Your 10-Day Hawaiian Island Honeymoon Itinerary

Trust us, one island is not enough

Updated 08/06/12
01 of 10

Day 1: The Big Island

Table and chairs on beach with tree

Courtesy of The Four Seasons Resort Hualalai

Morning

Touching down in Kona, you might think, "Um, have we landed on the moon?" Otherworldly black lava rock ripples across the sunny Kona-Kohala Coast, where you'll find all the top resorts. Pick up a rental car—driving through the lunar landscape is half the fun—and ride 15 minutes to the insanely luxurious 243-room Four Seasons Hualalai, where you may catch a glimpse of Cameron Diaz or Rachel Zoe. Think seven outrageous pools, an apothecary-style spa, and an open-air gym worth setting a wake-up call for.

Afternoon

Park it at the adults-only Palm Grove pool with a yuzu-margarita shaved ice (like a snow cone—with booze).

Evening

Stay in for a seaside farm-to-table feast at 'Ulu Ocean Grill—75 percent of what's in the kitchen is sourced from local farmers.

02 of 10

Day 2: The Big Island

Woman in bathrobe looking out at ocean

Courtesy of Fairmont Orchid

Morning

The Big Island's got 11 of the world's 13 climate zones, and the way to see them is from a helicopter. With Blue Hawaiian Helicopters, you can fly over tropical rainforests, snowcapped Mauna Loa, and Kilauea, an active volcano with incredible red rivers of molten lava.

Afternoon

Decompress with a traditional lomilomi massage in an outdoor cabana at the Fairmont Orchid's Spa Without Walls. This resort is a little more low-key than the Four Seasons and sits on a small, lovely beach.

Evening

Split the kalua-pig quesadillas, warm local goat cheese, and signature original wok-charred ahi at Merriman's, a hyperlocal restaurant in tiny Waimea—the heart of Hawaii Island's emerald-green ranch country.

03 of 10

Day 3: The Big Island

Man and woman walking on shore

Courtesy of Island of Hawaii Visitors Bureau

Morning

Drive to golden Hapuna Beach, a half-mile-long stretch where you can lose hours picnicking and sunbathing.

Afternoon

Throw on a cover-up and explore Hawi, an adorable old mill town now full of brightly colored galleries and cafés. Do a dessert lunch of Kona-coffee ice cream at Kohala Coffee Mill.

Evening

The sunset views are amazing from Manta & Pavilion Wine Bar, which is set on a bluff. Pick from 48 wines by the glass and share pupus (appetizers) like Kona kampachi sashimi.

04 of 10

Day 4: Maui

Hotel room

Courtesy of Ritz-Carlton Kapalua 

Morning

Nothing beats room-service macadamia-nut pancakes on your balcony.

Afternoon

You're moving on to Maui (it's a half-hour flight), a honeymoon go-to for its fabulous, everything-you-could-dream-of-is-right-there resorts. One of the glitziest is the Ritz-Carlton Kapalua on the northwest coast, which has a 10,000-square-foot pool and elegant island-style rooms with to-die-for marble bathrooms.

Evening

After a swim (three beaches are within walking distance), try your first poke—raw tuna, Maui onion, and soy sauce—at the Ritz's sleek Kai Sushi.

05 of 10

Day 5: Maui

Landscape view of ocean at Kalama Park

Getty Images 

Morning

Your best chance of spotting Laird Hamilton is at Colleen's at the Cannery, a café in Haiku with hearty breakfast burritos, healthy tofu wraps, and strong espresso drinks. The surfing icon pops in after riding "Jaws," the monster break nearby.

Afternoon

Inspired by Laird's abs? Take a surf lesson with Maui Sports Unlimited at Kalama Park in Kihei, where the waves are more manageable than "Jaws."

Evening

It's a little touristy, but oceanfront Lahaina, a historic whaling village close to the Ritz, has some standout restaurants. Order the scrumptious Kona-coffee roasted rack of lamb at upscale Lahaina Grill.

06 of 10

Day 6: Maui

Chairs and tables with umbrellas by pool

Courtesy of Grand Wailea

Morning

Roll out of bed and walk the nearly two-mile Kapalua Coastal Trail, which has stunning views of Molokai Island.

Afternoon

Head south to Wailea Beach—home to more five-star hotels—for bodysurfing and great people-watching. Kick off happy hour with fancy umbrella drinks at the Grand Wailea resort's Bistro Molokini, and watch out for whales offshore.

Evening

Tomorrow will be jam-packed, so do an early dinner back at the Ritz's hillside fine-dining restaurant, Banyan Tree. Request an ocean-view table, and go for the branzino in miso broth or cumin-crusted hapu (sea bass).

07 of 10

Day 7: Maui

Car driving on Hana Highway

Royce Bair / Getty Images 

Morning

Pick up the famed 42-mile Hana Highway—a series of some-600-odd hairpin turns among cliffs, waterfalls, and primordial trees—just past the boho town of Paia. It's about three hours east to time-stands-still Hana, where Oprah goes to chill.

Afternoon

Don't miss Maui's only black-sand beach at Wai'anapanapa State Park.

Evening

Stay for dinner at the luxe Travaasa Hana and crash in a sea-ranch cottage. Or drive to Paia (the return goes quicker—about two hours) and check into the wallet-friendly Inn at Mama's Fish House.

08 of 10

Day 8: Kauai

Woman relaxing on hammock by beach in Princeville, Kauai

M.M. Sweet / Getty Images 

Morning

Hop a 40-minute flight to Kauai, nicknamed the Garden Isle. If you've seen The Descendants, you'll recognize the wildly lush, mountainous landscape. Stay on the north shore and splurge on the Princeville Resort. While shooting the film, George Clooney loved this cushy resort with butler service and a pool overlooking Hanalei Bay. For a more affordable option, go the condo route at the nearby Hanalei Colony Resort and cook in. The cozy units are actually two-bedrooms—it's like having a suite.

Afternoon

Try stand-up paddling, the core workout that's got Rihanna hooked, with Hawaiian Surfing Adventures in Hanalei Bay.

Evening

Back in colorful Hanalei town, strong mai tais (followed by karaoke on Mondays) are the favorite at super casual Tahiti Nui.

09 of 10

Day 9: Kauai

Resort on water with vegetation

Courtesy of Grand Hyatt Kauai 

Morning

Today you're road-tripping to the sunny south shore. Ride ATVs through the trails of Kipu Kai, a working cattle ranch.

Afternoon

Poipu Beach is a series of golden, palm-backed crescents with great wave action. After bodysurfing, you're due for massages in a garden hale at the Grand Hyatt Kauai.

Evening

On your way back north, stop in Kapaa and dine at Kintaro, a buzzing sushi and teppanyaki place that's big with locals.

10 of 10

Day 10: Kauai

Waimea Canyon helicopter view

Getty Images

Morning

See the Napali Coast's 4,000-foot-high cliffs and 14-mile-long Waimea Canyon—a mini version of the Grand Canyon—on another helicopter adventure with Island Helicopters.

Afternoon

Ginger-lychee caipiroskas by the pool, anyone?

Evening

Break out your best dress for Princeville's Makana Terrace, which has dramatic Makana Mountain views. Ask the sommelier for a bottle of wine that's $10 more than you usually spend—and settle into a serious discussion about your first-anniversary return trip.

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