My Bougie Bucket List: Luxury Trips I’d Take if I Won the Lottery

My bucket list of luxury vacations

I know it’s not even Q4 of 2024 but since I already have the rest of my year planned out travel-wise (USA, Portugal and hopefully some Christmas markets in Germany, to name a few woohooooo!!) I’m already looking ahead to next year and trying to figure out where I can go in 2025 and…

It should come as a surprise to absolutely NO ONE that I basically need to win the lottery to be able to afford all the travelling I want to do! Being a full-time corporate working girlie helps me fund my travels for the most part, but if I won the lottery I could 1. Travel full-time instead of having to work around my vacation days and 2. Be able to afford some bougie, super glamorous trips that are currently way out of my price range.

So if I ever just disappear with no notice and end up on one of the following luxurious vacations, you’ll know that I’ve won the lottery and am off living my absolute best life. A girl can dream, right?!

Here is my bucket list of the top 5 dream luxury vacations that I would do if I won the lottery. And yeah, it was hard to choose JUST 5.

1. Yacht Week in Croatia

I’m beginning my list with something I’ve been saying for YEARS that I would loveeee to do. If you’ve never heard of Croatia’s Yacht Week, it’s basically exactly what you think it would be – a week of sailing around Croatia on a yacht, spending your days chilling and sailing from one port to another with a stop in a bay to cook lunch, swim, or exploring the islands, and spending your nights at unreal parties and exclusive events.

There are various destinations/routes you can choose from, but the Original Croatia Route is the one I would opt for. If I won the lottery, I would of course opt for the premium yacht obviously. And of course I would book out a private yacht so it’s just me and 11 friends. And OF COURSE I’d add in a “host” who would cook all of our meals for us on board. A week island hopping on a private yacht while having all of your meals cooked for you and your needs look after by a full crew on board, and attending insane parties all night long? Yes please!!

2. Maldives

I feel like every second spent in the Maldives would be like being in a live screensaver. True PARADISE.

The Maldives consists of a bunch of different islands, and usually a hotel will have it’s own. If money was of absolutely no concern, I’d stay in one of the Overwater Hideaway Villas at Soneva Secret. This hotel, which only opened this year, has only 14 villas. And get this – each villa it’s OWN DEDICATED ASSISTANT and PRIVATE CHEF. 

You arrive to the remote resort by seaplane and can choose between a floating villa or beachfront villa. And the villas START at $3,200/night. I prefer a more local and authentic experience, but you best believe if I had the winning lottery numbers, I would absolutely be balling out on a high-end luxury floating villa in the middle of the clear water of the Maldives. And while there I would of course do a sunset dolphin cruise, visit the spa, and swim with turtles. Obviously.

3. Alaskan Cruise

The total opposite to the floating villa in the Maldives, another luxury vacation that is on my bucket list is an Alaskan Cruise. If I won the lottery, I’d do a VERY fancy one of course. I wanna see giant glaciers, tons of wildlife (especially huge bears and whales), and just all of the beauty the Alaskan outdoors has to offer. But I’d also love to learn more about Alaska’s history and culture. 

The Alaskan Cruises by Silversea look fab. They’re all-inclusive, have the highest crew-to-guest ratio, are all small boats, and focus on Alaska’s outdoors. As of now they are for the higher-tax-bracket gals, but if I won the lottery this is something I’d love to splurge on.

4. Luxury African Safari

Another ultimate bucket list goal/life dream is to do an African Safari. I’ve never been to Africa before, but I know I will be absolutely CAPTIVATED by it.

Imagine winning the lottery and going on the ultimate African getaway!!! Like I cannot deal. Heaven. And with my lotto winnings I could choose a luxury safari experience. I’d love to make my way from Kenya to Tanzania – taking a hot air balloon over the Masai Mara to watch the great migration, exploring the city of Nairobi, doing a nature trek in the Serengeti. Ugh doesn’t that sounds like a once-in-a-lifetime trip?!

AndBeyond have an East African Safari tour inspired by Conde Naste where guests stay at some amazing luxury camps in Kenya and Tanzania and let me tell you – if I won the lottery I would book it (over $14,000/person for 12 days) in a HEARTBEAT. One of the camps even has giraffes coming up to the windows!!!! UGH, PARADISE!

5. A Las Vegas Getaway

This may sound SO cliché, but I think if I won the lottery, Vegas would be a surprising contender of somewhere I’d go..! Hear me out:

I really have NO interest in going to Vegas. Like truly, zero. It wasn’t on my top 5 US bucket list I did years ago. And one of those reasons is that I feel like you have to spend a lot of money to have fun there. Which I do not have. I’m more of a FREE or CHEAP fun type of gal.

But if I won the lottery….

I feel like it would be so fun to pay for me and my best girl friends to take a once-in-a-lifetime trip to Vegas! We could go to some fancy schmancy dinners, blow a bunch of money in the casinos, hit up some exclusive pool parties by day and some exclusive clubs by night (with a VIP area booked and bottle service, of course), and just have a super glamorous time.

And of course since money is of no concern, I would book us the Two-story Sky Villa at the Palms Resort because why not? It’s complete with a private pool with a view, 24-hour butler service, massage room and fitness center. 

Basically the ONLY way I’d go to Vegas is if I won the lottery and could ball out and bring a group of girlfriends with me!

So there you have it – 5 bougie vacations that are completely out of my tax bracket but that I would LOVE to do if I won the lottery.

But really though…

It’s fun to think about luxury vacations in places my bank account and bucket list could only dream about, but at the end of the day – I love the type of travelling I do. I love travelling on a budget, finding local experiences, going off the beaten track, eating the local cuisine, and trying to find less touristy spots. Ultra-luxurious vacations are probably amazing, but I’m happy enough travelling within my budget. And even though I’m not actually a lotto winner, I’m still very lucky to be able to travel a lot between having a full-time job and not having unlimited funds.

So really, there’s no complaints here! (Although I wouldn’t complain if I won the lottery either, of course).

What is on your luxury vacation bucket list? Where would you go if you won the lottery?

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