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Morning

Spend some time away from the sand and surf by heading up the Haleakalā Highway (Route 37) to the coolness of Upcountry Maui. At ’Ulupalakua Ranch you’ll find the Tedeschi Winery. Tours of the winery are free, and you can taste the full range of products in the restored cottage of King David Kalākaua.

Retrace your path back along Route 37 to visit Makawao, once a cowboy town and now a shopper’s haven. There are tony boutiques and art galleries housed in western-style buildings. Pick up some lunch at Rodeo General Store’s deli or sit down at Duncan’s Coffee Co., both on Baldwin Ave., the town’s “main drag.”

Afternoon

Continue down Baldwin Avenue to the Hui No’eau Visual Arts Center. Inside and outside, works by local artists are created, displayed, and sold. Traveling right to the end of Baldwin Avenue will take you to Pā’ia for great people watching – and more shopping. Once a plantation town, then a hippie haven, and now a windsurfing mecca, Pā’ia offers an adventure in browsing for unique clothing at Jagger’s (see Jaggers), work by local artists at Maui Hands, and antiques at Pā’ia Trading Company (see Pā’ia Trading Company).

For a late afternoon spectacle, the waters off Ho’okipa Beach are filled with the colorful sails of windsurfers and kite boarders. Finally, end your day with a fresh fish dinner at Mama’s Fish House (see Mama’s Fish House).

Morning

Take a leisurely drive – there’s no other way on Moloka’i – to the spectacular Hālawa Valley on the island’s far eastern end.

Begin in Kaunakakai with a breakfast of sweet bread from Kanemitsu Bakery (see Kanemitsu Bakery). Stock up in town with snacks and drinks for a picnic.

From Kaunakakai, take Route 450 heading east. Be sure to notice all the ancient fishponds still intact along the coastline. About 11 miles from Kaunakakai you’ll see, in quick succession, St.Joseph’s and then Our Lady of Sorrows (see Our Lady of Sorrows Church)– both built by Father Damien in the late 1800s. Step inside to experience the history.

The road to Hālawa is winding, narrow, and extraordinarily scenic. Take your time to enjoy it – pull over, stop for a picnic or a snack, or to snap some photos, and immerse yourself in the glorious surroundings and clean, fresh air.

Afternoon

Hālawa Valley is absolutely perfect: a high waterfall cascades into the stream that winds through the valley and eventually reaches the ocean. The base of the valley is a great place for a picnic if you haven’t already eaten, or to kick back and feast on the views.

Once you’ve luxuriated in the tranquillity of the valley, retrace your journey back to Kaunakakai in time for an afternoon swim and dinner at the Oceanfront Dining Room (see Oceanfront Dining Room).

Early Afternoon

Head west along Route 30 from the Kā’anapali Resort area, and stock up on snacks and beverages at the quaint HonoluaStore in Kapalua (see Honolua Store).

Stop at either D.T. Fleming Beach or Honolua Bay (see Honolua Bay) for an invigorating swim in summer or the thrill of watching experienced surfers in winter. Drive carefully along narrow Route 30 from Kapalua all the way around to Wailuku. The road, barely wide enough for one car at points, twists and turns with the coastline, hugging the mountainside with sheer drop-offs to the ocean below.

Late Afternoon

After you travel through the lush Honokohau Valley,stop at Nākālele Point for a short hike to experience the awesome force of the blowhole. Here the vivid red-hued cliffs drop to the ocean below and trails along the bluffs offer terrific ocean views. The wide expanses of grassy bluffs are great for a picnic.

After another brief stop at Mile Marker 16 to try ringing the Bellstone, continue along the route through the tiny village of Kahakuloa. A few miles farther finds you at Kaukini Gallery (see Kaukini Gallery), which displays and sells the work of local artisans.

From here you will soon return to “civilization,” passing through the communities of Waihe’e and Waiehu. Continue “home” along the main highways.

Morning

Slather on the sunscreen, grab a mask, snorkel, and fins, and put on your hat for a morning of Maui’s fabled sun, sand, and sea. The trade winds here normally pick up between 11am and 1pm, so early morning is the time to claim your spot at any one of the sparkling white beaches that line the Kīhei/Wailea coast. Kama’ole I, II, or III, Keawakapu, and Wailea (see Beaches) are all perfect for swimming, snorkeling, body boarding, or just plain sunning. Farther south, Big Beach at Mākena is entirely idyllic, and La Pérouse Bay shelters fabulous snorkeling and kayaking spots.

It’s best to be out of the sun well before noon, and that’s a good time to head to Alexander’s Fish & Chips, Kīhei Caffe, or one of the many food stops that dot South Kīhei Road.

Afternoon

The Hawaiian Island Humpback Whales National Marine Sanctuary provides a good after-lunch activity. You’ll learn about the wonders of Hawai’i’s marine life, most notably the gentle giants that winter in these waters. Binoculars and viewing stands are available at no charge. Right in front of the sanctuary’s office deck, and easily seen with the naked eye, are the remains of an ancient fish pond (currently being restored).

There’s a small park adjacent to the sanctuary’s buildings where you can enjoy an afternoon snack or a thirst-quenching drink at a shady table.

Morning

Begin with an early morning visit to Haleki’i Pihana Heiau, perched on a bluff overlooking Maui’s central valley. Take Route 340 from Kahului, make a left turn onto Kūhiō Place, and finally, turn onto Hea Place to reach the Heiau (temple). Maui’s ancient chiefs would have surveyed their domain from this very spot.

Head back up Kahului’s Ka’ahumanu Avenue all the way to the misty crags of ’Īao (see ’Īao Valley). Imagine the ali’i (royalty) enjoying this lush valley as you hike in the coolness of the tropical greenery and take a refreshing dip in a the sparkling stream.

A ten-minute drive out of the valley to Wailuku will bring you to Bailey House Museum (see Bailey House Museum) for a look at precontact life on Maui. Bailey’s own paintings also provide an interesting glimpse into how the island looked when the Protestant missionaries arrived in the 1820s.

Afternoon

Grab a quick, local-style lunch at Sam Sato’s or Wei Wei Noodles & Barbecue, both in the nearby Wailuku Millyard.

Next, you come to the island’s plantation era, vividly displayed at the Alexander & Baldwin Sugar Museum. And to bring you back up to date, end your day by picking up some pūpū (snacks) at one of the many markets in Kahului – Safeway, Ah Fook’s, Foodland – then head to Kanahā Beach Park for a sunset picnic.