What’s the Best Summer Vacation You’ve Ever Been On?

Alright – I'm going to admit up front that this is probably the most selfish post I've ever written for M$M. Usually I try to put out something that's really insightful or interesting enough to start off your day on a positive note.

But, every once in a while I want to try to take advantage of the fact that I have 100,000+ people that I can go to for wisdom or their experience on certain topics.

I've always been so surprised how many people are willing to take time out of their days to write lengthy emails to me about various subjects, and I promise that I try my best to read and respond to all of them (even though I fail sometimes).

So here is my one selfish request: My wife and I are going on a vacation this summer and need help deciding where haha

I know a lot of you are big time travel junkies and “travel hackers”, so I figured the best people to ask were well…you.

Related: Should people travel if they have debt?

We're behind on the travel thing…

Like a lot of millennials, we've waited a while to really get our lives “started”. Most of our early twenties were spent being super cheap and saving up money for things like our wedding or paying off debt.

Travel was just another one of those things that fell by the wayside, but now that my income has risen a bit and I have more flexibility with my schedule – we're trying to do some catching up.

So far, we've done three big vacations:

1. The Bahamas

This was actually for our honeymoon, and we stayed at one of the big all-inclusive chains. It definitely wasn't cheap, but I guess we just wanted to splurge a bit because we had never really done anything before.

It was honestly incredible, and somewhere that I'd 100% go back to again. Our resort was on the Great Exuma (Ex-Zoom-uh) island in the Bahamas chain (which I constantly pronounced “eczema” on accident…aka the skin condition haha).

The water was straight-up incredible, and even though the island was pretty scarce as far as things to do, we still did enough in the week we were there to have a great time.

Also, I jumped in the pool with my cell phone in my pocket and lost every picture/video that we took on the trip. The phone is still sitting in a bag of rice two years later.

My wife was pissed, but these are just the type of things that I do.

2. Whitehouse, Jamaica

Last summer, we decided to do a vacation at the same big all-inclusive chain. This vacation totally blew for a couple of reasons.

The biggest one was that my wife's father passed away on our third day there. It was a horrible situation, and I doubt we'll ever go back to Jamaica because of how traumatic that was. Who knows, but I doubt we will have “good vibes” about Jamaica in the near future.

Read also: The Real Reason I Live Debt-Free

It was really hard to get back to the U.S., but we did manage and were able to take care of everything we needed to.

The other reason the vacation wasn't that cool is that we were tired of the all-inclusive thing. Sitting around on a resort and eating/drinking unlimited amounts is definitely nothing to complain about (fully aware that this entire post is a first-world problem), but it just felt like a repeat of our honeymoon in a place where the water wasn't quite as nice.

We did do some zip-lining in the jungle, which was by far the highlight of the trip. I had a GoPro strapped to my helmet and got some incredible footage, which I completely lost about two weeks later when I stupidly tried to ride a surfboard backwards behind our boat and dropped the GoPro to the bottom of the 18 feet deep creek we ski at.

Again, my wife was pissed, but these are the type of things that I do.

3. Anna Maria Island, Florida

This was the cheapest of our vacations, and easily my favorite so far. If you haven't heard of Anna Maria island, you need to go. The water is incredible, it's cheaper to visit than a caribbean island, and there's just a ton to do.

We stayed at normal beach hotels and a bed and breakfast while we were there, and it was cool to switch things up.

After staying there for about 5 days, we wanted to seriously move to Florida. But…the houses cost $1,000,000 plus and there are more tourists on the island than locals.

Related: The 50/50 Split: Renting versus Buying

After talking to a bunch of the local people we met there, we decided that it might be a better idea to purchase an investment property there some day instead of trying to move there.

I didn't destroy any electronics on or after this trip (so far).*Fingers crossed*

4. Whatever place we pick from your suggestions

This summer – we want to do something in the caribbean again. We aren't cold weather people, and we prefer something tropical.

I'd love to hear your suggestions in the comments (or email, whatever works). I will just ask that you provide some specifics on the hotel/resort you stayed at and any money-saving or fun stuff to do tips you might have.

If you have something non-caribbean, I'm open to being convinced to go there haha.

Thanks in advance!

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Posted in: Travel Hacking