Jetting off to the Caribbean might seem out of reach but it’s surprisingly not. I tried to find a route that was not only low on cost but low on layover time as well. This ended up being a combo ticket of both Frontier and Spirit Airlines. The times matched up fairly perfectly to make the tickets work out and the price was phenomenal ($177.50).
During the MCO layover (3 1/2 hours because our flight arrived early), instead of opting to wander around the airport or hang out at the gate for a few hours, I used my AAA card to get into The Club at MCO at Terminal A. This might seem like an unnecessary expense off hand but it’s not. During the 8:30 am – 12 pm time we were there, we managed to fit in breakfast, lunch, snacks, and a few drinks. There was ample seating, plenty of outlets to charge your electronic devices, a little office center with printers, restrooms, and showers. Well worth the price of admission.
San Juan Weekend Getaway – Stay
We used Booking.com to book a room for Da House in Old San Juan, which was right in the middle of all the action of the town. The hotel is a historical site and features a romantic bohemian vibe. There is no elevator but there is a beautiful staircase to lead you to your room. Our particular room didn’t have windows that looked outdoors, they looked into the hotel, which sounds a bit odd but it was actually really nice.
Outside of our bedroom window 
Bedroom
There were several little nooks within the hotel for reading, playing games, or just having a glass of wine. There’s a 24-hour pool on top of the hotel that can be accessed from the 4th floor. I will warn it’s a bit small and more the size of a hot tub. Music travels throughout the hotel from a classic record player in the lobby.
San Juan Weekend Getaway – Dining x Play
This section is combined because there are many, many things to do in San Juan, but I was quite content venturing around to different restaurants and bars. It’s quite difficult to find really good any Puerto Rican food in Charlotte, so it was my preferred thing to do while I could.
Caficultura – This is my must go to spot in Old San Juan. I discovered it during our Carnival Cruise last summer and have been 3 times since. They have the most amazing hot chocolate I’ve ever tasted and I love that it gets just as much design love as the coffee-based drinks. All of the food items look amazing, but I’ve only ever gotten the croissants with the guava butter … beyond amazing.
Smoke It and More – This is not just a smoker’s hangout, as the name suggests. This smoker’s paradise has unexpectedly amazing drinks and food. There’s no smoking in the shop, from what I could tell, so you don’t have to worry about it killing your food and drink plans.
The best Rum Punches are located here (they’re also only $4) and even more surprisingly, some damn good sushi. We did a traditional spicy tuna roll and a local Hoja Borica, which features plantains two ways. You think you don’t want it but you do.
Los Yeyos – We only stopped in for drinks, but I’ve heard the food is delicious as well. It’s a bit of tight squeeze but that adds to the appeal. The walls are covered with memories of visitors past and, unfortunately, I forgot to leave my mark. They had dollar shots of various drinks, so we stopped in to try a few because why not.
Punto de Vista – This rooftop restaurant was recommended to us as having the best mofongo in Old San Juan and I’ll have to agree. I hadn’t had mofongo in YEARS and it was the one meal I was dying to have on this trip. Punto de Vista gives the option of a sweet sauce or a creamy garlic sauce, which I went with and it was amazing.
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Roundtrip Frontier ticket from Charlotte to Orlando: $37.10
Roundtrip Spirit ticket from Orlando to San Juan: $140.40
The Club at MCO: $39 (with AAA card)
Taxi to Old San Juan from the airport: $24 (only accept cash)
Da House: $129
Food & Drink: $75 – $100
