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Why I Vacationed in Puerto Rico and You Should Too

Yoga at El Morro |

It’s the time of year when Canadians flock south to get some sun and sand, choosing all-inclusive resorts mostly in Cuba, Dominican Republic, Mexico, and Jamaica. I understand the need to flee. After a couple months of wearing 3 layers to go out your front door and spending all your non-working time in the dark the craving for sunshine and sandals becomes insatiable. A need to recharge the batteries and drink our faces off to both congratulate ourselves on getting this far and steel ourselves for the remainder of winter.

For those of us on the East Coast, the cheapest sun vacation we can find is an all-inclusive. I mean, how else could you spend a week on a beach with all the food and alcohol you can drink for under $800? I can barely fly home to New Brunswick for that price.

To All-Inclusive or Not?

So when the inevitable pull south starting tugging on me last year I thought about those all-inclusives. I’ve never been to one. I looked into resorts in Cuba. Tested out various dates and price points. But when it came right down to it, I just couldn’t do it.

It just didn’t sound like very much fun solo. Never mind that I’d have to pay the dreaded single supplement, so the ultra cheap vacation became a $1400 week drinking alone. Surely there was somewhere a little less isolated with more activities that I could visit for similar money? I’ll also admit – and maybe it makes me a travel snob – but the thought of spending so much money to have the same travel photos as everyone else in Newfoundland…. well…

I Chose Puerto Rico.

Not only did they have beaches and rum but I could stay right in the heart of San Juan’s Old Town and explore on foot. There were also things like bio bays, kayaking, snorkelling, stand up paddle boarding, and food tours to keep me occupied. I could fly down there for not much more than a flight to Toronto. Sold.

I met a lot of Americans and some Europeans but almost no Canadians. Guys! You’re missing out. The All Star Island has a lot to offer the Canadian snowbird. And it’s an easy place to travel. Everything is in American dollars and most people speak some English, many fluently.

San Juan, Puerto Rico |

Old San Juan is a pretty, pretty place filled with candy coloured buildings and is steeped in history. It’s incredibly walkable and you can explore most of it in a day or two. I started off with a great food tour that not only filled my belly with yumminess but got me acquainted with the town.

Mostly though, I just wandered and photographed.

San Juan, Puerto Rico |

San Juan, Puerto Rico |

San Juan, Puerto Rico |

Fortaleza in Puerto Rico |

I did a guided tour of Fortaleza – the seat of government – and even had an exchange of words with the current Governor. I poked around the house built for the first Governor of Puerto Rico, Ponce de Leon. Made some friends with the local cats, as I do.

Bacardi Distillery in Puerto Rico |

I drank free rum at the world’s largest rum distillery. Tip: the Bacardi tour used to be free with two drinks but now costs $12 and includes just one drink. I drank my first pina colada at the bar that invented the drinks…or at least claims to.

Mallorca in Puerto Rico |

Then there’s the food… oh the food. Sure it’s starchy and fried but that makes me think that Newfoundlanders would love it. Bring on the plantains! Oddly enough, I found it harder to get good Puerto Rican food in Vieques but had no trouble getting a burger.

I can’t rave enough about the bio bays! Words can’t begin to describe how cool it is to be kayaking in the dark and see the water glow with every paddle stroke. Simply amazing. Put it on your bucket list. Now.

Vieques Sugar Mill in Puerto Rico |

I spent more time out in nature than I believe I would’ve at an all-inclusive. On the main island I went hiking at El Yunque National Forest, kayaking at Farjado, and stand up paddle boarding and a lot of beach walking in San Juan. Over on Vieques I did some more kayaking along with snorkelling, horseback riding, a little more hiking/exploring, and some good old beach bumming.

Whether you’re looking to shop in cute boutiques, try new food, soak up the sun at crystal clear beaches, or do all the activities, Puerto Rico has you covered.

Would you consider choosing Puerto Rico for your next winter break?


  1. Peter Parker says:

    May 16th, 2015 at 10:06 am (#)

    Are these reptiles harmful… I am scared of reptiles.

  2. Melissa Hogan says:

    May 19th, 2015 at 12:01 pm (#)

    Nope! Not that I know of anyway. The little lizards on Vieques were cute and would just run away if I got too close. The iguana at El Morro was more interested in sun bathing than in the people nearby.

