Hearts in Hawaii: A Luxe & Cultural Wedding Journey Through Maui

A Culture-Focused Maui Destination Wedding Week for Luxe Explorers and their Guests

Experience the best of Maui — from black sand beaches to waterfall hikes, private poolside pampering to unforgettable sunset views — with this curated wedding week itinerary designed for couples who crave both luxury and adventure.

Stay: Wailea at one of the resorts (we love the Wailea Beach Resort, Four Seasons, and Andaz)

Best Time of Year: April-May or October

Best Form of Transportation: Rent a Car or Hire transportation for tours

🌺 Ideal Week-Long Destination Wedding Itinerary on Maui

Where tropical elegance meets once-in-a-lifetime adventure

Planning a destination wedding on Maui means more than just a beautiful ceremony — it’s an entire week of connection, celebration, and unforgettable moments with your closest people. From waterfall hikes on the Road to Hana to poolside massages and a sunset sendoff, this curated itinerary blends luxury, relaxation, and Hawaiian culture for the ultimate wedding week in paradise.

Here’s your day-by-day guide to the perfect Maui wedding week:

📅 Monday–Tuesday: Arrival + Island Vibes

Guests arrive on the island and settle into the serene beauty of Wailea Beach, checking in to your resort of choice. These first two days are all about adjusting to island time — relaxing, exploring the resort grounds, and soaking in the tropical elegance Maui offers.

🌺 Tuesday Evening: Welcome Luau at Wailea Beach Resort

Kick off the celebration with a Welcome Luau Dinner at the iconic Wailea Beach Resort. With premier seating, guests enjoy an immersive cultural experience featuring traditional Hawaiian music, hula dancing, fire performances, and island-inspired cuisine.

🌿 Wednesday: Road to Hana Adventure

The day brings a bucket-list experience — the legendary Road to Hana.Guests can:

• Drive themselves using the self-guided Shaka Guide app, or

• Join a group with pre-arranged transportation for a more relaxed journey.

Stops may include:

• Scenic waterfalls

• Tropical gardens

• Hike through Haleakalā National Park

• Lunch in Hana for a local flavor experience

🌊 Thursday: Ocean Day – Dive, Snorkel, or Sunbathe

Give guests the flexibility to tailor the day to their pace:

• Scuba diving adventures for certified guests

• Snorkeling excursions in Molokini Crater

• Or simply a relaxing beach day along Wailea’s soft sands

💆‍♀️ Friday: Private Pool Day at Olakino

Treat your guests to a day of pure indulgence at the Olakino Pool, a wellness-focused adults-only oasis.Features include:

• Poolside massages

• Private cabanas

• Lunch + cocktails served throughout the day

In the evening, invite guests back to the pool area for a private dinner under the stars, blending elegance with barefoot island charm.

💍 Saturday: The Wedding Day

The big day is here! Celebrate your love with a ceremony and reception in one of Wailea’s breathtaking venues — whether it's a seaside lawn, beachfront chapel, or cliffside terrace. Every detail reflects your shared spirit of elegance, adventure, and aloha.

🌅 Sunday: Sunrise + Sunset Reflections

After a well-deserved sleep-in or spa visit and brunch, close out the week with a sunset gathering at Haleakalā National Park. Watching the sun dip below the clouds from 10,000 feet is a spiritual, unforgettable experience — a poetic end to a magical week.

✈️ Monday: Farewells + Departure

Guests check out and head home with a newfound love for ʻohana, carrying with them memories of love, laughter, and the spirit of aloha that made this wedding week truly one-of-a-kind.

Ready to Begin the Planning Journey?

Inquire Here