6 Romantic Small Towns In Hawaii For A 3-Day Weekend

Romance is all about immersing yourself in each other’s company at select spots where intimacy and unique experiences bring you closer together. Hawaii is known for its romantic destinations, attracting couples in budding relationships, honeymooners, and those celebrating milestone anniversaries, or reigniting the proverbial flames of passion. With eight major islands dotting this expanse of the Pacific Ocean, couples can discover intimate inns like Maui's Paia Inn, luxe accommodations at resorts like Kauai's 1 Hotel Hanalei Bay, and private hideaways at sheltered retreats like Puakea Ranch on the Big Island. These six romantic small towns in Hawaii for a 3-day weekend are idyllic escapes to connect with each other, free of life's distractions.

Paia, Maui

Surfing is big on Maui’s North Shore, where the chill vibes instantly relax couples seeking one-on-one time. There is no surfboard required to benefit from lovely Paia’s warm locals and laissez-faire Bohemian attitude that makes everyone feel welcome. Its tiny footprint is made for walking hand in hand through the colorful town, where Paia Inn’s dreamy king guest rooms are designed for intimate moments in luxe boutique-style comfort, with private porches overlooking lovely gardens and hints of the ocean. Settle in for the Japanese-inspired dishes at the inn, seated under the palms just steps away from the beachfront, where you can kick off your sandals and meander along the shoreline with ample opportunities for stolen kisses under the stars.

Float side by side as the waves gently roll beneath you at Baby Beach, where windswept sand dunes and a wooded area create a feeling of seclusion. Make reservations for at least one dinner at Mama’s Fish House, where you can share beachside Mai Tais and feast on gorgeous, straight-from-the-ocean seafood. Take the short drive along the scenic Hana Highway to watch the sunrise at Ho’okipa Lookout and stop at Wailele Farm to see Twin Falls if you have the time. Here, one can grab a cold brew made from 100% Maui-grown coffee while exploring the gently cascading falls to cool off after their hike.

Hanalei, Kauai

Get lost in the captivating beauty of Hanalei, where lush green mountains, golden sandy beaches, and impossibly blue waters earned Kauai the title of "Garden Island." 1 Hotel Hanalei Bay is a north shore retreat, where dedicated "VIP gurus" craft customized couple's escapes for exceptional stays. From private pickup in a luxury SUV to daily sessions with an expert Body Architect, duo pampering keeps you focused on each other while everyone around you caters to your needs.

Spend your Saturday morning discovering the flavors of Kauai at the Hanalei Farmers' Market, where you can sample fresh fruits and vegetables, sip freshly squeezed juices, and savor home-baked goods from the farms and producers of the North Shore. Pack your delicious market finds for a paddle along the Hanalei River in a two-person kayak or BYO SUP. Couples can also enjoy sweet and freezy treats from Wishing Well Shave Ice in the afternoon and dine on luscious, globally inspired dishes in an intimate 1860s plantation cottage at Postcards in the evening.

Koloa, Kauai

Learn more about each other with a romantic luxe stay in Koloa, where creativity and coastal charm blend effortlessly. Just a short drive away, Hanapēpē Art Night adds a lively cultural touch to your weekend, when local painters, sculptors, and craftsmen open their studios for an evening of music, conversation, and gallery browsing. The festive atmosphere invites thoughtful discussions and shared discoveries, making it a memorable date-night outing without pulling focus from your Koloa base.

Back in Koloa, wander through Old Koloa Town, where plantation-era storefronts now house art galleries, boutiques, and relaxed cafés. Stop by the Koloa History Center to gain insight into the island’s sugar plantation roots, then stroll toward nearby Poipu Beach for golden-hour views and the chance to spot Hawaiian green sea turtles resting on the sand. Stay in a secluded bungalow at The Lodge at Kukuiʻula, where private lava rock outdoor showers and access to the club’s upscale amenities set the tone for intimacy. After dinner at ʻUmeke Kitchen + Bar, wander along Kukuiʻula Harbor to watch the sunset before slipping back to your private retreat. Spend a leisurely morning biking to the lodge’s 10-acre farm to pick fresh flowers and produce, then lounge by the infinity pool overlooking the Pacific.

