In May 2014, my wife, @threadtherapy, and I, got married in Anguilla, British Virgin Islands, a tiny Caribbean island just north of St. Maarten. It was a destination wedding for just our closest friends where we booked two breathtaking mansions on a cliff overlooking the ocean.
Our wedding had it all: emotion, tears… body shots. It was wilder than both the bachelor and bachelorette parties — combined.
Needless to say, our wedding was AMAZING. Far beyond anything we imagined or, frankly, thought we could pull off. Despite how our incredible photos look, the wedding was actually affordable! And since you are all part of the Life, Tailored family, I’m going to show you how we paid for all of this ourselves (and, of course, with some help from our guests), and we managed to make our out-of-pocket expenses between $20,000 and $30,000.
1. Have Two Weddings: Friends and Family
Since my wife and I are located in New York City, we knew our wedding was bound to be expensive. Renting out the rooftop of our building would have cost $10,000 for the wait staff alone, not including $150/person for food, entertainment, etc. And since we’d be having it in our own stomping grounds, our invite list was sitting at around 120 people.
Our solution? Split the wedding.
We invited only our closest friends to a destination wedding, and threw another family wedding at a much cheaper venue.
2. Find The Perfect Venue (ie Vacation Rental)
Here are a list of some of our other favorite villas from LuxuryRetreats, and a sneak peek at where we’re having our reunion. We stayed at Ani Villas for our wedding, the staff was top-notch and we can’t wait to plan our return trip.
Ani Villas, Anguilla
$10,714 – $14,714 night
Casa Kimball, Dominican Republic
$2,400 – $5,000 night
Tip: Look for rentals in the offseason to save up to 50% off typical rates.
Sand Villa, Anguilla
$2,400 – $10,000 night
Mahatma House, Bali, Indonesia
$775 – $1,340 night
Celadon Villa, Koh Samui, Thailand
$1,000 – $1,800 night
Malee Sai 5 at Sava Villas, Phuket, Thailand
$1,500 – $3,200 night
Lime Samui 2, Koh Samui, Thailand
$1,150 – $2,200 night
3. Invite Your Closest Friends And Ask Them to Participate
We wanted our wedding to be something everyone remembered forever, so we found the best villa on all of LuxuryRetreats (they use pictures of it on all their marketing materials).
The villa we picked we couldn’t have afforded on our own, so what we did is ask our guests for help. We told them that we were planning our wedding at the Ani Villas, and we were inviting them for 5 nights. We would cover all their food, drinks, entertainment, excursions, and more.
In exchange, we didn’t want any wedding gifts, no bridal showers or any of that stuff “you’re supposed to have,” but we ask that you contribute $1,000 per person to help us pay for the villa.
We thought of the wedding as a mini vacation for everyone, and when else can you go to a 5 star resort for just $200/night and get a personal chef preparing all your meals?
4. How to Book the Villa
You want to book in the offseason. This is when rates are 50% lower than average because people typically don’t want to travel. I would suggest not booking anything in the Caribbean when it’s hurricane season, but every other time would be awesome.
Apparently May is a low season in Anguilla. In New York, the day we left it was 45 degrees, and when we arrived in Anguilla it was 79. Also, when we looked at the weather in Anguilla, it showed rain all 5 days. It didn’t rain a single day we were there.
By booking in the offseason, this saved us about $20,000.
To pay for the villa, you’re going to have to put down 25 – 50% upfront, with the remaining funds owed about two months prior to arrival.
We asked our guests to pay 25% upfront, and the remainder once we got closer. We used Venmo to accept all the payments and it was super easy.
5. What To Wear For Your Wedding
I bought a Bonobos linen tuxedo with a 30% off coupon and got it tailored three times to ensure the perfect fit.
This was paired with a linen shirt from John Byron from their resort collection that was custom made to my size, all done online.
For shoes, I went with Swims loafers available from MrPorter.com.
Previously we covered what Ledbury suggests you wear on your wedding day including an awesome tuxedo shirt.
We also did a roundup on the best men’s wedding bands to complete the look.
I bought the Bonobos suit when they had a 30% off coupon, and since I had referred a ton of people from Life, Tailored, I actually had enough credit to get the full suit for free. The shirt was also gifted to the blog, and I bought the shoes from eBay for about 50% off the original price. Finally, I had the suit tailored by Alba Dry Cleaners, who I had previously built their website, so the tailoring was also comped.
This thriftiness is possible for anyone, you just have to be patient, be educated, and plan out what you buy and when.
