Maui in Style: Ka'anapali, Road to Hana & Haleakala
Beach Vacations
Trip Overview:
Bask in the gentle rhythms of Maui on this eight-day journey, where each day blends island beauty with moments of pure indulgence.
Begin in Ka’anapali, where the scent of plumeria drifts on the breeze and evenings are crowned by a sunset sail across the Pacific, the horizon brushed in gold and rose.
Slow your pace in Kapalua, a place of quiet elegance, where pristine beaches and lush golf courses offer serene days under the Hawaiian sun. Journey south to Wailea, pausing for a private-guided drive along the legendary Road to Hana, a ribbon of coastal highway lined with waterfalls, rainforest and hidden black-sand coves.
Greet the dawn atop Haleakala, watching the first light spill over the vast volcanic crater in a moment that feels almost otherworldly. Wailea’s calm waters and crescent beaches invite restful days, whether by the shore, in the spa, or exploring local dining and artisan shops.
From start to finish, this escape captures the soul of Maui—its wild beauty, its warm spirit, and its timeless invitation to slow down. It’s a journey for travellers who want more than a holiday; it’s a chance to be part of the island’s rhythm, returning home with the scent of the ocean still in your memory.
Highlights:
- Begin in Ka’anapali, where ocean breezes and sunset sails set a serene Maui rhythm.
- Unwind in Kapalua’s peaceful embrace, surrounded by pristine beaches and rolling green landscapes.
- Follow the Road to Hana, discovering waterfalls, rainforest canopies, and hidden black-sand shores.
- Watch sunrise from Haleakala’s summit as light spills across the vast volcanic crater.
- End in Wailea, where calm seas, coastal dining, and soft sands invite complete relaxation.
Included Services:
- Private arrival and departure airport transfers
- 7 nights in deluxe accommodations
- Private transfer from Kapalua to Wailea
- Shared Deluxe Ka’anapali Sunset Sail with private transfers (max 40 guests)
- Private Deluxe Road to Hana Tour
- Shared Haleakala Sunrise Tour (max 24 guests)
- 1 Breakfast, 1 Lunch
Excluded Services:
- Travel insurance
- International and domestic airfare & airfare taxes
- Entrance fees to sites not explicitly listed as included
- Meals and beverages not mentioned
- Gratuities
- Items of a personal nature
- Passport & Visa fees if applicable
Transfer: Kahului Airportto Kapalua HI
Hotel: The Ritz-Carlton Maui, Kapalua (5 Star Rating)
The Ritz-Carlton Maui, Kapalua offers an elevated ocean-front retreat set on 54 lush acres along Maui's northwest shoreline. Guests enjoy beautifully renovated guest rooms and suites, featuring private lanais, luxurious marble bathrooms, and serene tropical decor. Rejuvenate in the full-service spa, savor Pacific-inspired cuisine at onsite restaurants, and unwind beside multiple ocean-view pools, including an adults-only sanctuary. Outdoor enthusiasts will appreciate the well-appointed fitness center, tennis courts, and assigned access to two championship golf courses. The resort's calm elegance is reflected in warm, attentive service-creating a refined yet relaxed atmosphere that invites guests to connect with Maui's natural beauty.
Day 2: Deluxe Ka’anapali Sunset Sail
Transfer: Kapalua HI to Kaanapali Beach HI
Enjoy stunning panoramic views of the West Maui Mountains, kissed with rainbows, aboard Maui's newest sailing catamaran. Step away from the bustle of a crowded restaurant and slip into sunset at tables set for intimacy and comfort. Allow yourself to be lulled into relaxation while the world-class Trilogy Crew members serve several tasty pupus (appetizers), signature cocktails, and knowledge of Maui's history and marine life. Departing from world-famous Ka'anapali Beach, sip and sail with Maui's oldest and most experienced sailing company!
Transfer: Kaanapali Beach HI to Kapalua HI
Day 3: At Leisure in Kapalua
Day 4: From Kapalua to Wailea
Transfer: Kapalua HI to Wailea HI
Hotel: Four Seasons Resort Maui at Wailea (5 Star Rating)
At Four Seasons Resort Maui at?Wailea, every detail radiates effortless island elegance from the koi-pond courtyards to the soothing salt-water pools framed by manicured gardens. The 383 guest rooms and suites, many with private lanais and ocean views, range from sleek Club-Floor retreats to expansive three-bedroom Lokelani residences with gardens and butler-level service. Daydream by one of three pools adults-only infinity, family waterfall, or serene fountain while cabana attendants ensure iced treats and comfort. The spa blends indoor and open-air hales with Hawaiian-inspired treatments, and championship golf, pickleball courts, boutique shopping, and refined eateries complete the serene luxury.
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Day 5: Private-Guided Deluxe Road to Hana Tour
Enjoy one of our world's most scenic and captivating roads circling around Haleakala. Tour around Maui's eastern volcano to see countless waterfalls, lush rainforest, breathtaking mountain views, and magnificent ocean scenes. Hana Highway features over 600 coastal turns and nearly 60 bridges, mostly one lane. Swim in a freshwater pool by a waterfall and in the ocean at Wai'anapanapa's black sand beach. We'll take care of the required park reservation in Hana, provide lunch, cold drinks, and more. Let our experienced guides take the wheel, and enjoy a full day tour along this historic road of awe inspiring views.
Day 6: Haleakala Sunrise Tour
The Haleakala Sunrise Tour offers guests an opportunity of a lifetime to view the sunrise from atop Haleakala! This tour includes an exciting and informative guided vehicle tour of Haleakala National Park along with the Upcountry and North Shore areas. Our NAI Certified Interpretive Guides will share with our guests the rich Culture and History of Maui along the way. After sunrise, guests will have an opportunity to visit the historic areas of Kula, Makawao Town, and Pa'ia.
Day 7: At Leisure in Wailea
Day 8: Depart from Maui
Transfer: Wailea HI to Kahului Airport
