Vieques! I've been to mainland PR 3 times and Vieques 3 times and much prefer Vieques. The beaches are spectacular and quiet. The bio bay is very cool. Lodging is mostly inns, house rentals or the W Hotel ($$$).
We went last year and loved it so much we are going again this year! We did Old San Juan last year (kids loved the forts), the caves, the bio bay in Fajardo, hiked to the top of El Yunque, and then spent three days on Culebra.
This trip we are spending one night in San Juan (to go back to the forts) and a week on Vieques. We rented a house via homeaway.com (there are nine of us this time).
We found it was cheaper to fly into San Juan, rent a car for the week, fly out of the little airport on the other side of the island (leaving the car in the lot), and then rent another car on vieques (they won't let you bring the rentals on the ferry), than flying directly to Vieques from San Juan.
We stayed on Vieques for a week a few years ago and loved it. We rented a nice house through VRBO. The highlight for us was the Bio-bay trip at night where tiny luminescent creatures light your body up in the warm water. I think the guy who did Avatar (Cameron) must have been there at some point. It is one of the highest concentrations of these beautiful little creatures in the world. There are also a lot of horses on Vieques and it is not highly developed commercially. The beaches are beautiful (and more and more are being reclaimed from their former navy use.)
I second the Vieques bio-bay experience. It is the one experience that permits you to swim in the water rather than just boat through it. That has it's pros and cons, however. You may want to wear a swim shirt and possibly leggings and swim shoes. Due to the water conditions in the bio-bay, there are a lot of jelly fish. My daughter was stung badly on her leg, but no one else on the boat was. She lived, and although she said it was worth it, she would not do it again without wearing more protection.
If you do plan a trip with this experience in mind, plan your trip for moonless nights. A bright night will ruin the trip and they don't even go during a full moon.
Vieques is beautiful. We flew into San Juan, took a van to the hotel, stayed a few days at El Conquistador and rented a car for a day trip to hike El Yunke which was fun. (My daughter loved swimming in a waterfall, even though it was freezing water in March!) Then we took a ferry to Vieques and stayed at the W hotel for two days. It was lovely, but extremely expensive and was our only option due to my daughter's age. Many terrific sounding lodging options are restricted to adults only.
I really enjoyed shopping in Vieques, btw. We met a very nice woman who drove a taxi. She gave us her card and happily acted as our personal driver for day trips to the beautiful beaches and for shopping while we were in Vieques. As I recall, her rates were very reasonable.
@sac before I babble on forever could you narrow down the types of things you guys might like to do, what area of the island you may already have been n mind and anythings you wouldn't like.
I've got tons of activities and places I could send you too and I know my way around the island pretty good, so, what are you more or less looking for?
We did a few days in old San Juan and then took the ferry to Culebra- gorgeous beaches, very undeveloped in a god way, lots of interesting places to stay run by highly unique ex-pats.
Would definitely recommend renting a car and exploring around. Very easy to do so. We went years ago so my memory is hazy but I remember we only spent a few days in Old San Juan and the rest of the time driving all over the island and staying in different places. Highly recommend the bio bay in Fajardo (we didn't have time to get over to Vieques) where we canoed and then swam in the bay.
We did a long weekend in Old San Juan and really enjoyed it but wouldn't have wanted to stay any longer. 3 days was enough but that was also after spending a week in the Virgin Islands. We stayed at Hotel El Covento and absolutely loved it and highly recommend it.
Our number one activity is birding and we are working with a local guide on a 5 day/4 night birding tour for part of our trip, but we will still have a first night in San Juan and then 3 more days and nights after the tour. Interested in lodging suggestions for one or two nights in San Juan and the bio bays for sure. Also zip-lining and/or snorkeling. We don't really 'lie in the beach', but are usually 'on the go'. But we mostly will go places that will have good accessibility for my MIL who will be with us and has limited mobility, so lots of sightseeing by car plus walker/wheelchair accessibility will be good. No, she won't be zip-lining.
Dates are set and we already have plane reservations.
+2 for El Convento in Old San Juan. You can walk to everything--historic sites, restaurants, shopping.
Edited to add: I just caught what you said about your MIL. In terms of being in the middle of everything, El Convento is ideal, but I'm unsure how accessible the local streets are (narrow, cobble stone, etc.). It is a lovely old building, but I keep thinking that it has steps here and there all over the place that might be difficult to navigate. If the hotel seems interesting to you, contact them directly for some insights about if it might be the right place for your MIL.
That stinks, I was going to say +4 for El Convento. We had gotten a suite for us and 2 kids (or two adjoining rooms, I don't remember) and it was perfect and the breakfast (included) was yum.
I would recommend the Caribe Hilton for the part of your stay in San Juan. It's away from the Condado beach madness and a short bus/taxi ride to Old San Juan. For dinner, stop at El Jibarito in Old San Juan. I think it's on Calle Sol. Authentic food at reasonable prices. Enjoy!
It looks like we can get a VRBO or similar for our last three days in PR and now just need to find a hotel for our first night. Our birding tour covers the four nights in the middle. We would love to have stayed at El Convento or others mentioned above but so far have not found anything suitable to our needs (minimal or no stairs plus larger or extra beds, since our men are too tall for the couples to share anything smaller than a Queen) for a one night stay on February 27th, preferably in or near Old San Juan. Additional suggestions welcome!
sac