Home Destinations 10 Things To Do in Key West That Don’t Include Water

10 Things To Do in Key West That Don’t Include Water

by Penny Sadler
Key West shopping on Caroline St. @PennySadler 2013

Shops on Caroline St.

Key West, Florida evokes images of turquoise waters, sunny skies, palm trees, lazy days fishing – in short, just about anything to do with water. But, what if you don’t swim, don’t have a boat, and just want to enjoy the scenery and whatever else Key West has to offer? Is there anything happening that’s not on or in the water?

The answer is yes! I recently spent the better part of a day and a night there, and never got in the water. I enjoyed it so much I’m still dreaming of palm trees and fluffy white clouds drifting across azure blue skies. 

The main industry is tourism, and the locals know how to make the most of what their slice of paradise has to offer. Key West is one of the friendliest places I’ve ever visited, and people are happy to help you or just engage in conversation.

Here’s my top ten list of things to see and do in Key West. All of them are family friendly, and most of them are free – or at least, very very affordable.

Key West Trolley Tour @PennySadler 2013

Old Town Trolley Tour

Old Town Trolley Tour This is the first thing I’d recommend. It’s a great way to get oriented to the island, and the tour is only an hour and half long. I really did know more about the island afterwards. Our guide was, of course, a native Floridian who grew up in Key West. Some of his aside comments were pretty hilarious and he gave a very thorough tour.

Be aware that there are a number of different trolley tour vendors and some are a bit more expensive than others. We were offered a two day pass for $30.00, or a one day pass for $20.00. Since we were leaving the next day, obviously the one day pass made more sense. When you buy your ticket(s) make sure to ask what time the last tour leaves. You can hop on and hop off at most stops, but if you take the last tour of the day, you will be limited as to which stops you can get back on.

Details here

Key West, Shipwreck Museum, @PennySadler 2013

Shipwreck Museum

Key West Shipwreck Treasure Museum

Much of the culture of Key West developed around salvaging wrecked ships. In fact, it was once the main industry of the island, and made Key West the richest city in Florida.

1 Whitehead Street

Bicylce Key West @PennySadler 2013

Ride a bike

Take a Bicycle Tour

If a trolley tour isn’t your thing, ride a bike. Key West is small and compact, so riding a bicycle makes sense, as parking a car is a bit of a hassle, (and you don’t need it). You can take a self guided tour, or go with a tour company like Key Lime Bike Tours. Most B&B’s offer bike rentals and a map.

Basically you can see everything you’d see on the trolley tour. If you go on your own, you won’t get the local scoop, though.


Hemingway Home Museum

If you’re a literary sort, don’t miss Hemingway Home and Museum. Hemingway lived in Key West for over ten years and completed A Farewell To Arms within seven weeks of moving to Key West. The history of Key West and Hemingway are legendary, and if you’re a Hemingway fan, I think it’s a must see.

907 Whitehead St.

Key West home of Ernest Hemingway for 7 weeks. @PennySadler 2013

Casa Antigua

Casa Antigua and the Pelican Poop Shop

If you can’t get enough Hemingway, stop by Casa Antigua where Hemingway stayed for a few weeks upon moving to Key West. I discovered this place on an early morning walk, but they weren’t open yet. An annual literary festival and competition, Hemingway Days is held here.

314 Simonton St.

Key West Light house @PennySadler 2013


Key West Lighthouse and Museum

Also on Whitehead St. is the Key West Lighthouse, now a museum. Climb the eighty-eight steps to the top for a wonderful 360 degree view of the island. There’s also a small museum that runs a short film with history of the island and some of the original lighthouse keepers.

938 Whitehead St.


Food is always a big part of a memorable trip. Whether it’s something simple like a refreshing gelato on a summer day, or a regional dish that you won’t find anywhere else, a good meal is often the most cherished vacation memory. Key West has a bit of every type of cuisine, with a strong Caribbean influence, and of course, seafood.

The weekend I was in Key West was Lobster Fest weekend. I ate lobster cooked in ways I never could have imagined. I tried the honey tempura battered deep fried lobster on a stick and lobster mac and cheese. I’m really a traditionalist and prefer my lobster steamed or grilled with butter, but the lobster mac and cheese was too delicious. I was happy I had someone to help me eat it!

Italian espresso at Duettoo @PennySadler 2013

Espresso at Duetto

For dessert, I couldn’t resist checking out Duetto, a real Italian gelato and coffee shop. The owner is originally from the Piemonte region of Italy. My travel companion, who just happens to be from Italy, had an espresso and pronounced it the real deal. I had a pistachio gelato – tasty – but I still think it tastes better in Italy.

Key West, Duetto cafe, @PennySadler 2013


Key West the southern most point. &#64:pennySadler 2013

Photo op!

Create a Photographic Souvenir

It’s kitschy, but as you can see people line up to have their photo taken with the buoy at the Southern Most Point in the United States. There is a trolley stop nearby and you can get off for the photo op, then catch the next trolley.

Key West Harbor, @PennySadler 2013

The Harbor

Take a Walk

Just because you don’t have a boat doesn’t mean you can’t enjoy walking around the marina. There’s shopping and restaurants, and you never know whose yacht may be docked there.

