It’s about time you got away for the weekend. I mean, really got away. I’m talking about a weekend vacation, not just a weekend trip.
The first and most essential thing you’ll need for such a weekend away is someone special — your girlfriend, for example. There’s not much better than a romantic weekend away with her. Seriously, I bet you can’t think of anything better.
The next thing you’ll need is a destination. Now, I need you to trust me on this, you can’t go wrong with Hawaii. I repeat, no matter how often your girlfriend thinks you’re wrong, when you choose Hawaii, you will always be right.
You’re probably now asking yourself, “But which Hawaiian island do I choose?” as the anxiety over making such a massive decision brings you to your knees. Chill out, go to Maui. Decision made.
Maui is the ideal Hawaiian island for a romantic weekend away. Why? Think of it how one Maui local described the island to me, “If Oahu, Hawaii’s most lively and populous island, and Kauai, Hawaii’s sleepy, nature-filled island, had a baby, that baby’s name would be Maui and it would be the most perfect place ever.”
The last thing you’ll need is a plan. An itinerary for a romantic weekend on Maui. No, scratch that — an itinerary for a perfect romantic weekend in Maui. Lucky for you, I put in the hard work of visiting Maui to create such an itinerary. You can go ahead and tell your girlfriend you planned the whole thing yourself and I won’t say a word.
WHERE TO STAY: FOUR SEASONS RESORT MAUI AT WAILEA
First things first, you’ll need a place to stay while on Maui. Choosing the right resort is a big decision as it sets the tone for the trip and it’s where you’ll spend a fair amount of time. And you, being the perfectionist that you are, won’t settle for just any resort. You want a resort that is the perfect setting for the perfect romantic weekend. You want a resort that lights the flame of love with gasoline and a flame thrower, not just a matchstick.
Well my friend, I’ve been to such a place and it’s called Four Seasons Resort Maui at Wailea.
Located in Wailea (a.k.a. Maui’s Beverly Hills), Four Seasons Resort Maui is home to 380 oversized rooms and suites, three world class restaurants, three spectacular pools and one amazing white sand beach.
For the perfect room, go with an Ocean View Prime Room which features an ultra-comfortable king size bed, extra large lanai (Hawaiian for balcony) and a huge (and sexy) marble bathroom complete with a spacious rainfall shower.
You can find more tips and suggestions on Four Seasons Resort Maui throughout the itinerary below, so keep on reading.
If you’d like to take an in-depth look at Four Seasons Resort Maui, check out this review from Trevor Morrow Travel.
This perfect romantic weekend will require you to take a Friday and a Monday off work. Yes, maybe this article should have been called Perfect (Long) Romantic Weekend: Maui, but that just didn’t have the same ring to it.
DAY 1 - FRIDAY
Welcome to Maui! Day 1 will have you arriving on the island in the early afternoon. From there, you’ll kick this weekend off with a thrill by exploring Maui from above. After that, it’ll be straight to Four Seasons Maui to settle in and eat dinner at one of the island’s best restaurants.
12:00pm – Arrive In Maui
To make the most of your short time on Maui you’ll want to arrive as early as you can on Day 1. Your best bet is to fly through Los Angeles where three carriers have direct flights that will get you to Maui’s Kahului airport by 1pm. They are:
Delta – Departs Los Angeles at 7:55am and arrives on Maui at 11:38am
United – Departs Los Angeles at 8:44am and arrives on Maui at 12:25pm
American - Departs Los Angeles at 9:05am and arrives on Maui at 12:55pm
After landing, make your way out of the airport and pick up a rental car, which will be essential for the weekend ahead.
2:00pm – Helicopter Tour With Blue Hawaiian Helicopters
Blue Hawaiian Helicopters is Hawaii’s premier helicopter tour provider with outposts on Oahu, Kauai, the Big Island and Maui.
On Maui, their operations center is located at Kahului airport. Since you’re already at the airport and since you’re time on the island is limited, drive over and take a tour.
