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48 hours in Key West

48 hours in Key West

We only had a week in Florida, so we decided to spend a few days in St. Augustine and a few days in Key West. If anyone is wondering it is around 8 hours drive between the two cities. Despite it being a busy week, it was a blast. Now, I’m not sure I’d recommend these two particular cities back to back considering the drive, but I will definitely recommend visiting these two cities in general.

Now, my family is a bit different from the typical family vacationing nowadays, we are all over 21, which really is a glorious time and opens up some new doors.

Before the Vacation

Now, we did a little planning before our Key West trip. We booked three things beforehand.

  1. The hotel. My father is a big believer in rewards programs and we tend to work with Marriott. We stayed in the Fairfield Inn, which the rooms seemed a little small for four people, but they were still nice. We especially liked the pool and free breakfast.
  2. Sunset Cruise. We did some online research and found Sebago Tours – they had fantastic reviews and a variety of options. Be sure to book online for the discount!
  3. Dry Tortugas. This was a bucket list item for my mother. So we booked tickets for the four of us.

48 Hours in Key West 

The First Day – Kicking Off Our Trip With a Bang

Since St. Augustine is further north, we stopped there first. After a day of rest, we started our trek down to Key West. It was a long drive. Knowing that we would get in around 4 pm, we booked our sunset cruise to be that night to kick off our Key West trip right.

We got into the hotel and were welcomed by a warm smile and a cool drink that tasted like a virgin daiquiri. After changing into cooler clothing because of the heat down there, we threw the address for Sebago in our GPS and were on our way. Thankfully, Sebago emailed me confirmation information and gave more detailed instructions because we were not familiar with the area.

We found a parking lot that you could pay a decent price of parking for 24 hours nearby and we went over to check in an hour before the cruise. They say to get there a half hour before the cruise starts, but we wanted to get our tickets then check out the local shops.

Nestled between a clothing store, a photography shop, and some food places, is the Sebago Cruise office. You walk in and are instantly greeted by big smiles. Of anywhere I went in Key West, I did not meet anyone more helpful or kind.

Now, there are a variety of cruises to choose from. We considered the Champagne Sunset Cruise or the Captain’s Choice Sunset Cruise. We went on the Captain’s Choice. It is a smaller ship, only seating a max of 20 people, which I thought was perfectly comfortable and intimate. At the office, we were given our tickets, and then we were told when and where to meet.

We browsed the local shops and I fell in love with the local art. We also were amazed by the free roaming chickens and roosters. They are all over the place. I couldn’t believe seeing a rooster, chicken, and babies right outside a store. You hear roosters crow wherever you go. Also, expect to see iguanas. These massive reptiles aren’t quite as commonly found outside shops, but I certainly saw a few.

We had plenty of time to drop off our purchases at the car then meet back up for the cruise. We started the cruise with the usual safety warnings, a drink in our hands, and an introduction to the cruise staff (an experienced, knowledgeable, and funny Captain and a prompt, quick to assist, and fun bartender/deck hand). These two people helped make the cruise even more enjoyable. Also, don’t worry, despite it being only a 2-hour cruise, there is a decent sized bathroom.

Our cruise party had only 14 people and it was a great number. Plenty of space inside the cabin and out on the deck. We cruised around the harbor and out further, back in forth in the area. We got to hear about the local interests, take in the beautiful sights, and sip on a variety of drinks. They have different wines, sangria, basic bartending alcohols, and a bunch of beers. I was a fan of the sangria, but that’s my go-to drink when I’m on a tropical vacation.

After sailing around for a while, they broke out the food – caprese and olive skewers, mini sandwiches of turkey or roast beef, shrimp, and little chocolate pastries. I suggest not coming that hungry. Please have a snack or something beforehand because you will start off drinking. However, I will say that after having all that food we really weren’t hungry for dinner (except my father, but he’s always hungry). If you have small meals throughout the day, then this is more than enough. It compliments the alcohol and lets you enjoy your surroundings.

Although there wasn’t a sunset due to the hurricane not too far away, it was still my favorite part of the trip. The views and overall cruise were the perfect start to our Key West adventure.

Our cruise included people only over 21, but they still have soft drinks and water in case you don’t want to drink. Even if I wasn’t 21, I would certainly enjoy this! A little tip, be sure to bring cash to tip. These people work hard and do a great job so remember to bring a little something to show some gratitude.

Many people were requesting suggestions from the Captain and Bartender for food, which they typically took into account specials like half-priced drinks and appetizers that usually only locals know. So be sure to ask a local if you don’t already have plans for dinner.

We were stuffed from the cruise so we went back to the hotel for an early night sleep – we were exhausted.

Day 2 – Dry Tortugas and Local Flavor

We had to get to the terminal for the ferry ride to Dry Tortugas a little early. We used the parking lot and pass that we bought yesterday that lasts for 24 hours – a purchase I would recommend if you’re going to the same area often.

Before we boarded the large boat, the crew briefed us about what you can and cannot do on the boat and the island. Be sure to pay attention.


