Surprise Hawaii Trip

Surprise Hawaii Trip ~ Kristy Wicks

December is my favorite time of the year… Not only because it’s a holiday month but because it’s also my wedding month. This year Jeff exceeded all expectations with a surprise Hawaii trip to Maui. He has never done this sort of thing on his own before so you can imagine how surprised I was.. Emma was in on the whole thing. (of course).

I found out we were leaving only a month beforehand to give me time to prepare. It was time that I definitely needed to make sure I had work taken care of while gone. I had to save enough time to to get all my holiday and vacation shopping done. (the most important part.. Lol)

Before leaving, Lilly Pulitzer reached out to me about a separate collaboration during the holiday period. The partnership couldn’t work out due to the timing of my trip, so instead they sent me a few of their newest arrivals to wear while I was away in Hawaii. So fun! I’ve always loved Lilly Pulitzer and own several pieces. Emma also wore Lilly often in college – the brand was very popular with sorority girls because they used to make items that incorporated the greek symbols mixed with each sorority’s colors. Emma had pillows, tumblers, key rings, and even clothing. You name it, she had it.

It was perfect timing hearing from Lilly Pulitzer because I knew I would be needing special pieces for this trip. It was our 29th Anniversary after all. (who can believe that?!?!) Her line fit in perfectly with everything Hawaii related in regards to design, colors, and patterns.

We left bright & early on a Monday morning & flew from SFO to Maui direct. One of the nice things about having a husband who travels a lot, is having the opportunity to visit the United executive lounge in the airport and getting upgrades on the plane if available. Nothing like starting a trip off on the right foot. (especially for someone like me who has been a Flight Attendant for years)

Once we landed in Maui, we grabbed a cab to the Grand Wailea. The hotel is around 30 minutes from the airport.. perfect timing for me to catch up with all of you. ;) If you’ve never stayed at the Grand Wailea before – it’s a Waldorf Astoria luxury hotel. It’s extremely popular for weddings as they have the cutest little chapel on site with the most romantic setting. Families also love it because it has a gazillion water slides, and a lazy river!! The last time we visited this hotel Jeff and Emma lived on the slides. I on the other hand prefer the lazy river. ;)

Upon arrival we were greeted with the most beautiful lei which the girl wrapped around my neck.. I felt immediately spoiled. The entire hotel was decorated to the hilt for Christmas and everything looked amazing.

Surprise Hawaii Trip ~ Kristy Wicks.52

Surprise Hawaii Trip ~ Kristy Wicks

Surprise Hawaii Trip ~ Kristy Wicks

Jeff was able to get us a beautiful ocean front room which had the most beautiful view of the chapel. Perfect for our anniversary.

Surprise Hawaii Trip ~ Kristy Wicks

Isn’t the chapel so beautiful?

The first night we decided to head down to the beach to watch the sunset with a cocktail. We stopped to take pictures. After that we had a low-key dinner at the hotel and crashed early. Such a nice relaxing first night.

Surprise Hawaii Trip ~ Kristy Wicks (52)

Surprise Hawaii Trip ~ Kristy Wicks

| Dress: Lilly Pulitzer | Shoes: Vince Camuto (similar style here) | Earrings: Nordstrom (similar style here) | Lips: Pillow Talk by Charlotte Tilbury & Frost Bite by Jouer | Highlight: Rose Gold by Jouer (another one I love here) |

Surprise Hawaii Trip ~ Kristy Wicks

Day 2: Jeff and I walked the property, lounged by the pool.. slept by the pool…swam in the pool… and lounged some more. (with a few lava flows in between) Dream day! Topped everything off with a great read: The Couple Next Door.. so juicy.

Surprise Hawaii Trip ~ Kristy Wicks

| Sunglasses: Versace (similar look here) | Swimsuit: Robin Piccone | Coverup: Surf Gypsy | Bag: Lilly Pulitzer |

|Nails: Time for Napa by OPI | Lips: Hue by Mac and Nude Dior ‘Addict’ Ultra-Gloss | Shoes: Jack Rogers |

That second night night we had cocktails at the Grand Wailea bar then walked next door to the Four Seasons to eat a yummy dinner at Spago. I was expecting the vibe to be very romantic and relaxed because it was a mid-week night at the beginning of December, but we walked into a jam-packed restaurant full of corporate people and families. The nice part? There was candlelight and we had the sweetest waiter in the world. We felt special and everybody around us disappeared.

