Key West is a place that has been on my bucket list for YEARS! My older sister moved to Clearwater Beach, Florida many years ago and I’ve constantly talked about making the trip down to explore the Keys while I visited her.
Well, that finally happened! 🙂
I actually did a full Miami to Key West Road Trip, but I have to admit.. the highlight of that week long trip was definitely Key West! The adorable island feel, bustling nightlife, adventurous excursions, gorgeous sunsets, and beautiful beaches…. Key west had it all!
Even though the weather was not great during my few days there, I still think it’s such a wonderful place to travel to. And the bad weather just gives me another excuse to travel back to Key West to experience it all over again! 😉
In this Weekend in Key West itinerary, I go over a perfect 3 day itinerary, things you should know before finalizing your trip, common questions about the keys, must-pack items for this specific trip, my tips on where to stay, and a bonus section incase you want to extend your time in the Keys!
There’s a chance this free guide contains affiliate links. This means that I may make a small commission (at no extra cost to you), that goes towards little Rosie’s dog treats! This trip was also hosted by Capitana Key West & Florida Keys Tourism, but all thoughts and opinions are always my own.
Key West Itinerary Overview
Day 1: Key West Sight Famous Sites & Sunset Catamaran Cruise
Day 2: Day Trip to Dry Tortugas National Park
Day 3: Boat Tour to Sand Bar + Sunset Celebration in Mallory Square
Where is Key West?
Key West is the further point of the continental USA and the last key you can drive to on a Florida Keys Road Trip. Something I didn’t realize when doing my Miami to Key West Road Trip was how narrow the highway is. There are many keys to explore along this 3 hour drive, but they are not necessarily “towns” that you can get off the freeway and walk around.
Everything is right off the highway, so if you want to go from your hotel to dinner, you need to go on the freeway and drive. For some reason I thought each key had a little town to walk around and explore?!
Well, Key West was by far the most commercialized key that had a walkable downtown area. There are tons of things to do like boat tours, bar hopping on Duval Street (the famous main street), shopping in the historic Mallory Square, and so much more. Key West is the main Key in the Florida Keys and should definitely be the main focus of your trip!
Plus, it’s the closest key to the popular Dry Tortugas National Park!
Where to Stay in Key West
I was very surprised how easy it was to get around either by bikes or Uber / Lyft! If you called and Uber / Lyft, they came within seconds, which I thought in such a touristy and remote spot, there would not be any available but that was not the case!
Key West is pretty small, so you really can’t go wrong with the area that you choose to stay in. For me, I preferred to stay a little bit away from the hustle & bustle (not right in the downtown area), that way I could get a hotel that was right on the water & had it’s own private beach for relaxing!
I chose to stay at the brand new hotel, Capitana Key West!! It’s an opal property, which if you’ve never stayed at an Opal Property before.. you can thank me later 😉 They provide bottomless complimentary water bottles (which is always such a pain at hotels needing to buy a case of water), wrist band key cards so you don’t forget or lose them, & all the rooms are suite-size (ya know.. with a couch, kitchenette area, and ocean-view balcony).
If you would rather stay right in the downtown area, click here to check out hotels near Duval Street!
Weekend in Key West Itinerary
Like I said before, Key West is a very small place! I don’t think you need more than 3 days to see everything and have plenty of time to relax. In this perfect itinerary, you will be getting the perfect mix of touristy sites, adventure, relaxing, and best food recommendations!
And as always, I’ve listed a “Bonus Ideas” section at the bottom of this guide incase you want to extend your trip or swap something out! I have a ton of fun ideas for large groups too! 🙂
Okay, let’s dive in!!
Day 1: Touristy Site Seeing + Sunset Catamaran Cruise
On your first day in Key West, you are knocking out all the touristy sites! Key West is a very walkable island, with most of the sites walking distance from each other.
If you would prefer to bike ride, bike riding is extremely common in the Keys! There are a few bike rental shops around, but my recommendation is Eaton Bikes! They are located only a 5 minute bike ride from your starting point, affordable & have great reviews.
TIP: Or if you want to truly embrace your vacation mood, you can rent golf carts to get around the downtown area 😉
All of these stops are in walking order, so you can start from Stop #1 and work your way up! If you do all of the stops listed here, you should still have plenty of free time to explore shops, stop at a few bars along Duval Street, and relax a bit before the Sunset Catamaran Cruise 🙂
Stop #1: Southernmost Point Sign
Your first stop is the Southernmost Point Sign, which get’s BUSY. I would highly recommend showing up here first thing in the morning if you don’t want to wait 20+ minutes in line to get your photo taken..
I made the mistake of stopping here late in the afternoon and the line was down the block!! I ended up just snapping a quick photo from the side and calling it a day. Even the photographer side of me didn’t want to wait in a line that long!!