I like to read the names of the boats and see what flags they are flying. It’s also fun to just observe people who live and work on boats – such a different lifestyle.

key west marina, Usher's yacht. @PennySadler 2013

Key West Marina

Right by the Marina is Kermit’s Key Lime Pie. Kermit sells just about anything you can think of key lime flavored, and they’ll let you sample everything. You can also buy a slice of key lime pie to go, or eat it on their patio.

Kermit's Key West, Florida, &364;PennySadler 2013


The Porch Key West, Florida, @PennySadler 2013

Key West, Florida

Enjoy great color and architecture, especially in the old historic center.

Sailing into the sunset @PennySadler 2013

Key West Sunset

Watch the Sunset

Finally, the quintessential Key West experience, sunset at Mallory Square. About 6:00 pm the square fills with entertainers of all varieties, but I was mesmerized by the sunset and watching the boats sail by.

There you go, I think that’s at least ten things you can do, and never put even your big toe into the water.


From, 10 Things To Do in Key West that don't include water by Adventures of a Carryon

All materials ©pennysadler 2013. All rights reserved.

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Graff May 11, 2015 at 11:56 am

You missed the very best thing! An amazing scavenger hunt! http://Www.keywesthunt.com

clothing sale December 4, 2013 at 5:08 am

Excellent work, some incredibly good tips! I truly appreciate you crafting this blog post and the remainder of your website is excellent!

Penny Sadler May 12, 2014 at 10:46 pm

You would!

Michael May 8, 2015 at 8:07 pm

Avoid the Old Town Trolley and take the City View Trolley instead. Same route with newer more comfortable equipment for half the price.

Penny Sadler May 8, 2015 at 10:23 pm

Hey Michael, Thanks for the tip. I thought the Old town Trolley was fine and the price seemed reasonable compared to some others we checked, but we were on such a short time frame I can’t say for sure.

Claudia August 29, 2013 at 8:24 am

oh WOW I want to go there!

Penny Sadler August 29, 2013 at 10:45 pm

but Claudia, you’ve been there! 🙂

Leroy December 27, 2013 at 2:28 pm

She’s missing out!!!

Penny Sadler December 27, 2013 at 2:47 pm

I agree!

Gabi (The Nomadic Family) August 28, 2013 at 3:56 am

Penny,thank you for sharing.Really great post.

Melissa August 26, 2013 at 12:40 pm

Great post! Now I’m kicking myself for not making it to the Hemingway Museum the last time I visited Key West!

Penny Sadler August 27, 2013 at 9:34 am

You’ll just have to go back!

Leroy December 27, 2013 at 2:30 pm

Am guilty too many times I visited KW, never went into HWH…..shame on me

Mary @ Green Global Travel August 25, 2013 at 1:58 pm

Thanks for the great non-water suggestions. We’re hoping to get to Key West next year and your tips will certainly come in handy!

Penny Sadler August 25, 2013 at 2:06 pm

I can totally see you guys there. You’ll love it.

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Cat of Sunshine and Siestas August 22, 2013 at 1:47 pm

KEY LIME PIE. And drinks. That’s all I would do if I went back!

Penny Sadler August 22, 2013 at 2:17 pm

LOL it could be done!

Marina K. Villatoro August 22, 2013 at 11:17 am

Can’t wait, love this post. Just because of this, I am now extending our trip which was originally for 2 nights for 3 nights. there just seems sooo much to do!

Penny Sadler August 22, 2013 at 12:08 pm

Hi Marina, That is great to hear! Have a great time and thanks for visiting!

Adam August 21, 2013 at 10:32 am

I enjoyed this list and glad to see Hemingway on it 🙂

I think my favorite thing to do in Key West is still eat a key lime pie, though!

Penny Sadler August 21, 2013 at 10:39 am

It was yum!

Tom Bentley (@bentguy1) August 20, 2013 at 7:14 pm

Penny, I had a great time in Key West a little while back. The historic cemetery is a great place to photograph. Blue Heaven and 7 Fish were both colorful, fun and tasty places to eat. I’m pitching an article around, but haven’t found an editor to bite yet.

Penny Sadler August 20, 2013 at 7:21 pm

The Trolley Tour actually took us past the cemetery. I actually love visiting cemeteries, but my travel partner – not as much. Good luck on the article. Would you write my “hooks?” If I could figure that out, I’d pitch a few too! 🙂

Terry at Overnight New York August 20, 2013 at 1:56 pm

The Hemingway House Museum looks inviting. Lots to do on dry land!

Penny Sadler August 20, 2013 at 7:21 pm

Terry, I think Hemingway House would be your “thing” for sure. Also the Pelican Poop House. The Lighthouse is literally across the street from Hemingway House. Yep, lots to do on land.

Lauren@GreenGlobalTravel August 20, 2013 at 12:39 pm

I bet the water is amazing in Key West, but would get very tiresome of being out on the water most of the time. Thanks for this list of other things to do! Safe travels 🙂

Penny Sadler August 20, 2013 at 12:54 pm

It is! You guys would love it!

Penny Sadler August 19, 2013 at 12:30 pm

Well I’m disappointed I had no time. The water there is spectacular. But, I did get a great feel for the place and people.

wanderingeducators August 19, 2013 at 12:23 pm

To think, I’d never have discovered ANY of these, bc I’d be in the water all the time! Thx for the tips!

Maria August 18, 2013 at 9:18 am

Nice tips – it’s true, I think Key West and think water activities… or, I used to *grin*

Penny Sadler August 18, 2013 at 9:24 am

Haha. You’ll never think about Key West in quite the same way.:)


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