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Holidays With No Limits: Where Would You Go?

Even if we have a wonderfully generous budget for our annual holidays and trips, almost everyone has their limits! It’s one thing to invest is a gorgeous hotel or elaborate day tours when you’re traversing the globe. But it’s another to imagine private jets, butler service and private dinners on the beach. Not to mention, this is even more wonderful to dream when you could take all your best friends along for the ride.

Luckily, many companies worldwide are starting to see the value in letting their employees take a real, genuine break – and a luxurious one at that. There’s a great tradition among (mostly) new companies to incentivise their employee to take real vacations from work. This CEO is offering thousands of dollars on top of regular salaries to totally go off the grid. And here’s a list of the 20 best companies to work for that offer holiday incentives such as unlimited paid time off.

It’s fun for all of us to dream up elaborate vacations if we won the lottery or happened to work for one of these amazing companies encouraging real, quality time off from the grind. Here’s our top three scenarios that would be the ultimate travel experiences with our squads if money was REALLY no object.

One Night in the Caribbean Blowout

Almost twenty years ago, a famous furniture store in Massachusetts took all their employees on a one-day incentive trip to Bermuda, just to say thanks for all their hard work. We can’t imagine how fun it could be to take 1200 of your closest friends to the Caribbean. We’d love to re-create the experience. The rise of chartered flights may made this dream closer to a reality as well – but we’re dreaming here, so let’s think big. A short trip allows a giant group to go all out and not worry about responsibilities at home. We could do everything and nothing – from renting out a private beach area for exclusive swimming and snorkeling, to a fully-catered seafood feast right on the shore. The hotel itself would accommodate our group, as we’d fill the whole place with just us, so all requests would be catered to immediately. Keep those pina coladas coming!

Massive West Coast Music Festival: VIP-Style

Music festivals and large gathering outdoors are our thing. We’ve had a blast all over the world at live music gigs, whether they are all weekend long in Virginia, in the cheery muddy woodlands southwest England or in a far off sunny locale like India. While it’s part of the experience to be among the crowds, many music festivals offer incredible VIP tickets for those who want to enjoy the music in an elevated sense. We’d have so much fun inviting a dozen friends to splash out in glamping teepees at Coachella in California or swanky apartments and private viewing platforms included with VIP at Primavera Sound in Barcelona.

3-Month Volunteer and Chill Session in Thailand

One of the biggest challenges for getting the group together for a holiday is time. Time off is a precious thing. Much of it goes toward family obligations, weddings and even being sick. To have real, solid time away with those to love is invaluable. With unlimited funds, we could pay to allow our friends and family to take tons of time off and join us on a big trip abroad.

Recently, we found Thailand to be super friendly for groups and would enjoy taking a big group to this beautiful country. Chang Mai especially in the north welcomes digital nomads and those looking for a more laid-back lifestyle to indulge countless coffee shops, nature, street food, music and traditional culture. There’s opportunities nearby to volunteer with elephant sanctuaries as well, so you and your squad could give back to the community while you take months of luxurious time off.

If money was no object, where would you travel to? Who would you take with you? How long would you go?

Eileen Cotter Wright

Author Eileen Cotter Wright

Eileen Cotter is a freelance travel journalist and owner of Pure Wander. She's our resident expat extraordinaire and falls down a lot in yoga class. Follow her on Twitter @Crooked_Flight

More posts by Eileen Cotter Wright

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