A 48-Hour Itinerary for Romance

From cascading waterfalls to stunning ocean views to delectable dining, the island of Oahu is made for exploring with someone special. In honor of Valentine’s Day, we’re gushing about our favorite dreamy spots for relaxation, reconnection, and adventure. 

Day 1 

3 pm: Check In

For a grand gesture, book our Executive Suite where you’ll enjoy a king-sized bed, two bathrooms, a kitchenette, and wet bar – a must-have for chilling some bubbly. Relax on your two private lanais and take in sweeping views of Waikiki and the Ko’olau Mountains. 

4 pm: Take a Dip

Cool off with a swim in our heated outdoor pool and lounge on the sun deck surrounded by lush foliage. Read the latest issue of your favorite magazine or catch a catnap in the Hawaiian sun. 

6 pm: Watch the Sunset 

Take a short 5-minute walk to Waikiki Beach for the spectacular nightly show. Find a spot on the sand and wait for the sun to sink below the horizon. Look out for the elusive green flash! 

7 pm: Dine on Surf & Turf

Visit the trendy Kaka’ako neighborhood for an indulgent meal of PRIME steak and over-the-top cocktails at Ya-Ya’s chophouse & seafood. After dinner, stroll through the district to admire the street art murals and pop into an of-the-moment craft bar or local brewery for a nightcap.  

Photo: Hawaii Tourism Authority / John Hook

Day 2 

8 am: Explore the Island 

Rent a car or book a tour to discover the stunning coastlines, majestic mountains, and quaint towns outside of Waikiki. One of our favorite drives is along the naturally rugged and scenic Kaiwi Shoreline on the southeast side of the island.

2 pm: Swim in a Waterfall 

At Waimea Valley, take a short walk through the lush rainforest and gardens, and you will be rewarded with a cool dip under Wailele waterfall. 

4 pm: Share a Shave Ice 

With shave ice stands and shops sprinkled around the island, you won’t miss an opportunity to get romantic by sharing this sweet treat doused in your choice of flavored syrups, such as guava, lilikoi (passion fruit), and pineapple. 

6 pm: Picnic Under the Stars 

Back at the hotel, walk a few short blocks to Waikiki Market to pick up a variety of local favorites like, poke bowls, musubi, and malasadas for a picnic spread like no other to enjoy on the golden sands of Waikiki Beach. 

Photo: Hawaii Tourism Authority / Joe West

Day 3 

8 am: Go Whale Watching 

Start your day by boarding a catamaran to get an up-close view of the annual humpback whale migration. From November through May, the gentle giants come to Hawaii to give birth in our warm waters (and you can be witness to it!). 

12 pm: Check Out 

A hui hou (until we meet again)! As you depart, we hope you take with you new memories and renewed love for each other.  


Surfing Header Photo: Hawaii Tourism Authority / Tor Johnson