My Tropical Dream Wedding at the Four Seasons Maui at Wailea in Hawaii
When Kenny and I got engaged, we actually had no idea where we wanted to get married. We knew we wanted somewhere tropical, of course, and we imagined a destination wedding, but we were torn on where to do it. We toyed with the idea of Mexico, and actually had a big trip planned to tour venues we liked in Cabo and Punta Mita, but we fatefully decided to go to Hawaii first.
We went around the Big Island and toured countless hotels and venues, before hopping over to Maui to do the same. We were touring a few places, but out of all of them we decided to stay at the gorgeous Four Seasons Maui, because it was already our top choice from the research we had done online, and I wanted to make sure we knew what the guest experience would be like for our guests staying there. Immediately, when we checked in, we fell in love with the FS Maui for our wedding.
There’s a reason the Four Seasons Maui has the pristine reputation it does. It’s because it is, truly, the best. The service, the food, the location, the VIBE. You feel at home there, but also on the best vacation of your life. Everything about the hotel just screamed to Kenny and I as ‘our’ place. And, as we did a walkthrough with one of the Four Seasons Maui’s events team planners Stephanie, the venue, in Kenny’s words, ‘checked every single box’ we had wanted in a destination wedding venue. Whereas other places we toured were nice, but were missing one aspect we wished for here or there, Four Seasons Maui was perfect in every way.
The ceremony location on a lawn overlooking the beach with one of the most stunning views in the world, check. The reception area would be in the same place as the ceremony, and could fit our 170 guests with a huge dance floor, a band, gorgeous string lights and moonlit palms, check. The cocktail hour before the reception would be in the Plumeria Gardens, with breathtaking sunset views, check. The after party would be in a ballroom where we could go late into the night with a DJ and dance our hearts out at the Tropical Disco of our dreams, check. AND on top of all of the dreamy wedding day perfection, we could have a beachfront rehearsal dinner in the sand followed by a pool party the night before the wedding, taking over the Four Seasons Maui’s Serenity Pool and swim up bar and having the welcome party of our dreams. It all, quite honestly, felt somewhere between way-too-good-to-be-true and so, so right.
Table of Contents
Why we chose the Four Seasons Maui for our wedding
My number one priority when it came to finding our perfect wedding venue was the guest experience. Kenny and I had always imagined a destination wedding where our closest friends and family would be on VACATION with us, staying at the same resort and vacationing together, not just coming and going for the wedding day.
Looking back on our wedding, one of our favorite parts about it was that it truly felt like adult summer camp at the Four Seasons Maui all week. It was unreal having all of our friends and family there with us. We truly took over, with around 70 rooms booked in our wedding block (!!!!!!), and SO MUCH Kenny Flowers everywhere! (Especially the Wailea print, which we designed inspired by Wailea for the wedding!)
We loved that the FS Maui has a very upscale, elegant vibe, but it’s also FUN. Which was so perfect for Kenny and I, and the wedding we had imagined!
I loved the idea of a destination wedding because of this vacation aspect, and the fact that we could have so much more quality time with our loved ones, spread out over the weekend. So I wanted to choose a hotel that our guests would love as much as we did!! The Four Seasons was the perfect choice for us because a ton of our guests had never even been to Hawaii before, let alone Maui, and I knew it would be the dreamiest vacation for them!
Most people stayed a minimum of 4 nights, with some of our friends staying a full week or more. Kenny and I stayed 8 nights total. Which was the perfect amount!
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THE WEDDING WEEK LEAD-UP
The wedding week
We flew from California first thing on Monday of the wedding week and got to the FS Maui by about 10am. We are so happy we came early in the week because we had a couple days to get those last minute things done before most of the guests arrived (NECESSARY!!) We worked on the guest goodie bags, had our marriage license appointment (you have to do in person in Hawaii!), had meetings with our wedding planner, etc. etc. and got ready for the big week! I also booked a hydrafacial at the spa, and mani and pedis for my mom and I so we could be ready for the weekend! The FS Maui spa is amazing and I highly recommend. Most of our guests got at least one treatment while they were there! Everyone was obsessed.
