A Weekend in Puerto Rico (2026 update)
This is an old post, updated for 2026
In 2013, a friend and I decided to do something relatively spontaneous and find a cool place to go for the weekend. She had been yearning to visit Puerto Rico, so we decided to bite the bullet and book a quick 4 day trip. I’m a bit of a PR veteran, having been there many times in the past to visit family. However this was my first time going as a “tourist” and I was excited about experiencing the island from a different perspective.
Granted, four days is not enough time to complete a comprehensive trip to La Isla Boricua, but we made the most of it. There are a few “must sees” for any first timer to PR; I’ve decided to point out a few of those, as well as highlights and pointers that made our trip so much fun!
Air
At the time, I was spoiled because I lived in Florida; San Juan is a 2 hour flight from Miami and 2.5 hours from Tampa. Although I’m now in DC, there are still several direct flights to San Juan with reasonable pricing. And don’t forget…no passport needed to go to PR!
Accommodations
I decided to book two hotels over the course of our 3 night stay in Puerto Rico in order to have different experiences: the serenity of a beach resort and the energy of a vacation in the city.
For the first two nights, we stayed at the Gran Melia Golf Resort in Rio Grande (which is now the Hyatt Regency Grande Reserve). This resort is located about 20 minutes east of San Juan and is an extremely easy drive if you utilize the expressway and toll road. We rented a car to give us the independence to move around at our convenience (more on that later); parking at the resort was $15/night. The resort is situated on a peninsula, so the drive to the property is quite lovely. You’ll pass the resort golf course en route to the resort.
The public areas of the hotel are gorgeous. The hotel is VERY Caribbean; there are no exterior walls, allowing the breeze from the sea to drift through the hotel. There are 5 restaurants and 2 bars located at the main property, giving guests plenty of choices when it comes to dinner and drinks. Since Puerto Rico does not have any all-inclusive resorts, all meals and drinks are paid a la carte. The swimming pool is one of the largest I’ve ever seen, complete with a swim-up bar. And of course, there is the beach, with its plethora of beach chairs and hammocks for guests to enjoy. There is a convenience store onsite (The Market), which sells almost everything under the sun at “resort premium” prices (I just made that up). The public areas also feature free wi-fi; I saw plenty of guests lounging in the lobby areas with their laptops and iPads. 🙂 (2026 update: Wi-Fi is now free throughout the entire property)
All of the guest rooms at the resort are Junior Suites or better, so they are very spacious. The resort is pretty massive, so there are golf carts available to help guests navigate the resort.
I found the property to be a very serene and relaxing resort. No one was in much of a hurry, and due to the time of year, the resort wasn’t very crowded. We were seated almost immediately at the on-site restaurants, and bar service was quick and efficient. We did have to stand in a short line to check-in for our rooms, but it was nothing to complain about. The resort is in a remote location, and if you don’t have a rental car you will be forced to dine at one of the on-site restaurants. They also did not offer much in terms of nightlife; a small band playing at the lobby bar was our entertainment. So if you’re looking for a resort with an active nightlife, this is not the place for you.
For our final night in PR, we relocated to La Concha Resort in the Condado area of San Juan. As soon as we arrived to Condado, we knew this was going to be a completely different experience. The traffic was CRAZY and there were pedestrians all over the place. Once we arrived, we were struck by the modernity of the resort. It really felt like we were on South Beach! The public areas are very contemporary and the pool area had a really cool two-tiered design with a full-service grill situated nearby. Just north of the pool was the beach, which was relatively small but did the trick. A continental breakfast is available at the lobby bar in the mornings and a full breakfast buffet is set up in the Voga Italian Restaurant.
We had an oceanview room with two double beds. The windows/sliding door were floor to ceiling, with an incredible view of the water. We were really pleased with this room. It had the all-important iPhone charger/alarm clock, a refrigerator that was NOT a minibar (I know, right?), and tons of closet space. Since we would only be there one night, we didn’t really take advantage of that. Wifi is also available throughout the resort.
La Concha also has their “upper tier” option for guests looking for an upscale vacation, with their guest rooms in THE Suite Tower. Those staying in this all-suite area of the resort have access to a private, adults-only swimming pool/beach area.
Since Condado is such a pedestrian-friendly area, there are a plethora of bars, restaurants and clubs within walking distance of the hotel. Old San Juan is a 10 minute cab ride away, and the airport is about 10 miles east, so there really is no need to rent a car if you plan to stay here.
I’ll end Part 1 of this post here, and return in the near future to discuss the fun stuff: Puerto Rican FOOD, fun, and getting “got” at the rental car counter! Until then….