Maui, Hawaii: The Perfect Romantic Getaway

Fly into Kahului, pick up your rental car (essential on Maui), and drive the 45-minute coastal route to Ka'anapali or Wailea — the resort strip along Maui's western and southern coasts where the ocean is consistently calm, clear, and warm. Check into your resort as the late afternoon sun turns the Pacific gold, then walk down to the beach for your first contact with Maui's extraordinary water. The resort strip has excellent beach access and the water here is some of the clearest on the island. Tonight, walk the Ka'anapali Beach Walk to the Black Rock headland for the cliff diving ceremony at sunset — a nightly torch-lighting and cliff dive performed by resort staff at the exact site where the ancient ali'i (chiefs) once performed the same ceremony.

• ✦ OGG arrival and rental car pickup
• ✦ Resort check-in and beach first swim
• ✦ Ka'anapali Beach Walk sunset stroll
• ✦ Black Rock cliff-diving ceremony

The Molokini Crater is the eroded rim of a volcanic caldera that rises from the ocean floor 3 miles off the Maui coast, creating a protected crescent that is home to 260 species of reef fish and extraordinary water clarity. Your boat departs from Ma'alaea Harbor at 6:30am on calm pre-wind morning water, arriving at the crater for 2 hours of snorkeling before the afternoon charter crowds. The back wall of the crater drops 350 feet and is accessible only to divers, but even snorkeling the upper reef reveals an astounding density of parrotfish, Moorish idols, green turtles, eagle rays, and the occasional white-tip reef shark. The afternoon is yours for the beach — Wailea Beach at Wailea is one of Maui's finest.

• ✦ Molokini Crater snorkel excursion
• ✦ Sea turtle and eagle ray encounters
• ✦ Wailea Beach afternoon
• ✦ Sunset at Mama's Fish House in Pa'ia

This requires the hardest thing about Maui: a 2am alarm. Drive the winding 38-mile Haleakalā Highway from the coast to the 10,023-foot summit in the dark, joining a line of cars winding above the clouds before dawn. The reward at the summit is one of the world's great natural spectacles — standing in the cold (bring a jacket: it's 40°F at the top) above a cloud layer that stretches in every direction as the sun breaks the horizon and turns the volcanic cinder landscape purple, red, and orange. The Haleakalā crater is one of the largest in the world — 7.5 miles wide and 2,600 feet deep — and at sunrise it resembles the surface of Mars more than anything on earth. Descend to Kula for upcountry farm breakfast and lavender farm stop before returning to the resort.

• ✦ Haleakalā summit at sunrise
• ✦ Above-the-clouds crater viewpoint
• ✦ Upcountry Kula farm and lavender fields
• ✦ Ola's restaurant dinner in Makawao

The Hāna Highway is 64 miles of the most extraordinary coastal driving in America — 617 curves, 59 one-lane bridges, and a progression of waterfalls, rainforest, black sand beaches, and sacred Hawaiiancultural sites that has been drawing visitors to the remote Hāna coast since tourism began on Maui. Leave at 7am to beat the traffic. Major stops: the Twin Falls at the highway's start (swim in the cool waterfall pool), the Ke'anae Arboretum for a walk through taro gardens, the black sand beach at Waiʻānapanapa State Park (reserve entry in advance), and the sacred 7 Sacred Pools at Ohe'o Gulch within Haleakalā National Park. Book dinner at the Ka'uiki or Hotel Hāna-Maui dining room for an extraordinary farm-to-table evening at road's end.

• ✦ Twin Falls waterfall swimming hole
• ✦ Ke'anae Arboretum taro garden walk
• ✦ Waiʻānapanapa black sand beach
• ✦ 7 Sacred Pools at Ohe'o Gulch swim

The return from Hāna via the unpaved back road around the island's southern tip (check road conditions — it's 4WD recommended) takes you past Kaupo Gap's dramatic volcanic landscape and the fishing village of Nu'u with its ancient fish ponds. Drive west through the cattle lands of Upcountry Kula to the old whaling town of Lāhainā — a National Historic Landmark district with the largest banyan tree in America (its aerial roots cover an entire city block), the historic harbor where 19th-century whaling ships docked, and an extraordinary array of art galleries and restaurants along Front Street. This is old Hawaii meeting contemporary Maui at its most compelling.

• ✦ Back road return through Kaupo Gap
• ✦ Lāhainā banyan tree — largest in America
• ✦ Historic Lāhainā waterfront
• ✦ Front Street art galleries and dinner

From December through April, the waters between Maui, Lāna'i, and Molokaʻi host the world's largest humpback whale congregation — 10,000 whales winter in the warm Hawaiian waters before returning to Alaska. A 2-hour whale watching cruise from Ma'alaea Harbor virtually guarantees sightings at close range: mothers teaching calves to breach, males competing in elaborate bubble-net displays, and the extraordinary sound of whale song transmitted through the boat hull. In the afternoon, drive the 50-mile coastal route north through the old sugar town of Pa'ia and along the North Shore, where the biggest winter waves on earth roll into Peahi (Jaws) and Ho'okipa Beach. Watch pro surfers from the clifftop viewpoint and eat shave ice in Haliimaile on the way home.

• ✦ Humpback whale watching cruise (or snorkel cruise in summer)
• ✦ Ho'okipa Beach North Shore surf viewpoint
• ✦ Pa'ia town lunch and shave ice
• ✦ Final resort sunset cocktails

A final Maui morning at the resort pool or on Wailea Beach, taking in the last views of the Maui Channel and the islands of Kaho'olawe and Molokini floating in the hazy distance. Pack up and drive the 45 minutes to Kahului Airport for your mainland flight — the drive north along the coast offers one last glimpse of Maui's extraordinary landscape, the cane fields and the sugarcane-rich interior, the mountains above in their perpetual cloud cap. Maui has a way of recalibrating the nervous system over a week — the combination of natural scale, warm water, and aloha spirit produces a specific kind of ease that lingers for weeks after the return flight.

• ✦ Final Wailea Beach morning
• ✦ Resort breakfast and checkout
• ✦ Coastal drive to Kahului Airport
• ✦ OGG departure