How to Plan the Perfect Valentine's Day Getaway to Hawaii

Sunset on Oahu.(Photo by Ka)

With Valentine's Day approaching, Travel Agent brings you the most romantic spots to celebrate the occasion on the Hawaiian Islands of Maui, KauaiHawaii Island, commonly referred to as The Big Island, and Oahu.


Looking to pop the big question to your loved one in Oahu? First wining and dining him or her in Waikiki could increase a client's chances of getting a yes. Waikiki is the main hub for tourists looking for some shopping, dining, activities and luxury resorts.

When it's time to propose, we suggest any of Waikiki's beautiful beaches. The best beach for some secluded romance, however, is Diamond Head Beach. This a great spot for some light water sports or sunbathing, but the best part is that there are hardly any people on Diamond Head Beach. 

Another unique option for proposing in Oahu is located not too far from Diamond Head Beach. At the top of Leahi, commonly referred to as Diamond Head, is a 760-foot tuff crater that is often considered one of Hawaii's most famous landmarks.

It only takes a short drive or bus ride to get to Diamond Head Crater from Waikiki. This moderately challenging trail includes two sets of stairs, totaling 175 steps, as well as dark, underground tunnels and old military bunkers that require a flashlight. 

If you plan to hike on Saturday morning, be sure to swing by the Kapiolani Community College Farmer’s Market, a farmers market showcasing locally grown food and produce. And don't forget to bring the ring.

Romantic Resorts

The most romantic resorts on Oahu are Turtle Bay Resort and Outrigger Waikiki on the Beach

The biggest hook for Turtle Bay Resort is its recently completed Beach Cottages. The Beach Cottages are set away from the rest of the resort in a secluded parkland on the shore of the bay that gives Turtle Bay its name. From their private lanais, guests enjoy views of Turtle Bay in the foreground and the Pacific just beyond. The cushioned, woven-wicker loveseats on the lanai provide vast views of the ocean’s activities.

Each 740 square foot cottage has vaulted 15-foot ceilings, polished Brazilian walnut floors, contemporary furnishings and upgraded marble bathrooms with Kalista deep-soaking tubs. 

Additional offerings include a pre-visit online advisory service, an on-arrival greeting with a fresh lei and local artisan snacks, an amenity-of-the-day exclusive to the Beach Cottages, robes and slippers, Hawaiian aromatic teas and robust Hawaiian coffees, and an assortment of beach accessories.


The most romantic feature at Outrigger Waikiki on the Beach is the views it offers of the previously mentioned Diamond Head. 

The resort completed a massive renovation in 2012. The Outrigger Waikiki on the Beach now features all newly renovated guest rooms and corner suites with views of Diamond Head, the Pacific Ocean or views of Waikiki. 

The new oceanfront swimming pool is surrounded by a new pool deck tiled in natural stone with a glass surround for unobstructed ocean views. The interior of this property also has received a facelift with all guest rooms receiving new carpet, furniture, draperies and paint, along with new glass lanai railings in all oceanfront rooms and suites, which help showcase the impressive view from these rooms.


Also, romantic clients should mark their calendar for spring of next year when the Four Seasons Resort Oahu at Ko Olina opens it doors, representing the first Four Seasons Hotels and Resorts property in Oahu. It replaces the old JW Marriott Ihilani Ko Olina Resort & Spa.

The Best Venue for Weddings or Vow Renewals

If you're looking to tie the knot this Valentine's Day and they want to do it in a church, the best place is Kawaiahao Church, the first Christian church built on Oahu in 1842.

Known as the "Westminster Abbey of the Pacific," Kawaiahao Church is made of 14,000 coral slabs from ocean reefs that were hauled from the sea by native laborers and missionaries. The church and the grounds were named a National Historic Landmark in 1962.

The Most Romantic Lookout

Looking for a beautiful background to smooch your baby in front of? Head to the Nuuanu Pali Lookout. Just a five mile drive northeast of downtown Honolulu, the Nuuanu Pali Lookout offers incredible views of the Koolau cliffs and Windward Coast. 

