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All-Inclusive Vacations In Your 20’s: Are They Worth It?

Insiders guide on what a Dominican Republic vacation would be like in an all-inclusive resort

Note: On the rare occasion Cassidy accepts guest posts, they tend to be from her best friend of over 10 years who has a completely different idea of travel. The opportunity arose for her to ask Kelsey (post author & bestie) to document her experience in a place Cassidy has neither been, nor experienced this particular style of traveling which she found may be of interest to readers.

Approximately one year ago, I found myself driving down I-93 south, the skyline of my favorite city laid out in front of me. The August sun was shining, and I rolled down the windows on my little Saturn Ion which was packed to the brim with my lifelong possessions. I was in the process of moving out of the dirty, cheap first apartment of my adulthood, and moving into a gorgeous new apartment just outside of Boston. I was leaving behind the roommates that were more like strangers than anything else, and moving in with my two best friends.

Our new place was right next to the commuter rail, two miles away from Davis Square, with the cutest little breakfast spot within walking distance. Most weekends we woke up hungover, but my friends and I pulled on our shoes and headed out the door anyway. We would trudge down the street in pursuit of the most delicious breakfast sandwiches we’ve ever had whilst reliving the details of the previous night.

A few weeks after moving day, I sat at my new kitchen table with my best friend and closest confidant, Beth. We were eating breakfast together and discussing what we’d be doing that weekend, probably going into Boston, or having people over to see our new place. Suddenly, she perked up, turned to me, and I knew by the look on her face that she was about to say something insane.

Insiders guide on what a Dominican Republic vacation would be like in an all-inclusive resort

“Oh my god, we should totally go to the Dominican this summer!”

This Dominican vacation was something we had discussed at length in the past, but it ended up constantly falling through the cracks while we moved on to other things. Not giving it much thought, I said, “Sure, that’d be fun” and went back to eating my breakfast. I didn’t think anything would come of it.

Like the majority of my friends, Beth and I met in college. We found ourselves sandwiched between sweaty bodies on an alcohol-stained apartment couch in the middle of a party. We bonded instantly. She is one of the few whose friendship proved to be something worth holding onto, and we grew together instead of apart over the years. One thing everyone knows about Beth is that she is very Type-A. She’s a planner who prides herself on her organizational skills. While I went on preoccupied with my usually daily stresses, she was behind the scenes, planning out our Dominican summer for us.

Insiders guide on what a Dominican Republic vacation would be like in an all-inclusive resort

For that, I am grateful, because all I had to do was say “I’m in” and the rest was pretty much taken care of. When it comes to travel, or basically anything, I’d like to think that I’m very “go with the flow.” I usually let other people decide my weekend plans for me. I don’t really care where I am or what I’m doing, as long as I’m surrounded by the people that I love, with a glass of wine in my hand (I’m also a sucker for a good rooftop view.)

After rounding up a group of people to join us on our Dominican adventure, we booked a villa in Puerto Plata for the first week in June. We researched flights and ended up booking right around Christmas time. Later, we were set up on a payment plan, where we’d pay a certain amount of money each month to cover the cost of the villa and its all-inclusive perks.

Insiders guide on what a Dominican Republic vacation would be like in an all-inclusive resort

Finally, this was turning from fantasy to reality.

I honestly couldn’t believe it. A vacation is something that really shouldn’t seem so far-fetched, but for me, it was. I hadn’t taken a real vacation since summer 2012, when my parents took my two siblings and I to Florida. This is better known in my household as the “family vacation from hell.”

In college, I wasn’t able to study abroad, or go on spring break trips because I was a on a varsity sport and an athletic scholarship, so I had to be around for practices as well as competitions. We had to always be on, present and training. Instead, I looked on in envy at pictures of my friends gallivanting around Europe, or on the beach in the middle of March while I trudged through cold, New England winters. I’ve only been out of college a short time, and this is the first opportunity I’ve had to do something like this, so I wasn’t about to give it up for anything.

Over the next few months, our Dominican getaway became an obsession.

We installed countdown calendars on our phones, so we’d know how much longer we had to wait, right down to the second. We wrote list after list: things to pack, things to buy, travel tips and what we planned to do while we were there. I went to bed at night dreaming of the luxury resort, the private beach, the cabanas and, of course, all of the delicious fried food I was planning to eat when I got there. In preparation, I put myself on a rigorous workout plan to shed those few extra pounds I’d put on since college (that happens to everyone, right?)

