While doing research for our anniversary trip to Vieques, I considered two options for getting to the island: the ferry from Fajardo or a flight from San Juan. The ferry did not save us that much money, at least in comparison to the extra effort it required, and so we decided on the connecting flight from San Juan. To make it even easier, United has a relationship with Cape Air so we were able to book the entire flight from Houston to Vieques in one purchase. I think it saved us some money to buy them together through one airline, rather than separately through two vendors.
More importantly, this United Airlines umbrella ended up being a HUGE bonus after their incoming flight was delayed and we missed our connection to Cape Air. If we had booked separately, they would not have been responsible for our overnight hotel. Luckily, they were and we even got a meal voucher too. Not that it was a good situation, but at least we did not have to add surprise expenses to the disappointment. We made the most of it by exploring Old San Juan that evening.
However, I would highly recommend trying to get into San Juan as early as possible so that you do not have a similar issue. In addition to having time to spare for delays, it is much easier to land in daylight than figure out Vieques roads at night. If you can only find late arrivals, then spend a night in San Juan and enjoy a meal in Old San Juan. While I was ready to get my beach vacation started, having a mofungo in Old San Juan was a memorable highlight from the trip as well.
Early the next morning we prepared to ride in the smallest plane that I have ever been in. I am not going to sugarcoat it, this flight was both nerve-wracking and yet exciting. Be ready to be honest about your weight and to be assessed by size so that the plane is evenly distributed in load. I did not get to sit next to Dave, which is hard when nervous, so prepare mentally if you are a nervous flyer. It is about safety, so no need to be high-maintenance on this.
Also, there is no air-conditioning on the planes though the pilots left the windows open as long as possible for a fresh breeze. I would recommend you wear cool clothes. If you nervous-sweat like I do, then perhaps some quick dry clothing as well. There is no room for carry-ons so be ready to hand over everything to go into storage, even your purses ladies. The seating is tight and you feel every movement of the plane glide. It is not like a commercial airliner where motion is stabilized. Being in the cockpit with the pilots is wild, but at the same time reassuring to see calm navigation. It took me a moment to settle in and calm down before I started to enjoy the views. The flight is less than 30 minutes and I was counting each second, but it was quick and painless.
When we landed in Vieques, I took a deep breath and wanted to kiss the ground. The airport is tiny and adorable. For security and order, the bags are unloaded onto the smallest luggage carousel that you will ever see. It almost seems like you should just get your own luggage out, but that is obviously against the rules. I noticed that the W Hotel seems to have their own little fancy lounge area. Whatever.
The biggest difference between coming and going is that you should arrive early to return home, because the only thing that makes the end of vacation in Vieques easier to handle is the delicious food at Isla Nena Cafe. So damn good.
The other option is to take a ferry, which is detailed here. As airfares increase, we might consider doing this another time but it does require a cab ride and then a longer trip to the island. However you get there, enjoy your trip and be sure to appreciate every moment…