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Our Key West Vacation

Every Labor Day weekend we try to go on a trip. It’s a combination of a three-day weekend and usually my birthday weekend and we like to celebrate a little. We typically go to Las Vegas, but we weren’t in the mood to gamble this year, so we decided to fly into Key West for our first time ever.

When we go to the Florida Keys, we typically fly into Miami and drive through all the Keys. This was a different experience, but when you’ve only got five days to spend there you want to savor every minute. We flew into Key West on Wednesday, and we took the earliest flight we could to A) get there as soon as possible and B) hopefully avoid any delays or cancellations from the airline. It’s also so nice not having to deal with a car down there. It’s so hard to find parking and not having to deal with that was a relief.

Key West Airport

Wednesday – We landed, left our bags with luggage porters and headed down to Duval Street. We stayed at the Bahama House, and it was a fabulous spot. A spacious and clean condo with a pool in a great location that’s close to all the action. First stop: We knew we wanted to get Cubanos at Cuban Coffee Queen and that did not disappoint. It is probably one of the top Cubanos on the island. We bar hopped up and down Duval Street that afternoon while we waited for our friends to arrive. We also did our favorite happy hour at Alonzo’s Oyster Bar, which is one of the best happy hour deals in Key West. It was the quietest night in Key West in terms of people in the bars and on Duval Street.

Thursday – Ryan and I had lunch at Bo’s Fish Wagon, which was a new spot for us. On the outside it is really unassuming, but the food is incredible. All the fish is brought in fresh, and you can tell! In the afternoon, the four of us did a food tour with Key West Food Tours. This is the third time Ryan and I have booked with this group, and we absolutely love it. It’s a great way to see a lot of the island and try a lot of off-the-beaten-path places. They do food tours and cocktail tours and I’d recommend both. This was the cloudiest day we were in Key West, so we watched the sunset at Sunset Pier. We also stopped by Berlin’s, a dark and romantic speakeasy. Classic cocktail list and a great view of the harbor. We finished off our night watching The Durtbags at Durty Harry’s.

Friday – Friday’s lunch included lobster pizza at the Seaside Cafe, something I tried for the first time in March and fell in love with. It was also insanely hot that day so went to Dante’s for a pool party. If you like Vegas-style pool parties, buckets of beers and DJ’s bumping the best songs, you’ll love this place. That evening we did a sunset cruise with Sunset Watersports. This is something we try to do every year. It’s a fun boat ride and includes unlimited cocktails.

Saturday – We wanted to climb to the top of the Key West Lighthouse, which is one of the best views of Key West you can find. It’s $17 to climb to the top and see the museum and it’s absolutely worth the price of admittance to get that fantastic view. We stopped at Ram’s Head for drinks after, which was also a new spot for us. Fabulous drinks and food there. We hit up Alonzo’s again for happy hour before the highlight of the day: I managed to get us reservations at Latitude’s, the only restaurant on Sunset Key. You take a short boat ride out to the restaurant and get some of the best views in the Keys.

View from the top of the lighthouse

Sunday – For lunch we stopped at a spot we’d never been to The Eaton Street Seafood Market. Ryan and I had walked by this place a hundred times but never gone in and WOW – we were absolutely missing out. We had the yummiest lobster roll, but they have tons of options for any seafood you could possibly want. For happy hour we went to The Boat House, which is another awesome option for happy hour in Key West. We finished the night by having dinner at one of our favorite little Italian spots, Mangia Mangia.

View at Latitudes

Things to consider:

  • Flying directly into Key West eliminates the need for a car, which is so nice. Parking is nearly impossible down there, so we stuck to walking and Ubers. You can also easily rent a bike or scooter to get around.
  • It is extremely hot in September. The temperatures were in the high 80s/low 90s but the humidity is around 80-85%. Be prepared to sweat A LOT. If you’re staying for a week or longer, plan days where you just lounge by a pool. We’re typically in Key West in March when temps are high 70s/low 80s and cools down a lot at night. Major difference!
  • Can’t get into your hotel room? Book a luggage porter! We landed at noon but couldn’t get into our Airbnb until 4PM. We didn’t want to drag our bags all over Key West, so we called up Paradise Porters and they took our bags and delivered them to our house when we were ready.
  • Wednesday night when we arrived it was very quiet on Duval Street, but by Saturday it was hopping. We are used to being there when it’s very busy (spring break season) so Friday/Saturday was more of what we were used to in terms of the amount of people out and about.
  • September is typically a month where many of the restaurants in Key West close to give workers a break before October and Fantasy Fest kick off. Everything was open when we were there through Labor Day weekend, however a lot of restaurants were closing the day after Labor Day for the entire month. This meant a few of the restaurants we went to were very limited on food options due to being closed in September. Just something to consider!

I’ve got our whole trip saved in highlights on my Instagram under Key West ’22 if you’re interested in seeing even more of what we ate, drank and saw. If you ever have questions about booking a trip there, please don’t hesitate to reach out!

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