Your Romantic Oahu Getaway: A 3-Day Itinerary

So you have three days in Oahu with your partner and the options on where to go and what to do are overwhelming? Never fear, our team is here!

Consider the following possible itinerary that will ensure you see some of the very best this island has to offer:

Day One in Oahu

Begin by checking into your chosen lodging. Two excellent accommodations we’d like to highlight are the Makaha Condos and Beachfront Hauula vacation homes. The gorgeous waterfront condos of Makaha feature their own pools and ocean view lanais. If you choose here, make sure to spend some time out on that extended lanai to soak in the sun and soft ocean breezes. Following a salty day at the beaches, you’re sure to appreciate a cool dip in your own private pool waters. Or, maybe you want your own private beachfront? If so, then check in at the Beachfront Hauula Getaway. This vacation rental is located just a short drive north of Lanikai Beach and offers its own private wavefront patio that you just might find yourself unable to leave. So go ahead and unpack, unwind, and enjoy a glass of wine as you dip your toes in the backyard beach. 

Wherever you’ve chosen to lay your head at night, we recommend heading out to Honolulu on your first day of adventuring. Honolulu is an exceptional capital city with a rich array of activities and sights to see. Start your afternoon visit here with a coffee and light pastry from Kona Coffee Purveyors. We recommend getting it to go and enjoying a lazy walk around the downtown streets here to enjoy a little window shopping with your coffee sips. Kona Coffee Purveyors is also just a couple of blocks from AinahauTriangle, Fort Dereussey Beach Park, and Waikiki Bay — all of which offer exceptional backdrops for a romantic stroll. 

As the day grows long, consider booking a dinner and show event at Rock-a-Hula. Rock-a-Hula takes aspects of a traditional luau and merges it with a modern, rock-and-roll style of the show. Here, you can feast on gourmet Hawaiian-style cuisine just like you would at a traditional luau show, but, in addition to your fire knife performances and hula dances, you’ll also enjoy celebrity impersonators and more classic American rock that results in a really unique Hawiian-American concert-style show. 

Or, if you’re not big on impersonations and dinner theater, then maybe instead make dinner reservations at Azure. Azure is an upscale Royal Hawaiian seafood restaurant that is located within this same neighborhood and has a beautiful patio and cabana overlooking Waikiki Bay. You can’t go wrong with any of the menu items here, but for a nice romantic dining experience that will highlight the best, we recommend the four-course tasting menu. 

Day Two

Get an early start on your second day of adventures and head to the opposite end of Oahu for an exhilarating morning hike along the Makapuu Point Lighthouse Trail. This is a fairly easy paved hiking trail that generally takes an hour to complete out and back and offers incredible coastal views. If you’re lucky, you may even catch sight of migrating whales! Or, take the much shorter trail down to Hanauma Bay for a remote beach experience. Post-hike, whichever hike you choose, head on over to the town’s beloved Island Brew Coffeehouse. Island Brew Coffeehouse is located in a cozy shopping district with a patio overlooking the harbor. They offer incredible espresso drinks and have an impressive breakfast and lunch menu that includes acai bowls. 

Go big on your meal at Island Brew Coffeehouse and then enjoy a relaxing coastal drive up to Lanikai Beach with its own mesmerizing coastal and mountainous vistas. Lanikai Beach is well-known for its clear waters and excellent snorkeling conditions. Which, Aaron’s Dive Shop is just around the corner and offers affordable 24-hour snorkel gear rental and purchase. The beach sands at Lanikai Beach also have their own appeal with their soft, white, seemingly endless composition. All of these facets make for perfect lounging conditions if you and your partner feel like a little suntanning at this point (and who wouldn’t want to pause and bathe in the Hawaiian sun?).  

If you are itching for some late afternoon activities on your romantic Oahu getaway, then consider a visit to either (or both) the nearby Hoomaluhia Botanical Garden and Byodo-In Temple. Both offer relaxing day trip opportunities where you and your lover can meander landscaped grounds without heavy crowds.

For your last evening in Oahu, go to Sunset Beach Park just west of your vacation rental. Its name won’t disappoint you as this is one of the best places to go and enjoy incredible evening views of the sun dipping into the horizon. Plus, thanks to its distance far from bustling places like Honolulu, after the sun goes down you can enjoy spectacular star-gazing.

Day Three

As the final day of a three-day vacation to Oahu, take your time checking out of your vacation lodgings. When you’re finally ready to close the door to your suite, enjoy a morning hiking the trails off of Palii Highway. This road cuts through the center of the island and features gorgeous and romantic sights like the Nuuanu Pali Lookout, the Likeke Falls hiking trail, and the Lulumaha Falls trail.

In the afternoon, complete your journey to Honolulu and visit the prestigious Honolulu Museum of Art (HoMA). HoMA has its own outdoor cafe and coffee bar where you can enjoy some light fare in a picturesque courtyard before browsing its excellent collection of art, which includes pieces by Monet, Picasso, Van Gogh, and Georgia O’Keefe. 

Finally, to close out your romantic vacation in Oahu, grab a pair of cocktails at Bar Leather Apron. Located in the heart of Honolulu, this is a swingy bar with a nice speakeasy vibe that also serves up some delicious tapa items. 

Learn More About Oahu

We hope this possible three-day itinerary gives you some good ideas on where to stay, dine, and visit on your romantic tour of Oahu. Of course, it is by no means all of what this island has to offer. Be sure to check our other pages to learn more about Oahu’s best of’s.