Instead of going straight home after work, I would head down to the company gym and jump on the treadmill for a few miles, until I was sweaty and exhausted. I tried to switch it up and keep things interesting, sometimes by lifting weights, taking a weekly HIIT class, and throwing in a nice hard spinning session every so often. No way was I going to show up on the beach looking anything less than my best. This vacation might have drained my bank account, but at least it was keeping me honest.

Insiders guide on what a Dominican Republic vacation would be like in an all-inclusive resort

Finally, after almost an entire year of waiting, it was time to head to the airport. We grabbed 3 am Ubers, coffee, and jumped on a plane to Puerto Plata.

Overall, the all-inclusive life was a good choice for our group. We were pretty well catered-to during our time in the Dominican Republic. There were maids who cleaned our villa and cook for us. All of our drinks and meals were “free” and in no short supply. Our days were spent enjoying the gorgeous beaches and cabanas. While I would definitely go again, I can see why people our age (broke twenty-somethings) would choose otherwise. All-inclusive’s are expensive. I easily dropped two grand over the course of a year on this trip, even after the pretty hefty discounted rate we received for being members of the resort. But, everything was provided and taken care of which is what I preferred.

Along the way, I collected some tips that proved to be helpful while staying at an all-inclusive in the Caribbean if it’s a vacation you’ve ever considered:

Bring cash, specifically tip money.

The staff are relentless when looking for tips, and will straight up ask you for them after hauling your luggage to the car. You’ll find out that the level of service declines pretty quickly if you don’t tip. They accept American dollars which will save you the hassle of going to the ATM and having to exchange the pesos you get out of it. Also, souvenirs and postcards were necessary purchases for me while I was down there so the cash was much-needed.


This one seems like a no-brainer, but it’s one that I cannot emphasize enough: sunscreen. Sunscreen. SUNSCREEN. I was unfortunate enough to get burned on both our first AND last days there, which gave me few opportunities for relief. And if sunscreen doesn’t work: aloe, aloe, aloe.

Insiders guide on what a Dominican Republic vacation would be like in an all-inclusive resort

Don’t shy away from excursions.

These were definitely the best parts of the trip. Though the prices can seem intimidating at first, there are affordable options (our waterfall excursion was only $50/person) and they were absolutely worth the money. Pay in cash to avoid the 9% tax they tack on to credit card purchases (see first tip above.)

Spring for the international data, especially if you’re in a big group.

It’s inevitable that you’ll split up at some points, and it’s key to stay in communication with each other to coordinate dinner plans, and just to make sure no one gets lost. The wi-fi on the resort can be expensive and spotty, so data is definitely your best bet. Just be sure to keep your head out of your phone and stay in the moment while you’re there. Trust me, everyone will still like your Instagram posts when you get back to the states.

Be aware of how much you’re drinking.

At an all-inclusive resort, it’s easy to lose track of your drinks. Taking shots at a swim-up bar with your friends can be super tempting. Fruity drinks are readily available without any bar tab hanging over your drunken head.  One day, I was at the pool drinking with my friends, and I later woke up in a Cabana with no memory of how I got there. Luckily, I was unharmed, albeit a little embarrassed. This would’ve been scary if I wasn’t in a group of nine, but after that I made sure to go easy on the alcohol.

Insiders guide on what a Dominican Republic vacation would be like in an all-inclusive resort

Most importantly, choose your travel partners wisely.

This can make or break a trip, excursion or vacation. Make sure to surround yourself with people you love/trust or at least those with similar interests. Groups can be hard, there’s a ton of conflicting personalities and problems tend to feel heightened in an unfamiliar place. It really can ruin a vacation to have someone constantly dragging anchor from too many Mai Thai’s or complaining throughout the duration of your stay.

It’s important to talk as a whole about what will work, and also not work during your time together. Worst-case, those who want to sleep in all day can band together. Also, consider people who are going to push you just enough to try new experiences that you might not otherwise!

Would you stay at an all-inclusive? If you have in the past, did you find it worth the money? Let me know in the comments, Cassidy Jean @ Jetplane Jean has never been to an all-inclusive resort and would love to hear your thoughts on it as well!

Insiders guide on what a Dominican Republic vacation would be like in an all-inclusive resort


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