Stop #2: Southernmost EVERYTHING
Next up, explore the entire “Southernmost Point” area, which I found hilarious!! There’s a Southernmost Point Bar, Southernmost Point Café, Southernmost Point Hotel, Southernmost Point Beach… you get the point, don’t ya? 😉
All of these sights are right next to the Southernmost Point Sign, impossible to miss!
Be sure to follow along on Instagram: @MyPerfectItinerary
Stop #3: Hemingway’s House & Museum
Next up, head to one of the most famous spots in Key West, Hemmingway’s House & Museum, to see some 6 toed cats. 😉
Ernest Hemmingway was a famous author who settled in Key West in 1928 and built one of the largest houses of that time. He built the only pool in Key West that cost $20,000 back then (AKA a fortune!!), which is still there today.
He received his first cat, Snow White, from a ship’s captain that had a rare gene that caused the cat to have six toes. Till this day, there are snow white’s decedents roaming the property that all carry the rare gene of having six toes! Even if you choose not to tour the museum, you can still walk by the property to try to spot one of these cute cats! 🙂
Stop #4: Key West Lighthouse
Right next to the Hemingway House & Museum you can climb to the top of the Key West Lighthouse! It only takes 88 steps to get to the viewpoint at the top and on a clear day, you can see over 15 miles out.
Admission is super affordable (only $14 as of 2022), click here to buy your discounted tickets online!
If you are going for a special occasion (oh I don’t know, a proposal?!), you can rent the entire lighthouse during sunset! This cute package include access to the museum, grounds & Lighthouse during the prime time of the day and you also get a wine & food basket to enjoy! 🙂 Click here to check it out!
Stop #5: Blue Heaven for the Best Key Lime Pie in Town
Blue Heaven is a historic restaurant in Key West, especially known for having the best Key Lime Pie in town! It was unfortunately under construction on my trip, but my friend who used to live in Key West said this place is a MUST for breakfast or lunch!
You can have your toes in the sand, listen to live music, and yummiest Key Lime Pie in town!
Stop #6: Mile Marker Zero
Next up, head to Mile Marker Zero which marks the beginning and end of US Highway 1! This is a pretty touristy stop that I wouldn’t go way out of your way to see, but lucky for you… this walking tour takes you right past it.
This exact spot is off the corner of Fleming Street & Whitehead Street, where you can find the Mile Marker Zero sign. There are also a few “End of the Road” gift shops to grab a souvenir 🙂
If you start your day around 9am and complete these 6 stops, you should finish them all around 1pm! That leaves you plenty of time to wander the downtown area, hop in a few bars / shops, and head back to your hotel to freshen up for your Sunset Catamaran Cruise!
The main thing to do in Key West is anything on a boat. You will see a million tours offering to take you out to sand bars, snorkeling cruises, and of course.. sunset catamaran cruises!
I have done many sunset catamaran cruises in my lifetime, but this one was unique because they had a live band on board. Which I now learned.. is a MUST! 🙂 We luckily got paired on board with, what Joseph and I think, were professional dancers. They were putting on a show during the cruise and putting everyone else to shame, ha!
The exact tour I chose was Fury’s Sunset Catamaran Cruise which had bottomless wine, beer, and margaritas. They also had food & a live band on board.
Day 2: Day trip to Dry Tortugas National Park
One of the most famous things to do in the Florida Keys is take a day trip to Dry Tortugas National Park. Located 70 miles off the coast of Key West, you can snorkel in protected and clear waters, learn about the history of Fort Jefferson, relax on the white sand beaches, and so much more!
You can only access this National Park by sea plane, personal boat, or Ferry. The ferry (which is definitely the most cost-effective way) operates a little differently than a standard ferry..
There is only one ferry time per day, so unless you have your own boat or are taking a sea plane, the only people going for the day are the people on the ferry with you. The ferry ride is 2 hours long and comes with:
- Breakfast and Lunch
- Snorkeling Equipment
- Restrooms on board
- Cash Bar (only on the way back to Key West)
- 45 Minute Tour of Fort Jefferson
The ferry is two hours each way, so you would get about 4 hours to explore the island. Even though the ferry feeds you Breakfast & lunch, you want to make sure you pack anything else you need since there are no shops or restaurants when you get there.
If you would rather have a luxury experience and also get to see Dry Tortugas National Park from above, you can travel by Sea Plane! You can opt in for half day or full day tours, giving you 2.5 or 6.5 hours to explore the park.
After you’ve completed your adventure-filled day, here are some ideas for when you get back to Key West (which is around 5:15pm if you are doing the ferry):
- Have dinner at the best fresh sea food spot in Key West, Half Shell Raw Bar!
- Watch the sunset celebration in Mallory Square (you will be doing this tomorrow for sunset, but it doesn’t hurt to see a beautiful sunset twice!)
- Go bar hopping along Duval Street.
- Relax at The Capitana’s Hotel Hot Tub!
