Itinerary help -Maui

Question

Hi - we are a family of four, kids 5 and 8, traveling to Maui for 9 days in March. Looking for advice on what part of the island to stay and where. We are an active family and I would like to explore different parts of the island. Should we plan to stay in two locations to access different areas? Or plan to stay in one area as a home base and travel from there? My original thought was staying in upcountry or north shore for the first few nights as a base to explore that area from, then going down to the south shore or west shore for a resort stay to relax, but I am not seeing many lodging options in upcountry/north shore area. As for resorts, I typically prefer quieter, smaller, more boutique resorts, which not sure if that exists? It seems more big resort or condos? Any help is appreciated. thanks.

Answer

It sounds like you have an exciting trip planned to Maui! Since you’re an active family with young kids, you’ll want a mix of adventure and relaxation, and it’s a great idea to explore different parts of the island. Let me help you break down your options for lodging and itinerary.

As for where to stay, Maui offers diverse landscapes, so having two different base locations is a good idea. This allows you to explore more of the island without spending hours in the car each day. Let’s look at both options:

Option 1: Stay in Two Locations

Staying in two different areas will give you a chance to experience different aspects of the island and reduce the time spent on long drives. For a family-friendly trip, I’d recommend splitting your stay between the Upcountry or North Shore and the South Shore or West Shore.

Upcountry or North Shore for Exploration (First Few Nights): Upcountry offers a cooler climate and a more laid-back, rural atmosphere. It’s a great base for exploring nature and hiking, especially for young kids who enjoy outdoor activities like the Haleakalā National Park and Makawao (famous for its paniolo heritage). In addition to the park, you can take the kids on a farm tour, visit Surfing Goat Dairy or Kula Botanical Garden to enjoy the scenery.
South Shore or West Shore for Relaxation (Second Half of Your Trip): After a few active days, head to the South or West Shore for a more traditional resort experience, but still with a quieter vibe. Both areas are near great beaches for swimming, snorkeling, and other water activities, and the resorts tend to be more family-friendly with pools and direct beach access. The Wailea area on the South Shore is more relaxed and less crowded than the North Shore, with upscale boutique resorts. The Ka'anapali Beach on the West Shore is a great option if you're looking for good resort amenities, restaurants, and shopping without the crazy crowds of large Waikiki-style resorts.

This option is great because it lets you explore different parts of Maui with ease. The drive between Upcountry and the South Shore (or West Shore) is about an hour and a half, but you won’t have to make it every day. You can break up your days with activities that are close to each base. However, keep in mind that Upcountry and the North Shore areas may not have as many lodging options, especially if you’re looking for boutique hotels instead of large resorts.

Option 2: Stay in One Location

If you prefer the convenience of staying in one place, I’d suggest staying on the South Shore or West Shore as your home base, which gives you easy access to many of the island’s attractions. From here, you can easily do day trips to the more remote parts of the island. It’s ideal for families with young kids who need a more predictable schedule and don’t want to keep packing up and moving.

Wailea (South Shore): Wailea is a great option for a family stay. The area has smaller, quieter resorts compared to the larger resorts found in Ka’anapali. Plus, the beaches here (like Makena Beach and Keawakapu Beach) are some of the best on the island for families, with calm waters and great snorkeling spots. There are also upscale hotels and resorts like Hotel Wailea (an adults-only resort, but nearby hotels offer family-friendly options) and The Fairmont Kea Lani which has a family-friendly atmosphere. Wailea is also close to La Perouse Bay and Molokini Crater for snorkeling tours.
Ka'anapali (West Shore): If you prefer a resort feel, Ka'anapali is ideal for families. The area has a good selection of family-friendly resorts with direct beach access, perfect for your afternoons by the pool or beach. Nearby attractions include Whalers Village for shopping, dining, and cultural activities. The beaches here are perfect for kids and there’s easy access to Lahaina Town for historical sites and restaurants. The drive to Haleakalā National Park or the Road to Hana from here is about 1.5 to 2 hours, but you can plan these trips for specific days.

This option is less hectic than moving around to multiple areas and allows you to settle into one location with easy access to local beaches, restaurants, and shopping. However, you may miss out on the Upcountry or North Shore experience, which offers a different vibe and access to more rural adventures.

Accommodations Options

Since you prefer quieter, boutique-style resorts, here are some recommendations for both the Upcountry and Resort areas:

Upcountry/North Shore: While not as common, there are a few boutique options in Upcountry and the North Shore that offer a more intimate experience. Consider places like The Plantation Inn in Makawao (North Shore) or the Andaz Maui at Wailea (South Shore) for a quieter resort experience. Alternatively, smaller inns and guesthouses like Hana-Maui Resort in East Maui offer peaceful stays with scenic surroundings.
Wailea (South Shore): For a smaller resort feel, Hotel Wailea is a boutique option for adults, but you may also enjoy The Fairmont Kea Lani which offers spacious villas with a quieter atmosphere. Both are family-friendly, but still maintain an upscale, serene vibe compared to larger, high-traffic resorts.
Ka'anapali (West Shore): Try The Westin Nanea Ocean Villas or Montage Kapalua Bay for a more boutique feel. Both are luxurious, but more intimate than massive resorts in the area, and have quieter pools and beaches.

Ultimately, the decision to stay in one or two locations depends on how much you want to explore each area. For a balanced experience of adventure and relaxation, splitting your stay between two locations might be the best option, though staying in one base could be a good alternative if you prefer more downtime and don’t mind longer drives.

Either way, Maui has so much to offer, and you’ll have an amazing time exploring the island with your family!