keywest sunrise

A Day Well Spent in Key West – Things to See and Do for First-Timers

Honestly, I had no expectations of Key West. I would usually do a thorough research of the places I’d travel to beforehand, but I didn’t for this one and boy, was I pleasantly surprised!

We started the day early. After we’re done with workout and breakfast, we headed out at around 9am to set the day in motion. You just follow the crowd and head straight to Mallory Square. You won’t get lost or miss it, I promise. Once you step on cobbled stones, gaze upon a wooden tower that is the Shipwreck Historeum, and get drawn in by kitschy souvenir shops and juice bars at the lively Sponge Market, you know you’re already there.

old town trolley

If you haven’t decided yet whether to do a DIY walking tour or book any of the recommended tours in advance, you can check out an array of museums within walking distance (show it on the map – mark it) and day tours which starts from here such as the Old Town Trolley and Conch Train Tour which both offer an entertaining sightseeing tour like no other. I took the former and it’s definitely worth every penny – I was laughing my ass off the entire time. I’m amazed how this trolley drivers/tour guides can do the same thing over and over again without losing enthusiasm. They must really love what they do and it shows!

Southernmost Point of Continental USA

You can also book other special interest activities around Key West such as a ghost town tour (yes, it’s the 5th most haunted place in the US apparently!), riding on a glass bottom boat, snorkeling, etc.

If you end up going with the Old Town Trolley (they have a booth in Mallory Square) which is a hop on hop off tour, there are stops along the way that might arouse your interest like the Ernest Hemmingway Home & Museum, Duval Shopping Street and Bar/Restaurant Strip, Bahama Village Market, and the iconic Southernmost Trolley Stop – you better get a photo taken here! Otherwise, you didn’t really go to Key West!

View the interactive map complete with information on route and stops here. You can compare OTT and CT here (show routes and offers) –

Interactive Key West Map

So while husband is doing his Rum & Cigar tour, I hopped on the Old Town Trolley to do some exploring myself. I was so ready except for the chilly gushes of wind shocking my brain cells since I only brought summer clothes, meaning short shorts and thin sleeveless clothes, with me. I really wasn’t warned about this. So if you’re going in late March, I’m warning you now. At least bring a scarf or a hoodie with you like the veterans who were with me constantly asking me if I wasn’t feeling too cold. Hell yes, of course – but I didn’t want them to give up their windbreakers for me so I had to suck it up and pretend to be tough.

As I have said earlier, I found this tour quite entertaining and really informative. I was really quite impressed that’s why I didn’t get off until it was on its way back to stop #1 and I was about to meet husband anyway to make our way to the Southernmost Point Buoy, the most photographed spot in Key West as it’s believed to be the southernmost point of continental United States. And for that reason, expect to wait in a long queue for a few minutes until you get your turn to pose beside it. Don’t worry though, it moves at a relatively quick and steady pace and nobody dares to cut in line. When you’re done, you may want to walk further towards Atlantic Blvd or wait for the trolley to drive past again and hop on it to reach the coastline and maybe hang out by the beach. We didn’t do this anymore as I forgot my sunscreen and this pregnant lady was already starting to get “hangry”. So we headed to Kermit’s Key Lime Pie shop and cafe to try the delectable key lime pie of course! Also had fish and chips at their café – it’s a substantial portion! I think I have already eaten so much seafood on this cruise trip than when I was back in the Philippines a year ago. You know we don’t really have access to fresh seafood in Frankfurt all year long.

Before going back to our ship, I picked up a few things; I meant a pile of delicacies to bring back to my food cabinet, family, and friends.

Verdict: Two thumbs up for Key West! We would have loved to stay for a night or two to explore a bit more, simply chill at one of the nice beach bars and restaurants, walk around the neighborhoods and gawk at the pretty pastel-colored houses. There’s always the next time and I’ll make sure I stay for at least a night for the ghost hunting tour! Ahwooo.

a day in keywest


Key West looks amazing- it has been on my bucket list for a long time now. Thanks for sharing your tips!

Next time you go, take a drive on the 7 mile bridge. It’s a spectacular ride. Glad you got to enjoy a piece of Key West (and some real Key Lime Pie)!

Jayashree Sengupta

Never been there…. But definitely will… But your article virtually took me there

Great guide! I went to Key West a few years back and ever since then I make the chocoalte coverd key lime pie on a stick every summer!! It’s hard not to buy key lime flavored EVERYTHING to bring back home.. I bet your family and friends had fun trying the differnt treats!

Wow! Looks interesting this place.. I wish to explore it now too.. 😛