How to Spend the Best 5 Days of Your Life


At Life, Tailored, we believe in living the best life possible. Growing up, my family couldn’t afford to take vacations, and I honestly believed when I became an adult, I would be relegated to the same fate. That is, until I started to do my research. Last year I discovered the power of credit card points, and since then have taken a $16,000 flight on Singapore Suites flight to Europe for just $500.

After that unbelievable trip, I wanted to share the fun with my friends, so I decided to figure out how we can all enjoy first class service on an economy budget. So last year I began planning The Best 5 Days of Your Life Trip.

Myself, and 14 friends stayed at a super luxury villa in the Dominican Republic, all for less than $300/day including unlimited food, drinks, and excursions.

You can checkout the details of our amazing trip below, and learn how you can live the same type of life, tailored to you.


Where You’re Going: Casa Kimball


Casa Kimball is a super luxury villa in Cabrera, Dominican Republic. The villa itself can sleep up to 16 people, with 8 bedrooms, 8.5 bathrooms, and a handful of additional air mattresses to accommodate all your guests.

The villa is absolutely breathtaking, as you can see from the pictures. The pool is the staple of this property, and is easily the nicest any of us had ever seen in person (or online, for that matter).  All 100,000 gallons of water is yours for the next 120 hours, and it’s wonderful.


What to Do at Casa Kimball

Just staying at the Casa Kimball property is amazing. On the property they have a 100 meter, 100k gallon pool, pool volleyball, ping pong, cliffside jacuzzi, billiards, full bars, and board games.

But the Best 5 Days of Your Life aren’t all going to be enjoyed in the confines of the house, no matter how amazing the house is.  So we’ve also added a list of unbeatable excursions and activities to give your vacation that over-the-top feel you’re looking for.

Here’s what’s on your list.


Zip-lining in the monkey jungle. This was an awesome experience. Located about an hour and a half from the villa, we went up into the mountains of the Dominican Republic, and went down 7 different zip lines. At $75 per person, everyone was super pumped after this trip.  The guides are amazing, the course is crazy fun, and at one point you even endure a 50ft “free fall” drop.

Booze cruise on a private catamaran. Having gone on a boozy catamaran last year for our wedding, we knew this was a must-have. We started out the day on the catamaran around 11am with appetizers and drinks. This was followed by snorkeling at preselected snorkeling spots with thousands of bright fish and coral, paddle boarding, and open sea cruising all accompanied by plenty of beer and liquor. Bookings cost around $2,500 for the entire day.

Private DJ & karaoke party. Being able to stay on the property and enjoy the villa really complimented this experience. We had a full setup of DJ equipment including strobe lights, smoke machines, and awesome music. We did Karaoke on one night and the DJ the following night, and each booking was only $250 a piece.  The DJ and Karaoke master was the same guy, and him and his team definitely know how to make sure you have a great time.

Salsa and merengue dance lessons. I’m admittedly a terrible dancer, and haven’t ever taken a dance lesson. We had a team of 5 come to the house, and teach us how to dance for three hours (it was the same team that did the karaoke and DJ), and I loved it. I even learned how to merengue. At $150 for the entire event, get this!

How to Get There in First Class for Free


To get to Casa Kimball, you want to fly into Puerto Plata (POP), which is 1 1/2 hours from the villa. From New York, you have two options for direct flights: JetBlue and United. You want to fly United because JetBlue doesn’t operate a premium cabin to POP (they will be rolling out Mint Class to Aruba and Barbados beginning Nov 2015 — checkout our review of Mint Class, we loved it), but United offers Business class to POP.

To get your flight on business class the Life, Tailored way, you’re going to use points to fly for free. The easiest way to accrue United miles is via the Chase Sapphire Preferred (right now there’s a 40,000 point signup bonus) card which earns 2x points on all dining and travel purchases. We put all our meals on here, and the points add up quickly dining out in New York.

For a roundtrip Saver ticket, you need just 60,000 miles. Just by signing up for the card, you get 50,000 miles, so you’re almost there.

What’s In Your Carry On Bag


The flight from Newark to Puerto Plata is a quick 3 hour ride, so I packed just the essentials for the flight. I discovered Monocle magazine last year on my Singapore Suites class flight, they actually had a copy for me to read on the 9 hour trip. The magazine, for those of you who have never heard of it, is basically a combination of The Economist and GQ. They cover International affairs, luxury lifestyle, as well as what to wear and where to buy it. I even picked up their Monocle Guide to Better Living which adorns my coffee table at home. Basically, for the modern gentleman, it’s the only magazine you need.

In addition to my reading material, I just picked up a pair of the Bose noise canceling in-ear headphones. I owned a pair of the over-ear version, and while they were good at canceling out the noise, they made my ears hurt on long flights. Also, due to their size, it made it tough to pack light. From my experience on two flights now, I would rate these in-ear headphones better than the Bose over-ear. My wife also owns the Beats by Dre noise canceling headphones, and these in-ear are the best of them all.