Extra tips:

  1. If you get seasick, be sure to bring medicine for nausea.  
  2. DO NOT leave anything at the terminal. It will be closed when you get back and there is no getting in.
  3. Bring an extra water bottle. The reusable kind because they provide water at only certain times on the boat and you have to pay for the rest. So bring waters for the family and fill up at the water jugs to have more.
  4. Bring a jacket or something for the ride back if you are planning on sitting inside instead of outside. After a long day in the sun, it tends to feel rather cold inside.
  5. Bring a bathing suit, a change of clothing, towels, and anything else you want to do, like snorkel gear. However, if you don’t have your own snorkel gear, you can borrow some when you get to the island.
  6. Bring good walking shoes, it doesn’t matter if they are flip flops or tennis shoes. Make sure they are comfortable.
  7. Did you also know that you can submit a photo to be voted on to win money? There’s more information on the boat about the contest.
  8. Bring plenty of cash to tip. You can tip the tour guide, the bartender, the boat crew, and so on.

The ferry ride took a while, but everyone sleeps on it anyway. Now, breakfast and lunch are included, but we had breakfast at the hotel. Instead, we grabbed the cereal packets as snacks to have throughout the day, before and after lunch.

You can take a tour of the island, which I heard was really good. We just immediately went to one of the areas for snorkeling. The beach is typically busy, but once you get out in the water there’s plenty of room.

Be careful of the possibly strong tide. However, my family scuba dives so it didn’t really affect us.

I loved seeing the sea life! Despite the storm making things a bit harder to see, I still enjoyed snorkeling for a while and then just swimming around in the perfectly cool water.

After a few hours of swimming, we had the perfect break for lunch. You go back to the ship where there’s a huge galley with a variety of sandwiches, non-alcoholic drinks, and sides like hummus, chips, and potato salad. You can keep going back if you need, so you can get plenty of food.

We decided to walk around the fort after lunch. We went around reading about the history. I was astonished in what they had to overcome and what they went through. Just be aware that if you go to the higher levels that it’s a lot of narrow stairs and no railings, so you might want to stay on the ground if you are worried. If you are not, be sure to be careful, but the views are breathtaking from the top of the fort.

Afterward, there was just enough time to change and get a good seat back on the boat. Be sure to check in that you and your family members are on the boat, this is making sure that no one gets left behind.

On the trip back, the bars are open. They can make anything from a virgin (or alcoholic) daiquiri and other mix drinks to handing out a refreshing beer. Of course, you have to pay and tip, but for the long boat ride, it can be a nice reprieve.

Once we got back to shore, we went back to the hotel to freshen up. Then we went out for dinner. We heard from a local that a restaurant called Hogfish Bar and Grille was way out there, but worth it. The local was right – it is out there, but the food and drinks were good. It’s a local and tourist eatery, which is a good sign, right? It’s more of an outdoor covered restaurant and bar, where you sit on picnic tables and look out at a local marina.

If you enjoy seafood, you need to try a few things in Key West. I recommend the pink shrimp and the hogfish. Both are local delicacies. I think the Key West pink shrimp are bigger than some typical shrimp with some good flavor. While the hogfish is ugly it does taste good. You can get hogfish in a wide array of ways and you’ll often find them at the majority of seafood restaurants in Key West. If you’ve never had it and enjoy trying new seafood, I suggest trying it at least once.

At HogFish, we had some appetizers, drinks, sandwiches, and the famous key lime pie. I enjoyed my key lime mojito and my parents loved their local beers, as well as all of the food. Now, if you leave Key West without having a key lime pie, you are missing a key piece of their legendary cuisine.

After a night of rustic seafood, we went out shopping again. There are so many stores that offer anything from clothing and souvenirs to sweets and local street food. You can go down the main streets downtown or check out Mallory Square and other plazas.

If you still have the energy, you’ll be there in time for the Sunset Celebration. You can browse vendors, watch street performers, and enjoy both the crowd and the sunset. You will see people on crowded hotel tops and balconies to enjoy the legendary sunset.

Just be aware that there will be crowds and traffic because it is a festival during the summer.

Day 3 – The Final Morning Before Hitting the Road

We decided to spend our last morning by sleeping in and taking a dip in the pool. This allowed us to be nice and relax before the long car ride. However, I know others that used this free time to tour a few hot spots like the homes of Ernest Hemingway or Harry S. Truman. The Hemingway home and museum is supposed to be inspiring! Just we warned, if you are allergic to cats (like my father), I might not advise it. They have kept breeding the cats Hemingway had while he was alive and now there are a lot!

We checked out from the hotel and hit the road. Alright, alright, my final bit is not technically Key West, but it’s one of my favorite restaurants on this trip and this one had some of the best prices, so I have to mention it. On Key Largo, there are two restaurants called Mrs. Mac’s Kitchen 2 and Mrs. Mac’s Kitchen the original. Both are delicious, so it doesn’t matter which one you go to.

The majority of the people that go here are locals. It has anything from seafood and steaks to sandwiches and salads. The prices are reasonable, the portions and large, and the people are friendly. This quaint eatery allowed us to leave the Keys in bliss. We had fresh seafood like fish tacos, shrimp and fish, and crab cakes. While you are there, you need to try their Key Lime Freeze. It’s only around $4 and it’s huge, plenty to split between two people.

Our trip to Key West was busy, but there was still plenty more to do. Despite going non-stop, we loved every minute! Click here to check out the Florida Keys website to see more attractions and vacation options.

Some or all of these attractions provided discounted or free tickets for the purpose of review, but as always our reviews and opinions are our own. 

What to do when you only have 48 hours in Key West