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The Hawaiian Islands | Explore Maui's & Lanai's Beauty

Sample Itinerary


Hawaii, Maui, Lanai

Trip Duration

8 nights / 9 days

An ideal escape for those seeking low-key relaxation amid some of the world's most spectacular beauty, Maui, Hawaii's Valley Isle, and Lana'i offer an immersive vacation experience to reconnect with nature and with your loved ones.

Below is just a sample of the immersive itineraries our Destination Specialists can create. Click on the experiences links in the itinerary to see other curated excursion choices offered by Journese. Our Destination Specialists are happy to book our hotels and excursions highlighted in the itinerary below, or let them know if you would like something customized. And, feel free to offer our non-hyperlinked suggestions to your clients to further explore the destination.


Day 1 Continental United States / Maui

Board your comfortable flight as you prepare to immerse in the Aloha spirit. Upon arrival, pick up your pre-registered Hertz Jeep Wrangler and enjoy the scenic drive to Grand Wailea for a six-night stay in a Deluxe oceanview guestroom, including daily breakfast. Set on 40 acres of tropical gardens and overlooking famed Wailea Beach, this resort offers a welcome respite from the hustle and bustle of everyday life.

Spend your afternoon poolside, lazing in the sun at the adults-only Hibiscus Pool, or, for those more adventurous, slide down the resort's three-story lava tube slide.

This evening, enjoy Hawaii seasonal cuisine at Humuhumunukunukuapua'a, named after Hawaii's state fish. Situated on a floating lagoon and featuring a thatched roof, this restaurant with acclaimed chef dining offers fresh Hawaiian ingredients. Savor the Taste of Hawaii with the chef's local sashimi selection, pickled ginger and wasabi, followed by steamed ohana style Hawaiian snapper as you gaze at the ocean before you.

Day 2 Haleakala Sunrise Excursion

Rise early this morning as you embark on Maui's most famous natural wonder, Haleakala Crater, rising 10,000 feet above sea level. The Haleakala Sunrise Excursion is a once-in-a-lifetime experience, head through Maui's upcountry to Haleakala National Park to witness the glory of dawn over the dormant volcano's summit. Enjoy a continental breakfast upon arrival at the park and full breakfast upon your return.

This afternoon, enjoy a well-deserved nap in the comfort of your room as you listen to the waves lap on Wailea Beach. Afterward, refresh in one of the resort's nine blue water pools, and then take a leisurely walk along the soft sands of Wailea Beach.

Tonight, dine at Bistro Molokini, where you will enjoy casual, locally sourced fare. Enjoy wood oven-fired hamakua mushroom pizza with caramelized Maui onion, roasted garlic aioli and fine herbs. Complete your dinner with tropical tiramisu, created with passion fruit lady fingers, macadamia tuile, and vanilla and mango mascarpone cream.

Day 3 Resort Water Adventure

After your scrumptious breakfast, enjoy a Botanical Tour with the resort's Director of Landscaping, learning about the native Hawaiian flowers, plants, and fruits on property and their significance to the island. Afterwards, enjoy a complimentary scuba lesson for first-time divers, then continue your water fun as you kayak and paddle board in the warm ocean water.

Take a lunch break as you enjoy light bites in the pool at Grotto Bar amidst the waterfalls, slide and grottos. Delight in seasonal fruit and homemade banana bread, followed by the impossible burger with caramelized onions, Maui Gold pineapple, sprouts and mango bbq sauce on a brioche bun. Top it off with a coconut mojito. This afternoon, head to the Wailea Canyon Activity Pool. This 2,000-foot-long, 25,700 sq. ft., 770,000-gallon pool area includes nine individual pools on six different levels, connected by a lazy river with whitewater rapids and gentle currents. Enjoy four jungle pools, five intertwining slides, a whitewater rapids slide, a Tarzan pool with rope swing, a sandy beach pool, six waterfalls, caves, three Jacuzzis, the world's first water elevator and a swim-up bar. Or, head back to the ocean to explore Maui's colorful marine life.

This evening, enjoy a romantic sunset dinner on the beach with Cabana Dining. Toast your champagne glasses as you celebrate your connection with nature and each other while dining on an amuse bouche, followed by ahi tartare and a wild arugula salad, seared day boat scallops with smoked tomato beurre blanc and crispy potato cakes and chef's hand-crafted dessert.

Day 4 Snorkel Adventure

Today, enjoy one of Maui's "must-do" experiences as you explore Molokini crater on a Snorkel Adventure. Board a catamaran to sail the Hawaiian waters, visiting two snorkeling locations- Molokini and the shallows of the Maui coast line, home to many Hawaiian honu (sea turtles). Enjoy Mom's homemade cinnamon rolls for breakfast and BBQ teriyaki chicken for lunch.

Return to the resort to relax by the pool or play tennis before turning in for the night. This evening, enjoy your ocean view from the comfort of your room as you enjoy in-room dining.

Days 5 - 6  Island Exploration

Explore the island today, heading north to famed Kaanapali Beach where you can laze on the powdery sand or try your hand at parasailing. Indulge in lunch at famed Duke's Maui, with ocean views stretching to Lanai and Molokai. After lunch, stroll to Whalers Village to enjoy some island shopping.

This afternoon, head farther north to explore Kapalua, with its lush, green backdrops. Try your hand at one of Kapalua's championship golf courses overlooking the blue waters of the Pacific. On your way back to your resort, stop at Morimoto at Andaz Maui at Wailea Resort to delight in beachfront dining, savoring renowned Japanese sushi and cuisine.

The next day, venture out to Iao Valley State Park for a nice hike along the lush valley, through the botanical garden and along the flowing river. Learn the culture and history of this sacred site, which was where King Kamehameha I conquered the Maui army in 1790. Or, enjoy the short hike leading to Twin Falls Maui Waterfalls in Haiku. Stroll through towering bamboo trees, search for native wildlife, then take a dip in one of the two refreshing waterfalls.

Day 7 Maui / Lana'i

Say Aloha to the island of Maui as you return your Jeep Wrangler and board your inter-island flight to the secluded island of Lana'i. Settle into your Oceanview guestoom at Four Seasons Resort Lana'i for a two-night stay.

Stroll to Malibu Farm, perched above Hulopoe Bay, to enjoy a lunch of organic, locally sourced food poolside. Many of the fruits and vegetables come from the restaurant's own Harvest Garden. This afternoon, take a self-guided walk along the trails of the island, taking in the breathtaking views of this secluded paradise. Return to the resort for a stroll on the soft sand beach, followed by a quick dip in one of the resort's lagoon-style pools.

Conclude your day with fine dining at Nobu Lanai, enjoying fresh-caught fish and intimate sushi bar at the Cliffside terrace showcasing amazing Pacific Ocean views.

Day 8  Lana'i Discovery

Begin your day with a guided sunrise hike to Pu'upehe, one of Lanai's most iconic landmarks. Learn about the native history and traditions of Pu'upehe from your expert guide, who will also describe the living environment of the beach region. This afternoon, charter a catamaran to snorkel in secluded waters and listen as humpback whales sing, concluding with breathtaking views of the spectacular sunset as you sip our champagne with your loved one.

Day 9 Lana'i & Maui / Continental United States

Stroll to The Break to enjoy Hawaiian Coffee and a build-your-own acai bowl as you take in the amazing scenic view before boarding your inter-island and transpacific flights back home, reminiscing about the natural wonders you discovered and planning your next bucket list vacation.

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