The Life, Tailored Beach Vacation Manual


Whenever it starts getting cold, I look for beach vacation ideas and new destinations to explore. This past Winer, we went on a killer beach getaway. Below is our guide on how to recreate this for yourself.

Traveling in style means much more than arriving to an immaculate destination.  More than wearing the perfect outfit for your travels.  And more than what airline you take for your jet setting adventure.

Having the perfect vacation means all of this and then some.  We’re here to help you make your vacation tailored perfectly, from the minute you get to the airport, to your last drink on the beach, all while saving some money.  This is how you take a Life, Tailored beach vacation.

The Perfect Destination

This post was written after we suffered through the Winter of Hell this past 2014. Winter in New York seemed to last from November into April, and after this sustained misery, we had to get out. This is our beach vacation escape plan.

Choosing the perfect destination is obviously a key essential in any great trip.  You want a beach, you want the white sand between your toes and you want the sun to be just perfect.  There a hundreds of places to go to get all of this, but taking a trip to an island in the middle of nowhere isn’t in everyones budget.  We suggest staying stateside, but feeling like you’re a million miles away.

Our choice vacation spot: Atlantic Beach, Florida.

The Flight


Not all modes of transportation are equal, and when you’re planning the perfect vacation, you want perfection from start to finish.

We recommend JetBlue.  The tickets are extremely reasonable and the modern planes come with all the right amenities.  The best part?  The extra legroom.  There are few things worst than having the guy in front of you insist on turning his seat into a bed, leaving your knees hitting the seat.

JetBlue seats start out a little roomier than the average, but for a small upgrade you can enjoy up to 38″ of stretching space.  By purchasing the “Even More” seats on JetBlue you get treated to more than just legroom.  Even More space also includes Even More speed, which gives you a faster route through security at participating airports.

JetBlue Even More Space


The cost to upgrade to even more space is $30-40 per flight, and the fact that it lets you show up to the airport 30-45 minutes later than usual is a godsend, especially if your flight departs before 7am.

We recently took this flight from JFK -> JAX, and it was just about two hours long. It was short enough that we couldn’t finish watching Hunger Games 2.

It was 45 degrees in NYC when we left, and when we landed it was 78 in Jacksonville, two hours have never meant so much.

JetBlue has begun offering First Class aka Mint Class (pictured above) on flights from JFK to LAX, and will be expanding to JFK to SFO come the end of 2014. I’m saving up points to be able to pickup this flight, which goes for about $1200 roundtrip. Unlike traditional first class meals, JetBlue is going to have the likes of Saxon & Parole cater the meals.

Use TSA Pre ✓ To Breeze Through Security


Of course if you aren’t traveling from one of the designated airports that allows you to utilize the Even More speed option, there is another route you can take.  TSA Pre Check is a huge time saver, and a travelers dream.

The difference between TSA Pre Check and the normal hour long line you stand in is unparalleled.  The line is speedy, and you don’t have to remove half your wardrobe when you hit the front.  You are allowed to keep on your shoes, belt and lightweight jackets.  You also can leave all your liquids, gels and other randomly questioned items in your bag with your laptop.

Of course due to safety reasons not everyone is eligible for TSA Pre Check.  Click here and learn how to find out if you qualify, and how to speed through security for your next trip. You don’t need a reservation for TSA Pre Check, if you just get there early, my visit only took 45 minutes without a reservation.

The American Express Platinum card offers a free ($100 credit) towards the GOES program, which is the International version of TSA Pre-check, and also includes TSA Pre-check. The only issue is signing up for GOES requires a reservation, which can often take months.

Travel Gear


Now that you know what plane to take, you need to know what to bring aboard.  Having the right luggage can save you time, a lot of hassle, and just makes everything run a little more smoothly.

A lot of men seem to forget, but you are allowed one carryon, along with one personal item.  Which means you can bring something that will fit in the overhead compartment and another bag that will fit under the seat in front of you.

Rimowa Topas Stealth


For your main carryon you can’t go wrong with Rimowa.  The Topas carryon (pictured above) is lightweight, durable yet flexible, and is able to fit all your necessities comfortably without going over the size limits.  Rimowa carries a number of models, sizes and colors. Once you own a Rimowa, there’s no going back. There are special hidden ways to pack it that allow you to fit almost anything you need in it. Rimowa Topas Stealth Cabin Aluminum 55CM Carry-on Case, $1,340

Jack Spade Duffel Bag


For your personal item, skip the backpack and opt for something a little more useful and spacious.  I have a number of different sized duffel bags that all fit under the seat in front of me.  Our favorite duffel bag right now is the Jack Spade Colorblock Carryall Duffel.  Available for $328, it is a bag that will last you a lifetime, and is as stylish as it is practical.

