12 Things to Do on a 2-Day Road Trip to Key West

Key West is my kind of laid-back paradise. Seedy and unpretentious but colorful and warmhearted, this tiny island has never failed to cheer up and entertain me.  Salty-caramelized, hot and malleable with a twist of crazy – this is Key West life in my overly romanticized mind.

2 Day Road Trip to Key West Itinerary

Key West completes a string of The Florida Keys tropical islands, being the states’ southernmost point and a famous spot for tourists from over the world. 3-4 hour scenic drive from Miami to Key West is a destination by itself, with lots of fun activities offered by Florida Keys on the way.

Being a Miami local for I-can't-believe-how-fast-time-flies 10 years, I've visited Key West religiously roughly once a year. I never lack reasons for yet another crazy getaway to my beloved island.

As I am sort of trying to keep up with the travel blog here (oh, naive naive me, thinking this would be an easy task), I figured I owe it to myself and to a few readers I've managed to attract (again poor poor me, hoping readership would be popping like popcorn if only I keep writing) to publish one of those "10 things to do..." posts about Key West.

Without further ado, here’s my suggested itinerary for your very best 2-day road trip adventure through the Florida Keys to Key West!


(Head out at 7 am Saturday, get back by midnight Sunday)

1. Key Largo Snorkeling 

About an hour drive from Miami (this timing varies depending on the starting location), Key Largo is the first large island in the Florida Keys Archipelago. Book your snorkeling tour in advance as it is very popular with tourists and busy all year round. 9 am trip will give you an hour of snorkeling and you’ll be done by noon – wet, happy, hungry and ready to see more! 

Price: Under $50

Key Largo Snorkeling

Key Largo Snorkeling

Key Largo Snorkeling

2. Robbie's Tarpon Feeding

While rather controversial, tarpon feeding is enough fun and unusual activity for me to pass on. Right after the snorkeling tour I suggest you head to Robbie’s (30 min drive) to have lunch, relax in an atmosphere of local charm and reggae style live music, feed tarpons and watch pelicans trying to steal both the fish and the thunder.

Price: Under $10 (feeding fish, not yourself)

Robbie's Tarpon Feeding

Robbie's Tarpon Feeding

Robbie's Tarpon Feeding

3. Seven Mile Bridge Scenic Drive

The Oversees highway connecting Florida Keys islands is a 113-mile chain connected by 42 bridges, one of them 7 miles long. The Seven Mile Bridge was among the longest in existence at the time it was built. Should I go into details how beautiful this drive must be? Yeah, it’s pretty amazing. The water colors are magnificent, ranging between all shades of aquamarine, emerald green and blue. Sit back, enjoy the views and maybe ponder a bit over the beauty of our world and the treasure that is our life.

Price: Free

Seven Mile Bridge Key West

Seven Mile Bridge Key West

4. Bahia Honda Beach and State Park

Bahia Honda Beach and State Park is a great spot to take a break from driving and stretch your legs. Spend some time on the beach, have a few refreshments (if you brought any along) and walk a short trail to the abandoned Rail Bridge. The views are amazing here, so take a camera!

Price: Under $10

Bahia Honda Beach and State Park

Bahia Honda Beach and State Park

Bahia Honda Rail Bridge

5. Seafood Feast

30 min drive from Bahia Honda and the road splits in two – you are entering Key West! Accommodations on the island are rather pricey but always packed – definitely book a room beforehand and go for a nice Victorian B&B over a generic hotel room (not much difference in price but a lot in experience). If you follow my itinerary, you’ll arrive around dinner time and the options here are endless. I say, you can’t visit Key West and not indulge yourself in a seafood feast! My personal favorite is Alonzo's Oyster Bar – fresh oysters, clams, mussels, shrimps, conch ceviche will please any seafood gourmand out there. And if you are in time for 4 - 6:30 happy hour – just keep eating! It’s half priced.

Price: Happy Hour Under $50 per person

Alonzo's Oyster Bar

6. Sunset Watching

It is cliché for a reason. When in Key West, go to Mallory Square and watch sunset. With a tropical drink in hand. Pink rainbow in the sky and on the water, sailboat silhouettes against the setting sun, music, laughs, happy faces – even crowds of tourists somehow complement this place rather than spoil it. 

Take a walk along the plaza to watch street performers and arts showcasing - while nothing spectacular, the atmosphere is fun and cheerful with a cherry of bizarre on top. 

