Luxury Top Tips for Puerto Rico: We won a trip there. No, really! vacations

Top Tips for Puerto Rico: We won a trip there. No, really!

OutOfOffice.com's latest winners tell us their top tips for San Juan and Puerto Rico


James Glynn and Tomek Mossakowski enjoyed a stunning trip to Puerto Rico courtesy of OutOfOffice.com, Puerto Rico Tourism and Norwegian Air.

We were so surprised when we won a trip to Puerto Rico. That’s because most British people – let’s be honest – don’t really know where or what Puerto Rico is. Unlike other destinations in the Caribbean – Barbados and its posh beaches, the legendary parties of Jamaica or the crumbling splendour of Cuba – Puerto Rico has remained outside the imagination of most UK holiday-goers.

Thanks to Norwegian, you can now get there non-stop, meaning no layovers in Miami with horrendous queues at immigration. This is good news for the sun-seeker and even better news for us, two gay Brits who’d never won a competition before but were lucky enough to win this one.


About Out Of Office


Out Of Office is a luxury tailor-made travel company with a focus on delivering exclusivity and inclusivity. Our passion for global adventure is matched only by our deep commitment to delivering exceptional five-star service.

Everything we do is customised and designed especially for you – our valued customer – based on your exact personal requirements. Each member of our team is widely travelled. This means you get access to first-rate travel insights and the best possible advice from our team of luxury travel experts.

Enquire Now

And good that we did: Puerto Rico is beautiful, bizarre, wacky, hispanic, American and African all-in-one, with some world-class beaches (often topping Trip Advisor’s best beaches in the world list) and with loads of culture to keep the curious satiated.

Our holiday began when we flew on Norwegian’s brand new Dreamliner 787 plane (no, really!). They’re spacious, sleek and speedy, with very cool details like wifi, a power socket in every seat, huge windows that dim at the touch of a button and – best of all – a card-reader so that you can pay for drinks at the touch of a button. This, after two wines, two beers and some champagne, turned out to be a pretty dangerous innovation!

james glynn and tomek mossakowski

We dined at one of San Juan’s most up-and-coming restaurants, Santaella, where visiting Americans dressed in smart shirts and sneakers queued out the door while trendy locals clinked cocktail glasses at the bar. We journeyed through the tapas menu, falling in love with a soft-tortilla taco stuffed to its floury brim with generous chunks of fresh tuna.

The next morning, we moved to The Wyndham, a huge resort only 30 minutes outside of San Juan. The buildings, facilities, pools and service were fantastic, but best of all was its close proximity to some of Puerto Rico’s best tourist sites.

Renting a car from the hotel, which in true American fashion was super quick and easy, we drove up to El Yunque, a gorgeous rainforest in the hills. Lush, wet and chirping and squawking with life, this National Park was one of our best experiences, apart from a brief scare over the ‘Puerto Rican Adder’ (it doesn’t exist, James tricked me). The paths in the rainforest were easy to navigate, taking us through hills thick and dark with life. All paths diverge on a huge waterfall and pool called La Mina, where we resolutely stripped off and jumped in. After swimming under the roar of cascading water, we felt thoroughly beaten but refreshed, and trotted back into the jungle still soaking but smiling.

Also nearby was Luquillo, the most idyllic beach we visited. It’s a brilliant quirk of the country that the most beautiful beaches are all public and arriving there was an experience we won’t forget anytime soon. It was wonderfully curved, with soft white sand and shallow water, just perfect for bobbing in. Better yet, the beach was filled with locals looking to relax as they popped upon bottles of the local brew Medalla beer, refreshing if a little light for European tastes. Stretching along the beach were the kioskos, 69 kiosks selling an array of foods to the hungry. After some serious splashing around in the sea, we wandered along the kiosks, choosing some delicious deep-fried delights to have with beer, before getting a few scoops of ice cream and eating them under the slight shadow of a palm as we looked on at paradise.

After the Wyndham, we stayed at San Juan Water and Beach Club in the Isla Verde area, a buzzing stretch of beach just next door to San Juan’s airport. Don’t think that means it wasn’t nice: some of Puerto Rico’s best stretches of sand are in urban spaces and this beach had everything from wonderful water to serious party vibes. We sipped pina coladas (which were invented in Puerto Rico, FYI) as we watched locals race along the horizon on jet skis. San Juan is great for its mix of locals and tourists, lending everything a feel of authenticity.

tomek mossakowski

In the evenings, we explored San Juan’s gay nightlife, stopping off at gay-friendly bars in the Old Town or watching the sunset from the rooftop bar of our hotel. The Old Town is easily the city’s biggest attraction. Houses of myriad colours, complete with balconies drenched in flowers, run along hilly streets, everything resembling an old Spanish town. The cobbled streets lead to all sorts of delights: crumbling buildings, huge castles or views of the historic port where pirates tried (and often failed) to land before being blown to bits by the cannons that still stand proud on the edge of the city. Puerto Rico is a history-buff’s dream, whether it’s its Spanish roots, African touches or American modernity that fascinate you.

We’ll remember lots of things about our trip: the slow, staccato way the locals speak in their lulling island tones, or the crazy mix of food (croquettes and mofongo aka plantains on every menu, a Burger King on every corner), or caramelising ourselves under the big, bright Caribbean sun. Perfectly sized, always friendly and suitably un-resorty, Puerto Rico was a great destination for two gay travellers.

Why book with us?

Personal Service


We want to ensure you have the best experience with us so we’ll keep working on your itinerary until perfect. You will have your own personal dedicated member of our team who will help build the perfect trip for you.


Call our travel experts on +44 (0)20 7157 1570

Our 5* Reviews


We pride ourselves in the number of clients that are referred to us by our existing customers. Our 5* Trustpilot rating is important to us, so we encourage you to browse our reviews. They speak for themselves and that's why you are in safe hands.


Make an enquiry


Phone

020 7157 1570

Email


To start planning your luxury trip, tell us more about your travel plans and we'll match you with one of our experienced travel specialists. You can speak to us via phone, email or video call.

Open 7 days a week.


All the prices on our website do not include flights. We can, of course, arrange them for you.


Your trip
Your details

Please enter your destination and details.

  • $2,000-3,000
  • $3,000-5,000
  • $5,000-7,500
  • $7,500-10,000
  • $10,000+