5 Places to Get Engaged in Puerto Rico

I've been writing about Puerto Rico for a long time now. (More than six years, in fact.) After two books, countless blogs, and thousands of reader emails (thanks guys!), I've picked up a few trends. Things that people tend to ask for, or ask about when they visit the island. One is food and restaurants. Another is all about romance.

Over the years, so many people have asked me for advice on where to get married, where to go for their honeymoon, and where to get engaged. I've even had a few readers share their honeymoon stories with their fellow readers (thank you Jody and Adam). But a recent email made me realize that I haven't shared my ideas on where, exactly, one should go if he or she is looking to pop the question. I gave that some thought and came up with these 5 picturesque spots. And if you choose any of them for your big moment, you better tell me about it!

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    Tim Draper/Getty Images

    I remember the first time I walked down Paseo La Princesa, the broad promenade that hugs the ancient city walls as it snakes around what was once the boundary of Old San Juan. The tree-lined street, lined with food vendors and local artisans, was serene, quiet and lovely. And in the distance was a large fountain at the end of the paseo, overlooking the bay.

    The fountain is called Raíces, or Roots, and it represents the diverse ethnic groups (native Taíno, Spanish and African) that make up modern Puerto Rico. And as day turns to night, it transforms into one of the most romantic spots in San Juan. Framed against the setting sun, it's a beautiful spot, ideal for a proposal.

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    At a Fortress

    You actually have several candidates if you want to propose within the walls of an ancient fortress. And by the way, if that sounds about as romantic as proposing in front of a prison, that's because you haven't seen these fortresses!

    Castillo San Cristóbal and El Morro are historic monuments with panoramic views and several breathtaking spots to choose from. My recommendation would be in front of a garita, or sentry box. These little towers just out from the corners of the ramparts, offering a bit of seclusion as well as a truly iconic backdrop.

    The lone drawback is that you'll be proposing during the day, and if that strong Caribbean sun is out, you'll want to be dressed casually.

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    On a Beach

    This one was so easy that I thought I'd try to narrow it down; after all, Puerto Rico has about 300 beaches to choose from. But I'm guessing that, if you want to propose, you'll also want a bit of privacy. So how about a beach that you can practically claim as your own (if you're lucky)?

    That still leaves a huge number of places to choose from, but I'm going to force myself to narrow the list to three:

    1. Navío Beach: I love this beach in Vieques for a few reasons: for one, it's off the beaten path, so it tends to be less crowded. But even cooler than its privacy is its secret room. Just past the curve of the beach along the ​left-hand side, there's a natural cave that's accessible only when the winds are calm and the tide is low. It's a magical spot for a proposal... just make sure you've secured those rings!
    2. Carlos Rosario: On Culebra Island, Flamenco Beach rules, but I fell in love with Carlos Rosario as soon as I saw it; a short hike from its more crowded sister, I was the only one on this lovely beach when I showed up, and I even came across a deer on the trail.
    3. Rincón: Known for having some of the most spectacular sunsets in Puerto Rico, the beaches here are less crowded and ideal for long strolls. And if you've chosen to stay at the magnificent Horned Dorset Primavera, you'll have a view like this.
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    Photo © Zain Deane

    Puerto Rico's gentle rainforest has waterfalls, scenic overlooks, its very own mythology and the soundtrack of the coquí to serenade you as you find the perfect trail, and the perfect place, to propose. Personally, I would take the Mount Britton Trail to reach the peak and enjoy its unparalleled views.

    Continue to 5 of 5 below.
  • 05 of 05

    At a Restaurant

    Again, your choices here are numerous and range from rustic eateries to chic dining establishments helmed by superstar chefs. And again, I had to struggle to narrow my suggestions down. This is a personal bias, but I wanted to avoid hotel restaurants; I also looked for local cuisine, because, after all, you're in Puerto Rico. And I came up with Casa Lola.

    Not only did I love the food here (courtesy of Chef Roberto Treviño), but I also loved the historic mansion that once belonged to Lola Milagros Cedeño. This Puerto Rican fine dining establishment is all intimate nooks and niches, with private rooms, intimate corners and even a private cellar that you can reserve for a very special dinner.