What to Wear

Packing for a beach trip is always easier than heading to a cooler climate since you’ll most likely be able to hang in swim trunks everyday.

For this trip, I packed 5 pairs of trunks for each of the days, and packed 7 shirts that match with the trunks so I could keep the same trunks on for breakfast, lunch and into dinner.


Orlebar Brown

Orlebar Brown makes investment grade trunks. They are made of a polyester blend that is comfortable, fast drying, and looks great in pictures (as you can see). Also, my favorite feature of the trunks is the adjustable tabs on the side. I go into every trip with the tabs as tight as possible, then if I’ve done my job, by the end of the trip, I’ve loosened them all the way into relaxed mode.


Retro Marine

I got a pair of these from my wife for Christmas and absolutely love them. They are about 1/3 the price of the OB’s, and have a more beach-only vibe. They have a drawstring waist and come in a softer fabric that make them great for lounging by the pool.



I brought a pair of Isaora sweatpants for the travel, on the flight, and for when the thermostat dipped at night. I got into Isaora last year when I was looking for workout clothes that looked good and functioned well without having a big “U” or swoosh all over them.



Proper Cloth

This is my favorite custom shirt maker, and I love that they now have relaxed shirts. I got my first custom made denim shirt from Proper Cloth a month ago and have worn it more than a dozen times. I cut it a bit shorter in length than dress shirts, and a little bit wider in the cut to give me room to breathe while relaxing. The final touch is the ASW monogram on the stomach.


Gant Rugger

My goto brand for relaxed Americana favorites. I got this blue and white naval stripe cotton sweater and break it out every spring, summer, and fall. I love the simple stripes in the sweater, and since I’ve worn it for a couple seasons, the cotton is extra soft.


Kit & Ace

These are soft, incredibly versatile, and comfortable shirts.  I discovered Kit & Ace last winter, and immediately bought 6 shirts after wearing the one.  They’re from the founders of Lululemon, and from the success they had with LL, they used their money to start buying a ton of cashmere clothing because it was so soft. Well, as you’ll know, cashmere pills making it unusable after 10 or so wears, and is strictly dry-clean only, which can get expensive and is inconvenient. So with Kit & Ace, they developed technical cashmere, which is just as soft, but can be machine washed. Needless to say, once you try these out, you’ll be hooked. They’re not cheap, and tees start at $79, but once you try it you’ll agree it’s worth it.




Whenever I travel anywhere where there’s water involved, I pack my Swims. Swims created shoes that go seamlessly from the beach to the bar. The aspect I love the most is being able to walk around in the ocean, in the pool, and not having to take off my shoes. Also, since they’re so functional it means it’s one less pair of shoes I need to pack.

Travel Essentials


Mr Natty Hair Clay

Wherever I travel, I always bring along my Mr Natty hair clay. Since I have longer hair, this stuff helps to give it shape and prevent my hair from curling up or the dreaded Alfalfa.


Monocle Travel Domino Set

Whenever you’re traveling, you never know when a flight cancellation could turn into a 6 hour layover at an airport, and that’s when you want to be prepared with games. I picked up this awesome travel domino set made of birch plywood crafted by Monocle for a trip to Martha’s Vineyard and now travel with it on every trip. What I like is the tiles are lightweight yet strong. You can slam them down without worrying about snapping them. Plus, they don’t add too much heft to your bags the way ivory dominos would. Dominos itself has multiple variations of games to play from the simple matching game to more complicated betting styles. Regardless of how you play, this $75 set will last you a lifetime.


Monopoly Deal Card Game

Monopoly has been masterfully converted into a card game, and it’s extremely addictive. When I first brought this out to the group, people were skeptical. Mainly because the Monopoly board game is highly due to luck. The card game, however, has multiple elements of skill to it. We ended up playing this game until 2am on multiple occasions of our trip, and will not be going on any future trip without packing it.

Day 1 Outfit

Day 2 Outfit

Day 3 Outfit

Day 4 Outfit

Day 5 Outfit

How You Can Make This Happen

When you book Casa Kimball, included in your booking for an additional $75/person/day is the personal chef experience. This includes breakfast, lunch and dinner prepared on-site by your personal chef.

Casa Kimball costs between $2,900 – $5,000 per night, depending on high or low season. Luckily, low season is May – August, giving you 3 full months to book your trip at the lowest price point.

If you book in low season with 16 guests, your cost per person is just $906 for 5 nights in a super luxury villa.

That’s just $181 per person, per night.

This doesn’t include tips, excursions or food, which adds in an extra $500 or so per person, but still we’re talking about extremely affordable luxury.

To book with CasaKimball, head to their website and let them know that Life, Tailored referred you. They’ll hook you up with a discounted stay.  Enjoy the Best 5 Days of Your Life!

Where Are We Going Next?

You know it’s a great trip when you start planning the next trip at the end of the one you’re one, and that’s just what we did on the way home from Casa Kimball. We’re excited to work with our next partners to help us plan out our trip. So if you would like to see your brand or villa on our next trip guide, drop us a line.

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