Puerto Rico is the only Carribean island owned by the United States, therefore it is easy to travel in and out of and a fabulous place to stay! You don't need a passport to go through security and the flight time isn't bad at all. If you're ooking for a Carribean getaway, Puerto Rico is just the right amount of fabulous.
Our first night we stayed on Ashford Avenue in downtown San Juan and ate at one of the street vendors on the beach! They made chicken on a stick and fresh lemonade (with rum and brown sugar). If you have the opportunity, eat from the street vendors because that is the true local food and it's cheap! I drank a lot of fresh coconut water- they keep whole coconuts and just slice the top off!
The next three nights we stayed at a resort in Rincon (the surfing capital!). It was beachfront so I rolled out of bed and slept on the beach most afternoons. While we stayed here, we rode horses on the beach (with Pintos r Us), went snorkeling along the reef and swam at night in the bioluminescent bay, and went parasailing along the coast (I HIGHLY recommend doing this! The view of the island was incredible), and spent the afternoons lounging at the resort.
The following two nights we moved to a villa in downtown Rincon (more of a local vibe than a touristy one!) and it was fab. We booked this through air bnb and it was such a great place! If you're traveling in a group I would say try to use air bnb- since you meet the owner privately. There are so many incredible places that are not your basic Mariott that will help you experience a town and its culture. This was by far my favorite place we stayed! It had a full kitchen and balcony and pool with a view. While we stayed here, we hiked the El Yunque National Rainforest, and ate at a local beachfront restaurant, Copa Llena, every night! I would definitely get a mango mojito anywhere you go- Bacardi is made in Puerto Rico, so it's their specialty!
The last two nights we went back and stayed in downtown San Juan and toured the San Juan National Historic Sites. We walked through the Fort San Juan de la Cruz, which is where the Spanish spent 250 years fortifying the Island of Puerto Rico and controlled the Carribean with. We also walked down to the SJ Gate that evening, I would recommend walking in the evening when it is close to sunset. Also, the Capitol building has one of the most fabulously painted ceilings I've ever seen. If you have time, walk through the churches too. No matter what religion you are, you can appreciate the beauty.