Sanibel Island, Florida

Key West Travel Guide

After spending the entire month of May in Key West, I feel like we had a really good grasp on the most drool-worthy food, incredible experiences and what’s actually worth spending money on in the Southernmost Point of the United States.

First, here are some things you should know:

  1. May is the off-season (when we went) and it was so lovely! Less people, discounts galore and tropical weather. It’s a sweet spot in between the spring break rush and when summer travels start. We would highly recommend going this time of year to get the most bang for your buck.
  2. Food is simply expensive here. Get used to it. Look around for happy hours and food deals in order to save a little cash. Just ask any local – they are more than happy to fill you in on their favorite spots.
  3. Sometimes, buying is less expensive than renting. We bought this $70 inflatable 2-person kayak with two oars on Amazon Prime. Most kayak rentals are at least $25 per person, per hour. Even if you are flying and not driving, you could easily sell this before you left. Another example: scooter rentals. Scooters are a really fun way to get around the island. We bought mine for $800 before coming to The Keys and a good deal on a scooter rental is $125 a week. I could easily sell it for what I paid, so it ends up not costing you anything.
  4. Comparison shop, especially with touristy excursions or tours. Getting a good or bad guide can make or break the experience, so do a quick Trip Advisor search before you book.
  5. You don’t have to stay in Key West, especially if you have access to a car, bike or scooter. we stayed in Stock Island and I could literally walk to Key West, but it saved us a significant amount of money versus staying on Key West itself. As a bonus, I feel like we got a much more authentic experience and met a lot more locals being one island over.

Now onto the can’t miss experiences of Key West:

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1. The “Do-It-All” Excursion from Sunset Watersports

This was by far the best value in Key West for an excursion. For $129, you get to do everything for a day. Let me explain. A 2 hour jet ski package in Key West can easily be $200. Splurge on this one thing and you will save yourself a ton of money. For six hours, you get to go on a large charter and do the following, all-inclusive: jet ski, dolphin watching, paddle boarding, kayaking, snorkeling a ship wreck, parasailing, water trampoline, inter-tubing, water slide (plus more I’m not even listing) plus a free lunch and open bar (on the way back). We had so much fun and we got a fluke day where there was only 8 of us, when capacity is 120. We negotiated for the parasailing to be included (normally $10 more per person) so I’m sure you could as well.

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2. Go wine tasting at Key West Winery

I’ve been wine tasting almost everywhere, but The Key West Winery is a completely different experience. It is all about their fruit wines served in an informal environment. All of their wines are made from different varieties of fermented fruit (think kiwi, strawberry, blueberry, peach, etc.) and they taste amazing. Even Zach – who isn’t one for wine – was more than happy to sample some flavors. We bought a Groupon so for $45, you got a bottle of wine, two “adult pouches” of wine (perfect for bringing to the beach) and a wine tasting for two. Best of all, they let you choose the flavors you want to sample. Just a block away from the Southernmost Point, this is a can’t-miss. Truth be told, we went back twice.

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3. Have a decadent happy hour at Better Than Sex

This place is something that just has to be experienced. Everything has a well, sensual, theme (as the name implies). All of the drinks are served with a “rim job” (i.e. caramel or chocolate dimmed rim) which is incredible. They are known for desserts as well, but in my opinion, the drinks were better. My sugar-loving husband disagrees.

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4. Have brunch at The Banana Cafe

This cafe is so charming and located right in the heart of Key West, on Duval Street. Request to sit up top or at the bar. The coffee is fantastic, the mimosas are on point and Zach said the crepes are can’t miss. I even “cheated” for lobster mac-n-cheese and the decadent dish was 100% worth it.

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5. Have a dinner where the locals dine, at Hogfish

Hogfish is one of those local spots where the environment is relaxed, the food is incredible and you always walk away wanting to come back. They are best known for their daily specials, which give you as fresh of seafood as you can possibly get. I had a avocado shrimp ceviche one day that is out of this world. Their red sangria is amazing also.

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6. Walk down Duval Street

This street is really the heartbeat of Key West, it’s where all the cutest shops, great restaurants and well, action, is. At night, it comes alive and has a similar vibe to New Orleans. During the day, you will find people with exotic birds doing side shows, artisans and everything else you can image.

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7. Go kayaking through the mangroves and in the open ocean

The one thing that surprised me is that the water surrounding The Keys is so shallow. Make sure you watch the tides and go when the water is up. You can explore mangroves and kayak in The Atlantic Ocean or The Gulf of Mexico, depending on which way you go. We saw stingrays, barracudas, jellyfish and parrot fish while kayaking. Bonus points if you bring a wine pouch and go around sunset.

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8. Witness a sunset on the dock of Higgs Beach

There are two main beaches in Key West: Higgs and Smathers. We really loved Higgs, especially because of the amazing dock, which is perfect for sunsets, sunbathing and watching fish below.

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9.  Visit The Key West Butterfly and Nature Conservatory

This is one of those things you do expecting very little. But wow, this butterfly conservatory is downright magical. They even had flamingos and it is a very interactive experience.

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10. Scuba dive to the Vandenberg Wreck

This is one of my biggest regrets of our Key West trip. We couldn’t get the timing right to get certified and do this dive. Every single review looks incredible!


Perfect length of trip: 1 week

Ideal timing: May, less crowded and good weather

What to pack: Easy breezy blouses, sundresses, shorts, sandals, rompers and bikinis

What to splurge on: Excursions and diving

What to save on: Any trolley tour, just walk!

As always, thank you for reading.

Make sure to check out some of my other travel guides:


(Affordable) St. Thomas

Cartagena, Colombia

Quick Trip NYC


  1. Gigi Wrote:

    What Beautiful pictures & fun experiences, thank you fir sharing this!

    • Brenna Wrote:

      Aw thank you, Gigi!