How to Do a Working Holiday (and still feel relaxed!)


Laptop, camera, lenses, chargers, hard drives, agenda, notebook, cell phones, point-and-shoot. Perfect. All packed for the perfect beach vacay.

Okay, okay, okaaaaay. It probably doesn’t sound like what most people would normally pack for a beach vacation (or any relaxing vacation for that matter), but when you work for yourself, taking a week off isn’t really a four-word phrase that applies to you. I don’t have a team who can run the ship for me when I’m away, so the only way I can usually escape Toronto is to do a working holiday.

When I got the invite to head to Dominican Republic earlier this month with Air Transat to join a few fellow bloggers in experiencing the brand’s Luxury Collection resorts, it was EXACTLY what I needed. Resorts are perfect for balancing out work and play – all the planning is done for you, the service is round the clock, and everything you want is at your fingertips. What I didn’t expect was how unbelievably seamless everything was from the moment we arrived at the airport to the second we landed back in Toronto a week later.

So, what exactly makes for a great working holiday? Well for me, it’s all about getting stuff done in a relaxing, inspiring environment so that you I can arrive home refreshed and without a week’s worth of work to catch up on.

Before booking your own working holiday, here are five things I found that made my Dominican trip the PERFECT working vacation:

An easy flight experience
We upgraded to Club Class on our Air Transat flight, which, for a working holiday, is a must in my opinion – with no distractions, the plane ride is my favourite place to get work done, and the more convenience, the better. Spacious seats, dedicated flight attendants and upgraded food and drink is soooooo worth it to me (not to mention a dedicated check-in desk and the fact that your checked bags get first priority off the plane). You can also upgrade in economy to Option Plus, which gives you priority check-in and boarding plus extra in-flight conveniences in-(starting from $89 round-trip).

Dedicated relaxation time
Sure you want to keep on top of things, but it’s also important to take advantage of the ‘holiday’ portion of your trip. The resorts we went to had UNREAL spas, lively swim-up bars and white sand beaches with cabanas and beds – set aside a few hours each day to really relax and unwind and disconnect from your workflow.

Good WiFi
“Free WiFi” – the magic words when it comes to travelling with me. I don’t care how much of an internet-reliant princess this makes me sound like, but the first question I ask when deciding on where to go is ‘How good is your WiFi?’. All of the resorts we stayed at had WiFi throughout, and not just WiFi, but GOOD WiFi – in the lobby, in our rooms, even on the beach, making it easy to keep up with emails and social media posts.

The whole point of a working holiday is to escape your routine and be able to work remotely from a beautiful destination, while at the same time relaxing and re-energizing. Having a personal butler at the resort or 24-hour room service at your fingertips are the things that make life easier for you – meaning you can focus on getting work done, so you have more time to play (and sip on pina coladas!).

Inspiring spaces
As someone who works remotely, one of the biggest challenges is finding inspiring spaces to work from (my condo makes me go stir crazy). You’ll also go nuts on a working holiday if you’re cooped up in your room all day, so aim to find a new work spot each day that inspires you and still makes you feel like you’re on holiday. I tackled e-mails from the beach, perched at a resort coffeeshop, slouched on the sofas in an open-air lobby and even whilst soaking in my balcony Jacuzzi.

Where to Stay

From the moment we checked in to our first hotel and were welcomed with cool eucalyptus towels and sparkling wine, I knew that Transat’s Luxury Collection was the ONLY way I wanted to travel from that point forward (either that or have Damien meet me with a glass of sparkling every time I come home). The best part about sharing every awesome experience on social media was knowing that none of it had been set up specially just for us as bloggers – everything the hotels offered us was available to all other guests as well (the wanderlust vibes were real).

Take a peek at the five incredible properties we stayed at, all with something a little different to offer and perfect for the freelancer who wants to mix business with pleasure.


Excellence El Carmen

Our first hotel of the trip, this was also my favourite. Aesthetically, it was totally my style, from the minimalist buildings to the modern pools and restaurants, but it was also adults-only, so was quiet, chill and had a young professional clientele.
(from $2,039 per person)

Working holiday highlights:

  • 24-hour room service (breakfast in bed is key)
  • A cute coffeeshop with pastries and delicious lattes (caffeine is also key)
  • Free calls to Canada and USA from your room (um, amazing)
  • Beds on the balcony (for when you want to work outside)
  • The most incredible hydrotherapy spa for the ultimate recharge at the end of a long day
  • And for a beach-time recharge, ‘coco loco’ pina coladas, which are made with fresh coconut water and served in the whole coconut – officially my new favourite drink


Paradisus Punta Cana Resort

Walking into this resort’s open lobby was like walking into a jungle – big palms everywhere, ponds with flamingos and turtles, and the sound of birds chirping throughout. A totally different vibe from the first hotel, the Paradisus Punta Cana is an eco-resort, but with all the luxe amenities too.
(from $2,259 per person)

Working holiday highlights:

  • Kid-friendly, for those that need to bring their littles along
  • Upgrade to Royal Service, giving you separate check-in and out, separate adults-only pool, and a private beach area
  • Five pools and 12 restaurants to choose from


Iberostar Grand Hotel Bavaro

Oh man, this place is luxe. Palatial and grand, the Iberostar is classic in style and impressive in service. Part of a larger resort complex, this private adults-only resort offers a more luxury experience, but still gives you access to the other properties and their amenities.
(from $2,569 per person)

Working holiday highlights:

  • Personal butler service, who takes care of all your needs during your stay (if you want a hot Jacuzzi run every day at 4pm, he’s on it)
  • A state-of-the-art fitness facility, so you can start your day with yoga, spin or kickboxing
  • Beautiful spa to get everything from massages to sun burn treatments
  • Massive buffet, with fresh juice and omelettes to get your day started on a healthy note (or a chocolate fountain and pastry bar to treat yo’self)


Paradisus Palma Real Resort

Although we only checked in to this hotel for a day, I immediately fell in love with its grand courtyard and incredible pool. And even though this hotel was family-friendly, it wasn’t too loud or wild for those adults looking for a relaxing getaway.
(from $2,269 per person)

Working holiday highlights:

  • Family-friendly for those vacationing with kids
  • Upgrade to Royal Service, giving you separate check-in and out, separate adults-only pool, and a private beach area
  • Add-on an incredible meal at Passion, a AAA 4-Diamond restaurant by seven Michelin-star chef Martin Berasategui
  • Have a nightcap at the resort’s cocktail bar, where a mixologist serves up unique blends


Secrets Cap Cana Resort & Spa

We ended the trip on a high note, checking in to the newly opened Secrets Cap Cana. Beautiful from every angle, this resort had the most luxe rooms of the bunch, with a massive shower for two and a huge memory foam bed (best part of a holiday is catching up on zzzzz’s!). Preferred Club members also get access to the private Seaside Grill, with alllll the seafood.
(from $2,059 per person)

Working holiday highlights:

  • Personal butler service for Preferred Club members (perfect for days when you have a lot to get done in your room)
  • Bedside tablet to schedule spa appointments or order room service
  • 24-hour café (with delish coffee), for when you need a late-night jolt
  • Personal jacuzzi on the balcony (for when you want to brainstorm in the bath)
  • Quiet beach with excellent WiFi and great service
  • Beachfront suites available with personal infinity pools


This trip was done in partnership with Air Transat,
however all opinions, images and unforgettable memories are my own.

For more of the Air Transat Luxury Collection in Dominican Republic
and other destinations, check out the Air Transat website.


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