Key West Itinerary (4 Days in Key West, Florida)

Key West is a town full of character and charm where deals are not difficult to find.  Flying directly to Key West is often not the most cost effective way to get to the Keys. Check out the ferry from Ft. Myers or drive along the famous Overseas Highway US 1 from Fort Lauderdale or Miami.


Key West Itinerary 1

We started our trip in Fort Lauderdale, rented a red Mustang convertible, and drove south to the Florida Keys.  If you take this route and pass through Key Largo, I highly recommend The Conch House.  Awesome food and drinks with the best key lime pie we had on our trip.  We timed our drive to get to Key West right as the sun was setting, providing some beautiful scenery. Fair warning, I do think the Overseas Highway has a little too much hype around it. If it works well to save you money, go for it, but I wouldn’t go out of my way to make the drive.  We ended our night with some slushy adult beverages at the Flying Monkey. Be sure to check with your hotel for coupons.  Most restaurants and bars we went to offered deals and promos for tourists and our hotel offered us buy one, get one drink vouchers for most of the bars.


Key West Itinerary 2

Started the day at Harpoon Harry’s, a 50’s style diner then picked up some bikes from the shop next door. Key West is a very bike friendly town and bikes are a great way to see the town. Aimlessly Riding around looking at all the houses and landscapes was a fun way to spend the morning.  We then stopped by the famous Kermit’s for some chocolate dipped key lime pie. Kermit’s offers just about anything you can imagine in key lime, cookie mixes, coffee syrup, wine, etc.  and is a perfect place to pick up interesting by usable Key West souvenirs for your family and friends.  After dinner we ended the evening with a sunset party cruise which leaves the dock just before sunset then offers drinks and dancing as the sun sets.


Key West Itinerary 3


Started day three checking out the harbor which offers some great restaurants on the water to grab lunch or breakfast at. Again, check for special offers, you can likely get them for the restaurants here too. Then we headed to the not so typical tourist attraction, the Key West Cemetery.  Touring a cemetery is weird you say? Well the Key West cemetery has the typical Key West character and is a bit quirkier than other cemeteries. Here you can find gravestones with inscriptions such as “I told you I was sick” and “I’m just resting my eyes”.  Next we went out on the water to view some sharks. If you find sharks at all interesting, you will really enjoy this tour.  Finally we ended the evening at the dessert restaurant Better Than Sex.  I highly, highly recommend dining on desserts at Better Than Sex. They offer a great dessert menu and serve glasses of wine with chocolate or caramel dipped rims. Absolute heaven.


Key West Itinerary 4


Day four we spent exploring the more classic attractions of Key West. Stopped my Hemingway’s house and toured Truman’s annex. Then stopped by the Southernmost Point and took a picture (expect a line to take a picture with the famous statue any time you go).  Finally we climbed to the top of the Key West Lighthouse to enjoy a view of the city from above before our journey home. Definitely recommend checking out the lighthouse, they offer student and AAA discounts on the fee to get to the top.

Overall Key West is a very interesting town with plenty to do and see and great deals if you look for them.