Set more than 1,000 feet above the Oahu coastline amid mountain peaks shrouded by clouds, the stone terrace overlooks the areas of Kaneohe and Kailua, Mokolii and the University of Hawaii’s marine biology research center, Coconut Island. Other notable landmarks that can be seen are Hawaii Pacific University’s Windward campus, Kaneohe Marine Corps Base and the Hoomaluhia Botanical Garden, which is part of the Honolulu Botanical Gardens.

Hawaii Island

Mauna Kea Beach Hotel sits on one of the most romantic beaches in Hawaii.

Widely considered the best hotel on The Big Island, Mauna Kea Beach Hotel has become a landmark on Hawaii Island, having recently completed its 50th year of pampering A-listers in the Aloha State.

The hotel is situated on Hawaii’s best beach, Kauna‘oa Beach, and uses its tastefully designed rooms and views to keep guests from wanting to leave.

When Travel Agent toured the property last year, we stayed in a Plumeria Beachfront Suite. There’s one of these per floor. Ours had two bathrooms, a living room with a dining area, and a bedroom with a king-sized bed. The best part of the room is that the terrace offers both garden and full ocean views. The flatscreen LG TV in the living area rotates so guests can be entertained while dining or while sitting on the couch. There are also ocean views from the king bed and the tub located in the bathroom.

The spa has four single treatment rooms and one “luxury” couples suite, which includes a whirlpool Jacuzzi tub. Couples interested in a tasty pre-dinner cocktail should sip on Mauna Kea’s signature drink, The Frederico, which is made of Bacardi Light rum, Jack Daniel’s, pineapple, passion fruit, guava and orange juices with a splash of grenadine. Be careful though, as these cocktails pack quite a punch and are easily deceiving since the taste of the whiskey and rum are overshadowed by all the fruit juices.

For love birds looking to tie the knot, with any three-night stay, full wedding coordination services are available, including assistance with venue location, bride and groom lei, officiant, photography services, cake, music and salon services. Packages are also available.


Romantic Views

Couples in love should be sure to sneak a photo at the Akaka Falls State Park, located along the northeastern Hamakua Coast. Couples can take in two gorgeous waterfalls on one short hike. As you follow the paved footpath, you'll first see 100-foot Kahuna Falls. Clients should then continue to follow the loop around the bend, where they'll discover Akaka Falls, which plummets 442-feet into a stream-eroded gorge. This hike takes less than an hour.

For Thrill-Seeking Couples

View above Hawaii's Big Island on board Paradise Helicopters. // Photo by Joe Pike

Flying in a helicopter may require a little taste for adventure, but there is also nothing more romantic than holding hands with your loved one as you literally fly somewhere over the rainbow.

We highly recommend Paradise Helicopters, which just wrapped up its 15th year in business. It offers A-listers tours of everything from active volcanoes oozing with plumes of molten lava to valley tours where countless numbers of waterfalls can be spotted to coffee tours where passengers can land and taste some traditional Kona coffee.

The company is located in several of the Hawaii islands and its Kona office is located at the Kona International Airport (KOA), which is about 45 minutes south of the resort. Paradise Helicopters can arrange transportation for all guests.

There are a total of 17 pilots working for Paradise Helicopters. We were told three of Paradise Helicopters’ pilots are former Marine One pilots. Marine One is the call sign of any United States Marine Corps aircraft carrying the president of the United States. Many of the other pilots are ex-military pilots. Besides perhaps some of the safest pilots you can hope for, all pilots are experts in the topography of the island.

We experienced the Volcano & Kohala Landing tour, in which we were supposed to see lava activity and also land at one of the many waterfalls on the way. The waterfalls were spectacular and require a short hike to get to. 

We weren’t lucky enough to see any lava because of poor visibility and generally poor weather conditions, but we did fly over a few rainbows. In fact, rainbows are quite common to spot, but also aren’t a guarantee. If VIPs see one, however, spotting one from the ground will never be the same. High above, they appear to be closer to full circles than simple arches. 

