A Couples Weekend in Key West

We travel as a family at least 5 times a year around the country. However, my husband and I always make time to do at least one couples getaway once a year (more if possible). Since we live in Miami, FL, a road trip to the Florida Keys is high on the bucket list. We drove down to Key West for a couples getaway and had a blast relaxing, eating and enjoying the outdoors. Here is my review on what to do, where to eat and stay for a couples weekend in Key West:

First of all, if you would like the simple itinerary of what we did, click on my post - a Key West Weekend.

We drove down to the Florida Keys from Miami around mid afternoon and were excited about the beautiful 3 hour drive ahead. We did not stop until we reached Key West because we were hungry and wanted to eat where our friend had recommended. If you are planning on stopping through the Keys, check out my post - Best Restaurants in Marathon FL (it is a little over half way down the Keys) or this detailed post on the Miami to Key West Drive with 25 stops along the way.

HogFish Bar and Grill

This was our first stop just before we hit the main downtown area of Key West. It is technically located in Stock Island, which is just 5 minutes outside of the main Key West tourist area.

What a great meal! This place is the "Keys" - a very local type spot with fresh seafood, great drinks, and nice waterfront dining. They are open for breakfast, lunch and dinner, and on the weekends have live music. I highly recommend making this a stop on your weekend in Key West.

Better than Sex Desserts

When I heard about this place, I was a little unsure due to the name. It is a dessert only restaurant! Besides a traditional ice cream shop, I didn't know places like this existed. Let me start off by saying that this is adults only... all of the desserts here have explicit names and the artwork in the place shows "some skin". Many of the desserts are also plated in a "suggestive manner" (if you catch my drift). I repeat - this is not a kid friendly place!

Now that we are past that part, you really do need reservations to this dessert restaurant. It was packed when we arrived at 9:00 PM and luckily they sat us right away. The menu is brought to you in a tablet where you can scroll through pictures, descriptions and laugh at the clever dessert names. In addition to the desserts, there are dessert type drinks with liquor, beer and wine options. I ordered one with chocolate infused into my Cabernet and loved it.

Let me say that Better than Sex Desserts was a lot of fun and laughs! It is the perfect dessert and drinks place for a couples weekend in Key West.

Where We Stayed:

Hyatt Residence Club Key West Windward Point

This hotel was beautiful! The reason we chose this place was due to a special 4 day/3 night offer I was emailed since I am a Hyatt member. I am a budget traveler and am always looking for ways to save on travel, so when I was emailed a cheap rate, I jumped on it. See how I use hotel credit cards to travel for cheap or free and How to Get Free Hotel Stays. Well, the rate was so good that we asked our best friends to join us for an impromptu couples weekend in Key West.

Pros

- great rate

- huge 2 bed room suite with a full kitchen, large balcony, pool and ocean view

- quiet and away from the hustle and bustle

- nice, relaxing pool and very good bar

Cons

- not walkable to downtown (had to take a taxi - Uber is not allowed here)

- close to the airport (could hear the planes landed and arriving)

- had to sit through a 2 hour vacation club presentation (that's the catch to get the good rate)

Here is a video tour from our balcony:

Check rates to Key West resorts on the picture below:

Glazed Donuts and Red Buoy Coffee

What a tasty donut! We took a quick little drive to this breakfast place and immediately loved the robot theming. Their coffee was flavorful and the donut selection was on point. They had everything you would expect from a donut shop with some local twists (key lime of course). If you love a good donut, you must come visit this place.

Kayak Adventure

After an early breakfast, we headed to the marina for our kayak adventure through the mangroves. We used a company called Lazy Dog Adventures for our kayak and snorkel tour- we loved them!

If you are staying in Key West, they offer to pick you up on their shuttle for free, but since we were already planning on driving to breakfast, we drove the extra 5 minutes to them. Once we parked, there was a check in station and we quickly got our gear and kayaks ready to go for the 2 hour adventure.

After some quick basic instructions we were off with our small group of about 5 kayaks and our guide. She was so knowledgable on the surrounding area/wildlife and gave us great pointers on how to steer, slow down and enter/exit the kayak (we are beginners).

Our favorite part of the entire kayak adventure in Key West was going through the mangroves. There was an area that we had to go through that was too shallow due to low tide and instead of paddling, we had to use our hands to pull ourselves through the mangroves. It was quite a workout and a little nerve-racking, but looking back on it... very fun! Check out the video below to see how we did it!

Part of the tour also included a snorkeling stop. They provide you with masks and snorkels but we brought our own full face snorkel mask. It was our first time using it so we were both very excited about testing it out. Sadly, the water visibility was not great, but we loved how the mask worked. If you are ever down in Key West or even in the Lower Keys, you should check Lazy Dog Adventures out. They were a great company with very knowledgable guides and have a variety of tour options. Click the picture below to look at the tours they offer.

Lunch at Hurricane Hole Marina

We were going to drive back to Key West, but were starving so decided to just stay here where we parked our car at the start of the kayak adventure. I am glad we did because this place was great! We had their fresh catch and each ordered a frozen beverage. It was a delicious lunch.

Hurricane Hole Marina Restaurant

After an exhausting morning, we just wanted to relax. We headed back to the hotel pool to change and have some drinks poolside.

Then, it was tourist time. We took a taxi and toured Duval Street (this is the famous main street in downtown with all the bars and shops). We were dropped off on Mallory Square and strolled around Duval Street and meandered over the side streets too. There were tons of souvenir and gift shops with crazy T-shirts and funny signs along the walk. Be aware- many of these places are not kid friendly and curse words are found very frequently in print.

After having a drink at a couple of bars, and doing some shopping, we walked to the end of the street where the famous Southernmost Point sign was. We took the touristy picture (after waiting 10 minutes in line) and then walked back and saw the Hemingway House and Little White House. I would have loved to tour the grounds of each place, but we were hungry and needed to get back to the main area for dinner.

Check out the best selling tours in Key West:

Hot Tin Roof

This was another fantastic meal! It is located in the Ocean Key Resort right in Mallory Square and offers some of the best waterfront dining and Latin/Caribbean fusion in Key West. We purposely made dinner reservations to catch the sunset and it was well worth it.

They have numerous tables by the windows and have outdoor dining too. This place was more of an upscale restaurant, and had delicious appetizers, seafood, meats, drinks and desserts.

On the last morning of our couples weekend in Key West, we slept in and enjoyed the pool until it was time for lunch. We headed back to Mallory Square and took a small ferry to Sunset Key (an island just 2 minutes offshore).

Latitudes - Sunset Key Cottages

Once you step off the ferry boat, you feel like you have been transported to the Caribbean somewhere. I don't know why, but the water was more beautiful here than a few yards away in Key West. It is a residential community, and there is one company that manages vacation rental cottages on the private island. This is where the restaurant, Latitudes, is located.

It is open for breakfast and lunch, yet for dinner there is a dress code enforced. We were dressed pretty casual and it was not a problem. For the budget conscious travelers like myself, please note that the prices are also much better during lunch (hence why we came at noon).

The food was amazing! The views were amazing! The whole island was amazing! After lunch, we walked around the beachfront for a few minutes and took the ferry back to the "main land" of Key West.

We left right after lunch and drove back to Miami after a terrific couples weekend in Key West. Pin for later - click below.

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