The first thing we did when we arrived was stop at Costco to stock up on provisions for the week. We got lots of wine to keep in our rooms for entertaining friends, Hawaiian goodies for the goodie bags (I get into those details below), and anything and everything else we’d need for the week.
BTW – we brought most of what we’d need for the wedding over with us in checked bags, or shipped directly to our wedding planner at the hotel. Things like tropical disco party favors, guest book, name cards, etc all got shipped directly to her, but we also had a lot we had to bring with us! I mean look at how many bags we brought with us.
(No, this isn’t ALLLLL my wedding week outfits and skincare routine, but that was a lot of it, too). And yes, I brought my wedding dress with me on the plane (here’s how I did it).
The week of the wedding
Every morning in Maui, Kenny and I would wake up, grab the free Kona coffee outside of DUO, and walk the Wailea coastal walk to get some exercise and start the day! Sometimes on our way back we’d go straight into the ocean to go swimming with sea turtles or we’d head to breakfast or the pool after!
It was our Maui morning routine and we loved it so much. I miss it just thinking about it!
Wearing this alo yoga set – my fav!
Mornings during the wedding week leading up to the big day were so incredible
Our guest goodie bags
On Wednesday, a lot of our guests started to arrive. We had the hotel deliver their goodie bags to them in their room (and anyone not staying in the hotel, we delegated this task to family friends to deliver theirs!)
We gave each guest an ‘Aloha’ jute bag, with a custom Kenny Flowers shirt and/or sarong (shirts for men, sarongs for women) in their size. Kenny designed a special print for the wedding guests inspired by the dress I wore the first night we ever met!!!!! The guests LOVED it, and it was so fun seeing them all wear it all weekend and afterwards! (It’s called the 703 – after our wedding date, and is one of our favorite prints! It’s now available on our site here)
Above you can see me on the first night I ever met Kenny in college in the original print! We took that print and made it our own, adding little elements of our life together throughout it, and that’s what we gifted our guests!
and we put them all together in these aloha bags!
(I also gifted each of the bridesmaids a bottle of wine I picked out especially for them in their goodie bag!), and these stickers off of Etsy were great! I always think it’s nice to have a good bottle of wine in any hotel room to have on your balcony or getting ready for a dinner, etc! My girls loved it and ended up having group room happy hours with them.
THE SNORKEL / SAIL
Thursday: Wedding party sail & snorkel
On Thursday morning, we had our first official wedding event – a chartered sail & snorkel with our wedding party, their plus ones, and our parents! It was SO much fun. We rented this sailboat, and sailed off to Molokini! Molokini is a famous crater off the coast of Maui that is SOOOO beautiful – we saw so many fish and the water was crystal clear and sparkling blue. It was amazing. We told everyone to wear the Wailea print if they had it (this was one of the prints we designed for the wedding, called The Wailea – we launched it in 2020, and gifted the girls at my bachelorette party and the guys at Kenny’s bachelor party swimsuits in this print).
It was a lot of people’s first days in Hawaii (and first time to Hawaii!) so it was SO fun getting out on a boat and doing some snorkeling, and definitely so fun having everyone wearing the same print, highly recommend matching swimsuits if you’re planning a boat trip!
Friday: Pool day at the hotel
Friday morning, Kenny & I rented a poolside cabana for the day at the Four Seasons Serenity Pool, and had a floating breakfast to kick off the day!
After breakfast, we treated my two maids of honor and Kenny’s best man Brooks to IV’s from NextHealth. If I could give every bride and groom ONE best piece of advice going into your wedding weekend, it would be to get an IV the morning before the wedding! It was recommended to us by the Four Seasons team because they recently brought on NextHealth full-time to the resort and they offer IV’s and booster shots for jet lag, hangovers, weddings and more. It’s just an IV of vitamins that help avoid hangovers so with one IV we were full of energy and didn’t get a single hangover or even feel tired in the LEAST on the whole wedding weekend. It really was like magic. They recommend doing it one day before the wedding for maximum benefits! The NextHealth team came to our balcony to do them, which was awesome and so convenient. It took about 45 minutes, and everyone was RAVING about how good they felt all weekend.
