Dream Honeymoon Itinerary: 6 Nights on Lanai, Hawaii

Four Seasons Resort Lanai
Overlooking Hulopoe Beach from the Four Seasons Resort Lana’i

I’ll be honest with you: I never really considered myself a Hawaii person. In fact, when my husband Cory and I were planning our honeymoon, it wasn’t even on our list. Instead, we thought about destinations like Italy and Croatia, and ended up doing a combo between the two. We even went to Paris for a shorter first anniversary trip. The fact of the matter is we ALWAYS seem to pick city vacations over beach vacations like Hawaii, and while they are amazing, we end up coming home kind of exhausted and over-run. Lately, I’ve been looking for something different!

So when the opportunity to visit Hawaii came up a couple months ago, I definitely had to adjust my mindset. What activities were we going to do? What sights were we going to see? I’m so used to spending WEEKS if not months planning every moment of every day of a trip, that it was so refreshing to realize that this could be a vacation that was different than anything else we’ve done before. Sure, we wanted to do SOMETHING, but we also wanted plenty of time to, well, do NOTHING, too. It turned out that we found the perfect place to do this: The Four Seasons Resorts Lana’i.

Oh yes. I bought a “sailing” dress for this trip. More on that, below!

I cannot even begin to tell you how amazing a time we had. By the end of our trip my husband and I were like Jell-O, which is exactly what we wanted (and needed). And on top of that we were never bored. Thanks to the hotel we had what I think is the best honeymoon (or second honeymoon for us) trip ever. The itinerary was so great I just had to share it with you, below! Yes, this is going to be a “splurge” trip if there ever was one, but trust me when I tell you that if you don’t do it on your honeymoon, you might never do it! So get that Honeyfund out and start saving!

A note about Hawaii honeymoon/vacations: Initially when we were planning our trip, I envisioned traveling to at least two different islands and spending at least four nights on each. Honestly, I’m so glad we didn’t! While Hawaii is in and of itself a relaxing place to go, there is actually a ton to do based on your preferences. We thought about visiting both Lana’i AND Kaui, or Lana’i and the Big Island, but I soon realized that if you want to island hop you’ll almost always have to do it via a connecting flight in Honolulu. And a lot of times the flights can get delayed, which can potentially eat up a whole day. The beauty of spending the majority of your honeymoon on Lana’i (aside from how stunning the island/resort is) is that you can fly into Maui and take a 45 minute ferry to the island, which means you don’t have to deal with flights or delays (unless that delay is caused by you being too relaxed to get up! LOL). Personally I really liked the way we planned it, below, but if you have extra time and do want to explore two islands, I would highly suggest just adding more nights on Maui to the front or back end instead. I hear amazing things about Wailea (especially the Four Seasons there) and that could be a great way to do two islands without the stress of adding another flight in. But that’s just my personal preference!

OK, ready? Here’s what we did for our Hawaii “honeymoon,” day-by-day:

Day 1: Fly into Maui’s Kahului Airport (OGG)

We live in LA, which means the flight into Maui is pretty easy for us. We took an 8:30 a.m. flight and arrived a little after 11. It’s three hours earlier in Hawaii, which is great because it basically means you have the whole day. We were departing the next day for Lana’i and I wanted to be close to where the ferry would pick us up, so we stayed at the Westin Maui Resort Ka’anapali. The rooms were nice and since we were staying on points and have Starwood status, we got upgraded to a really pretty ocean view. Our room wasn’t ready when we arrived, so we had lunch by the pool and then changed into our suits as soon as we dropped our bags off in the room. After a couple hours in the ocean we got dressed and headed to Lahaina, where we had yummy cocktails and drinks at Fleetwood’s on Front which is, you guessed it, owned by Mick Fleetwood from Fleetwood Mac (I was a little too excited about the chance to run into him, considering he apparently comes in all the time). While the town of Lahaina is cute, if we were staying more than one night I would have definitely most likely preferred to stay near Wailea, as I mentioned above. Lahaina and the area around where we stayed is a bit touristy and not really our vibe, but to be honest you’re still in Hawaii so it’s pretty awesome. 🙂  After dinner and given the time difference we hit the hay early (like 9:30, which was amazing! lol), and got ready for our short journey to the Four Seasons Resorts Lana’i the next day.

On the ferry.