Of course along with what you’ll need while you’re away, you need to make sure to pack the must-haves for on the plane.

Bose Noise Canceling Headphones


The best treasure to keep in your duffel bag: The Bose QuietComfort 15 Noise Canceling Headphones.  Awarded best noise canceling headphones two years in a row by Trip Advisor, these keep the crying kids off of your plane and allow you a peaceful flight whether you decide to finish up that last minute work or take a nap until your final destination.

These Bose made our list of the best noise canceling headphones of 2014.

Pop Rock Breath Mints


Our secret travel companion are these poprocks breath mints. It is basically crystallized (sugar-free) mints, that clean your teeth, and make your mouth feel fantastic.

After a long flight, I like to pop these in as we’re making our landing, and the popping is a nice pick me up that helps my mouth feel fresh, and I’m ready to get onto my destination.

The packages are $29.50 for a 60 count box. Just $.50 per pack, pretty awesome. Order a couple cases, your friends will love these things.

They’re by, and I recommend the peppermint flavor.

What to Wear


Aside from the headphones,  you need to make sure you have all the right things in your luggage for the perfect beach vacation.  Fortunately, beach clothes are easy.  You don’t need many shirts, and you can wear a swimsuit all day long.  But this doesn’t mean you shouldn’t put some thought into it.

Here are your essentials to keep your trip perfect from start to finish.


Swims Loafer.  Perfect for the water, but stylish enough to throw on with some chinos.  Swims makes the perfect shoe for any beach vacation and it would be a mistake not to bring a pair (or two.) Swims Penny Loafer, $159.


Onia Swim Trunks.  Pictured here is the Charles, Onia’s 7″ gingham print classic trunks.  They are the perfect trunks for any stylish man.  No flowers, no graphics, just the right cut and an even better look. Onia Swim Trunks, $145.



M.Nii Surfrider Windbreaker.  Available at EastDane, this lightweight windbreaker is perfect for the ocean breeze without making you sweat.  Stylish and put together, this is a great vacation jacket.  And the lightweight nylon easily rolls up to fit in your bag should you never need it.
M.Nii Surfrider Windbreak, $240.


Bonobos Irish Linen Shirt.  Assuming you’ll spend more time on the beach and less time in steakhouses, don’t bother bringing your entire office wardrobe with you.  One good, versatile button down will do the trick.  Try something like this slim fit striped button down from Bonobos, wear it with a few less buttons in the morning, and throw it back on properly buttoned for dinner.  After all, you’re on vacation, no need to fuss with your outfits. Bonobos Irish Linen Shirt, $98.


484 Selvedge Jeans by J. Crew.  Pair your button down with a great pair of beach vacation pants, like these white selvedge denim jeans from J. Crew. Perfectly slim (but definitely not skinny) these jeans are exactly what every stylish beach-goer needs. J. Crew 484 Selvedge Jeans, $155.



A.P.C. Striped Sweater.  The A.P.C. striped sweater from Mr. Porter is perfect for casually throwing on when you’re on the go.  Unfortunately beach vacations don’t always know you’re on a beach vacation, and they don’t plan the weather accordingly.  Don’t get caught off guard if you get a chilly day thrown at you, make sure you have a good sweater.  This should be that good sweater. A.P.C. Striped Sweater, $220.

Where to Stay


After your amazing plane ride, you don’t want to kill the mood by showing up at a “resort” that is akin to a Motel 6.  If you’ve followed us so far, this is not the time to stray.  If you want to stay at the beautiful palace pictured above, then spend your vacation at One Ocean.

This immaculate luxury resort is perfect for relaxation, no matter what relaxing mean to you.  Right on the ocean with exquisite views, this resort also features golf, ocean view dining, a top notch spa and more.

Plus, upgrading is easy.  The staff are friendly and accommodating, and if you slip them that extra twenty you may just find yourself with an ocean view right from your bed.

Don’t believe all the hype?  Check out this Floridian paradise for yourself.  Click here and book the best beach vacation you’ve ever had.

One Ocean Resort


When checking in, make sure to ask if there are any upgrades available. Oftentimes, there are rooms available, and just asking can grant you an upgrade.

