We arrived in San Juan on a Thursday night, and spent the first night in a nondescript airbnb located in Ocean Park, which is an upscale, residential neighborhood of San Juan (I don't recommend spending much time here, but we were just staying for one night before moving on).
The next morning, we hopped in a pre-booked taxi, which charged us $70 for the hour-and-change ride to Fajardo, which is where the $2, hour-long boat ride to Vieques departs. The restaurants and mini-marts around the ferry dock all had prominently-displayed signs advertising Dramamine, meant to prevent the type of mass-vomiting scene we once endured on a boat in Playa del Carmen.
The airbnb we stayed at for our three nights on Vieques was owned by a rule-abiding, mid-60s woman who seemed more German than Bostonian. She, along with all the expats we met on the island, had acquired an island-type eccentricity borne of living in a town with almost as many horses as people for one too many years.
We stayed in Esperanza, which is the main town next to Isabel Segunda, where the boat docks. The malecon lining the water is filled with overpriced, touristy restaurants, but highlights included the house-made hot sauce at Belly Button's (you can buy several-ounce bottles to take home) and a drink called the Dirty Banana at Bananas, which consists of Kahlua, Amaretto, blended banana, chocolate sauce, and whip cream (skip the watered down Piña Coladas).
For food, we had decent coffee and baked goods at the bakery that sits several blocks back from the water in Esperanza. Good luck, though, because true to island style, the bakery opens when they want for as long as they want, and they were out of bread when we stopped by.
Forget the food; beaches are the true highlight of Vieques. We enjoyed Sun Bay, which is the large public beach within walking distance of Esperanza. It is at least a mile long and has several shady spots. Horses grazing on the grass set back from the beach add to the atmosphere, and a food stand will pour all manner of liquor into a split-open coconut for $8 (we opted for an ice cream bar instead).
You can walk from Sun Bay to Media Luna, which has shallower water, but is smaller and less shady. Playa Navio lies several hundred muddy feet beyond; be prepared to brave several large puddles that span the length of the dirt road. All three beaches are sparsely populated.
We ate mofongo for the first time that night, which is a mash of plantain or yucca surrounding your choice of meat or fish (we opted for chicken). It was sold to us as the best mofongo on Vieques, and while certainly better than the American-style food that dominates Esperanza, it wasn't award-winning.
We also visited Blue Beach, which was harder to reach but equally beautiful as the other three. Our last night, we took a tour of the bioluminescent bay, which is filled with microorganisms that glow a fluorescent green when disturbed by your hand or the tip of a kayak oar.
Almost all Puerto Ricans speak English, which was a surprise. The island resembles Latin America in its architecture, weather, and music blasting from rolled-down car windows, but its priciness and the predominance of English are unlike any other Latin region I've visited.
Next up, San Juan!