A helicopter tour makes for a great first activity on the island and a great surprise — pending your girlfriend is the adventurous type who likes surprises of course. Surprise or not, it’s the perfect way to start your trip off with a thrill as well as get an overview of the paradise you just landed on.
Blue Hawaiian offers six different tours of Maui, but to fit with your schedule you’ll want to go for the 30-minute West Maui tour, the 50-minute Hana/Haleakala tour, or my personal recommendation, the 50-minute West Maui and Molokai tour.
Note: Tour times change daily depending on the tour, the demand and the weather. Usually afternoon tours depart anywhere from 1pm to 3pm. Make sure to call ahead and ask what times tours will be leaving on your desired date.
To learn more about Blue Hawaiian Helicopters, check out this article and video from Trevor Morrow Travel.
4:00pm – Arrive At Four Seasons Resort Maui At Wailea
Welcome to your romantic home away from home for the next three nights. After walking through the stunning open air lobby and effortlessly checking in, get acquainted with your room and refuel with the welcome plate of cheese, crackers, fresh fruit and bottle of champagne which has been awaiting your arrival on your coffee table.
From here, just unpack, get comfortable and take a walk around the property. Get ready to say “wow” about 50 times.
7:00 - Dinner At Spago
Having traveled long and far, you won’t want to leave the resort tonight. So, just make your way to the lobby level where you’ll find the Hawaiian outpost of Wolfgang Puck’s Spago. Dine outside at an intimate table for two overlooking the resort’s fountain pool which lights up beautifully at night. Toast to being on Maui, to being with each other and to an unforgettable weekend ahead.
DAY 2 – SATURDAY
You can’t come to Maui, even for a romantic weekend, and not explore the island. Although you may be tempted to just lounge on the beach all day, memories are made by discovering new frontiers together. That’s why day 2 will be your most active and take you way above sea level to experience a side of Maui you probably never knew existed — Maui’s Upcountry. Back at Four Seasons Maui after a long day on the road, a relaxing reward will be waiting for you.
2:30am - Wake Up
No that’s not a typo. This morning you’re getting up early to view the sunrise at the summit of Haleakala, a dormant volcano at 10,000 feet elevation.
You’ll want to be out the door of the Four Seasons by 3:00am, but luckily there will be complimentary coffee and pastries waiting in the lobby. Tell the concierge the night before that you’d like your car to be ready for your departure to Haleakala and they’ll have warm blankets placed in the car for you. The summit of Haleakala can be as cold as 30 degrees Fahrenheit in the early morning, so you’ll want those blankets (and a coat…and an extra coat when your girlfriend wants your coat) when you’re at the top.
4:45am – Arrive For Sunrise At Haleakala Summit
Arrive at the summit early, well before sunrise, to do some of the best stargazing you’ll ever do in your life. Then hide the lone tear that will run down your cheek when you experience the beauty that is the Haleakala sunrise. Although getting up this early might sound absolutely ridiculous, it’ll turn out to be a fun, unique and memorable experience to share together.
Stick around at the summit for an hour or so after sunrise and watch as everyone else leaves, leaving you and your lady with the place almost to yourselves.
*Make sure to check what time the sun will rise during your stay and adjust your wake up and departure time accordingly. You may be able to sleep in longer.
To learn how to view the Haleakala sunrise like a pro (she’ll appreciate that you did your research) check out this article and video from Trevor Morrow Travel.
8:30am – Breakfast At Grandma’s Coffee House
After sticking around and exploring the summit for about an hour, then driving an hour down from the summit, it’ll be approximately 8:30 and definitely time for coffee. For a cup of authentic and organic island joe, head to Grandma’s Coffee House, a cafe and coffee roaster favorited by locals and visitors who happen to drive by. They grow their own coffee beans right on the slopes of Haleakala which are then roasted in-house using the same 100-year-old roaster that Grandma herself used to use.
Breakfast options include everything from scrambled eggs to french toast to fresh fruit — but don’t leave without sharing a pineapple-coconut square (my personal favorite). Although tempting, make sure not to over eat as you’ve got a great lunch ahead of you.
