From the boardroom to the beach: Your business travel guide to South Maui

Maximize your business trip in Wailea and Kīhei with insider tips and things to do in Maui after your meetings.

Edited by Taylor Cahan | November 25, 2025

Blend business and leisure in South Maui

South Maui is where business travel and island adventure blend seamlessly. Here, the “bleisure” mindset comes to life as you move from meetings to golden-hour strolls, savoring the best of Wailea and Kīhei between work commitments. With a little planning, you can unwind on the Wailea Beach Path, experience a traditional lūʻau, or catch a performance at the Maui Arts & Cultural Center (MACC) — all within the after-work window. This guide is built for travelers who want to make every hour count, with actionable tips, local insights, and a focus on the top things to do in Maui.

Where to work in Kīhei and Wailea

Productivity comes easy in South Maui, where a tranquil atmosphere and inspiring views help you make the most of every workday. Drop in at The Cohana coworking space at the Maui Research & Technology Center in Kīhei for access to conference rooms, fast internet, and office supplies — perfect for video calls, in-person meetings, and focused project time. Many local cafés, like the spacious Da Green Coffee Bar and Island Vintage Coffee Wailea, also offer strong Wi-Fi and comfortable seating for a change of scenery. Popular spots tend to get busy, so aim for early mornings right at opening or the mid-afternoon lull.

For those seeking a seamless blend of work and relaxation, Hilton Grand Vacations Club Maui Bay Villas provides suite-style accommodations with spacious living areas, full in-suite kitchens, and private lanais overlooking the ocean. After a productive day, step outside for a sunset stroll or a refreshing dip in one of the resort pools.

Insider tip: Since Hawaii-Aleutian Standard Time (HST) is typically 2-3 hours behind the West Coast and 5-6 hours behind the East Coast, plan your calls and deep work for early mornings to open your afternoon and evening for leisure activities.

Golden-hour nature escapes

When the workday winds down, South Maui’s natural beauty is just steps away. The Keālia Coastal Boardwalk along Maalaea Bay in Kīhei is a favorite for spotting native Hawaiian waterbirds and catching the soft light of sunset (open daily, 6:30 am to 7:00 pm). For a classic Maui experience, the Wailea Beach Path offers a paved, oceanfront walkway perfect for evening jogs or leisurely strolls as the sky glows pink and gold. If you wrap up your day after lunch, consider a quick drive Upcountry in the afternoon for a tasting at a local farm or distillery, then stay to watch the sun dip below the horizon.

For a stay that puts you right on the Wailea Beach Path, Grand Wailea, A Waldorf Astoria Resort features lush gardens, a world-class spa, and unparalleled ocean views at every turn. Don’t miss the resort’s morning beach yoga sessions, indoor-outdoor restaurants and bars, and signature Grand Lūʻau experience at sunset.

Cultural events and live music

Evenings in Maui are made for live music, art, and community. The Maui Arts & Cultural Center (MACC) in Kahului hosts concerts, artistic performances, and gallery exhibitions throughout the year. The venue is located on the North Shore, about a 20- to 30-minute drive from Kīhei or Wailea. Other cultural events include live music most nights at South Maui Gardens and weekly Polynesian dance performances, traditional island wood carving demonstrations, and ukulele lessons at The Shops at Wailea open-air mall.

For longer trips, group travel, executive stays, or company events, Ho’olei at Grand Wailea provides luxury villa accommodations for residence-style living. Access 22 meeting rooms and 100,000 square feet (9,290 square meters) of indoor and outdoor meeting space, plus a full catering and conference staff on hand.

Insider tip: After work, take the team to Monkeypod Kitchen in the Wailea Gateway Center for craft cocktails and pupus (small bites). For client dinners, Humuhumunukunukuāpuaʻa at Grand Wailea offers an impressive dining experience.

Reservations for island excursions

Some of Maui’s most iconic leisure experiences require a little advance planning. For sunrise at Haleakalā National Park, secure your reservation up to 60 days ahead for entry between 3 am and 7 am. Sunset and stargazing visits are also memorable and don’t require a reservation. Popular attractions like Waiʻānapanapa State Park in Hana and ʻĪao Valley State Monument in Wailuku both require non-residents to reserve entrance and parking in advance. If time allows, consider booking tours and activities like snorkeling, diving, paddling, and seasonal whale watching to maximize your Maui visit. You might even add a few extra days to your trip to make it a true vacation or bring your loved one for a romantic getaway.

Disclaimer: We used AI assistance to generate this content. All information was reviewed by Hilton's team to ensure it meets our standards for accuracy and ethics, allowing us to better match your travel needs and connect you with the right stay.

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