• media-iconmedia-icon
    Youtube
  • About
  • Equipment

Anguilla Four Seasons Friendscation

Facebooktwitterredditpinterestlinkedinmail
P

eople will forget what you said, they’ll forget what you did, but they’ll never forget the way you made them feel. This January, we invited 8 of our friends, some of whom had never met each other, and by the end of the four day trip, they all felt like family to each other. This is our guide to planning a friends vacation that will change everyone forever.

On a #Weication, You Turn Friends into Family

Photos courtesy of Capture

How We Were Inspired to Plan a Weication

The older we get, the tougher it becomes to spend time quality time with friends, and that’s why this year, to celebrate my 35th birthday, we decided to invite 8 close friends to spend 4 nights in paradise.



We partnered with the Four Seasons Anguilla to showcase how their 5 bedroom villas are the perfect #Friendscation destination.

In 2013, Wei and I got married on Anguilla and rented out two 5 bedroom villas at Ani Villas, and since that was such an amazing experience, we wanted to recreate that magic in 2020.

At Our Wedding, It Was #NoParents #NoRules

You haven’t been to the Caribbean if you haven’t visited Anguilla. There are 33 pristine, public beaches that pair perfectly with its laid-back vibe.

The island offers remoteness, relaxation, plus some of the best food in all of the Caribbean (excellent sushi, massive fresh lobsters and fine dining).

The best part is how accessible it is. JetBlue, Delta, and United all offer direct flights from NYC to St. Martin. After touching down in SXM, you’re whisked to the ferry terminal and in 25 minutes you’re pulling up to the ferry terminal in Anguilla.

The boat ride on FunTime Charters kicks off the magic of the island. From the front of the boat, you cruise past the forest covered mountains of St. Martin that look right out of Jurassic Park, and once you hit the open water there are more shades of beautiful blues than you can count.

With a cup of homemade Rum Punch in hand, and the wind whipping through your hair you feel like you’re in paradise and wish you never had to leave.

You’re staying at the Four Seasons Anguilla not only because of the immaculately designed property but because of that famous service with a smile. Everyone we encountered on property had a smile on their face and made our entire trip feel like a dream.

Here’s your itinerary for an amazing #Weication…



Day 1 – Welcome Dinner on the Beach

You’re going to start off your trip getting as close to that pristine beach as possible with a four-course dinner on the beach. Our concierge arranged everything and all we had to do was show up (and wear white).

We booked a Capture to memorialize our vacation, so instead of selfies, we have professionally shot and edited portraits we’ll hang in our home to remember forever this epic trip.

Day 2 – Pool Day

Kick off your trip lounging all day at your own private infinity pool. Your private butler will help coordinate any drinks, snacks or meals to be had while you’re relaxing poolside and will also help coordinate your dinner plans for the evening.

We got hooked on this new game, Farkle, that had us screaming “hot dice!” at every epic moment, game related or not.

Sunset Lounge Sushi

Sunsets, sushi and sake. Is there a better pairing in the world? Grab a glass of Whispering Angel and watch the sunset from the 100 meter infinity pool, then dry off and grab a table at the Sunset Lounge. We’re still dreaming about the beef bulgogi, firecracker roll and the Korean spiced wings.

Sink back into the couches with a Boulevardier in hand and listen to the sound of one of the local bands that play most evenings. Check the schedule for DJ Sugar, who was the DJ who spun at our wedding and also Mystyc Vybes, whose sound will remind you of Rihanna.

Day 3 – Massage, Wine & Paint

You worked hard last night taking in all the beauty and all those extra carbs, so reward yourself with a morning of pampering. Nothing puts us in pure vacay-mode faster than a couples massage.

Both Wei and I always fall asleep during the massages so we kinda miss the massage but also get the most satisfaction waking up and feeling amazing.


To tap into your creative side, get the gang together for a wine and paint session. I’ve never done this back home before and honestly had never even considered it, but this being my second time, I can tell you I’m hooked.

Painting is therapeutic.