After breakfast: kill some time by continuing down Kula highway (the term “highway” is used very loosely). The road quickly becomes a narrow roller coaster of ups, downs, twists and turns — and if it wasn’t for the Pacific Ocean in the distance, you may think you were driving through the rolling hills of Scotland. This is an incredible part of Maui that many people don’t associate with the island and visiting will add an unexpected element to your perfect weekend.
10:30am – Farm To Table Lunch And Tour At O’o Farm
Your friends at home (incredibly envious of your romantic weekend in Hawaii) will expect to hear stories of beautiful pools and relaxing beaches. What they won’t expect to hear is a story of how you visited a pristine organic farm tucked away in Maui’s enchanting Upcountry where you harvested your lunch from the garden, had it prepared by a gourmet chef in a rustic outdoor kitchen and ate it all with a spectacular view of West Maui from the farm’s vantage point at 3,500 feet elevation. Yes, this is something you can actually do and it happens at O’o Farms.
The farm tour and lunch runs from 10:30am to 2:00pm. To me, this sounds like a woman’s dream come true (and I bet you’ll really like it too). It’s also a one-of-a-kind wedding venue…just in case you’re looking…no rush though.
From here it’s about a 45-minute drive back to Four Seasons Maui, so you should be back by 3pm and have an hour to relax before…well, relaxing some more.
4:00pm – Couples Massage
You worked really hard today. You kept yourself and your girlfriend alive while driving on some of Maui’s most twisting and turning (ie. fun) roads. You ate a lot. And you gardened, kinda. Then there’s the fact that you got up at 2:30am! That in itself deserves a reward.
So now it’s time for the couples massage you arranged in an oceanside hale (Hawaiian for thatched hut). The spa at Four Seasons Resort Maui is world class and the vast list of treatments they provide will blow your mind. Make sure to work with a member of the spa team to help you choose or create the treatment that’s just right for the both of you.
7:00pm – Dinner At Kina’ole Grill Food Truck
Tonight, keep dinner simple, low-key and casual. To accomplish that, hop in your car and head a few minutes down the road to Kihei, a laid-back section of Maui with lots of local flavor. Parked at 73 Alanui Kealii Drive you’ll find the Kina’ole Grill Food Truck, a local favorite which came recommended from the beach staff at Four Seasons Maui.
For $14 you can get a made-to-order dinner plate which includes an organic green salad, white sticky rice, homemade macaroni salad and a choice of various main dishes like coconut shrimp, pineapple rum chicken, seared ahi tuna and mahi mahi. Just make sure to get there before 7:30pm when they stop serving.
DAY 3 – SUNDAY
You spent much of day 2 exploring Maui’s Upcountry (which can be tiring), not to mention waking up at 2:30am (which is most definitely tiring). That’s why day 3 will have you doing nothing but kicking back and not leaving Four Seasons Resort Maui once. Hallelujah!
9:30am – Breakfast In Bed
Breakfast in bed. Does it get any more romantic than that? No. No it does not. Make up for yesterday’s loss of sleep with a lazy morning together in your comfortable king size bed, accompanied by some pancakes, eggs and fresh guava juice. This is when you’ll start talking about how you should come back to Maui every year — which certainly isn’t the worst idea you’ve ever heard.
11:00am – Pool, Beach, Sleep, Repeat
Here it is. The moment you’ve been waiting for the entire weekend. It’s finally about to happen. Yes, I’m talking about doing absolutely nothing.
The only decision you’ll need to make for the rest of the day is which pool to sit by and which cabana to lounge in. There are countless cabanas to choose from, many set around the centrally located fountain pool and more set throughout the property between the fountain pool and the beach. There’s also a small hillside above the beach which houses a series of more private lounging spaces. All are complimentary and will be set up for you with fresh towels by the friendly pool attendants.
The pool attendants will also be on hand to handle drink and food orders, as well as occasionally come around with ice water, cold towels, cool cucumbers for your eyes, suntan lotion and refreshing Evian spritzes.
Then there’s Four Seasons Resort Maui’s iconic, adults only serenity pool, where a swim up bar and underwater music will keep you both entertained for hours. Reserve one of the luxury cabanas here for a fee or arrive early to snag two lounge chairs on the deck.