  3. John Daniel says:

    May 16th, 2015 at 10:22 am (#)

    Nice place for vacations.

  4. Cranky Migrant says:

    May 17th, 2015 at 1:05 am (#)

    Your images make it look very appealing to travel to PR. It’s one of my future destinations for sure.

  5. Melissa Hogan says:

    May 19th, 2015 at 12:03 pm (#)

    I wasn’t too sure what to expect on my trip but I really have a fondness for Puerto Rico now. Had a little something for everyone I think.

  6. Uelito @ Flashpacking the World says:

    May 18th, 2015 at 6:39 pm (#)

    Oh wow! I’d love to visit Puerto Rico one day! I have never been in the carribean. I love the architecture and colorful houses. Very beautiful photos!!! Thanks for sharing!

  7. Melissa Hogan says:

    May 19th, 2015 at 12:04 pm (#)

    This was my first time in the Caribbean too. Old San Juan was so fun to photograph and explore. I loved just kicking back in Vieques as well. Next trip I’ll have to explore more places like Ponce, Rincon, and Culebra.

  8. Drew says:

    May 27th, 2015 at 9:05 am (#)

    We love Puerto Rico. Went went there a few years back and had a blast. Spent time in Old San Juan, which was great, then heading to the far northwest coast. Basically no tourists at all. We walked on a white sand beach for three miles without seeing a single house or person. Beautiful island, easy to get to and more affordable than some surrounding islands

  9. Melissa Hogan says:

    June 2nd, 2015 at 8:41 am (#)

    That sounds fantastic! I walked for miles on Condado Beach but there were certainly people here and there. I’d like to get out to Rincon and try my hand at surfing again.

  10. Valerie says:

    May 30th, 2015 at 3:19 pm (#)

    Wow! Puerto Rico looks amazing <3 All these cute colourful houses… I really hope I get to go one day xx

  11. Melissa Hogan says:

    June 2nd, 2015 at 8:42 am (#)

    All the colours of houses was one of my favourite things about Old San Juan. So pretty.

  12. Francesca @onegrloneworld says:

    June 2nd, 2015 at 2:44 am (#)

    Thanks for this! Heading to PR next month! How did you get to Bio Bay?

  13. Melissa Hogan says:

    June 2nd, 2015 at 8:40 am (#)

    I did my Fajardo tour with Kayaking Puerto Rico and they picked me up in San Juan. In Vieques, I went with Blackbeard Sports.

  14. Brooke says:

    June 8th, 2015 at 1:17 am (#)

    I’ve had my eye on Puerto Rico for a while, but I haven’t heard many people promote it. I’m glad I stumbled upon your post to learn more about your advice and your adventure. I would love having so many outdoor options like hiking and snorkeling! I’ll have to check it out!

  15. Melissa Hogan says:

    June 8th, 2015 at 9:40 am (#)

    I hadn’t heard many people talk about Puerto Rico either when I went so I wasn’t entirely sure what to expect. Most of what I’d heard was from cruise passengers who just spent a few hours in San Juan’s old town.

    If/when you go, be sure to get out of San Juan after a few days and explore more of the island as well as Culebra and Vieques.

  16. Rachel says:

    June 15th, 2015 at 3:12 am (#)

    I love the lizard’s shot. He’s like; it’s so fun here under the sun, join me. :)

  17. Sleeper Scarf says:

    August 26th, 2015 at 10:05 pm (#)

    Great post! So many beautiful places I should go like PUERTO RICO….

    Thanks for sharing!

    Be sure to check out Sleeper Scarf for your next trip

  18. Monica says:

    August 18th, 2017 at 2:21 am (#)

    Did you stay in hostel or hotel? And what did you use for transportation? I am going next month by myself and trying to figure what to do out there.

  19. Melissa Hogan says:

    August 18th, 2017 at 9:09 am (#)

    I stayed in hotels while I was there (Gallery Inn and da House in San Juan, Bravo Beach Hotel and Malecon Beach House in Vieques). While in San Juan I just walked around the Old Town. In Vieques I rented a car for a day to explore the island and I also rented a car to drive myself from Ceiba back to the airport. When I did the bio bay kayaking, a shuttle van picked me up. Oh, but I did take the public bus in San Juan to get from the Old Town to Condado Beach.

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