Day 3: Private Boat Charter to Sand Bar
On the last day of your Key West itinerary, it’s time to end with a BANG! This is something that I plan on coming back to Key West to do because we ended up having a REALLY rainy day on our last day. All the local’s said it hasn’t rained like that day in over a year… so, just bad luck I guess? 🙂
Anyways, many local’s told us about their favorite activity in Key West which is taking a boat out to the sand bars! You can rent boats or go with a tour company, but their are many different sand bars a short boat ride away.
I would recommend packing some drinks and sandwiches and spending the day on your own little slice of paradise! Here is a fun private tour that takes you out to sand bars!
TIP: If you are sick of being on a boat (which hey, maybe Key West isn’t the place for you?!), I would recommend relaxing at Key West’s largest and best beach: Smathers Beach! You can rent paddle boards, kayaks, and relax under the palm tree lined sand!
Like how this photo was edited?! It was edited in ONE CLICK using my Preset Packs!
After relaxing in the sunshine all day, you will not want to miss Mallory Square’s nightly sunset celebration! Every single night (unless it’s raining) street performers and crowds gather to celebrate the amazing Key West Sunsets.
I would plan to get there about 30 minutes before sunset and stay at least 30 minutes after the sun sets when the colors really come alive!
For dinner, it’s time to head to Joseph & I’s favorite restaurant on Key West, LL’s Test Kitchen! It’s so easy to get sick of “beach bar food” after a week of eating it for Breakfast, Lunch, & Dinner. LL’s test kitchen has amazing, high quality food!
We opted in for the Pasta Carbonara and it was seriously to die for! And on top of that, the view from their wrap around deck is 10/10!!
Bonus Ideas for Key West
- Visit all the shops and museums in Mallory Square
- Tiki Boat Cruise – Think your own tiki bar, but on a boat! 🙂
- Get Cuban Coffee at Cuban Coffee Queen
- Spend the day at the most beautiful beach, Smathers Beach!
- Parasailing in Paradise – here is a great tour!
- Rent Jet Skiis – This tour takes you to a sand bar and past the entire Southermost point area!
- Kayak through mangroves – I did this in a different part of Florida and it was SO cool!
What to Pack for Key West
I never like to bore you with a long packing list, but I do always like to provide a few must-have recommendations for this specific trip! For traveling to Key West, here are some packing items I think you NEED!
If you are going in the water at any time, you need to wear Reef Safe Sunblock. There are living coral reefs just off the coast of the Florida Keys and they need everyone’s help to stay living! You can snag reef safe sunblock at almost any store, or you can grab my favorite one (SunBum) off Amazon! Click here for it.
This is my favorite sun hat that I recommend for all beachy destinations! It is super durable (perfect for travel) and not too big! And the perfect cherry on top… it’s super affordable!! Click here to check it out!
DUH, of course you need a good set of presets so you can quickly edit on the go! Lucky for you, I have a wide selection of presets that you can choose from starting at only $3.49 per pack!! Click here to check them out 🙂
How many days do you need in Key West?
I would say 3 days is the perfect amount of time to explore Key West. You could probably see most of the sites in 2 days, but I would leave yourself an extra day to relax and live the island life! This 3 day Key West Itinerary is perfect for seeing all the sites, day tripping to the famous national park nearby, and having tons of relaxation time 🙂
What is the best month to visit Key West?
Winter is busiest because the weather is the best (70 – 80 degrees with no humidity)! If you want to have nice weather but less crowds, I would travel during the shoulder season between March – May. I would not travel in the summer or fall if you want sunshine!
How long is the drive from Miami to Key West?
If you drive straight through from Miami to Key West, it would take you about 3.5 hours to complete. However, there are so many stops on a Miami to Key West Road Trip, so you should not drive straight through! Plus, there is often traffic that builds up on the main highway, since so many people are turning on & off it throughout the day.
Do you need a car in Key West?
I truly don’t think you need a car in Key West. The island is very small and easy to get around by bike riding, walking, or relying on Uber / Lyft. I stayed at the Capitana Key West, which was not in the downtown area, and had no problem getting around to the touristy sites!
Are Beaches Free in Key West?
Any beaches that are part of a state park or national park will be paid beaches. The biggest and best beach in Key West, Smathers Beach, is completely free and open to the public! Smathers Beach is located on the southeast side of the island, just in front of the airport. 🙂
Are there Alligators in Key West?
It is extremely rare to see an alligator in Key West. They typically do not travel that far down and would have a difficult time traveling on that narrow of a highway. If you want to see some alligators in the wild, I would recommend stopping at Everglades National Park!
Okay, that’s a wrap! I hope you found this Weekend in Key West Itinerary super useful and you have the best trip ever!!
Like I said before, I unfortunately went when the weather was not the best (which is SUPER rare for Key West). I already am itching to go back to explore all the things I didn’t get a chance to see!
Traveling to Florida? Here are some guides I think you would love:
- Miami Itinerary
- Miami to Key West Road Trip Guide
- Best Day Trips from Clearwater Beach, Florida
- 7 Day Itinerary to Clearwater Beach
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