The Ultimate 3 Day Key West Itinerary (With a Map of Key West)
Are you planning a Key West getaway but only have a few days to explore?
After growing up in South Florida, I’ve visited the Florida Keys more times than I can count and have done many day trips to Key West.
However, I finally got to experience Key West by itself on a weekend trip with my husband. We spent 3 days exploring all Key West has to offer, from snorkeling trips and sunset cruises to lazy beach mornings and mojitos on Duval.
We had a fabulous trip that didn’t waste a minute but still felt like a vacation. Because in my opinion, Key West is the perfect balance of relaxation and adventure if you plan it right.
So if you’re craving turquoise water, delicious seafood, and a little island magic, you’re in the right place. This post will cover everything we did with 3 days in Key West, with some small improvements!
For example, I recommend skipping the snorkel trip we went on and choose one that goes to an actual reef instead. I’ve also included some potential add-ons to the trip, like Bahia Honda State Park and the Seven Mile Bridge.
With these types of details and my local knowledge, you’ll be able to plan your perfect trip to Key West!
Key West Map
Before we get into this Key West itinerary, below is a detailed Google Map of Key West! It includes all of the restaurants, bars, and landmarks mentioned in this itinerary.
As you can see on the map, most activities are fairly close together in Old Town, with a few activities sprinkled in New Town. In general, you don’t need a rental car in Key West, unless you plan to explore outside of town!
I cover this more in the Getting Around Key West section at the end of this blog post, so make sure to read until the end for those tips!
P.S. Want to save this itinerary for later? I created a downloadable PDF version of this 3 day itinerary that you can print out for your trip! It also has the link to this map 🙂 Just click the link above and enter your email address so I know where to send it!
Day 1
Morning
On our first morning in Key West, we went straight to Blue Heaven, one of the most popular brunch restaurants in town. They open at 8am, and I recommend getting there as close to opening as possible. If you show up later in the morning, be prepared to wait!
We arrived around 9:30am, and the wait was already an hour. Luckily, they do have a little bar across the street, so we grabbed some Bloody Mary’s to kill time. There are also plenty of things to see nearby, like the Ernest Hemingway Home or Key West Lighthouse!
Because we had an hour and it was early in the morning, we walked down to the famous Southernmost Point Buoy for a photo! Located about 0.5 miles from the restaurant, it’s a 10-15 minute walk each way.
Of course, there was already a line formed here, so we opted to just snap a pic of the buoy itself without waiting for our photo in front of it. Our table was ready at this point, so we hurried back to the restaurant.
We sat in the outdoor garden seating at Blue Heaven, which is the perfect Key West vibe. We were visiting in November, so the weather was very mild and pleasant. However, if you’re visiting in the hotter months, come prepared with a fan and lightweight clothing!
The reason Blue Heaven is famous is of course, the food. I’m obsessed with Eggs Benedict, especially when they have lobster in them. We also got talked into a slice of their giant Key Lime Pie, which is a must in Key West!
After breakfast, it’s time to walk around Old Town Key West and explore the historic sites. There are a ton of things to do in the area, so you can choose a few (or all!) of them to fill your morning. Here are a few options!
- Climb to the top of the Key West Lighthouse
- Snap a picture at the Southernmost Point
- Tour Ernest Hemingway’s Home & Museum (make sure to look for the five-toed cats!)
- Explore the Key West Butterfly and Nature Conservatory
Another fun option is to go on a cultural and food tour in Key West! Key West is a blend of Florida, Cuban and Caribbean culture which means incredible food to try!! To be honest, I am so sad we didn’t do this on our trip, but it’s definitely on my list for next time!
Afternoon
There are some great lunch spots around this area, including The Lobster Shack, the Seaside Cafe at the Mansion, and Louie’s Backyard! We chose the Lobster Shack and were not disappointed.
Next it was time to head over to Fort Zachary Taylor State Park, a 19th-century fort and park located on the southern edge of Key West. Starting at $4.50 per person, the park is a great place to spend an afternoon without breaking the bank!
There is a beautiful beach within the park where you can swim, lounge, and even snorkel! Plus, you can tour the fort’s grounds and learn about the incredible Civil War history. We loved spending our afternoon exploring and lounging here with the gorgeous blue water as our backdrop!
