Barbados to Puerto Rico – Our Crazy Caribbean Journey

Not all travel days run like clockwork. This is something we’ve learned after 7 years of wandering around the world. And even though we were aware that mishaps can happen (and will), we weren’t prepared for our disastrous travel day from Barbados to Puerto Rico.

We arrived at the airport nice and early (we’re notoriously early for everything), and prepared to check-in to our LIAT flight.

We were those people at the check-in counter. The lineup was filled with anxious travellers waiting to get their boarding passes and drop off their heavy bags. We were holding up the line while rummaging around our packs, pulling out charging cords, books, laptops and trying to make the little neon sign on the scale read: 15 pounds.

Once the weight issue was sorted, we were told that we owed $800 for our flight tickets – which apparently we hadn’t paid for.

A Funny Acronym That LIAT Has Adopted From Its Passengers

We had our online Visa statement proving that we had paid, and we also had e-tickets, so this made no sense whatsoever.

We were then told that we actually didn’t have a seat on the plane, and that there were no flights to Puerto Rico for 2 days, possibly 3.

Excuse me?!

This wouldn’t work for us, as our flights were already booked to Istanbul from Puerto Rico.

Never had we ever experienced anything quite like this. When the extremely rude and uninterested LIAT agent didn’t want to help us, or explain anything to us, we contacted Expedia (who we booked through).

Expedia confirmed that yes, we had paid for the tickets and yes we were on the flight.

The Expedia representative actually contacted LIAT directly and sorted it all out for us!

After about 30 minutes, the supervisor appeared from the back room, made a few taps on the computer, and printed off our boarding passes – without saying anything, mind you. The only reason we knew what was going on was because we still had Expedia on the Skype call.

When we arrived at the gate, we were told the flight was delayed 2 hours.

travel from barbados to puerto rico
Waiting for our flight to eventually take off

At this point, we didn’t care, we were going to be leaving Barbados that night and we were just glad to be on the plane!

When we touched down in San Juan, Puerto Rico at midnight, we were eager to pick up our car that we had rented for 3 days, drive to our beachfront guesthouse and promptly pass out.

Unfortunately, no sleeping would be had until 2:30am.

flight from barbados to puerto rico
We’re finally in the air!

The shuttle to pick us up and take us to the rental agency nearby was to arrive in “10 minutes after we land”. After waiting 30 minutes, we called a second time. “Yes, sir, he will be there in 10 minutes”. We waited, and waited.

Nick ended up calling the company about 6 times from other people’s phones, until finally, they stopped answering our calls.

Our data on our SIM card from Barbados had run out after the second call to the rental agency.

After waiting for 2 hours at the airport, we decided to just take a taxi to our guesthouse, which defeated the purpose of having a rental car, as the cost of 1 day in the car is similar to a taxi.

We were also hesitant to leave because we thought we would be charged a cancellation fee for the car.

We were booked in to stay at the Numero 1 Guesthouse, and luckily, we had no issues with that portion of our travel day. We were greeted by the welcoming night staff and were shown to our room. Thankfully, our colourful accommodation was cooled in anticipation of our arrival – Puerto Rico was much more humid than Barbados!

where to stay in puerto rico the numero 1 guesthouse
Our room at the Numero 1 Guesthouse, loved working from the balcony 🙂

We were both exhausted, frustrated and in all honesty, bummed out. This was the start of our exciting 5 month trip, but so far, the first leg of the adventure had been a mess.

The following morning, we were able to think more clearly.

We contacted Expedia again and explained our car rental situation. We definitely should have booked with a reputable rental company like Alamo, rather than the random one we were having to deal with.

Just like the day before, Expedia dealt with the issue and made sure our credit card was not charged any thing at all.

Once that was finalized, we were free to get on with our time on the island.

We made our way downstairs for our complementary breakfast and were in awe of the view. Because we had arrived so late, we weren’t able to see the setting of the guesthouse, but in the light of day, it was before us in all of its glory!

The Beach

A gorgeous, long stretch of golden sand was literally right outside the guesthouse doors. In fact, we ate our breakfast on tables propped up on the beach, with the sand between our toes.

numero 1 guesthouse puerto rico
Not a bad view for breakfast!