I immediately forgot about all the anxiety I had about taking off from work and instead was zoned into my masterpiece.

Lynn, your instructor, will turn beginner’s into experts by the end of the one hour session and If you look at our final products, I bet you can’t tell which was the original and which was our creation.


For dinner, we ordered room service, played multiple rounds of Farkle and sat around debating and discussing whose art was best.

Off the room service menu, you’ve got to order the cheese plate, the grilled cheese and one of the salads topped with fresh mahi mahi or shrimp.

After you’ve unleashed your inner artist, it’s time to flex your musical talents. Head down to Waves, just a 5 minute walk on the beach, to sing karaoke. Waves is a tiny beach dive bar with only enough seating for 20 of your closest friends.

It’s a local favorite and a great way to hear captivating stories about the island from locals who know it best.

Day 4 – Sail the High Seas

The best way to traverse the 16 mile stretch of Anguilla is by boat, so for your final day on this magical island you’re hopping on a private catamaran tour. Go beach bar hopping, swim with the sea turtles and then head to Prickly Pear Island.

It’s an uninhabited island with a lone structure. Out of which they serve the best BBQ you’ve had outside of Texas.


Once you’re dropped off the boat, head to World Famous Elvis’ Bar where you can grab a local AXA beer and play corn hole all night long as the sun sets on the water beside you. Late night the bar plays live music and has an outdoor dance floor.

If you’d like to book your own #Friendcation or #Weication, reach out to the sales team and mention us. They’ll hook you up with something special and make sure every detail is taken care of so you can focus on making the most of your four days in paradise.

We flew down to SXM from EWR in United Business Class for just 54,500 miles each way. With flights during peak season hitting near $2,547, you get a nice $.0467 point per mile.

And remember the rule, if you’re using your points on any flight and get more than $.02 then it’s a good deal. If the price per point is below that, you’re better off using cash. For more tips on hacking airline miles, checkout our Youtube channel.

To take redeem the flight, we transferred points from Chase Ultimate Rewards. If you want to score 80k of Chase miles by signing up for a credit card with just a $95 annual fee, checkout this CardMatch tool and look for the Chase Ink Cash Preferred.

Slim-fit button-down poplin shirt by Club Monaco @ Mr. Porter

Glick Round-frame Sugnlasses by Moscot @ Mr. Porter

Men’s Caribbean Vacation Outfits

Cotton-pique polo shirt by Mr. P

So guys, I know it can be tough to figure out what goes with what, so I’m here to make it easy. One of the simplest ways to start looking your best is to simply copy what other guys are doing. So here are some ground rules for dressing for a beach vacation.

1. Always pack a pair of light jeans or pants. I went with a pair of white jeans. They’re gonna go well with anything, and in case the weather drops, you won’t be freezing.

2. Since we’re going to be near the water, I always try to pack pieces that are blue. The combination of the myriad of blues in the ocean water match really well to any shade of blue you’ll be wearing, and bonus points if you’re heading out onto the water.

3. No matter how warm you think it’s going to be, there’s always a chance of a cold front, and since I hate being cold, especially when on a tropical vacation, I always pack a sweater.

To fit in with the coral pink sands of Anguilla, I went with my Acne Studios pink cotton-jerysey sweatshirt from Mr. Porter. Its lightweight enough you can wear it on a windy day with shorts and soft enough you can wear it home on the plane to catch up on some Zzzs.

4. Always pants, never shorts after 3pm. I’m a short guy, and wearing shorts makes me look even shorter, so that’s why I always wear pants. Even if you’re normal height, wearing pants just adds authority to whatever you’re doing.

I just saw a preview of the new Curb Your Enthusiasm, and Larry tells the mailman, “if you’re gonna confront someone, you better do it in pants.”

So even though its 80 degrees out, grab a pair of linen pants (I love these linen drawstring chinos) and save the shorts for your swimwear.

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities. Lifetailored has partnered with Creditcards.com for our coverage of credit card products. Lifetailored and Creditcards.com may receive a commission from card issuers Additional 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.

More in Travel Guide