Surprise Hawaii Trip ~ Kristy Wicks

Yummy tomato salad

Surprise Hawaii Trip ~ Kristy Wicks

A sweet surprise at the end of the meal

Surprise Hawaii Trip ~ Kristy Wicks

Jeff looking cute in front of the restaurant

Surprise Hawaii Trip ~ Kristy Wicks

Don’t know why we didn’t take a picture of me.. I was wearing the cutest outfit from Lilly Pulitzer again with all the cutest accessories. I’ll add a shop the post below of everything I wore:

We had planned to go zip-lining on day 3 but due to the high winds they closed down all activities. They even delayed the big surf competition. We decided to do a couples massage instead.. it was amazing and I highly suggest it if you can swing it.

Surprise Hawaii Trip ~ Kristy Wicks
Surprise Hawaii Trip ~ Kristy Wicks

| Coverup: Chelsea28 (similar style here) | Bathing Suit: Becca | Shoes: Havaianas | Sunglasses: Gucci (similar style here) |

Wednesday night we went to dinner at Monkeypod, which is located a couple miles away from the hotel. We dressed up, looked super cute, and as I said in my Instagram story today.. we flubbed on the pictures. We need Emma to come and take pictures in the future. Next trip I’ll be on it I promise. I wore Lilly Pulitzer’s Black Poly dress. I love this dress!

Day 4 we rented a car and drove around the island hitting everyone’s favorite spots in Maui. So many of you had recommended Leoda’s Kitchen & Pie shop for their amazing food, especially the chicken and waffles which Jeff was all over. LOL He could not wait to try them. (I have to mention.. the customer service was also amazing and the place was jam-packed.. even at mid day)

I loved the touch of blue on the Christmas tree

The chicken & waffles did not let us down. Jeff said they were the best he’s ever had! The apple pie was also amazing…

Surprise Hawaii Trip ~ Kristy Wicks

They had tons of pie options

Once we left Leoda’s, we drove all around the island hitting some of the best scenic spots to view surfers and the ocean. We were so lucky to see tons of whales… so great because it’s not the time of year when they usually come in close. Just before dinner, we stopped at Ho’okipa Beach Park. It’s a great place to watch surfers and the large wave breaks. We have been told to go in the early evenings for the best lighting and sunsets and it was amazing. Unfortunately the winds were so strong that the surfers were not allowed to get in the water and we were blown all over the place. I was afraid Jeff was going to fall off the cliff taking photos!

After the beach we went to Mama’s Fish House for what we were told was the best food on Maui. I loved the entire vibe of this place. The views are amazing, and the restaurant had such an incredible ambiance. Our waitress has worked there for over 20 years and filled us in on a little bit of the history of this family-run restaurant. Mama actually lives right next door and still has a heavy hand on everything that goes on. She gave us some amazing guidance with our meal, what was fresh, etc. and we loved every bite.

Surprise Hawaii Trip ~ Kristy Wicks

Crab and avocado dip (Amazing!!)

Day 5:

We went to brunch overlooking the beach and took one last walk by the water before getting ready to leave. It was a short few days but any day away from the hectic schedules is always a nice reminder of why you’re in love.

Surprise Hawaii Trip ~ Kristy Wicks

| Dress: Lilly Pulitzer | Sunglasses: Ray-Ban | Shoes: Older Tory Burch (Similar style here) | Lips: Le Nu by Yves St. Laurent and Lychee by Jouer |

Suggestions for things to do while vacationing in Maui:

  • Stay at the Grand Wailea at least once – especially if you have kids.
  • Attend a Luau
  • Eat at Mama’s Fish House (Call for reservations in advance.. at least two weeks if you want dinner reservations).
  • Drive the road to Hana – lots of hiking, waterfalls, and beautiful beach views.
  • Go to Leoda’s for incredible pies & the chicken and waffles (food in general).
  • Go to the lookout point at Ho’okipa Beach for a great sunset and to watch the surfers.
  • Take a whale watching tour – the sights are amazing
  • Head to Maui Winery.. we didn’t get the chance to do this but everyone told us it is amazing!
  • Rent a car for a day or two to drive around the island.

While our anniversary trip might not have been as adventurous as most of our usual getaways, it was exactly what we needed during this busy holiday season. I’m so thankful that Jeff planned this… He knows me all too well. ;)


If you like reading about our travels, click here to see our Travel Guide to Mykonos.

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