Should the volcano portion of the tour be canceled due to unsafe weather conditions, the company will offer guests the opportunity for a modified tour to the Kohala mountains, where the waterfalls and valleys are absolutely spectacular. We were told the valleys and waterfalls are the pilots’ favorite tours.


Dining on The Big Island

Two of The Big Island's most touted restaurants tend to be Merriman’s Restaurant in Waimea and Roy’s Waikoloa Bar & Grill on the Kohala Coast. Honolulu Magazine has named Merriman’s the best Hawaii Island Restaurant for 13 consecutive years. And Roy Yamaguchi is a James Beard Award winner based on Oahu, but has locations in Waikoloa as well as Poipu on Kauai, and Lahaina on Maui, as well as Waikiki, Hawaii Kai and Koolina on Oahu.


Andaz Maui at Wailea Resort is one of Maui's most romantic resorts.

Andaz Maui at Wailea Resort, one of Hawaii's latest luxury hotels that caters to the young, chic crowd, is a great fit for couples looking to share their Valentine's Day vacation with another couple. When Travel Agent toured the property last year, the best room we saw was one of the three-bedroom villas, which we were told were popular amongst couples looking to travel with other couples. It really doesn't get more romantic than the outdoor plunge pool facing the ocean. Butler service is also available here.

The two features that we loved in all rooms were the full ocean views from both the bedroom and the shower. Partial ocean views from the shower or bath is nothing new at a luxury resort, but this was a full on, floor-to-ceiling view of the ocean. 

Other facilities at Andaz Maui include a 15,000-square-foot Awili Spa and Salon with 10 treatement rooms, a gym, a lobby lounge and meeting space. Another feature that we were impressed with was the resort's five pools, which include four that all lead into each other. In fact, three infinity pools all end up in one relaxing “lagoon.” The fifth is located separately and serves as the resort’s adults-only swimming pool.


Following a $15 million renovation of the former Residences at Kapalua Bay, the new all-suite Montage Kapalua Bay resort is a private oceanfront escape with an emphasis on luxury in a Hawaiian setting.

Montage Kapalua Bay offers 50 luxurious residential-style suites, ranging from one to four bedrooms. Montage Kapalua Bay also offers 54 Montage branded residences for purchase. Each room features large "lanais" (balconies), offering a panoramic view of the Pacific Ocean and neighboring islands. 

Montage Kapalua Bay's signature restaurant, Cane & Canoe, is reminiscent of a traditional Hawaiian canoe house, where locals and artisans would socialize, make sails, shave wood and weave baskets. The restaurant's interiors honor the Hawaiian culture with a comfortable, communal atmosphere with wood scrollwork, woven textures and vibrant floral touches.

For a more casual dining experience with some romantic views, the outdoor Sunset Patio offers an all-day menu suited for leisurely poolside dining. The adjacent Hana Hou bar will also serve as the perfect gathering spot to end the day and take in the Hawaiian sunset.


The Most Romantic Beach in Maui

Whether Kapalua Bay is the best beach in all of Maui can be up for debate, but most experts and Hawaii tourism officials agree that it is one of the most sheltered beaches in Maui. Because of the seclusion it offers, we recommend this beach for romantics looking for some privacy. The surrounding area is mostly dominated by the Montage Kapalua Bay and condominium communities, giving the impression that it is exclusive. But the bay is still open to the public.

The Most Beautiful Sunrise in Maui

Romantics spending Valentine's Day on Maui should pack a small bag with a blanket and camp out for a bit at the top of Haleakala Crater to see the best sunrise Maui has to offer. 

Rising more than 10,000 feet above sea level, Haleakala National Park is home to Maui's highest peak. Both tourists and locals are known to wake up early to drive up to the Haleakala Visitor Center. On a clear morning, seeing the sunrise from the summit of Haleakala is an unforgettable experience. If a proposal was part of your client's Valentine's Day plan, this is the place to do it. 

