JetSet: Puerto Rico

With winter weather setting in, we decided to head somewhere with sun, sand and surf. While all-inclusives are always fun, relaxing and easy, we wanted to try something different, so we booked a flight, hotel and car and jetted off to Puerto Rico.

If you’re like us, you don’t actually know much about this tiny Caribbean island other than that it’s where you flew into for your family cruise, so here’s a quick lesson: Puerto Rico is an “unincorporated territory of the United States“, meaning you can use American money and almost everyone speaks fluent English. It’s located in the northeastern Caribbean, east of the Dominican Republic, and the best part? You can drive from one end of the island to the other in only a few hours. 

Here are some of our favourite island hotels, restaurants and activities:

Old San Juan.

Where to stay:

We suggest starting your trip in the capital, San Juan. Old San Juan is absolutely breathtaking with colourful houses and store fronts lining the cobblestone streets. While there is no shortage of huge hotel chains, we’d suggest trying something a little different. Villa Herencia is a small, eclectic boutique hotel located half a block from the ocean in Old San Juan. If you’re looking to splurge, we suggest checking out El Convento next door, which is a converted convent complete with a rooftop pool and a beautiful courtyard. 

El Convento.

After spending a night in Old San Juan head over to La Concha Resort in Condado (also a sister hotel of El Convento). Condado is like the Miami of Puerto Rico, with luxurious hotels and restaurants lining the beach. If you’re looking for fun nightlife and a beachfront hotel, this is your place. 

Last but definitely not least, we suggest driving a couple hours west, where you’ll hit Isabela. There you’ll find Villa Montana, an idyllic little beach resort on the ocean. With old plantation-style villas and a restaurant that rivals any five-star here, Villa Montana is definitely worth checking out – we could have eaten their caramelized banana pancakes for days!

Eclipse Restaurant at Villa Montana.

Where to eat:

One of our favourite little roadside restaurants (just up the street from Villa Montana) was Ola Lola’s Garden Bar. Owned by a lovely American couple, the delicious food (insane burgers) is cooked right in the couple’s home next door. A popular “gringo” (foreigner) hang-out, the lights and open-air concept make for a pretty dreamy setting. 

Ola Lola’s Garden Bar. 
Just west of Isabela is Rincon, a haven for surfers and tourists. If you’re looking for a meal with a view, head no further. We tried Tamboo Tavern, one of many beachfront restaurants in this great little town and loved their “tostones” – essentially, plantain fries (very popular in Puerto Rico). 
Tamboo Tavern.
Back in San Juan, head to La Mallorca for delicious cafe con leche and the famous “mallorca con jamon y queso”, a pressed sandwich dusted with powdered sugar. For dinner, check out one of San Juan’s famous “OOF!” restaurants including Aguaviva,The Parrot Club, Dragon Fly, Toro Salao or Pina Colada, all great options for dinner and drinks. 
What to do:

Whether you’re into surfing, snorkeling or suntanning, Puerto Rico has something for everyone; they even have a world-famous rainforest called El Yunque, right outside of San Juan. 

El Yunque.
For great beaches and snorkeling outside of San Juan, we suggest heading to Aguadilla, Isabela or Rincon on the west coast, or heading east for a day trip to the little island of Culebra (Spanish Virgin Islands), just off of Puerto Rico, where you will find white sand and turquoise water. 

While you can definitely catch some waves in San Juan, most people head west to Aguadilla and Rincon for great surf. Adventurers will love some of the off-the-beaten-track surf beaches found there, especially because they never seem to be too crowded.

If you’ve never considered Puerto Rico for a trip, we hope we’ve highlighted some reasons you should check it out. It’s the perfect, easy way to vacation in the Caribbean.