After our IV, we went back to our poolside cabana and told all of our friends to meet up at this pool for the day until we had to leave for rehearsal! We hung poolside and then I got a blowout in the FS Maui salon before the rehearsal (they were really good! They did my mom’s hair too!) and then we got ready and met up with everyone in the hotel lobby!
Shop my bridal poolside looks:
THE REHEARSAL DINNER
Friday: Rehearsal Dinner & Pool Party
We rehearsed from 3:30 – 4:30, then had the wedding party to our suite for a quick drink before heading down to the rehearsal dinner festivities from 5-7:30! I get more into the full rehearsal dinner and welcome party play by play in this post here, but I’ll give you guys the quick gist!
Our rehearsal dinner took place in the sand at the Four Seasons beachfront venue, on a little bluff between the main beach and the hotel. It was SO beautiful. The decor & florals were all very warm, modern tropical. We had two long tables, and about 40 people total. My in-laws graciously hosted this beautiful event and we invited our bridesmaids, groomsmen, officiant, plus ones, and our immediate family (parents, siblings, and grandparents). The events team warned us it might be a tighter space for that many people, but it ended up being the PERFECT space for us. If we had any more we would have had to have round tables instead of long but the long were perfect for 40 people. The bar was right near the tables, and there was a little space where people gave speeches in-between the two tables!
The calligraphy was all done by Miss B. Calligraphy, who is so talented! I loved our signs!!!!! Photography by Anna Kim Photography
THE WELCOME POOL PARTY
We rented out the Four Seasons’ Serenity Pool from 8-10pm on Friday night for our welcome party the night before the wedding. Because the pool is only open to guests until sunset, they allow you to rent it out for private events at night!
THE WEDDING DAY
Getting ready with my bridesmaids
My bridesmaids, my mom, my mother-in-law and I all got ready together in the Ilima Suite, which was SO beautiful!!!! it was spacious and had the most beautiful tropical greenery outside! We had breakfast catered in from the hotel (SO good!), coffee and tea, and lots of champagne! It was so much fun and the best way to start the wedding day.
We all wore Kenny Flowers kimonos, of course! My white bride kimono is the same print in a silk burnout available here! The fans were a gift from Kenny’s nana – who had them hand-painted for us to match our kimonos!
My hair & make-up team
Cynthia Rose and her amazingly talented Kipona Aloha beauty team took care of us on the big day. I could not recommend Cynthia and her team more highly. Cynthia comes from a really impressive background in Hollywood and film industry and splits her time between LA and Hawaii. Everyone was SO happy with their hair and makeup, which made me so happy! The bridesmaid make-up artist used to be Paris Hilton’s personal makeup artist! So cool. My bridesmaids looked like absolute mermaid goddesses and everyone kept commenting on what a beautiful group (inside and out!) my bridesmaids were.
I felt like Cynthia did an amazing job emphasizing that she wanted me to feel like MYSELF on my wedding day, just of course with amazing makeup that would last all night long and that I’d feel amazing in. Her makeup style felt so natural and I didn’t feel like I had anything on! I also felt like my hair was absolutely perfect (an amazing feat for my naturally wavy, unruly hair in 85 degree humidity, sweat and dancing!). And more than anything, I really appreciated Cynthia’s calm, professional demeanor the whole day. She is truly a beautiful person and SO talented – I definitely want to work with her again for a photoshoot for my swimwear line Watercolors or anything else soon! My maid of honor was trying to hire her for her wedding on the wedding day, hah, which speaks to how impressive she and her team were! We loved them.
Kenny & the groomsmen
My wedding dress
The girls reactions to my dress!