Evening
To finish off our first day, we made our way to Mallory Square to witness the famous Sunset Celebration. Every day just before sunset, Mallory Square, located at the end of Duval Street, comes alive with food vendors, street performers, music, and more.
This is the most famous place to watch the sunset in Key West, so if you want a front-row seat on the seawall, arrive early! We got there about 30 minutes before sunset and it was already packed! But don’t worry, you’ll have a good view from anywhere, even if you have to stand.
We loved watching the sun slowly dip into the sea, as well as the gorgeous sailboats passing by in front of Sunset Key. So romantic!
After sunset, we had dinner reservations at Blackfin Bistro, which was one of our favorite meals from the whole trip! While it’s right on Duval Street, they have private backyard patio seating. It felt so romantic and intimate, and the food was delicious!
To wrap up the night, we headed out on a Key West ghost tour! It was so cool getting to learn about the spooky and haunted side of Key West. Turns out, there are a lot of ghost stories here!
Day 2
Morning
By our second day, we were itching to get out on the water, which is what the Keys are known for!! We chose to book a snorkeling and dolphin watching tour, which was fun but a little disappointing.
First, I want to note that when booking a tour that includes looking for animals in the wild, you definitely have to go in with the expectation that you won’t see them. We ended up seeing one dolphin at the very end of the tour, which was great!
Our disappointment was actually because of the snorkeling! This tour takes you to seagrass beds to snorkel instead of a true reef. After snorkeling extensively in the Upper Keys on beautiful coral reefs, this was a bit of a let down.
So, if your primary goal is to see lots of tropical fish in clear water, I would recommend booking this reef snorkeling adventure instead!
However, if you plan to snorkel in other parts of the Keys during your trip (like Key Largo or Islamorada), I actually recommend skipping the snorkeling in Key West, since the snorkeling is much more impressive in Key Largo vs Key West!
Instead, check out a boat tour to the sandbars or a jet ski tour around the island! These tours will allow you to experience the lesser-known spots of Key West on the water without crowds of people.
Afternoon
After our snorkel tour and spending all day in the sun, we grabbed a casual lunch at The Waterfront Brewery. Located right on the water (hence the name), the brewery overlooks the Key West History Seaport, full of boats in the harbor!
We had delicious nachos and cheeseburgers while watching football (this is a great spot for sports games). Plus, they have some of the best local beers you can try!
Once we wrapped up lunch, we decided to take a quick break back at our hotel to lay by the pool and recharge before going back out to Duval for the evening!
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Evening
In the evening, we headed back down to Old Town and grabbed pre-dinner drinks at Sunset Pier. There’s a small bar here where you can grab a to-go drink and walk along the beautiful pier.
Then, it was time for dinner at Hot Tin Roof at the Ocean Key Resort right next door. This was our fancy dinner for the trip since we were celebrating our 3 year wedding anniversary!
The second-floor patio seating at Hot Tin Roof is right above the pool and offers incredible sunset views. The vibes here were so good, and the food was delicious! The inside was gorgeous too, with dark wood paneling on a long bar, very Hemingway-esque.
After dinner, we did a tamer version of the “Duval Crawl”. This is the nickname for bar-hopping along Duval Street, as you will be crawling by the end!
Some of the most famous bars on Duval include Hog’s Breath Saloon, Sloppy Joe’s, the Bull and Whistle Bar, and the Smokin’ Tuna Saloon.
If bars aren’t your thing, don’t worry! There are other nighttime options on Duval Street. You can grab an incredible, adult-friendly dessert at the legendary Better Than Sex restaurant, which I am so sad we missed on our trip!
Another option is to see a drag show at Aqua Nightclub or La Te Da! There is a large LGBTQ+ community in Key West, and attending a drag show is a fun way to experience the local culture!
Day 3
Morning
On our last day in Key West, we decided to rent bikes and exploring the south side of Key West. There are plenty of places to rent bikes from, but I highly recommend Eaton Bikes! We were able to reserve our bikes online, and they dropped them off at our hotel for us!
Key West is extremely bike-friendly, so you don’t have to worry about following a particular route. We started from our hotel in New Town, the DoubleTree Grand Key, and made our way along the beautiful bike and walking path along A1A across from the airport towards Smathers Beach.
Smathers Beach is one of the only sprawling white-sand beaches in the entire Florida Keys. This man-made beach actually had white sand imported from the Bahamas because surprisingly, the Keys aren’t really known for their beaches!