We were up early enough to enjoy the peace and tranquility of the beach before the crowds arrived, which was exactly what we needed.

numero 1 guesthouse puerto rico
Ah, tranquility!

Our time in Puerto Rico was short, but very sweet. We weren’t sure exactly what to expect from this American-Caribbean Island, but our impressions during our quick trip there were all very positive.

ocean park beach puerto rico
The lovely Ocean Park Beach

The diverse atoll offers sand dunes, rainforest, beaches, salt flats and mountains. Had we more time, we would have explored further.

The Food

The food is a delightful blend of African and Spanish influences, and we enjoyed flavourful meals at the local restaurants. Mofongo was our favourite dish, and the fresh seafood meals on the beach were delicious as well.

what to eat in puerto rico chicken mofongo
Chicken mofongo
numero 1 guesthouse pamela's restaurant
An unforgettable ahi tuna meal at Pamela’s Restaurant, which is attached to Numero 1 Guesthouse

The Old Town of San Juan

The old colonial town of San Juan is a must-see. The glossy blue cobblestone streets were very unique and the El Morro Fort dominating the entrance to the San Juan Harbour is definitely worth a visit.

el morro fort puerto rico
Views over the Atlantic Ocean from the El Morro Fort

We wandered around for hours gazing up at the little balconies attached to colourful buildings and enjoyed the liveliness of the town.

san juan puerto rico cobblestone streets
The blue cobblestone streets were so cool!

El Yunque Rainforest

Even though we weren’t actually able to hike at the El Yunque Rainforest as planned, from what we’ve heard, and from the views we had on the drive up there (and from the drone!), this is a magical area.

If you’re interested in waterfalls and hiking, this is the place to go – although be warned, it can be very busy in the high season.

el yunque puerto rico
A bird’s eye view of El Yunque Rainforest

We’re excited to be returning to this island again in June. This is a place that we feel deserves more time. The latin music and culture mixed with the slow rhythm of the Caribbean was an intoxicating blend that made us wish we didn’t have to leave so soon.

In The End

Travel is always a bit of a gamble. Some days, everything runs smoothly and easily, while others, you wish you could just head back to bed and have a do-over. For us, sometimes it seems as though when it rains, it pours.

But no matter how disastrous a travel day may be, and no matter how many hiccups arise along the way, we always try to remember to be patient, keep our cool and figure out a solution to the problem. It’s all part of the life of a traveller.

When we arrive in a place as beautiful as Puerto Rico, we are reminded of just how lucky we are to be able to experience these places. Travel has its ups and downs, but that what makes it such a fun adventure.

Have you ever been to Puerto Rico? We’re heading back there in 5 months and we’ve already had so many great recommendations from readers so please, leave a comment and tell us what we should see and do when we return!

Also, Don’t Miss Our Quick Puerto Rico Video!

Like it? Pin it! 🙂

Barbados to Puerto Rico – Our Crazy Caribbean Journey

Written by

Goats On The Road

The team at Goats On The Road have a combined 100+ years of travel experience between them and have been to nearly country in the world. This site is 100% human written. We write useful articles for travelers, by travelers, WHO HAVE ACTUALLY BEEN THERE.

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35 thoughts on “Barbados to Puerto Rico – Our Crazy Caribbean Journey”

  1. Whew! What a hard start to a great trip. Good tips though about booking car rental with a reputable company. I was happy too to hear that Expedia gave you good service. It’s not the usual comment!

  2. HAHAHA! The latin’s “10 minutes” can be 10 hours or 10 days and it’s really annoying they can’t be honest about their ETA! I mean, we wouldn’t be angry if they said 5 days, right? At least we’ll plan our travels well instead of waiting for them for hours. Nonetheless, this is a very interesting trip and I hope you guys had a blast!

  3. Hi,
    i likes your blog and i regularly follow your post, every time you give us useful information that help us lot, thanks for sharing your views.