Price: Free

Sunset Watching at Mallory Square

Sunset Watching at Mallory Square

7. Bar crawling

Duval in Key West is Miami’s South Beach – it never sleeps, it is always crowded and perfect for bar crawling! Duval is easily my favorite among the two. I love its laid back atmosphere, shorter walking distances, cordial attitude, cozy appeal and devil-may-care craziness! Definitely go to Aqua to see a drag show and have some laughs. Just remember to leave your judgmental goody-goody self behind the doors – open-mindedness and sense of humor are a must! Then start bar hopping. Or crawling. Whichever you prefer. Listen to some live jazz, get frozen daiquiris, switch to a rock band, have shots with the bartender, meet the locals, drink some rum, meet strangers who can't remember if they are tourists, get temporary tattoo, dance on the bar… maybe a tequila shot? I am only kidding, but you get the point – Duval is a party paradise and a little party never killed nobody :)

Price: sky is the limit

Aqua drag show key west

Key West Nightlife


8. Jet-ski Tour

Any vacation gets better when you have a nice variety of activities. Being on an island calls for trying a fun watersport and Key West kindly (rubbing hands vigorously in anticipation of gain, in fact) offers a great deal of options: jet skis, kayaks, peddle boards, boats, etc. I suggest starting your second day with a Jet Ski tour. It doesn't damage your wallet as much as renting a boat, but gives you the same great opportunity to see and explore the island from another perspective, from the water. Throw in here tons of fun driving a Jet Ski and a refreshing sensation of wind slash waves coming your way (which is always a huge bonus on a tropical island with prevailing hot temperatures). Reserve your spot in advance not to waste precious vacation time.

Price: $100-$150

Key West Jet Ski Tour

9. Exploring the island on a bike

There are yet so many places to explore in Key West and, though all being in close proximity, walking all day long would run you out of steam. Biking provides an alternative which is fun, convenient and reasonably priced. Bike rentals are on each corner on Duval, together with scooter rentals as your second best option. Go on adventure without a destination and pedal along less crowded streets with no tourists, no hassle and only a red rooster here and there. Enjoy Key West’s joyful pastel colors architecture, quiet charm and abundant tropical vegetation. Check out scenic Roosevelt Boulevard and White Street Pier.

Price: Under $20

Bike Rentals Key West

Explore Key West like a local

Explore Key West like a local

10. Duval Street and Old Town

Duval is where you were bar hopping yesterday, remember? Probably not :) So, here’s your second opportunity to take delight in the distinct allure of this tightly built up street with its endless galleries, gift shops and cafes. Everything here is tourist targeted and so quite overpriced, but you can find some really ingenious pieces. Don’t buy anything for the asked price – bargain!

Refresh yourself and prevent dehydration (it's always hot and humid on the island) with cooled coconut water from the coconuts cut only a few hours (minutes) ago by the small-scale street entrepreneurs. These babies (coconuts, not entrepreneurs) are delicious, healthy and quench the thirst perfectly! 

Price: free to walk and watch

Key West Road Trip

Key West Duval Street

11. The Ernest Hemingway Home and Museum

After spending all day under the baking sun you are probably quite well done and crispy by now. If so, this is the best time to transfer your juicy, browned body into a well air conditioned room and to enlighten your mind with a piece of lore. I am referring to visiting the Ernest Hemingway Home and Museum – the former residence of the author. Take a guided tour or explore the house on your own – it’s just lovely either way. For those of you far from literature, history and all that jazz – there are 6-toed cats in there! Lots of them! Purring, sleeping, stretching furry weirdos who claim to be descendants of the Hemingway’s cat and refuse to leave the premises.

Price: Under $15

Ernest Hemingway Museum

6-toed cats

12. The Southernmost Point

You can’t leave Key West without a picture with the southernmost point buoy! It is a must and should not be neglected. It is like leaving Paris without seeing Eiffel Tower or London without a picture in a red telephone booth. It should be regulated, really. Police officers should be stopping cars leaving the island and demanding an image with passengers' happy faces next to the buoy and in case they’ve got none, giving them a warning and placing their mug shots on the wall of shame of people who DID NOT show reverence to the island’s pride. I am kidding, of course, and not trying to downplay the importance of the buoy :) It is an interesting spot with a history to it which one would want to know.  

Price: Free

The southernmost point Key West

In the end a few random suggestions:

Beer lovers consider stopping by the World of Beer Bar (500+ global beers).

Hot spices lovers and not cliché gifts seekers stop by Peppers of Key West (free sampling, names like “Anal Angst X-Hot Sauce” and over 600 sauces selection).

After you had a blackberry-caramel with a twist of pumpkin beer and tried a couple of “Ass in the Tub” hot saucers, have a romantic sunset photo session and be done. It’s time to go home!

If you read through until this moment - you are my hero and thank you for being so amazing! :)

Key West Sunset watching

Key West Sunset

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    1. Best one written so far because it comes from the heart......really liked it and want to make the trip down to try it all!

      1. Oh you know me so well, Mike! I guess I am slowly finding my writing style...which apparently is rather sarcastic :D And you would love Key West for sure!

        By the way, thank you for being my best follower! ;)

    2. Anonymous26 May, 2015

      Key West seems so magical! The sunset photos are reason alone to go. Thanks for sharing!

      Silly Medley: Lifestyle and Travel

    3. So many great things to do, love this list! Just added Key West to my travel bucket list!


      1. Glad to hear, Eden! Key West won't disappoint you :)

    4. You are amazing!! Thank you to share all details we need... Thanx for your time pretty lady😘

    5. You are more than welcome! :)

    6. Currently planning my trip to Key West and came across your list. Love it!

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