This beach is one of my favorite free things to do in Key West, thanks to the beautiful palm trees, white sand, and calm, warm waters. We spent our morning here relaxing on the sand and swimming in the sea before it got too hot and crowded!
Afternoon
In the afternoon, we ventured back down to Old Town to explore some of the other sites we missed on our first day. Around Mallory Square, there’s the Key West Aquarium, the Truman Little White House, and the Maritime Museum!
P.S. You can check out my full list of things to do in Key West for even more ideas!
It’s also fun to explore Duval Street during the day! We wandered down the road exploring all of the different boutique and souvenir shops. And of course, we had to stop in Kermit’s Key Lime Pie Shoppe for a slice of chocolate-covered Key lime pie.
All the bars are also open during the day and are typically are more kid-friendly at this time. You can grab a mojito at Willie T’s or a frozen drink at Fat Tuesday! Make sure to also check out my personal favorite: the Smallest Bar, which is the size of a jail cell!
Evening
In the evening, we finally got to do my favorite activity in Key West: embarking on a sunset cruise! As you probably know by now, the sunsets in Key West are jaw-dropping, and the best way to see them is from the water on a sailboat!
There are tons of different Key West sunset cruises to choose from, including dinner cruises, open bar cruises, and cruises with a dance floor! However, below is my top recommendation.
This is the tour we personally did and loved! It was very reasonably priced and included unlimited drinks and appetizers. Plus, there’s live music and incredible views the entire trip. While a sunset cruise is one of the best things to do in Key West for couples, they are also great for groups, families, and friends!
Our cruise lasted about 2 hours and was the perfect way to end our trip to Key West!
Sebago Watersports Sunset Sail
- Duration: 2 hours
- Cost: $80
- Rating: 4.5/5 stars⭐
- Includes: Open Bar, Live Music, Appetizers
Bonus Activities Near Key West
If you’ve got more time to spend, here are some bonus activities that are just a short drive away from Key West! Note, most of these activities will require a rental car to properly explore, and they are best visited on a half or full day trip from Key West!
These places are also great add-ons if you plan to drive and explore the Middle and Upper Keys on your trip! My personal recommendation is to plan a one week trip exploring from Key Largo to Key West. You can check out a video version of this below!
Bahia Honda State Park
Bahia Honda is one of my favorite places in the entire Florida Keys! This State Park is located just north of Big Pine Key at the foot of the Seven Mile Bridge. From Key West, it should take just under an hour to reach Bahia Honda.
Once you arrive, you’ll need to pay the $8 entry per vehicle, unless you have a Florida State Parks pass!
The park consists of 3 different beaches, Loggerhead, Calusa, and Sandspur! These beaches are picture-perfect Florida beaches, which is rare in the Keys! They have white sand and crystal-clear, shallow waters that are perfect for kayaking, swimming, and snorkeling!
My favorite part of the park, however, are the different views of the Old Flagler Railroad Bridge. This railroad bridge was built in the early 1900s by Henry Flager in order to connect the Florida Keys to the East Coast Railway.
At the southern tip of the park near Calusa Beach, you can actually walk up the Old Bahia Honda Bridge which offers incredible views to the park and surrounding waterways.
National Key Deer Refuge
Just before Bahia Honda State Park on your drive from Key West is Big Pine Key, where you’ll find the National Key Deer Refuge Visitor Center.
If you’ve never heard of them, Key deer are an endangered subspecies of the white-tailed deer that are unique to the Florida Keys. They are slightly smaller than your typical deer, and you can find them wandering throughout the Lower Keys!
While you might get lucky and see some deer while driving through Big Pine Key, the best way to see these deer is by going on one of the many hikes throughout the Refuge, which spans across 80,000 acres. You can read more about the different trails on the US Fish and Wildlife Service website here!
Stopping at the Visitor Center on Big Pine Key is a great way to learn more about the area and the protection efforts that are ongoing to protect the Key Deer. From there, you can drive over to No Name Key, where it is very common to see the deer on the side of the road!
Seven Mile Bridge
On the other side of Bahia Honda State Park, you’ll find the famous Seven Mile Bridge, one of the longest bridges in the USA! However, most people don’t know there are actually two bridges in this area!
The first is the current Seven Mile Bridge that you will drive over. Right next to it, however, is the Old Seven Mile Bridge.
