Hawaii, The Big Island
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 (left), 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. Rooms from $545; Four Seasons.
AFTERNOON Park it at the adults-only Palm Grove pool with a yuzu-margarita shave ice (like a snow cone—with booze).
EVENING Stay in for a seaside farm-to-table feast at Pahu'ia; 90 percent of what's in the kitchen (Hamakua mushrooms, grass-fed beef) is sourced from local farmers.
Hawaii, The Big Island
MORNING The Big Island's got 11 of the world's 13 climate zones, and the way to see them is from a helicopter. Fly over tropical rainforests; snowcapped Mauna Loa; and Kilauea, an active volcano with incredible red rivers of molten lava; Blue Hawaiian.
AFTERNOON Decompress with a traditional lomi-lomi massage in an outdoor cabana at the Fairmont Orchid's Spa Without Walls. (P.S.: This resort (left), a little more low-key than the Four Seasons, sits on a small, lovely beach. Rooms from $329; Fairmont.)
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; Merriman's.
Hawaii, The Big Island
MORNING Drive to golden Hapuna Beach (left), a half-mile-long stretch where you can lose hours picnicking and sunbathing; Hawaii, The Big Island.
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; 808-889-5577.
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; Prince Resorts Hawaii.
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: 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. Rooms from $399; Ritz-Carlton.
EVENING After a swim (three beaches are within walking distance), try your first poke—raw tuna, Maui onion, and soy sauce; it's like a ceviche—at the Ritz's sleek Kai Sushi.
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; Colleen's At The Cannery.
AFTERNOON Inspired by Laird's abs? Take a surf lesson at Kalama Park in Kihei, where the waves are more manageable than"Jaws"; Maui Sports Unlimited.)
EVENING It's a little touristy, but oceanfront Lahaina (left), 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; Lahaina Grill.
MORNING Roll out of bed and walk the nearly two-mile Kapalua Coastal Trail, which has stunning views of Molokai Island; Kapalua.
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 off-shore (left); Grand Wailea.
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).
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; Maui. 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; Hawaii State Parks.
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; Rooms from $545; Kauai. Stay on the north shore and splurge on the St. Regis Princeville (left). While shooting the film, George Clooney loved this cushy resort with butler service and a pool overlooking Hanalei Bay. Rooms from $1,000; The St. Regis Princeville Resort. (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. Rooms from $255; Hanalei Colony Resort.)
AFTERNOON Try stand-up paddling, the core workout that's got Rihanna hooked, in Hanalei Bay; Hawaiian Surfing Adventures.
EVENING Back in colorful Hanalei town, strong mai tais (followed by karaoke on Mondays) are the favorite at super-casual Tahiti Nui; Tahiti Nui.
MORNING Today you're road-tripping to the sunny south shore. Ride ATVs through the trails of Kipu Kai, a working cattle ranch; Kipu Ranch Adventures.
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 (left); Grand Hyatt Kauai Resort and Spa.)
EVENING On your way back north, stop in Kapaa at Kintaro, a buzzing sushi-and-teppanyaki place that's big with locals; 808-822-3341.
MORNING See the Napali Coast's 4,000-foot-high cliffs and 14-mile-long Waimea Canyon (left)—a mini version ofthe Grand Canyon—on another helicopter adventure; Island Helicopters.
AFTERNOON Ginger-lychee caipiroskas by the pool, anyone?
EVENING Break out your best dress for the St. Regis's Kauai Grill, which has dramatic Makana Mountain views. It's Jean-Georges Vongerichten's restaurant, so expect haute cuisine, like soy-glazed short ribs with green papaya–jalapeño puree. 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.