I wore this gorgeous Monique Lhuillier dress that I think was just made for our wedding. It was the perfect blend of beachy but elegant and chic, and I loved every part of it. I was a huge fan of the off-the-shoulder straps, but since I wore the dress all night dancing (yes even at the disco!!), I had the straps made removable so I could turn it into a strapless when we entered the reception and dance more freely! It was like having two dresses in one!
I got my dress from Bridal Galleria – the BEST place to shop for wedding dresses if you’re in SF or California!)
My bridesmaids dresses
When it came to shopping for bridesmaids dresses, I knew I wanted something vibrant, bright and tropical. The dull, muted tones that are so in style for bridesmaids dresses these days are just not ME, and I wanted something more fun and vibrant that felt more my style. Turquoise / teal has always been my absolute favorite color in the world, so I knew I had to find the perfect teal dress for my girls. When I couldn’t find anything ANYWHERE, I was in Bali shopping for fabrics for Kenny Flowers when I came upon the most BEAUTIFUL teal silk that I knew was made for my bridesmaids dresses. I bought a bunch of the fabric and found a tailor on the ground in Bali to take all of the girls’ individual measurements and customize a dress for each of them, so I brought these beauties all the way from Bali to Maui! I treated the girls to their dresses as a gift to them, because they’re my best friends in the world and I wanted to make sure there were as little expenses as possible for them for being in our wedding!
I wore a gorgeous new diamond tennis bracelet that Kenny gifted me on the day of the wedding, these diamond earrings from IVAR, my shoes were my something blue, and my mom’s emerald ring in my bouquet was my something borrowed. And, funny story, I completely forgot about putting it in my bouquet and in the hecticness of everything, mis-placed my bouquet at some point in the night and it was nowhere to be found the next day!!!! So it took my wedding planning team all day to track down the emerald, which had been taken away with the other flowers all the way to upcountry Maui. THEY TRACKED IT DOWN THOUGH, luckily before the bouquet was thrown out! Phewf.
The Wedding Ceremony
Florals by Dellables Floral Design
Before I walked down the aisle with my dad, I had what my planner called my ‘solo moment’ where I entered from the top of the stairs and walked down to the bottom, where I met my dad. This was so cool, I loved it!! I got to take it all in, and see everyone from above. I get chills just thinking about it. Kenny loved it, too, since that was the first time he saw me and he says I looked like his Angel coming from above!! (SWOON).
The girls reactions looking at over Kenny & up at me as I walked down the stairs!
The Cocktail Hour & Custom Coconuts
All of our guests were led to the cocktail hour which took place in Plumeria Gardens, a gorgeous venue with an ocean view and the absolute perfect spot for cocktail hour. We had gorgeous seafood towers and a ton of delicious passed apps. But my favorite part were The Catered Coconut’s custom coconuts!!!! This husband and wife team had a station set up where they were live chopping Maui coconuts it was sooo cool, and the hit of the cocktail hour! They had these custom wedding coconuts with our wedding logo and date on them, too. And, of course, the guests had the option to add spiced rum!
Our bride & groom signature cocktails. Kenny’s was the “Ditch Mai Tai” and mine was the Jetset’s on the Beach spicy marg.
Some of our guy friends absolutely nailing the ‘Tropical Elegant’ dress code, all wearing Kenny Flowers shirts under their blazers! Taylan, on the far left, is rocking the 703 shirt we gifted all the guests in their goodie bags!
This photo was a film photo taken by my friend @morganmariejones! I love it.
Did we do a first look?
No! We chose to not do a first look so that when I walked down the aisle was the first time Kenny saw me and it was the absolute best decision (for us)! To this day, Kenny says his best memory of the day was when he saw me at the top of the stairs making my entrance into the ceremony. And my favorite memory is his welled-up eyes once I got to him!!
The only downside of not doing a first look is that we had less time for photos, but since we take photos for a living, we never wanted our wedding day to feel like a photoshoot anyway. I chose Anna Kim for my photographer because I knew she could be up for the challenge of capturing the best moments as they happened – I wanted beautiful memories captured, not a staged photoshoot. She got the most gorgeous photos of us, in so little time! So we could spend more time at the celebration!