As mentioned above, Henry Flager built a railway in the Keys back in the early 1900s. However, a majority of it was destroyed in 1935 by a hurricane, and then the railway was converted into a roadway: the Overseas Highway!
And in 1982, this Old Bridge was replaced by a new bridge right next to it! Portions of the Old Bridge still stand today and now, it’s a very popular place to bike, walk, and fish. Or you can ride on the newly opened Pidgeon Key Express, a tram ride that takes you to the historic Pidgeon Key!
This is a great spot to add onto your Florida Keys itinerary, especially if you are already visiting the nearby Bahia Honda State Park. And it’s free to just walk along the bridge!
Other Things to Consider Before Visiting Key West
Where to Stay in Key West
Key West is only 4 miles long, so you might be thinking… how many places can there possibly be to stay? The answer is… a lot!
Key West has a few diverse neighborhoods, but the first decision you’ll need to make is whether you prefer the historic charm of Old Town or the modern amenities of New Town. These two areas split Key West down the middle: the eastern half and the western half.
Most people want to stay in Old Town to be near the action, but there are pros and cons to both areas, which I’ll dive into in the next sections!
For more hotel recommendations and a full deep dive, read my detailed guide on Where to Stay in Key West!
Staying in Old Town Key West
For those seeking a slice of Key West’s rich history and vibrant atmosphere, Old Town is the ideal choice. This area is known for its charming streets lined with Victorian-style houses, art galleries, and boutique shops.
When staying in Old Town, you’ll be steps away from the iconic sites. You can explore the Hemingway Home and Museum, soak in the vibrant energy of Mallory Square, and party the night away on Duval Street, then walk back to your accommodation!
Here is a list of the top Old Town Key West hotels!
- Almond Tree Inn (Moderate): Private, intimate setting right off Duval Street. Adults only.
- Ocean Key Resort (Moderate/Luxury): Incredible location right off Mallory Square and Sunset Pier.
- Pier House Resort & Spa (Moderate/Luxury): Right next to Ocean Key with small beachfront area.
- Casa Marina Key West (Luxury): Newly renovated and so luxurious with the largest private beach in Key West.
In addition to standard hotels, Old Town also has many vacation rentals and B&Bs since the area is so small and historic! These are worth checking out, since the hotels in Old Town can be expensive.
If you want to browse all the available vacation rentals in Key West, I recommend using cozycozy, where you can compare accommodations from more than 100 sites (including AirBnb, VRBO, and Booking.com) all in one place!
Side Note: if you’re staying in Old Town, I recommend skipping the rental car. You’ll be able to access everything you need via walking or biking. Parking in Old Town can be difficult and expensive, so it’s better not to have a car!
However, if you plan to visit other Keys during your stay, you’ll definitely need a car! I personally recommend doing an epic road trip from Key Largo to Key West so you can experience all the Keys have to offer!
Staying in New Town Key West
If you’re driving into the Keys, New Town is the first area you’ll come across. It’s where the airport is located, along with most of the “chain” hotels. This area is characterized by wider streets, modern conveniences, and a quieter ambiance compared to the lively energy of Old Town.
New Town provides a more relaxed environment, making it an excellent choice for those looking to unwind after a day of exploration. It’s also convenient for those who prefer to have modern amenities at their fingertips.
Hotels in New Town also tend to be a bit cheaper than those in Old Town!
Even though it’s a bit further away from the main Key West attractions, you still may not need a car if you’re staying in New Town.
This is because most of the hotels in New Town have free shuttles to Old Town that run multiple times a day. These shuttles make it easy to visit Old Town without having to worry about parking, or drinking and driving!
Here is a list of the top hotels to check out in New Town Key West!
- Havana Cabana at Key West (Budget/Moderate): Fun vibes and great for families
- Parrot Key Hotel & Villas (Moderate): Beautiful tropical resort tucked behind modern amenities
- Margaritaville Beach House (Moderate): Family-friendly resort right across from Smathers Beach
- The Perry Hotel and Marina (Moderate): Casual and pet-friendly resort on Stock Island
Getting to and Around Key West
There are a couple of options when it comes to traveling to Key West.
The Key West International Airport (EWY) is extremely convenient to fly into. It’s located right in the heart of New Town and just minutes away from Old Town. If you have the option, I highly recommend flying into Key West.