5:30pm – Option 1 – Dinner At Ferraro’s
Set just above stunning Wailea Beach, Ferraro’s is the place to go on Maui for a romantic dinner, even if you’re not staying at Four Seasons Maui. The concierge can arrange for your dinner reservations at Ferraro’s to coincide perfectly with the sunset — just make sure to request a table on the lower patio.
Order pre-dinner cocktails at your table as the pink and orange sky burns away and fades to black. As the light from flickering candles and torches takes over and sets a seductive mood, work through your appetizers and entrees (go with the special, likely to be a fresh and locally caught fish) as you recap the perfect weekend you’ve been having.
Finish with dessert as you linger for awhile, attempting to make this moment last forever.
5:30pm – Option 2 – The Ultimate Romantic Dinner
If you really want to take your sunset dinner to another realm of romance, book the Ultimate Romantic Dinner.
Included is a secluded private table set above Wailea Beach, a private consultation with the chef to design your very own five course meal and a dedicated server who will ensure everything is perfect.
This is the ideal place ask your girlfriend, the woman who has made this trip to paradise so wonderful, a very important question…will you do beach yoga tomorrow morning with me?
DAY 4 – MONDAY
Say it ain’t so! Yes, today is your last day on Maui. Day 4 will having you departing back to the continental United States in the mid afternoon, but not before finding some inner peace on a Maui beach or cruising along the Maui coastline.
7:30am – Option 1 – Morning Yoga With Maui Beach Yoga
Couples who workout together, stay together. That’s a saying, right? Maybe not, but either way, working out together and finding some inner peace together sounds like a really good idea. To help fight off the inevitable end-of-perfect-romantic-weekend anxiety, make sure to book a private beach yoga session with Candice, founder of Maui Beach Yoga.
Candice, an accomplished fitness expert who has been teaching yoga on Maui since the 1970′s, will meet you at one of Maui’s pristine beaches and lead you in an insightful and worthwhile yoga lesson no matter what your skill level. So whether this is your first time doing a downward facing dog or you can strike Pungu Mayurasana (google it) in your sleep, Candice is the woman to call.
10:00am – Option 2 – Outrigger Canoe
Would you rather sleep in on your last morning and squeeze in a little more time at Four Seasons Resort Maui? Well then start your day off at 10am by heading down to the beach for the morning’s last outrigger canoe trip. This complimentary activity, guided by the resort’s resident outrigger experts, is a great way to get out on the water, learn a bit of Hawaiian history and view the resort in all its glory. Just make sure to reserve your two spots in advance.
2:00pm – Departure
Yes, the time has come. Flying direct back to Los Angeles, three carriers offer flights which leave in the early afternoon and will have you back in the continental United States around 9pm. They are:
Delta - Departs Maui at 1:40pm and arrives in Los Angeles at 8:55pm
United - Departs Maui at 1:40pm and arrives in Los Angeles at 8:58pm
American - Departs Maui at 2:25pm and arrives in Los Angeles at 9:40pm
As you fly back across the Pacific, getting closer and closer to the “real world” you left behind just a few short days ago, use this time to think about how perfect your weekend was, how the person you shared it with made it ten times better and how you really need to take a lot more of these weekend getaways!
Don’t worry, I’ll hook you up with more perfect weekend itineraries soon.
WANT MORE MAUI? (Just Click On An Image Below)
I was hosted by Four Seasons Resort Maui during my stay, however, all thoughts and opinions are my own. Seriously, I want to take every girl I ever date to Four Seasons Maui for a perfect romantic weekend.
Photo Credit: Top Photo and Four Seasons Resort Maui photos provided by Four Seasons Resort Maui. Haleakala Sunrise, large photo by Ewen Roberts, small photo by Alex Ulanov. Grandma’s Coffee House photo by Ryan Healy. O’o Farms, large photo by Peter Liu, small photo by Chris Corrigan. Maui Beach Yoga, large photo by Peyri Herrera, small photo by Seabright Hoffman