Late afternoon at Ali’i Kula Lavender Farm, the air cools as the sun drops toward the ocean. From 3,600 feet up on Haleakala’s western slope, the whole South Shore stretches out below — Kihei, Wailea, Makena, and the blue line of the Pacific beyond. That view, with lavender rows in the foreground and beach towns in the distance, is the best argument I know for splitting your Maui trip evenly between Upcountry and the coast. Most visitors pick one or the other. This 6-day itinerary gives both the time they deserve.
Designed for first-time visitors and return trippers who skipped the high country, this route pairs South Maui’s reliable beaches and snorkeling with Upcountry’s cooler air, small-town character, and farm-driven food scene. You’ll base yourself in Kihei or Wailea for the whole trip and drive upcountry on alternating days. The towns, ranches, and farmlands on Haleakala’s slopes are close enough to the coast that you can be at a Kula food truck 45 minutes after leaving your hotel.
Upcountry Maui’s elevation, ranging from roughly 1,500 to 4,000 feet, means temperatures typically run 10–15°F cooler than the coast — a genuine relief on hot afternoons.
This itinerary works best for travellers who want to split their time between beach activities and exploring Maui’s agricultural highlands. It’s not the right fit if you’re set on spending every day on the water — consider a West Maui or full-coast itinerary instead. The key trade-off is driving time: Upcountry loops require 30–60 minutes each way from South Shore hotels, but the scenery and smaller crowds make it worth it.
First-time visitors
Families with older kids
Return trippers who missed Upcountry
| Day | Where | What | Time Needed | Key Tip |
|---|---|---|---|---|
| 1 | South Shore | Arrival, Wailea Beach, sunset dinner | Half-day | Book a 4:30 p.m. dinner reservation — sunset is around 6:00 p.m. |
| 2 | Upcountry | Makawao, Kula, Lavender Farm, Dairy | Full day | Komoda Bakery closes at 2:00 p.m. and is closed Sunday and Wednesday |
| 3 | Upcountry | Haleakala National Park, Paia | Full day | No sunrise reservation needed if you arrive after 7:00 a.m. |
| 4 | South Shore | Molokini snorkeling, Makena Beach | Full day | Book the early morning snorkel tour — afternoon winds pick up |
| 5 | South Shore + Upcountry | La Perouse Bay, sunset at Lavender Farm | Full day | Bring a jacket for the evening drive upcountry — it drops 15°F fast |
| 6 | South Shore | Last beach morning, departure | Half-day | Allow 45 minutes from Kihei to Kahului Airport (OGG) |
Day 1: Settling into the South Shore
Your first day is about shifting gears. After landing at OGG, pick up your rental car and head straight to your hotel in Kihei or Wailea. The drive is short — roughly 20 minutes — and the South Shore’s dry, leeward climate means you’ll likely see blue skies even if it’s raining elsewhere on the island.
Drop your bags and head to Wailea Beach or Kamaole Beach Park in Kihei. Both have calm, swimmable conditions in the afternoon. The sand is soft, the water is clear, and there’s enough shade from the beachside trees to keep the little ones comfortable. Spend an hour just floating — you’ve earned it.
Walk to a restaurant within resort distance — places like Wailea’s oceanfront dining options fill up fast. Reserve a table for 4:30 p.m. to catch the sunset around 6:00 p.m. without rushing. The kids can order early, and you’ll be back at the room by 7:00 p.m. for an easy first night.
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If you’re arriving on a late flight, skip the sit-down dinner and grab takeout from a local market instead. The first night is about rest, not a culinary tour.
Day 2: Upcountry Towns and Farm Stops
This is the day that flips your idea of Maui on its head. Upcountry looks nothing like the coast — rolling green hills, eucalyptus groves, and working ranches replace the palm trees and condos. The air smells like dirt and grass, and the pace is slower.
Start at Baked on Maui in Haiku for shakshouka or grab a guava malasada from Komoda Store & Bakery on Baldwin Avenue in Makawao. Komoda closes at 2:00 p.m. and is closed Sunday and Wednesday, so plan accordingly. Then spend an hour wandering Baldwin Avenue — the galleries and shops are worth the stop.
