Maui blends volcanic drama with gentle, family-ready beaches and a rich Hawaiian heritage. From the voyaging Polynesians to the 19th‑century whaling era centered around Lahaina, the island’s past still echoes in its place names, royal sites, and plantation towns. Today, Maui invites slow days in the water, scenic drives to Upcountry, and cultural stops that bring the island’s story to life.

For five days, you’ll base in two of the island’s best family hubs: Kihei in South Maui (calm shores and affordable stays) and Kaanapali in West Maui (golden sands, easy amenities, and great sunset views). You’ll snorkel, spot humpbacks in season, and graze your way through plate lunches, poke, and pancakes. A condo with a kitchenette keeps costs low while giving you sand-at-dawn flexibility with kids.

Practical notes: use reef‑safe sunscreen (it’s the law in Hawai‘i), obey ocean safety signs (Maui’s shorebreak can be powerful), and pack light layers for breezy evenings or a cool Upcountry morning. West Maui continues to welcome visitors; please follow posted guidance and respect any restricted areas as Lahaina rebuilds.

Kihei (South Maui)

Sunny, budget-friendly Kihei is beloved for its trio of lifeguarded beaches (Kamaole I–III), mellow mornings, and quick access to Maʻalaea Harbor and Wailea’s coastal path. With frequent food trucks and local cafes, it’s an easy place to feed hungry keiki after a sandy morning.

• Top sights nearby: Kamaole I–III (gentle entry, playgrounds), Keawakapu Beach (soft sand, sunrise walks), Ulua Beach (beginner snorkeling), and the Wailea Beach Path (stroller‑friendly coastal views).
• Great grabs to eat: Kihei Caffe (hearty breakfast), Coconuts Fish Cafe (legendary fish tacos), Nalu’s South Shore Grill (live music, Hawaiian comfort), Eskimo Candy (fresh poke bowls).
• Why base here: Affordable condos, family beaches with facilities, 15 minutes to Maʻalaea for excursions.

Stay in Kihei: Browse condos with kitchens on VRBO Kihei or compare hotels on Hotels.com Kihei. For a budget-friendly central base (not beachfront), consider Maui Seaside Hotel in Kahului.

Getting here: Fly into Kahului (OGG). Search fares on Trip.com flights or Kiwi.com. If you’re skipping a rental car on Day 1, prebook a shared ride: Arrival Shuttle: OGG to Hotels & Private Residences (often cheaper than multiple taxis with kids and luggage).

Family-friendly activities to book:

• Maui Ocean Center All Day Admission Ticket (world-class aquarium; great backup on windy mornings).

  

• Maui Afternoon Snorkel Aboard Malolo to Molokini or Coral Gardens (3 hours; kid-friendly, all gear included).

  

Kaanapali (West Maui)

Kaanapali Beach is a classic crescent of gold with easy facilities, beach walks, and sunset shows by Puʻu Kekaʻa (Black Rock). Whalers Village brings convenient dining, kid-favorite shave ice, and shops for forgotten beach gear.

• Top sights nearby: Kaanapali Beach and Black Rock (cliff-diving ceremony at dusk), Kahekili Beach Park (easy entry, showers), and Kapalua Coastal Trail (tide pools and lava rock views).
• Good family eats: Hula Grill Barefoot Bar (sand‑floor tables), Leilani’s on the Beach (excellent fish, kids menu), Duke’s Beach House (casual, hula pie), Fish Market Maui (counter‑service plates; great value).
• Why base here: Walkable beachfront, calm mornings for swimming, prime sunset and seasonal whale sightings from shore.

Stay in Kaanapali: Compare beachfront stays on Hotels.com Kaanapali or look for family condos on VRBO Kaanapali. Popular picks include The Westin Ka'anapali Ocean Resort Villas (villa kitchens) and, for a splurge up the road, The Ritz-Carlton, Kapalua.

Getting here from Kihei: Drive 45–60 minutes via Honoapiʻilani Hwy (morning departure avoids traffic). Budget for $10–$25/day resort or public lot parking depending on your property and plans.

Family-friendly activities to book:

• VIP Premiere Whale Watch Kaanapali Beach (Max 12) (Dec–Apr; small-group, eye-level views).

  

• Open-Air West Maui Sightseeing: Coast & Blowhole (scenic lookouts and coastline viewpoints; great for non-swimming family members).

  

Day 1: Arrive Maui (OGG) → Kihei Sunset and Easy Eats

Morning: Fly into Kahului (OGG). Compare fares on Trip.com flights or Kiwi.com. Typical West Coast–to–Maui flight time is ~5–6 hours; aim for an arrival before 2 pm if possible.