Day 2: Ferry from Lahaina to Lana’i

I had previously booked us tickets on the 12:45 ferry to Lana’i, which meant we had time to wake up, jog on the beach, and even take a swim in the ocean before we headed back to Lahaina (where Fleetwood’s was) to catch the ferry. We had about 30 minutes to spare so we ate lunch at a place right across from where the ferry is docked, and boarded the boat. The ferry almost feels more like a yacht, with great upper deck seating that allows you to soak up your surroundings (and even offers plenty of shade). The ferry ride to Lana’i felt like a great day trip even if you weren’t staying on the island. Seriously, it was gorgeous. The ride is an easy 45 minutes, and they bring you right into Manele Harbor. We got our luggage from the first floor of the ferry and proceeded down the dock, where we were soon greeted by a lovely Four Seasons Resorts Lana’i staff member who gave me the most gorgeous orchid lei, and Cory a kukui nut lei (I had seriously been waiting for this moment since we landed in Hawaii. I wanted that classic experience!). They packed our bags onto the shuttle and took us just a few minutes uphill to the resort.

When it comes to describing the Four Seasons Resorts Lana’i, I don’t even know where to begin. From the landscaping to the lobby and the awe-worthy rooms, the hotel recently underwent a billion dollar renovation, and it totally shows. Everything was immaculate and just, well, perfect. I hope our pictures can even do it justice!

The hotel grounds
Gorgeous artwork was situated throughout

Once we checked in and got to our room, we unpacked and basically proceeded to act like giddy schoolchildren over the fact that this was home for 6 nights. This room was AMAZING. Everything about the room was electronic, from the iPads on your nightstand to the automatic shades (and yes, even the toilet). We were in heaven. And being a hotel bathroom snob, I easily give this one 5-stars.

In terms of room type, we had a garden view room, which was beautiful, and I can only imagine how gorgeous a stay would be in an ocean view. We talked to another couple on their honeymoon there and they said it was spectacular (I was a little jealous, but actually really, really liked our view as well. I swear there’s not a bad room in the hotel!).

After we unpacked we decided to go outside and explore a bit. We ventured through the breathtaking lobby and down towards the pool, and were amazed by just how pretty the view was overlooking Hulopoe Beach. It now ranks as one of my favorite beach views ever, after having looked at it every day for a week! We decided to get a bite to eat by the pool at Malibu Farm, which has deliciously healthy food and probably the best pina coladas I’ve ever had (there will be several of these throughout the trip).

It’s like your own private beach.

We soaked it all in and headed back to the room to get ready for a 7:00 p.m. reservation at one of their four restaurants, ONE Forty, where we proceeded to have a lobster dinner that will go down in my book as one of the best lobsta’ dishes in the world. It was a Big Island lobster with garlic and roasted corn and some sort of shellfish broth that I’m day-dreaming about right now. If this was only the first night at the hotel, we were in for a definite treat.

Dinner. Yum!

Day 3: Reeeeeelax

Since we were still on our California time zone, it felt kind of amazing to wake up at 6:30 a.m. Each room has an Nespresso maker and Heath Ceramic mugs, which meant we made a ritual of having a cup of espresso every morning on our patio, overlooking the flora and fauna (not to mention birds!) from our balcony. I don’t normally workout on our vacations, but there was something about being here that just made me want to make the most of it, so we got dressed and headed to the gym, where they had cold towels and water and headphones waiting for us. Afterwards we headed back to ONE Forty, their main breakfast option, where we could choose from a la carte plates or what has to be the most extravagant (yet still somehow healthy) Asian/Hawaiian-inspired buffet anywhere. We of course opted for that (hey, we just worked out), and had everything from fresh sushi to omelettes to a freshly made juice and the craziest assortment of fruit (lychees nuts, anyone?) ever.

Morning ritual on our patio
View from breakfast

We changed into our suits and were down at the adults-only pool by 10 a.m. And considering we were still technically on PST, by 11 a.m., I had, yes, a pina colada in hand. We read. We swam. We ate (they deliver lunch on a tray right to your chair), and we ate all of the yummy treats they periodically came by with (like frozen grapes and mini strawberry shakes). Was this what a vacation was SUPPOSED to feel like? I feel like we’ve been doing it wrong the whole time!

This is my “you will photograph me drinking a pina colada” pose.
Lunch in bed…I mean by the pool.
Waterfall at the “Retreat,” the adults-only pool.
An insanely good mini strawberry milkshake they passed out poolside.

