fill up quick!
- Louie’s Backyard is another nice dinner option right on the water.
- For a more laid back option, consider El Siboney (a local favorite!) for some of the best authentic Cuban food you’ll ever eat, Seaside Cafe at the Mansion for lobster pizza and honey butter lobster biscuits, Garbo’s Grill for Asian fusion burritos, tacos, and burgers (it’s a food truck located at Hank’s, so it’s a good spot to start the night if you want to bar hop).
- After dinner, enjoy live music and bar hop wherever you feel called! Or enjoy your resort’s pool.
Day 2: Adventure on the Water
The second day is going to get a bit more adventurous! We’ll get out on the water then explore more of what the island has to offer.
Morning:
- Breakfast at Cuban Coffee Queen – The best way to start your morning in Key West is with a café con leche and a Cuban breakfast sandwich. Cuban Coffee Queen has a few locations but we like the location on the historic seaport (284 Margaret Street). This is where you’ll find the famous Welcome to Key West sign, too.
- After you have your coffee, wander the Historic Seaport. This is a fun area right on the marina with massive boats. A lot of tours leave out of this area and it’s fun to watch them. There are also plenty of restaurants and shops to explore.
Afternoon:
- Book a snorkel or sandbar tour – Getting out on the water is a perfect way to explore Key West. There are tons of great options. Here are some of my favorite tours:
- Jet Ski tour: This tour takes you 28 miles around the entire island of Key West.
- Dolphin and Snorkel Tour: This tour lets you mix dolphins and snorkeling at the coral reef. First, you’ll have the opportunity to see dolphins in their natural habitat. The captains know the most popular spots to find them. Then, you’ll go snorkeling (you’ll see marine life like tropical fish, but once in a while, sea turtles make an appearance) After snorkeling, complimentary beer and wine is available. Complimentary soft drinks are also available on board.
- Ultimate Adventure: This is one of my favorite tours in Key West and it makes me feel like a kid again. You will take a catamaran out into the water where you’ll then get an opportunity to ride jet skis, go parasailing, ride a banana boat, and play at the water park.
- As an alternative, you could visit Fort Zachary Taylor State Park. This my favorite beach in Key West and there is also a fort that’s interesting to visit.
Afternoon:
- Lunch at Conch Republic Seafood Company – Located right in the historic seaport (a perfect place if your tour leaves out of this area!) They are famous for conch fritters and fresh fish tacos.
- Take a Conch Train Tour or rent bikes to explore neighborhoods like Old Town, Bahama Village, and the marina area.
Evening:
- Sunset Celebration at Mallory Square – Street performers, food stands, and that classic Key West sunset over the Gulf.
- Night out on the Town
Day 3: A Little Bit of Everything on the Island
Morning:
- The first stop on your last morning is, of course, breakfast. Sarabeth’s is slightly more upscale for a quiet, nice breakfast (also great for recapping your trip and regrouping for what you want to do on your final day). Harpoon Harry’s for a more laid back atmosphere and key lime pie french toast (seriously, it’s sooo good). But honestly, like I mentioned on day 1, there are tons of amazing breakfast spots in Key West, I couldn’t possibly pick just one.
- If you’re more of a coffee person, check out my post on the best spots to get coffee in Key West instead (or do both breakfast and coffee!)
- Visit the Key West Lighthouse & Keeper’s Quarters – Learn about the rich history of the lighthouse then climb to the top for panoramic views.
Afternoon:
- Lunch at Salute! on the Beach – Located right on Higgs Beach with casual island vibes and ocean views.
- Spend some time at the beach afterwards if you have time want to relax.
- Visit the Key West Butterfly & Nature Conservatory – This place is dreamy. There’s tons of tropical foliage, flamingos, exotic birds, and tons of butterflies.
Evening:
- A sunset sail is a great way to end your trip. Choose a family-friendly sunset cruise or an adult-only champagne sail for those traveling without little ones.
- Relax by the pool, take a last walk along the harbor, or go bar hopping one last time on Duval Street. Any of these options are a great spot to end your last night. Do whatever your heart is calling you to do, that’s the spirit of Key West.
Tips for Visiting Key West:
- Parking can be tricky. Many hotels offer free bikes or walking access to everything.
- Sunscreen and hydration are musts — Key West sun is intense!
- Generally speaking, you don’t need a car once you get to the island. Some of the hotels (typically the ones located by the beaches) are a bit farther away from the heart of Key West. Many hotels in that area will provide a free shuttle. If they don’t offer shuttles, there are Ubers and taxis on the island.
- Don’t worry too much about fitting it all in – it’s impossible. Do what you can, catch the magic of Key West, and plan to come back again to do more of the things you didn’t get to.
Final Thoughts on Your Key West Itinerary
Three days in Key West is just enough time to fall in love with this quirky, sun-soaked island.
Whether you’re sipping mojitos in the shade, snorkeling in turquoise water, or watching the sunset paint the sky at Mallory Square, Key West is the kind of place you’ll want to come back to again and again.
I hope you have the best time!