6. How to Fly First Class to Your Wedding for Free
A first class wedding is not complete without flying first class to your wedding. By no means do we suggest paying out of pocket for a $10,000+ flight. This is Life, Tailored, so we’re going to show you how to fly first class for free (well close to it).
By using credit card points, we booked two first class tickets from NYC to St. Martin. We flew on United, and it costs 70,000 miles each way for first class, which is a total of 280,000 points for both of us.
To get this many points, I used my Chase Ink cards. They offer 5x points on purchases from office supply stores. I went to Staples.com and bought $200 Visa gift cards at $206, and then liquidated these into cash using ATMs, Venmo, the Post Office (by buying money orders).
Using the shopping portal from Chase, you also get 2x more points by buying on Staples, so I was getting 7x points for every $1 spent. I had to buy $34,285 worth of Visa GC to get the two tickets. It takes a lot of work, but it was worth it as we were sipping champagne in First Class.
This strategy can be scaled down to accommodate your guests as well. If they want to fly to your wedding economy, for free, you just cut down the amount of points. For instance, the Chase Sapphire preferred offers 40,000 points as a signup bonus, which will almost cover a roundtrip international flight. (60,000 miles needed)
7. Use A Concierge to Plan Your Wedding
My wife originally brought up the idea of paying upwards of $5,000 to have someone plan our wedding. The idea of having to pay someone to spend more of my money sounded ridiculous.
Luckily, we had a savior in LuxuryRetreats.
LuxuryRetreats offers a free concierge. She handled flowers, food, entertainment, and excursions. She even coordinated everyone’s flights to and from the villa, for a total of 21 people and about 15 different itineraries.
The wedding went off without a hitch (besides me losing my wedding ring on day one), and we didn’t spend a dime on a wedding planner.
8. Plan Excursions for Killer ROI
What we wanted to avoid with our wedding was what we’d experienced at so many other weddings. You’re assigned to a table with the third-cousin, and you only talk to the date you brought. The wedding is far from emotional, touching, or really all that fun.
To avoid that, we decided to plan the wedding over five days, with the ceremony on the fourth night.
This gave us four days for everyone, who came in barely knowing each other to bond, and create a pseudo-family.
To achieve this, we went on a ton of excursions together.
Nothing brings people closer together than being stuck on a boat in the middle of the ocean.
At first I thought excursions were a waste of money. I was wrong. Splurge on these. Your friends and wife will thank you for it later.
9. Get Beach Butler Service on the Beach
In addition to day boating, I highly recommend paying to have the staff serve you lunch on the beach. There’s nothing like eating on a white tablecloth 30 feet from the beach and feeling the sand in your toes as you partake in a three course meal.
10. Get a Photographer & Make It Candid
Instead of corny wedding photos of @threadtherapy and I peeking through doors to look at each other, we told our photographer Caroline Ross to catch us in the moment.
During dinner and dancing, Caroline was in the mix getting some of the most outrageous photos that everyone loves.
This photo captures it all. Our guests said this wedding was the most emotional, touching wedding, and also the most insane, balls to the wall party they’ve ever attended.
11. Keep The Ceremony Simple Stupid
We originally got a $13,000 estimate from our florists. It had the works, and what you would expect from any wedding you see on TV.
Instead, we went for a paired down version, and our final bill was closer to $2,000, and as you’ll see our wedding was just as beautiful, and we put this money towards our guests.
12. Write Kick Ass Vows
Instead of focusing on the flowers, we put our energy into our vows. Each of us wrote our own, if you need some advice, checkout our previous article.
We’ve had an interesting story together, and we shared all of our ups and downs in our journey together in our vows and afterwards, we had the whole audience in tears. One of our guests didn’t cry at her own wedding, but we got her to cry twice the day of the ceremony.
Take the time to write vows that mean something to you. Your wife, guests and you will thank me later.
13. Have The Bridal Party Give Speeches
Nothing is more fun and as exhilarating as both giving a great speech and listening to one. Both our groomsmen and bridesmaids gave speeches, and again everyone was either laughing hilariously or in tears.
Ask them in advance to prepare something. It doesn’t matter if they memorize it, but the stories they tell will bring tons of good (and bad memories)
14. Make It About You
The whole point of a wedding is to celebrate the union you two are now sharing. So that means make sure this wedding is everything the two of you want.
Forget parents, obligations, work, don’t sacrifice the celebration you two want because you feel guilty about not inviting someone.
When we decided to have a wedding of 21 people, there were a lot of people we had to say no to. That was tough, but it made the people we did choose that much more important to us, and made the wedding that much better.
You can always have a family wedding later where you fulfill those obligations to invite that couple that invited you, or that Grandma can attend. Remember, this should be your one and only wedding, so make it count.