However, you may find that flights into EWY can be a little pricey. While there are direct flights from around the country, it is still a small airport, which tends to mean higher prices.
Airlines like Silver and Allegiant often have cheap, direct flights though, so check to see if they fly out of your home airport!
The other option is to of course: drive! If flight prices into Key West Airport are too high, you can look into Miami Airport (MIA) or Fort Lauderdale Airport (FLL) and then make the drive down to Key West.
I touch more on this in my Ultimate Florida Keys Travel Guide, but I highly recommend this route so you can experience ALL of the Keys, not just Key West. The best option is to fly into Miami, rent a car, and make the drive from Miami to Key West.
Once you arrive in Key West, you don’t really need a rental car, even if you are staying in New Town. Most New Town hotels have free shuttles to Old Town. I highly recommend taking advantage of these shuttles or Ubers, because the parking in Old Town is hard to come by and very expensive! Old Town itsel is very walkable, no car needed.
So, I recommend dropping off your rental car when you drive in Key West and then flying out of the Key West airport, so you don’t have to drive the length of the Keys twice!
🚗 If you are planning a road trip, I love using DiscoverCars.com to compare pricing across multiple companies! Plus, they have a great 48-hour cancellation policy!
What to Pack for Key West
While I do have a full guide on What to Wear in Key West, here is a quick list of must-haves for your trip!
- Reef-safe sunscreen: this is extremely important! Most sunscreens are harmful to coral reefs (and your skin), so please choose a reef-safe sunscreen for your trip. I love Sunplus!
- Bathing suits and cover-ups: of course, you’ll need some swimsuits! I also recommend bringing long-sleeve shirts/rash guards you can wear in the water, as well as cover-ups for when you get out. The Florida sun is no joke!
- Sunglasses and a hat: do you see a theme here?! Preparing for the sun is so important!
- Waterproof sandals: I don’t go anywhere tropical without my waterproof Reef sandals! They are perfect for the beach, the boat, and walking around cities too.
Frequently Asked Questions
How many days do you need in Key West?
To experience all Key West has to offer, I recommend 3 full days! However, you can see the highlights of Key West in 2 days if needed, just expect some action-packed days. 2 days is ideal if you plan to visit other Florida Keys on your trip!
What is the best month to visit Key West?
My personal favorite time of year to visit Key West is in April or May. During late spring, the weather is absolutely perfect, the ocean is starting to warm up, and rain chances are low. If you want the coolest weather, you’ll want to visit in the winter months (November – February); however, this is the busiest time of year. Summer and early fall can be hot, humid, and have a high chance of hurricanes, so most tourists avoid visiting during this time. You can read more in my complete guide on the Best Time to Visit the Florida Keys.
What’s the cheapest month to go to Key West?
The cheapest month to visit Key West is typically in the late summer months into fall, so July, August, September, and early October. This is the heart of hurricane season, so make sure your hotels are refundable if you visit Key West during this time. In addition, hotel prices might be higher in late July/early August due to lobster season.
Can you walk around key West?
Yes! Key West is an extremely walkable town. Key West is actually divided into two sides: Old Town and New Town. The Old Town portion is the historic area that most people think of when they picture Key West (where Duval Street is). Old Town is very walkable and bike-able and not very car friendly! Parking can be expensive in Old Town. New Town is the more modern side of Key West where the larger hotel chains are, as well as the airport. New Town is not very walkable, but you can take a shuttle or drive to Old Town from here.
Final Thoughts
That wraps up my perfect 3 Day Key West itinerary. As you can see, Key West is more than just an island destination; it’s a kaleidoscope of history, culture, and natural beauty that is sure to leave you wanting more!
And 3 days is the perfect amount of time to spend in Key West to be able to see and do it all. Now that you know how to roughly spend your days, make sure to check out my full list of all the incredible things to do in Key West for more details to help you plan!
Or, check out my other blog posts about Key West below! ⬇️
The Ultimate 3 Day Key West Itinerary (With A Map Of Key West)
25 EPIC Things You Need To Do In Key West, Florida
Things To Do In Key West For Couples: A Complete Guide!
10 FREE Things To Do In Key West, Florida!
ULTIMATE Guide To The Best Key West Sunset Cruises
What To Wear In Key West: Complete Key West Packing List
Should You Visit Key West In January? Yes! Here’s Why
Should You Visit Key West In December? Yes! Here’s Why
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