Since we were booked for a Sunset Sail at 5 p.m., we adjourned from the pool and changed into our best yacht gear (as you can see below. Cheesy? Of course!! But I love it.) and checked into the Adventure Center in the lobby at 4:30. They took us via shuttle back to the dock we arrived at, and we were ushered onto a beautiful catamaran and introduced to the super nice crew. The Four Seasons packed a crazy good bento box filled with traditional Hawaiian pupus (appetizers) for us, and we had purchased a bottle of wine at the Manele General Store. This was, for the both of us actually, one of the highlights of the trip (the sailing trip, not the wine, though that was pretty great, too!). The crew set up fishing lines for us and dropped them into the water, so whenever there was a bite we got to bring them in! We sailed around the Lanai coastline, talked with the crew about the area, and felt like we were in another world for two hours. I would HIGHLY recommend it for anyone visiting the resort!

More yummy snacks!
Such a natural. 😉

We took our sea legs back to the resort (well, the shuttle did) and we dined on fresh tuna burgers at the Sports Bar. Such a perfect end to a perfect day!

Two glasses of wine later…

Day 4: Explore Lana’i

We’re up and at ’em at 6:30 a.m. again. Who am I, my mom?! I feel so accomplished before 9! Waking up early meant we got to take the time to explore the famous “Ocean Nine” at the Jack Nicklaus Signature Manele Golf Course. Built on lava outcroppings with three holes perched on cliffs, these have to be some of the most outrageous views of the Pacific anywhere. I’m not even a golfer and I wanted to start playing! If you ARE a golfer, you have to add this course to your list. Fun fact: Bill and Melinda Gates got married on the 17th hole!

manele bay golf course
The view from the golf course.
Just a couple of pro golfers.

After feeling like a pro at the golf course in my white sneakers, we picked up our rental Jeep Wrangler at the hotel and set off to explore the small town of Lana’i. In case you’re not familiar with it, it’s actually a fascinating town to learn about. There’s only approximately 3,000 people currently living on the island, and as of 2012, Oracle founder Larry Ellison owns 97% of it! Everybody we spoke to on the island seems really excited about that, as he wants to make it 100% green/self-sustainable with a lot of cool plans in the works. The island is known as the Pineapple Island, because it was once owned by Dole Pineapple, who had the majority of their plantations based there. Today, Lanai City has no stop lights and no shopping malls, just amazingly nice people and some super great poke that we were lucky enough to experience. If you plan to visit the city (and you should!) you have to stop at Lana’i ‘Ohana Poke Market for lunch, but make it an early one. A line starts forming before they open at 10:30, and they often sell out in an hour or two.

After filling our bellies with poke we stopped by the Mike Carroll art gallery. Mike is an artist who moved to Lanai from the mainland and paints beautiful scenes from the island. We got the chance to meet with him, where he told us about his wife, Kathy, who started the non-profit Lanai Cat Sanctuary to help create a home for the stray cats on Lanai. When Cory heard about this he almost died of excitement, so we made a beeline (after a cool stop at Shipwreck Beach), to visit the close to 500 cats they have living there. A large majority of them are up for adoption, and you can play with the dozens of cute kitties that run up to you when you get there. If you like cats this is definitely worth stopping by (and making a donation to support their great cause).

This is basically Cory’s dream come true.
Shipwreck Beach…one of our stop’s for the day
I only wanted to post this photo because I like my white shoes.

At this point we had done TWO things and I was ready to get back to the resort for some more R&R! We turned the keys to the Jeep back in (which was super fun to drive through the Hawaiian terrain), and relaxed before our 7 p.m. dinner at NOBU. Oh, did I mention this was one of the four restaurants at the resort?! Yeah, we’re spoiled! I dolled myself up a bit and we sat down outside overlooking the gorgeous beach and were wined (or shall I say Sake’d) and dined to our hearts content. Does anybody do it better than NOBU? It majorly knocked our socks off (well, Cory’s. I was in Hawaii living my best sandal life.)

Day 5: UTV Adventure

We scheduled a UTV experience (Utility Vehicle) for 9 a.m., and I admit that initially I felt like this was more a Cory thing and even considered not going. But I knew I would most likely never get a chance to go on one again, let alone in this magical place, so I figured why not! We checked into the Island Adventure Center at 8:15 a.m., and met our two drivers (who I loved). They took us and another couple (the ones who were on their honeymoon!) about 15 minutes out to a field with an Air Stream trailer, which was stocked with sunscreen, granola bars if we were hungry, water, helmets and goggles. Each driver took a couple, and they drove us through the grasslands and rainforests on Lanaihale mountain while teaching us about the history and culture of Lana’i.

Better than a cup of coffee in the morning!

