For my mom’s 70th birthday I gave her a gift she’d talked about for years: a return trip to Key West.
When we were younger, we went often. She was in her forties and I in my twenties. We camped once; hotel-ed it a few times; and this time around rented a room in a guesthouse.
Key West Express
We headed out to Key West via the Fort Myers Key West Express Ferry. The ferry departs at 8:30 so we were there and boarding at 8. Boarding went smoothly, and upon getting on the ferry we took our bags to the back and checked them in so we could enjoy the ride without lugging them around.
The ride was smooth and the day beautiful; we walked around a bit and then settled into a chair and watched a movie while eating a snack. The trip took a little over two and a half hours, so we were in Key West before lunch.
I’d booked the Author’s Guesthouse for a few reasons. One, it was a mile from the square, so fairly close. Two, it was off of the immediate busy streets so I hoped it would be fairly quiet at night. Three, it had free wifi, breakfast and a pool, perfect for cooling down on a very hot day.
The guesthouse turned out to be a quaint, quiet place to rest. I loved the décor, which followed the old-time feel, and the location: no traffic noise at night, pedestrian or otherwise. It was far enough off the main strip of Duval to be quiet but close enough for a quick cycle or walk. Breakfast was good, with yogurt, fruit, coffee, toast and juices, and it was housed on the downstairs patio area. Small, but enough for us.
The only downsides I found were the pool was more like bath water, which wasn’t refreshing (though it was pleasant in the morning when we went after breakfast) and the wifi was only available when we sat next to the pool (our room was upstairs and toward the back) or on the upstairs patio area, which wasn’t right next to our room. That was fine by me; I am okay with disconnecting when away, and, honestly, it’s the Key West way!
Speaking of . . . Key West!
Here’s the thing: Key West is super hot in the summer. I knew this. Originally I’d hoped to book the room for the winter months but things got crazy with work and I couldn’t. So when we stepped off of the ferry and the sun was beaming down, it was hot. As in fry your skin off hot! And we had a mile to walk to get our luggage to the room. At that point I thought the room was actually closer than that because we weren’t starting at Duval; it wasn’t. We got to the room drenched in sweat, but thankfully we were able to immediately check in because the room was ready.
The weekend itself was a blast. We tried to hit as many ‘touristy’ spots as we could, though we skipped Hemingway house (we’d both been there several times prior). I obviously took a nice long run around the island one AM, stopping to view the lighthouse, the Southernmost Point (where a fellow runner took my photo), and the ocean.
Key West can be what you want it to be. If you want to go and drink and party, there are plenty of opportunities. If you want to go and do some sightseeing, you can do that, too. Fishing and water sports are obviously a hit here, as is shopping – from tacky tourist stops to high end art.
If you’re planning a trip to Key West, here are some thoughts from my trip.
- Get a pass for the all day trolley or train around the island. There are several. We opted for Old Town Trolley since it was a buy one day, get one day free. The trolley offers 13 stops around the island and runs every half hour. The upside: You can get on and off at a variety of areas on the island, from the Mallory Square area to Hemingways house to the Southernmost point, and you can pick up a new trolley at the same stop every half hour, which is really convenient. The cost is not bad, especially considering it covers two days, and it is much better than a taxi fare (which we also tried). Some guesthouses and hotels offer discounts to the trolley, too. Also, the drivers tell a history of the island and you get to hear some great stories, such as why Ernest’s wife purchased a home near the lighthouse (think: bars) and how one bank became the idea of one of Ernest’s novels because they had refused to give him a loan at one point. The downside: If you are at stop 8 and want to get to stop 7 you’re going to ride for a while! The trolley only goes one way. Also, on super busy days, which happened our second day in town, some groups had to wait for the next trolley because ours was full. This only happened once, and when it did the trolley driver called back and let the company know they had people waiting.
- Plan for the heat and humidity. We live in Florida and are used to the weather, but even for us the heat and humidity were rough. Make sure you hydrate well, get out early and late, and take some dips in the pool when you can. Drink nuun! Or whatever it is that replaces your electrolytes.
- Get local for food. Skip the chains and enjoy some great food at some local places. We thoroughly enjoyed an easy lunch at Fisherman’s Cafe, which was right off one of the trolley stops. This is not a sit down restaurant, but one in which you order at the counter and, if lucky, grab a stool nearby. If not – which really isn’t bad either – you can find a bench on which to eat. The food and service were both amazing, and we tried yucca fries for the first time (delicious!). We had a dinner at Caroline’s Cafe on Duval, where the servings were large and the owner of the restaurant – along with the manager – stopped by the table to make sure everything was fine. It was!
- Enjoy a fun place to stay. Key West does offer the standard options, such as hotels, but you can also find a neat guesthouse if you look. The room was about the same cost as a hotel and I like staying in smaller guesthouses when possible. We got to meet the neighbors, the cat was quite friendly, and the lady who managed our place was very nice and accommodating.
- Take the ferry! The ferry was an amazing experience, from start to finish. The crew was great, they offered some food and drinks on deck, we got to watch a movie going each way, and even though we hit incredibly rough seas on the way home – seas that made me put my head down for a bit in hopes I would avoid throwing up all over the aisle – I would do it again.