  4. Looks fantastic the beaches are an amazing color.
    Transfers can be a hassle sometimes we had a really late driver in Rome. He then proceeded to drive like an idiot to the airport. My wife thinks we were lucky to survive lol

  5. This was a great read! Sorry to hear your trip wasn’t off to a good start, but sometimes, those hiccups (that are super annoying and upsetting at the time) are what make a memorable story for down the track, and possibly make the final destination that much better! Puerto Rico looks amazing and I hope we get to visit it someday soon! Love your videos too. I think we need to invest in a drone :p

  6. Awww sounds like it was a bit of a crap start, haha! The hotel view is amazing, and I remember mofongo! Yummy. Your video quality is incredible. Which camera and steady cam are you using?

  7. Wow! Clearly, the stars were not aligned for you on that day! But you are so right. Snafus are part of travel and as aggravating as it can be in the moment, you have to roll with it and sometimes take matters into your own hands. Also, bit sure what Visa you used, but Signature Visas often come with some protections and recourse for travelers if, for example, Expedia wasn’t there to help you out. Glad everything worked out, though!

  8. I’ve never been to Puerto Rico , but it’s now on my radar! I’ll most certainly stay at Numero 1 Guesthouse, that view from the deck is incredible. Based on your little time there, I can see why you’re looking forward to returning; beautiful beaches, scenic hiking, and good food (that ahi tuna looked like it was cooked to perfection)! Also, great video!

  9. I’m glad that your impressions of Puerto Rico were positive despite the hellish experience it took to get there! Kudos to expedia for sorting out the flight situation and making sure you were on it. That’s really wonderful customer service on their part.

    I’m glad you enjoyed Puerto Rico, and thankyou for reminding us that travel is about the good AND the bad days. Patience and a positive attitude is key.

  10. Yea, it seems you had a difficult start for this trip, but at least you were rewarded at the end. You could have spent a little more time there, Puerto Rico is really beautiful. I’ve been in San Juan many years ago, but I still remember its gorgeous beaches and rain forrest.

  11. Hello Goats On The Road,
    Seemed very tough of getting at the start, but you people managed .
    Sometimes such kinda off journey ends with a quite happy and surprising moments that we can never expect it off.
    Great Experience.! but somewhere I feel that such moments one has to really go through in order to learn or experience the hurdles and how to overcome the situations. 🙂

  12. Hubby and I say this phrase any time we are traveling to the Caribbean…..” Stay calm, heading into the island time zone! Have fun in Istanbul- you are visiting my favorite places !!!

  13. Hubby and I say this phrase any time we are traveling to the Caribbean…..” Stay calm, heading into the island time zone! Have fun in Istanbul- you are visiting my favorite places !!!

  14. Thanks for the comment Meg 🙂 We were stoked that Expedia helped us out for sure. I think we were a bit shocked becuase we hadn’t had any travel issues really for the past couple of years! Now we’re back in the game 🙂


  15. Thanks 🙂 We’re normally pretty good on Island time as we live in the Caribbean half of the year, but this was a bit much! lol. We had never flown with LIAT – and won’t again if we can help it. Istanbul is great! Thanks for the comment 🙂

  16. We’ve yet to travel to Puerto Rico but would love to – it looks absolutely amazing and the food looks delicious! Travel days are hard enough as it is without added stress and setbacks but it’s good it all got sorted out – will definitely be keeping Expedia’s helpful role in mind when we make our future bookings – and having a hotel and view like that to wake up to is a great way to wash away the stress and frustration from the day before!

  17. Having been an airline employee, I have to commend you… on several points: early check in (saves the day when there is a problem), calling Expedia for help (they are a great advocate), and most importantly, keeping your cool throughout. When we head out of country, we often use for our cars. Usually very good rates, but more importantly, they have been a great advocate for us when problems arise. Happy travels!

  18. It’s nice to hear how well Expedia worked for you. I use it whenever I can. Now I have another reason to do so.

  19. What a bummer of a travel day! I don’t know who you used for car rental, but rented a Jeep for 3 days from Payless and had a great experience. It was only $50 for 3 days 🙂 If you are looking for somewhere in the heart of Old San Juan we really liked Posada San Francisco hostel (private room).

    And Vieques is a must when you return! It’s such a fun, laid back island with spectacular beaches.

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