Fave 5: Things to pack for the beach

Spending a lazy, sunny day at the beach is as much a rite of summer as eating corn-on-the-cob and ducking out of work early to enjoy a drink on the patio. Too many times we find ourselves in such a rush to plant ourselves on the sand that we forget to pack some essential items. To keep your trip waterside as blissful as possible, we’ve done the work for you and rounded up the top five things you should bring to the beach. 

Beach Blanket

Make sure to match your bathing suit to your beach blanket.

A towel is important if you’re planning on taking a dip, but no one wants to sit on a soggy piece of terry cloth (at least, not us). Enter the beach blanket. You want one that is lightweight, large enough to share with friends and preferably in a fun colour or pattern. We love this throw from Anthropologie or this upcycled blanket from Etsy, but you can use an old sheet if you’re in a bind. 


The easiest sunscreen application. 

We don’t want to sound like a broken record, but we can’t stress the importance of wearing sunscreen this summer. Be sure to apply at least 30 minutes before heading outside and throw it in your bag to re-apply every 1-2 hours. We already gave some suggestions on our favourite organic sunscreen brands (read it here), but wanted to share one more. Lesa Hannah tweeted about this sunscreen “game changer” Janine Falcon introduced her to: Sun Defense Minerals by Eminence. This mineral-based face protector is easily applied with a brush and is hypoallergenic – perfect for those with sensitive skin. 

Hydrating drinks

We’re partial to this flask from the Drake General Store. 

As much as we love Ontario’s lakes, we wouldn’t recommend gulping it down if you’re thirsty. It’s extra-important to stay hydrated in the heat, so pack some hydrating drinks (and no, alcohol absolutely does not count) to bring with you. Water is always your best bet, but a refreshing home-brewed iced tea would work too. Gracie Carroll has an easy recipe over on her blog.

A good read

Can’t beat a great love story at the beach.

Whether it’s a trashy gossip mag or you’re re-reading Anna Karenina, a good read is a beach essential. We’re partial to fun, lighter reads in the summertime. Some of our top suggestions: Summer Sisters, Furious Love: Elizabeth Taylor, Richard Burton, and the Marriage of the Century, The Night Circus or Your Voice in my Head.

A cute cover-up

Better than cute, this cover-up is on sale right now at Shopbop.

After a day in the sun and sand, there’s nothing less appealing than putting on “real” clothing. Cover-ups are easy to throw on over you bathing suit whether you’re heading to the restroom or  wanting to keep that beach-y vibe going once you leave. The perfect cover-up should be lightweight, so its also perfect to throw on if you’re getting a bit too much sun. 

Fashion-able: Swimwear

Grab your Karen Walker sunnies, because with our guide to swimwear, bathing suit season is no longer the most dreaded of them all. For when days are scorching hot, we’ve got you covered from itty-bitty bikinis to sleek one-pieces.

Why wear one print when you can wear two? Mix and match with Zimmerman’s two-piece floral-weave bathing suit ($245). The fully padded floral top contrasts perfectly with the black basket woven bottom. Grab a towel – you’re gonna make a splash (we couldn’t help ourselves.)

Bring glamour to the beach in J. Crew’s Islet paisley ruched underwire bandeau tank ($108). The strapless bather has a pretty, neutral paisley print with a removable halter strap. Bonus for busty babes? The built-in underwire offers some serious support for full coverage. 

Look cool poolside in Old Navy’s animal print bandeau bikini top (about $15) and ruffled bottoms (about $15). These simple, classic mix-and-match pieces get a little oomph from the hot animal print and jewelled halter strap. Not a fan of prints? You can swap out the top for a huge selection of solid colours. 

For a little more coverage, but lots of style, Gap offers similar mix-and-match options that let you choose a different size for each piece. We love the pretty periwinkle-purple colour of this tankini (on sale for $17 right now!), and the deep V-neck still offers a bit of sex appeal without flashing all your goods. The bottoms (also currently on sale for $7) have adjustable ties on the side, which help avoid the dreaded squeezed-hips look.

Go get suited up and don’t forget the SPF!