Unique Key West itinerary in 2, 3, 5 or 7 days
This Key West itinerary guide provides you 12 daily plans to fit all the needs and like
In fact, besides considering the length of your vacation (from 2 to 7 days), I also consider the type of your holiday (couples, families, beach lovers, adventure junkies, etc).
We are all different, aren’t we?
But let’s jump right in
Table of Contents
You can read also
- Great areas of Key West to stay (for beaches, history, nightlife or a quiet time)
- The ultimate guide to a Florida Keys road trip
- Best 35 things to do in Key West and the Florida Keys (including unique gems)
- Where to stay in the Florida Keys (the 7 best islands)
- How to plan your best stay in Miami downtown or get the most out of Miami Beach
Best Key West Itinerary – In a nutshell
Here down a few quick points, however, keep reading for more detailed information
- How many days in Key West: in one week you can experience the entire island and do 2 or 3 days trips, if you want, to other islands of the Florida Keys. In 5 days you will be able to enjoy Key West as well as a day trip to another key like the secluded Big Pine Key or Marathon Island. In 2 or 3 days, you will get to love your time in Key West. Plan well in advance and you will be surprised by how much you can do in Key West in such a short stay.
- Key West itinerary in 2 or 3 days: book your accommodation close to Duval Street, the heart of the island, and explore from there the beautiful beaches, the historical place and organise one or 2 activities like snorkeling, jet skiing, sunset sailing or a SUP discovering experience. I have organised below 5 possible daily-plan for every type of vacation
- Itinerary in 4 or 5 days: with 4 or 5 days, you can even think to explore another island of the Florida Keys, besides enjoying Key West. Drive your own car or catch a public bus to Marathon island for example. Or why not the secluded Big Pine Key. Alternative seat and enjoy the many beaches of Key West and enjoy a couple of local trips for snorkelling and dolphins watching. Check out below four great plans for 4 or 5 days in Key West
- Itinerary in 7 days: Having a week in Key West is a real dream come true. Also, in this case, you can just relax the whole time with a few activities every second day. Alternatively, organise 2 or 3 day trips to explore more of the Florida Keys where every island has the own character, besides some amazing tropical beaches. You can also think to rent a bike for a week so you can easily cycle around Key West and reach the nearby keys with a quick ride. Read more below on my 7 days options
- 5 Must do attractions in Key West: it is always so hard to choose just 5 attractions, even more so in Key West, a small island with so many things to do. Personally, I suggest the Sails To Rails Museum to learn more about Key West history, with a fascinating exhibition, the Paddlin’ Madeleine for a sunset SUP tour, something really unique (organise directly with Madeleine), Mallory Square in Key West for sunset, the full-day Watersports Adventure Tour for a day of fun activities and the Jet Ski Island Tour for a real adventure around Key West. You can read my guide to 35 things to do in Key West and the Florida Keys for more ideas.
- Best 5 beaches in Key West: Another hard choice, because there are so many beautiful beaches. I start with Smathers Beach, the most popular of all, in the south coast, Dry Tortugas Island, remote (2 hours by ferry) but totally worth a trip there, the boutique Higgs Memorial Beach, with the surprising Salute! to have lunch, Dogs Beach, especially if you have your pet with you, and Fort Zachary Taylor Historic State Park, not only for the beach but also for a visit to the fort.
I recommend also checking out this organised guided tour if you are just after a ride through the most iconic spots and hidden gems of the island.
The other option is by bus with Key West Transit running the service within Key West and up to Marathon Island.
You can drive your car to Key West, but once on the island, I would personally forget about it.
I would consider it for going to a few beaches, but that’s pretty much it. Parking is not as straightforward, especially close to Duval Street.
In saying that, the car is great for a Florida Keys road trip (read my guide), because you will be able to stop wherever you want along the Overseas Hwy, including at the beautiful bridges for a few photos.
The car becomes also very handy if you want to visit other islands from Key West.
I usually use DiscoverCars.com, an online price comparison website, whenever I want to rent a car for one or two days. They have the best prices. Full-stop.
Key West Itinerary for 2 or 3 days
This is a typical weekend (2 days) or long weekend (3 days) trip to Key West.
My best advice for the weekends is to book all well in advance because good accommodations and tours are limited.
I usually book all in advance and cancel free of charge if I change my plans. Most of the booking platforms are very flexible in this respect, which is great for us travellers.
With a short stay, I suggest taking a hotel close to the central Duval Street. From there you can walk pretty much to everywhere.
You will be surprised to know that you will be able to see and experience a lot, even with just 2 or 3 days.
The important and essential thing is to plan in advance your stay with both hotels and activities based on your like.
It’s always nice to look for tours once on site, but with just 2 or 3 days, time is very limited. Besides, it can be disappointing to discover it’s all booked out.
And for this exact reason, I have written a handy guide with 5 Key West itineraries (for beaches, couples, families, action or everything), including 5 detail day-to-day plans, maps as well as photos.
With 4 or 5 days in Key West, you have essentially two options:
- relax in the island. In this case, check out my guide to 3 days in Key West and add an extra 1 or 2 days to chill out at one of the beaches. Or why not planning a ferry trip to the beautiful Dry Tortugas Island?
- explore more than Key West. This is more of an active trip where you take 2 days to explore other islands and beaches of the Florida Keys. For example, you could take a bus (FLiXBUS or Key West Transit) to Marathon Island and Sombrero Beach, or Big Pine Key and the secluded Long Beach.
If you drive your car to Key West, I also suggest spending the first and last day exploring other keys
I have actually written a guide to 4/5-days in the Florida Keys with four daily plans, including part of the stay in Key West. It is a great source of information to explore a totally underrated part of Florida.
In 7 days in Key West, you will forget about your busy life and it is going to be hard to go back 🙂
In my opinion, it would be such a pity not to include a visit to other islands of the Florida Keys if you are there for so many days.
Surely you should check out the Dry Tortugas Island easily accessible by ferry boat from Key West.
It is a fabulous day trip full of history, marine life and nature too.
As for the 5 days, if you drive to Key West, stop on the first and last day on another Key.
Key Largo, Islamorada, Marathon Island, Big Pine Key are all excellent destinations, all with the own character.
For example, Long Beach in Big Pine Key is a fabulous secluded place for a couple, but it could be a bit boring for a family with kids.
That is why I have written an ultimate guide to one week in Florida Keys keeping in mind 3 different kinds of vacations (couples, families and a bit of everything) with a detailed daily plan for each one.