Being on perpetual holidays, barefoot and sun-kissed… Impossible? Not quite: there is a handful of people on this planet who seem to actually live this dream life, hopping from one sublime off-the-grid escape to another, on a permanent quest for the endless summer. Who are they? Members of what New York-based journalist Julia Chaplin calls the Gypset (a cross between”gypsy” and “jet-set”), i.e. a crowd of semi-nomadic party enthusiasts who chose to embrace a bohemian lifestyle — in designer clothes.

7 Todos Santos Gypset Travel Todos Santos, Mexico

After portraying the colourful (and busy) gypset fashion in Gypset Style (Assouline, 2009), Julia Chaplin recently published a new volume dedicated to the ten top gypset getaways. Gypset Travel (Assouline, 2012) is worth leafing through for the photographs alone: the beautiful views of deserted beaches, lush green valleys, cute fishermen villages, romantic vintage campervans and perfectly tanned people will have you daydream about giving in to your free spirit and getting away from it all.

1-746-xxx From Rhodes to Bodrum, Turkey

If daydreaming does not quite do it for you, here are a few tips I picked up from the book to help you follow — at least a little — the tracks of those who live tanned and carefree all year round.

1. Get a location-independent job

The easiest way to join the Gypset seems to either be born in a decadent royal family, or to be — to any degree — blood-related to one of the Rolling Stones (there is quite a bit of glamourous namedropping in the book). However, if you are part of those who need to work for a living, there is still a way to travel most of the year: it is to take your work along with you.

Most gypsetters have nomadism-compatible jobs with a flexible schedule — fashion or jewellery design, photography, surfboard shaping… —, or choose to settle into a beautiful corner of the world and open a boutique hotel, a restaurant or — the ultimate gypset occupation — a Glamping business.

The most accessible way to everlasting wandering, though, is to join the freelance workforce and take up working remotely with your laptop and an Internet connection, by becoming a “digital nomad”. Check out Frankie’s post about this modern nomadic lifestyle, which is not necessarily as unapproachable as you might think!

A less extreme option is to save some cash throughout winter, then sublet your apartment and go live the beach life for a few months every year.

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Byron Bay, Australia

 

2. Pick less obvious destinations

Stromboli (Aeolian islands, Italy), Alto Paraíso (Mexico), Cabo Polonio (Uruguay)… All gypset destinations have something in common: they are hard to reach. Whether they are located at the end of a long and bumpy dirt track with no direction signs, beyond a beach that is only accessible by boat or on a tiny island where the only means of transport is donkey back riding, these hideouts are empty of any sunhat-and-promotional-T-shirt-wearing tourist, because getting there takes some serious dedication.

What we learn from this is that it is not because a place is not referenced in the must-see section of your travel guide or within a 30-minutes air-conditioned cab ride from the airport that it is not worth your attention. Do your research, buy a good old paper map and get off the usual tourist track! There are gorgeous beaches and adorable little towns out there waiting for you. For a little direction and inspiration, you can check out the Gypset atlas, or the Road Less Travelled guide, a great read which suggests lesser-known alternatives to overcrowded touristy landmarks.

 

3. Slow down

Rushing from one “unmissable” sight to the next and hastily gobbling a dry vapid sandwich before hopping onto the next bus does not always make for the most memorable holidays. What if, once in a while, you tried to ditch the fast pace of capital cities to get lost in nature, or ease off in a small laid-back town? Sure, there might not be much to see, but there is probably a lot to enjoy.

The gypset lifestyle might be utopian in many ways, but it is based on a good-life philosophy that is actually applicable anywhere: collecting moments rather than things, or sights. Go for a walk, a bike ride or a swim, read your book on the beach, round up some good friends and like-minded people, cook a nice dinner (or find out where the locals go for tasty, unpretentious food) and take the time to enjoy it. Gypsetters have long understood that time is the ultimate luxury!

2 North Goa Gypset Travel Aeolian Islands, Italy

 

4. Be spontaneous

The key to a less-ordinary lifestyle is great adjustability: don’t cling to your set plans too much. Follow unexpected opportunities, accept invitations to house parties, deviate from your intended itinerary when it feels right and embrace adventure when it presents itself (within the limits of safety, of course). “The true talent of a gypsetter, after all, is timing”, says Chaplin. “Knowing when to stay. When to leave. And when to return.”

Gyps Alto Paraiso, Brazil and Sayulita, Mexico

 

5. Avoid conventional hotels

Impersonal rooms, same old TV channels, standard continental breakfasts: although there are some mind-blowing hotels out there, most hotel chains offer a pretty predictable experience.

Why not decide on a nice B&B or guest house instead? They are usually cheaper, and chatting with your hosts will give you a better sense of the local culture — and might also get you a few insider tips!

Renting a local’s apartment for a few days or weeks, or sleeping on a stranger’s couch are also great ways to escape the classic tourist trail. A fair number of websites now allow you to go through thousands of offers: live local, live cheap!

 

6. Rough it

Secluded hideouts might sometimes mean no running water, electricity or reception. You may not be able to carry several pairs of heels or an elephant-sized makeup bag with you. You will have sand in your shoes, salt in your hair and might even have to skip a few showers.

Man up! That is all part of the adventure, and makes for fun memories. If you are in desperate need for a renewed wardrobe, check out small town markets for nice fabric and local inspiration instead of rushing into chain stores that flow the whole planet with the same clothes. For beauty emergencies, learn the country’s beauty tips. And for dramatic beauty emergencies, there are actually a few ways to cheat!

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7. Join the party

When you reach a place with the perfect vibe, don’t limitate yourself to admiring the sights. The easiest way to blend into the local culture quickly is to join the party! Ask around for the most popular dive bar, and bond with the regulars over a nearby-produced beer — or, better, sharing a bottle of the local moonshine! Follow the music you like, it will usually lead you to people who are on the same wavelength. And don’t forget: “Note to aspiring gypsetters everywhere: drunken dinners are a great source of invitations.”

5 Jose Ignacio Cabo Polonio Gypset Travel José Ignacio, Uruguay

 

Gypset Travel by Julia Chaplin (ASSOULINE)

Photo 1 (by Daniele Albright), photo 5 (by Adam Butler), photo 6 (by Julien Capmeil), photo 7 (by Anne Menke, in Gypset Style) and photo 9 (by Julien Capmeil) courtesy of ASSOULINE

Photos 2 and 8 (by Tap Ruspoli) and photos 3 and 4 (by Sybil Steele) via the Gypset.com Travelogue

mariecolinettravelettes Marie Colinet was part of the Travelettes team from 2013 to 2015. Originally from Toulouse, France, two years lived in Australia left her speaking English with an awkward Fraussie accent. In September 2015, Marie is starting the epic 6-month-or-who-knows-how-long road-trip along the Panamerican Highway that she’s been dreaming of since her teenage years — all the way from the U.S. to the very tip of South-America. You can follow her on Instagram @mariecolinet!