If a little action-adventure is desired, this is also a great spot for some incredible horseback riding.


The Makana Terrace at St. Regis Princeville offers casual all-day dining, and the menu is created with Asian influences.

Poipu Beach Park is often considered Kauai’s most popular beach. But since it draws a big family population because of its natural wading pool for young swimmers, it may not be the best setting for some quiet alone time with your loved one. Instead, we recommend the much more secluded and lesser-known Kauapea Beach, commonly referred to as This practically empty, half-mile stretch of beach is not easy to get to, as there are no public roads that lead to it. But that’s why it’s so unpopulated. “secret>

Instead, clients should take the Kuhio Highway past Kilauea and turn right on Kalihiwai Road.  Follow the road for less than a mile, turn right onto an unmarked road and look for the footpath at the end of the park. This leads to the west end of the beach. With enough seclusion to enjoy some privacy with your loved one, this is the best spot for a romantic picnic for two. 

The Most Romantic Resorts

The Lodge at Kukui‘ula in Koloa is an ultra-luxurious establishment that includes a collection of island-style cottages, bungalows and villas. Even though kids are welcomed and encouraged at the lodge, the Kukui‘ula environment remains calm and tranquil. We suggest guests take advantage of the relaxing atmosphere and visit one of the three pools or ask the staff to prepare a traditional Hawaiian pig roast in the authentic imu pit.

Not interested in the pig roast? Dine on the deck of the open-air plantation house, complete with views of the ocean (think fresh mango smoothies, fresh fish and sunsets).

The Spa at Kukuiula has a meditation garden, relaxation pool and six treatment rooms. The “Wet Ritual” is a must before any treatment. First, a steam will open the pores then your hair will be conditioned in a deluge shower, followed by another steam complete with a Kukui nut oil scrub. The last step will get your heart racing as you step into the cold plunge and hot dip. After your massage, take advantage of the posh spa products provided, including the sunscreen, which kept us protected from the sun the rest of the day. 

Romantics will also want to stay at the St. Regis Princeville, a stunning resort that overlooks Hanalei Bay. The large, opulent lobby is complete with a chandelier that reminded us of a floating jellyfish, and it set the mood for the rest of the resort (which was just as memorable). The Hanalei Bay is the focal point of this resort — as it should be with its bright blue waters and bobbing sailboats. 

Romantic Overlooks

Set on Kauai's West Side, Waimea Canyon is often described as "The Grand Canyon of the Pacific." The canyon stretches about 14 miles and is the setting for some of Hawaii’s best views. Clients can snuggle up as they lookout at some incredible deep valley gorges or they can travel a little further down Waimea Canyon Drive for the main Waimea Canyon Overlook, which offers views of Kauai's interior. 

Spread over 4,345 acres on a plateau 3,200 to 4,200 feet above sea level, Kokee State Park is covered in forest, wildflowers and hiking trails, making it an excellent spot to see native plants and colorful Hawaiian forest birds. The park also offers roughly 45 miles of the state's finest hiking trails. Some trails lead to views of Waimea Canyon, while others wind through wet forests with sweeping views of valleys opening up to the North Shore. 

Dining Options

Clients looking for a low-key, casual dining option should hit the town as there is a strip of about five small budget-friendly eateries all within walking distance of each other. Romantics looking to go all out, however, should dine at the St. Regis Princeville’s Kauai Grill. Kauai Grill’s cuisine is created by acclaimed Chef Jean-Georges Vongerichten, using fresh ingredients in dishes like the nut and seed crusted mahimahi and grilled Makaweli tenderloin. Clients should also check out The Makana Terrace at St. Regis Princeville. It offers casual all-day dining, and the menu is created with Asian influences, but the view is why you come here. 

Visit and keep visiting for all your latest Hawaii news. Be sure to follow Travel Agent's Joe Pike on Twitter @TravelPike.