A week is not perfect of course. The perfect amount time to stay in Key West is...as long as you can! For most visits Key West will be hotter, sunnier, livelier and way more fun than what you have waiting back home - so there is good reason to stay as long as you can. Plus there are hundreds of bars and restaurants and lots to do as well as great weather so you can chill by the pool and relax.
Here's how your stay might look over different time periods:
The cruise ship visit - a fleeting few hours
Cruise ships dock at Key West 350 times every year, up to 3 ships per day, so this is a common way of visiting Key West. You're here for a maximum of 6 hours onshore so you don't have much time.
Good itinerary: Most cruise passengers seem to take a ride on the Key West trolley tour - wizzing you round the island. As time is short, this is a good plan. It takes a couple of hours, although you can hop off part way through.
After that hit Duval Street and wander to a couple of bars.
If you want something a little more "Key West" go to Blue Heaven for your drink (you can eat there too). The place is one of a kind.
One day visit - rush, rush, rush
Yes, people do drive down Highway 1 for the day into Key West and back. It's accessible like that from Miami. Warning: don't get caught in the traffic, especially at weekends.
I think it's a bit of a missed opportunity, taking a room in a bed & breakfast and making it a long weekend is much better (see below).
Once you get here you won't have much more time than the cruise ship passengers, so see above for a recommended itinerary.
Long weekend - the "I wanna have fun vacation"
It's very possible to come and have a great time for only a weekend in Key West but it is very short time so I'm guessing that party and fun is on the agenda rather than restful and relaxing.
Check out the best cocktail places and restaurants in Key West - the links are at the top of my blog.
Again, be very careful of the traffic and congestion along Highway 1 if you're only coming for a weekend. Basically, if I was travelling I'd leave Miami at 6am at the latest on Friday or Saturday morning.
One week - The relaxation vacation
This is near to perfect. You get chance to wind down and not go at a frantic pace. You won't need to leave Key West - apart from visiting Fort Jefferson, see itinery below,
A week gives you the time to sample most of the best things about Key West.
Itinerary: Basically, you can do a few of the things in my list of top things to do - I would do the top 4 at least: the Conch train tour, walk Duval Street, Key West harbor and feeding of the tarpons, and go to the Custom house for a little Key West history.
I've got individual posts on all these things to do so go to the main article and click from there.
Also definitely do a seaplane trip to the Dry Tortugas islands, 70 miles from Key West, this will be a highlight - guaranteed!
Evening wise, here are my top restaurants and cocktail bars.
Two weeks - "The European holiday"
It's well known by Americans that all Europeans get more than 8 weeks of vacation every year (!!) and so all tourists from Europe can spend 3 weeks in Key West. (I am being ironic).
I have indeed managed to spend 2 weeks in Key West on one of my visits and there is:
- enough to do, although I, personally, would need to take a couple of days trips out of Key West if I was staying this long
- enables you to relax - check out the only good beach (the local's beach) on Key West
- ALMOST enough to get into the Key West local vibe
- Definitely go to Dry Tortugas by sea plane
Do lots of the the best things to do in Key West, including maybe the ones that are more genuine Key West - like tarpon feeding, Audubon House, the Key West museum.
7 years - the "I want to be a Conch" visit
Yes, people have visited for a week and stayed for years (qualifying to be a "fresh water Conch" as they call locals here, after staying here seven years!). Change your life and move to Key West, you won't be the first by a long way. There's even a popular book that's been written on the very subject - Google it.
Of course, you will also be asking:
- I know how long I can visit for, but WHEN should I visit? - which months are the best? - All months are NOT the same in Key West, there are big seasonal differences. Click here for my post on that.
- Other issues in planning a Key West vacation. Like how to get here, what's the weather like, what to wear, how formal is Key West? Stuff like that
- The cost of staying - Key West is expensive, and this will be BY FAR your BIGGEST COST. Click here for budget considerations and best budget /cheap accommodation. If cost is no object (lucky you!) click here for the best Key West hotels.