If you’re a bit more ballsy, go for the $20 trick. Slide the host a $20 and ask them if there are any upgrades available. It worked for me in San Francisco at the Clift Hotel. We got an upgrade to a corner room ($100 more) for our three night stay. Definitely beats the $20 cost.


The best room at Once Ocean are the oceanfront, simply breathtaking and worth the upgrade.

How to Book The Life, Tailored Way

How much you pay is equally as important as where you stay.

At Life, Tailored, we believe in getting the best product, but somehow finding a discount or sale we can maximize.

Here’s our insider tip for booking One Ocean.

We use for our booking. Their pricing is comparable with other sites, and in fact, sometimes can be more expensive than the hotel’s own website (which can actually work in our favor, we’ll cover that in a bit). has a frequent user program that allows you to get 1 free night for every 10 night stay. If you stay at 9 rooms with an average cost of $200, your 10th stay will be free up to $200. So effectively, we’re getting about 10% off our booking.

So with One Ocean, a $250 room becomes $225 via loyalty program.

Okay, so we’ve got that discount, how can we make it better?

Maximize Your Points & Discounts


We use to lookup referral programs for all online retailers. In our case, it’s showing us that we can get 5x Ultimate Rewards points when we book through their portal.

Ultimate Rewards is Chase’s loyalty program for their credit cards. I have the Chase Sapphire Preferred (which gives you 40,000 points on signup), and gets you access to Ultimate Rewards. Ultimate Rewards points are redeemable for $10,000+ First Class tickets to Europe, Asia, Australia, and anywhere you want to go.

My favorite cabin is the Singapore Suites Class that has a full bed, complete with Dom Perignon and rose.

So we click through the portal, get 5x points, plus the 10% off from

For a 3 night stay at One Ocean, at $250/night, that’s $750.

Since we’re using the Chase Sapphire preferred, we get 2X points on travel (including hotels).

So when we book using our trick, we get the following:

10% off — $75 for booking program
5x points — 3,750 points via Ultimate Rewards
2x points — 1,500 points via Chase Sapphire Preferred

Another kicker, when we booked One Ocean, the hotel was cheaper on their own website, so we used price-match guarantee. We sent in the price difference, and got another $50 taken off our bill. Pretty sweet.

What to Eat


Once you’re all settled in and are ready for some grub, you want to go to the places you should be going, not the first thing you stumble upon.  Put down your yelp app, we’ve obviously got you covered.

The first place you need to check out during your Atlantic Beach vacation is M Shack. (hint: adult oreo milkshakes)

This unrivaled burger joint is the creation of Matthew and David Medure, two brothers who took an old fashioned style burger joint and added some awesome fresh ingredients.  Check out their Atlantic Beach spot at 299 Atlantic Blvd.

Of course you can’t have milkshakes and burgers for every meal (although with burgers like that, maybe you could) when you are ready for a little more upscale of an evening head over to Mezza Luna.  With excellent food and wine pairings, this is your goto spot for your vacation date night.  I’d recommend something specific, if only I could make up my mind.


Mezza Luna
110 North 1st Street
Neptune Beach, FL

For the sushi lovers out there, you have to try Tamas Sushi.  Family owned and operated since 2000, this is some of the best Japanese cuisine you’re likely to find.  Trained in Japan at 18 years old, Tama-san worked as a sushi chef in his cousins restaurant for a number of years.  At 25 years old he was then asked to move to NYC and showcase his talents stateside.  After honing his skills in an American environment, he moved to Florida and eventually started his own delicious sushi restaurant, Tamas.

Sake is $6 for a large carafe, which you can’t beat. Order 4 of these and enjoy your super cheap, fresh sushi.

Tamas Sushi
106 1st Street
Neptune Beach, FL

Our Final Tips to a Perfect Beach Vacation


Follow our recommendations and have one of the most relaxing and joyous vacations of your life.  From packing the perfect suitcase to breezing through security, taking the small extra steps can ensure that you have the time of your life.

Keep watching Life, Tailored as we bring you more great vacation destinations, fun getaways, and other great ways to travel in style.  Enjoy your next beach vacation, and don’t forget the sunblock.

Remember, our goal is to get you all the things in life you want, at a discounted price. That is truly making your Life, Tailored.

If you enjoyed this article, subscribe to our mailing list and please tell your friends & enemies too 🙂

Like this:
Disclosure: This site has affiliate links. We may be compensated when users make a purchase or register to a third party website. For more details read our privacy policy.

Leave a Reply

Your email address will not be published. Required fields are marked *

More in Lifestyle