There were plenty of stopping points with crazy views onto the mostly untouched island, and the tour finished with a SUPER fun, fast ride over the terrain to the end. These drivers were total pros, and I was ready to go again! But alas, it was back to the hotel for the rest of the day “at leisure.”

One of the stops on the UTV tour.
Clearly having no fun.

Before dinner at the Sports Bar that night we took a quick 15-20 minute hike to Puu Pehe from the Four Seasons Resort Lanai for a heart-meltingly romantic view of Sweetheart Rock. We were the only two out there for the sunset, and it was felt like one of those moments you remember forever.

On the hike to see Puu Pehe
“Sweetheart Rock”

Day 6: Beach Day + Snorkeling

After waking up and having our morning coffee (in our robes) on the patio, this is when I REALLY realize that I, Lindsay Jones, am ACTUALLY RELAXED. Seriously, this never happens. Ever. I’m always thinking about what to do next and where I need to be and what I should be doing, as most of us probably are. But the thing is that I’m even like this on vacation, so being able to sit back and read (or not read), and look out onto the ocean and listen to the waves is mind-blowing to me. Isn’t this what honeymoons (and vacations!) are for? It’s Day 6 and I feel like we’ve had the perfect mix of relaxation and fun without being over-scheduled. The hotel actually figured out how to find my ZEN. I’m mush.

We eat another delicious breakfast today and this time decide to head down to Hulopoe Beach, which is a 3-minute walk from the hotel. We get set up with two Four Seasons beach chairs under an umbrella, and get masks and snorkels and flippers. I grew up in Miami (and currently live in LA), but I don’t think I’ve been in ocean water that felt as clean and amazing as this does. I didn’t even feel salty when I got out of the water! Hulopoe Bay is actually a protected marine preserve with a thriving coral reef system, which means you don’t have to go far from your chairs to see some amazing underwater life. We saw at least 10 different kinds of bright, beautiful fish, living untouched and happy right underneath us. Cory and I held hands and swam out to explore this reef at least four times during our trip here. It was so calm and relaxed…just like me, apparently! 🙂

Hulopoe Beach
Hulopoe Beach…so quiet and serene!
My jewelry for the day

At about 2 p.m. my husband’s Irish skin needed some indoor time, so we went back to the room, put some Hawaiian tunes on the TV, then headed to the golf course for the resort’s Rock N Range. This was such a fun couple hours where guests get to hit some golf balls on the range while drinking cocktails and listening to great music, all while getting golf tips from the Assistant Pro (who was SUPER helpful considering I’ve played golf 2-3 times in my life). A beer or two later I realized that I’m actually a left-handed golfer instead of a right, which only sort of accounts for how terrible of a player I am.

Having dreamt about THAT LOBSTER for the past few nights, we went back to ONE Forty for another amazing dinner, followed by some happy, full dreams of me winning the U.S. Open.

Day 7: The Last Day Blues

Does anybody else get seriously depressed on their last day of vacation? I was not ready to go home the next day!! In fact, I’m home now and I’m still not ready to be home! I wanted to use this day to do as much relaxing as possible, which meant more pool/beach time, a last pina colada, and a few more pages in my book before realizing I was too distracted by the ocean view and just wanted to stare at it for a couple more hours. This truly felt like the vacation of a lifetime, and I’m so glad we discovered this island! Even though the hotel has other guests on the property, you really feel like it’s your own private resort and there’s nobody there but the two of you. We soaked up our last full day of sun and celebrated an amazing trip with a delicious goodbye dinner at NOBU.

My fresh lei lastedthe entire trip!

Day 8: Goodbye, For Now

We boarded the 10:30 a.m. ferry to head back to Lahaina for a 3:00 p.m. flight, and made mental plans to come back for a special occasion. We also thought about how we could see if Larry Ellison, who owns the island, would be open to adopting us. Totally plausible, right?! Until then, we had to say Aloha to Lana’i and Mahalo for such a perfect trip.

Here’s a look at our “dream honeymoon itinerary” from the Four Seasons Resorts Lana’i

Arrival 1:30 p.m. Ferry
Dinner at ONE Forty 7 p.m.

5 p.m. Sunset Sail (check into Island Adventure Center at 4:30 p.m.)
Dinner at Sports Bar at Leisure

8:30 a.m. Ocean Nine Tour
10 a.m. Jeep Rental for the Day
Dinner at NOBU at 7 p.m.

9 a.m. UTV (check into Island Adventure Center at 8:15am)
Rest of day at leisure

Day at leisure
Rock N Range 3 p.m.-5 p.m. Manele Golf Course

Day at leisure

Departure 10:30 a.m. Ferry

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