What did people wear?
We asked guests to dress ‘tropical elegant’ for our wedding and everyone looked AMAZING. There were a ton of Kenny Flowers shirts with blazers and suits over, girls were in chic tropical dresses. Everyone looked really nice without looking over-the-top formal.
The Wedding Reception
We had the most beautiful modern tropical dinner reception in the same location as the ceremony on the Four Seasons Maui Oceanfront Lawn! They turned the whole space over from ceremony to reception in about an hour and used the same canopy as we got married underneath as our sweetheart table – which was so, so cool. And all of the gorgeous hanging florals were one of my favorite parts of the whole set up.
Our table names were all places that meant something to us as a couple!
We used sand dollar place cards with gold calligraphy from Etsy!
Our stunning florals were all by Dellables Floral Design
Our first dance
For our first dance, Shea Derrick and the Full Flavor Band played Kenny and my song, “If I Could Build My Whole World Around You” by Marvin Gaye. That song is so beautiful and special to us, and the band crushed it. I also had Kenny’s wedding ring engraved with “My world around you” – lyrics from the song!
Our Band & Music
We had both a band and a DJ at our wedding! We did a band for the outside reception part of the wedding (because Kenny and I both LOVE a good live band), and then we did a DJ for the disco (because who doesn’t want some epic rap, hip hop and pop music thrown into a wedding dance floor too!). There aren’t that many wedding bands in Hawaii, so it was one of the first things I was told to book when planning my wedding in Hawaii, we were SO lucky to have booked THE BEST wedding band on the island – Shea Derrick and the Full Flavor Band. EVERYONE was on the dance floor and they absolutely rocked it. They were the wedding band of my dreams!! Everyone was complimenting them for weeks afterward. They had the soul / fun dancing vibes we were going for, and we loved EVERYTHING they played!!! If anyone wants a copy of our wedding playlists, they’re on Spotify here!
The Fire Dancers!
We had three fire dancers show off their skills with a fire show and then lead us with torches to the disco! It was SO fun and a cool added element that was very Hawaii! For all the people who had never been to Hawaii before, this was so much fun because it was like being at a luau!
The Tropical Disco
A Maui County rule is that any outdoor event needs to go indoors at 10pm, but we assured our guests on the invitation that the party was truly just getting started, and at 10 we headed inside for “The Tropical Disco” after party, that went until 12:30am! This was a huge highlight of my night, and many of my favorite memories were just dancing our hearts out on this dance floor. Kenny was in charge of the EXPERT playlist and worked with the super talented DJ Liam Grist to have a night that everyone would remember forever.
If you’re having an after party, I highly, highly recommend props and costumes! It gets people loose and makes it soooo much fun. We got all of ours on Amazon (we loved the wigs like these, disco necklaces, sunglass sets, and of course leis, and Kenny got these AWESOME light up sticks that everyone loved customized with “C+K’s Tropical Disco” on Etsy here!
Our Photography & Videography
Our Maui wedding photographer was Anna Kim Photography. These photos speak for themselves but I obviously can’t recommend Anna Kim higher!!! She crushed it and captured all of the LOVE and FUN so beautifully all weekend! Also highly recommend having your wedding photographer do the rehearsal dinner/welcome party too!
Our videographer was Hi Focused – Jordan and his team are SO talented and were able to seamlessly capture every moment and put it together so beautifully. I will never get tired of watching our videos!!!! Watch our 7 min wedding video here!
All of our wedding vendors
If you reach out to any of our vendors, please let them know you heard about them from Jetset Christina!
Photography by Anna Kim Photography
Invitations by Gus and Ruby Letterpress
Hair & Makeup by Cynthia Rose / Kipona Aloha Beauty
Florals by Dellables Floral Design
Coconuts by the Catered Coconut
Band – Full Flavor Band
DJ – DJ Liam Grist
Calligraphy by Miss B Calligraphy
Fire Dancers – Manutea Nui E
Sunday after the wedding
We recuperated with everyone at the hotel on Sunday! It was so much fun. Pretty much everyone stayed until at least Monday, some Tuesday, so there were a ton of people just hanging on the beach and by the pool this day. This was how Kenny & I showed up to breakfast.