Makawao, Maui

The secluded destinations on the slopes of Mount Haleakala are reached by scenic roads shrouded in mist, where sheltered retreats like North Shore Lookout are idyllic settings for your romantic Makawao getaway. This boutique bed and breakfast is a couple’s hideaway in Upcountry Maui overlooking the North Shore coastline and West Maui mountains. Suites are intimate and tranquil with private lanais where you can snuggle up in a hammock or sit in companionable silence, wondering at the splendid landscape. Tour the B&B’s farm to experience a day in the life of rural Makawao, or wander downtown to explore the eclectic mix of shops where you can browse the collection of original art, prints, jewelry, and home goods at Maui Hands Art Galleries.

Hit the century-plus-old Komoda Store and Bakery for their famous donuts before venturing slightly further afield to The Sacred Garden. Take a contemplative labyrinth walk in the shade of a peaceful Kukui forest and stroll arm in arm through the gardens to find a secluded spot to share scrumptious morsels from your stash of stick donuts. Before leaving, visitors must explore the town’s “Paniolo” heritage at Makawao Public House, where traditional Hawaiian Cowboy foods introduce you to mouthwatering flavors, with satisfying beef dishes paired with a short but sweet red wine list.

Hawi, Big Island

Sunsets are a major attraction at the northwest tip of the Big Island, where the town of Hawi is reached via the winding Kohala Mountain Road through rolling countryside dotted with cattle ranches. The awe-inspiring landscape and verdant rainforests take you to your private sanctuary at Puakea Ranch, where the 33 acres of historic pastoral ranch land are the setting for your charming 1920s bungalow. Quaint gardens offer a sense of intimacy, where you can lounge on your spacious lanai, staring off at the ocean vista. A private hot tub and outdoor bathhouse add to the romantic feel of this enchanting stay, or you can take a dip in the lava rock swimming pool at the ranch's James Pond.

Fill a basket with fresh, locally grown produce and other goodies at the Saturday Hawi Farmers’ Market to prepare for a Sunday picnic at Pololu Valley Lookout. Relax, sheltered by towering cliffs, taking in the views of the deep blue ocean against the dark lava sands as you hike down. Dine on fresh island fish and classic Hawaiian-style cuisine at Hawi’s landmark restaurant, Bamboo Restaurant & Gallery. The historic plantation building is eclectic, bright, and filled with a friendly atmosphere where you can take your passion fruit margaritas up to the second floor to browse the art gallery and gift shop before dinner.

Haleʻiwa, Oahu

Escape the crowded tourist scene in Oahu along the palm-lined beachfront in Historic Haleiwa Town, where you can avoid the typical hotel towers and snuggle into your Ke Iki Beach Bungalow. The tiny patio made for two is set alongside a sweet little cottage surrounded by pretty private gardens, and a full kitchen allows you the luxury of spending your time in total isolation. Take advantage of complimentary daily yoga classes together under 100-year-old monkeypod trees, de-stress in the red-light sauna, and take an invigorating cold plunge before spending your day out and about experiencing the surfer town's somewhat quirky vibe at places like Haleʻiwa Store Lots.

Book a romantic sweetheart horseback ride at nearby Gunstock Ranch, where you can ride forest trails overlooking the ocean and stop for an intimate picnic at the ranch’s prime lookout point. Paddle the Anahulu River and drift under the Haleiwa Rainbow Bridge, or laze beneath the trees at sandy Pua'ena Point waiting for the spectacular sunset.

A Romantic Long Weekend In Hawaii

These six romantic small towns in Hawaii for a 3-day weekend are all about one-on-one time with your significant other, regardless of whether you are planning your first trip together or celebrating your silver anniversary. Couple-focused accommodations are made for intimate moments while keeping you close to experiences where you can get to know each other and share a laugh, from scenic drives along the Hana Highway and Kohala Mountain Road to paddling the Anahulu River and art crawls in Makawao and Hanapēpē to horseback riding in Haleiwa.