Afternoon: Grab the keys to your Kihei condo from VRBO Kihei or check in at a hotel from Hotels.com Kihei. If you’re not renting a car today, book the shared arrival shuttle. Shake off jet lag at Kamaole I or II—both have gentle shorebreak, restrooms, and lifeguards.

Evening: Dinner at Nalu’s South Shore Grill (teriyaki chicken, kalua pork, live music) or Coconuts Fish Cafe (two‑taco plate with 17 ingredients). Cap it with Ululani’s Hawaiian Shave Ice in Kihei—kids love the li hing mui or mango. Early night.

Day 2: Aquarium Morning + Snorkel Afternoon

Morning: Breakfast at Kihei Caffe (banana-mac pancakes, loco moco) or Sugar Beach Bake Shop (malasadas, lilikoi bars). Head to the aquarium: Maui Ocean Center All Day Admission in Maʻalaea lets kids see live corals, green sea turtles, and the walk-through tunnel. Expect 1.5–2 hours.

Afternoon: Join the Maui Afternoon Snorkel Aboard Malolo to either Molokini Crater or Coral Gardens (about 3 hours, typically from ~$90–$120 per adult; kids often discounted). Crew provides gear, flotation, and tips—ideal for first-time snorkelers.

Evening: Wailea dinner at Monkeypod Kitchen (happy hour for budget-friendly pizzas and pies). Walk a stretch of the Wailea Beach Path at sunset; look for honu (sea turtles) bobbing offshore. Back to Kihei for rest.

Day 3: Upcountry Pineapples → Transfer to Kaanapali (45–60 min)

Morning: Check out and point the car toward Upcountry. Grab pastries at Komoda Store & Bakery in Makawao (stick donuts are famous). Then tour a working plantation on the Maui Pineapple Farm Tour in Hali‘imaile—fun history, fields, and juicy samples (about 1.5–2 hours; commonly ~$75–$85).

Afternoon: Drive to Kaanapali (aim to arrive by 2–3 pm). Check in to a kitchen-equipped villa at The Westin Ka'anapali Ocean Resort Villas, browse Hotels.com Kaanapali, or a family condo via VRBO Kaanapali. Unwind at Kahekili Beach Park (north Kaanapali)—often less crowded, with easy parking and showers.

Evening: Wander Whalers Village. Dinner at Hula Grill’s Barefoot Bar (grilled fresh catch, kids burgers) or Leilani’s on the Beach (huli huli chicken, fish with macadamia nut crust). Watch the Black Rock cliff-diving ceremony at dusk.

Day 4: West Maui Beaches + Whale Watching (in season)

Morning: Coffee and acai bowls at Island Vintage Coffee (Whalers Village). Walk the Kapalua Coastal Trail for tide pools and blowhole‑like spray on windy days; or play in the gentle water at Napili Bay (arrive by 8 am for parking with kids).

Afternoon: From Dec–Apr, book the small‑group VIP Premiere Whale Watch Kaanapali (max 12 passengers; ~2 hours). Naturalists explain breaching and tail slaps; kids can listen to whale songs via hydrophone when conditions allow.

If you’re visiting outside whale season, opt for the Open-Air West Maui Sightseeing Tour instead for coastal lookouts.

Evening: Casual dinner at Duke’s Beach House (fish tacos, kids pasta) or Joey’s Kitchen (Napili Plaza; Filipino-Hawaiian plates at friendly prices). Ice cream stroll on the Kaanapali Beachwalk as the sky turns cotton candy.

Day 5: Last-Dip Morning → Depart

Morning: Early breakfast at Castaway Cafe (oceanfront omelets) or Java Jazz in Honokōwai (big menu, local art). Squeeze in a final swim at Kaanapali Beach or an easy snorkel at Kapalua Bay (hug the inside reef, watch currents). Rinse off and pack.

Afternoon: Drive 50–60 minutes to OGG. Return your car and grab snacks for the flight. If you need flights or last‑minute changes, check Trip.com or Kiwi.com.

Evening: Wheels up. Swap photos and plan a return during whale season if you visited in summer—or vice versa to try calmer ocean months.

Money-saving tips for families: Book a condo with a kitchen (VRBO has many) to handle breakfasts and easy pasta nights; pack a soft cooler for beach picnics from Foodland or Safeway; arrive at beaches before 9 am to secure free parking; and carry rash guards to cut sunscreen use.

Ocean safety basics: When in doubt, don’t go out; stick to lifeguarded beaches (Kamaole), watch for strong shorebreak at Big Beach, and keep kids within arm’s reach in the water. Always use reef-safe sunscreen and never stand on coral.