Our room at the Four Seasons
Kenny and my honeymoon suite
We stayed in room 594 for the full 8 nights we were in Hawaii, and it was absolutely incredible. This room is one of the Four Seasons Maui’s oceanfront prime one-bedroom suites, with1400 square feet of a 180-degree oceanfront view of the beach and neighboring islands, a huge balcony, Frette linens, configurable space, large outdoor living area and an awesome marble bar area that was perfect for entertaining friends throughout the week. Kenny and groomsmen got ready in here, too! We really felt at home in this room and it was soooo hard to leave. We’re already thinking for our anniversary we’ll come back and have to stay in the same room!
My parents upgraded themselves to one of the oceanfront Club level rooms at the Four Seasons (as did a few of our guests), which includes exclusive Club Floor privileges including breakfast, a full-service premium bar with complimentary alcohol, and private check-in and check-out. It’s basically the Four Seasons’ luxe all-inclusive option for alcohol, snacks and breakfast, and was perfect for them because they could entertain their friends in their room!
What Kenny and I would do differently looking back on the wedding week
This is a lame answer but I really have no regrets with our wedding, everything SOMEHOW ended up going so perfectly!!!!!! It really was a dream. I think you don’t realize when you’re going through the wedding process what parts of the weekend are going to mean the most to you. You think it’s going to be all the details, which were, AMAZING, don’t get me wrong. But really it’s the FEELING in the air that makes the weekend. And the fact that everyone you love is in one place with you!!!! In my experience at every wedding I’ve ever been to, the couple sets the tone for the party, so if you two are having fun, everyone else will be too! Kenny and I were BEAMING all week and weekend, and our friends could feel that. Everyone was thriving.
If I could go back, I would tell myself to stress less!! I feel like everyone says this, but seriously, it does all go by way too fast, and if you spend even a SECOND stressing, you’re wasting a moment of your precious wedding week! I was super stressed and doing all the last minute things up until Wednesday of the wedding week, when most people started arriving. After the celebrations started and people were there, I had no more stresses, but the stress leading up is REAL. And it takes some serious self care and knowing how to de-stress yourself around the even to make sure you don’t fall off a bridal deep end. I did a lot for myself in the lead up to the wedding – Kenny and I would go on our daily routine walks in Wailea, my mom and I booked massages in the spa, I got a facial on Wednesday before the wedding, and each night I would do meditations on my Spotify when I went to sleep so I’d sleep well and get necessary rest. I also would use cough drops all week because it’s so easy to lose your voice! I also took these apple cider vinegar gummies every day – they’re an anti-inflammatory and good for preventing losing your voice, as well as general digestion and health!
I’d also have a designated bridesmaid in charge of re-applying my lip gloss LOL. Such a random one, but for photos!!! I definitely never touched up my makeup (there was no time!!!!) and I had sweated it all off in the Maui humidity by like 8pm.
My best wedding day advice
Be the star of your wedding!!! Leading up to the wedding, you’re so often the producer, director, writer, editor, assistant all in one. But come that day, you and your husband are the movie stars. That is your JOB!!!!! Nobody wants you to be working behind the scenes or stressing about XYZ, they are there to watch you have the time of your life. So go do it for ’em 🙂
Don’t get pulled in a million different directions – spend your wedding night with your new husband or wife! I think it’s really important to stick together!!! It’s so easy to be pulled into a thousand separate conversation but you don’t want to look back on your wedding night and have all these amazing memories but not TOGETHER!
Have your parents sit on opposite sides of the aisle than you would think, so that his parents are looking at him during the ceremony, and your parents are looking at you!! My planner had this idea and we loved it!!!
All in all, Kenny and I could not have asked for a better celebration / vacation with all of our best friends and family! It was truly our dream come true and we wish we could re-live every second.
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