Drive up to Kula and spend an hour at Ali’i Kula Lavender Farm at 1100 Waipoli Road. The gardens are terraced on the slope, with views that stretch to the ocean. Lily loved the lavender lemonade, and Ethan was fascinated by the bees working the rows. The farm is compact enough that you don’t need a full afternoon — one hour is plenty.
In the parking lot of the Kula Longs Drugs (CVS), you’ll find Stewz Burgers, Thai Mee Up, and a wood-fired pizza truck. The picnic tables are shaded by palms, and the roosters keep things entertaining. It’s the kind of low-key lunch that works for everyone — no reservations, no wait.
Head to Surfing Goat Dairy at 3651 Omaopio Road for the afternoon tour. The goats are friendly, the cheese samples are generous, and the property has a relaxed farm feel. The drive from the lavender farm takes about 15 minutes. From the dairy, it’s roughly 35 minutes back to Wailea.
Day 3: Haleakala Summit and Paia
Haleakala National Park is the crown of Upcountry, and you don’t need a 3:00 a.m. alarm to enjoy it. Midday at the summit has warmer temperatures, fewer crowds, and the same staggering views of the crater.
From Wailea, the drive to the Haleakala summit takes about 1 hour 45 minutes. The road gains 10,000 feet in elevation, so pack a jacket — summit temperatures hover in the 40s and 50s even in summer. No sunrise reservation is needed if you arrive after 7:00 a.m., and the parking lot is easier to navigate later in the morning.
The Sliding Sands Trail descends into the crater from the summit. You don’t need to go far — even a 20-minute walk down and back gives you a sense of the scale. The trail is sandy and unstable in places, so wear sturdy shoes. Ethan counted seven nene geese on our walk, which was a highlight for him.
Drive down the mountain to Paia, the windsurfing town on the North Shore. Grab lunch at Paia Fish Market for casual seafood or Tinroof Maui for a quick plate lunch. Paia is small and walkable — you can cover the main street in 20 minutes.
If you have energy left after lunch, this family-friendly Hawaii itinerary has a similar structure and adds a few more kid-centric stops around Paia. Otherwise, head back to the hotel for a swim and an early dinner.
Day 4: Snorkeling the South Shore
The South Shore is Maui’s best snorkeling coast, and Day 4 is all about getting in the water. The leeward side has calmer conditions than the north or west, especially in the morning.
Book a half-day tour to Molokini Crater, a volcanic caldera about 3 miles off the coast. The water inside the crater is calm and clear, with good visibility for beginners. Tours depart from Ma’alaea Harbor and typically run from 7:00 a.m. to 12:00 p.m. The early departure is key — afternoon winds stir up the channel and make the ride back choppy.
After the tour, pick up a casual lunch in Kihei and head to Makena State Park (Big Beach) for the afternoon. The sand is wide and golden, and the waves are gentle enough for swimming. The park has portable toilets and limited shade — bring an umbrella. Entry is $5 per vehicle.
Walk off the sand and into a restaurant in Wailea for an early dinner. Many places let you book same-day for 5:00 p.m. tables. The kids will be tired from a full day in the sun, so keep it simple — a pizza place or casual grill works better than a long tasting menu.
Day 5: Lava Fields and Evening Upcountry
Day 5 splits its time between the South Shore’s wilder side and a return to Upcountry for a sunset perspective. It’s a longer day, but the variety keeps it from feeling rushed.
Drive south past Wailea to the end of the paved road at La Perouse Bay. The lava fields here are the youngest on Maui, and the shoreline is rugged and dramatic. The trail along the coast is flat but rocky — good for a 30-minute walk. The parking lot is small, so arrive before 9:00 a.m.
Head back to Kihei for lunch and a couple of hours at Kamaole Beach Park III. The beach has a grassy area that’s perfect for a break between swimming sessions. Grab a plate lunch from a local market and eat on the sand.
Drive back upcountry in the late afternoon for sunset at the lavender farm. The farm closes at 5:00 p.m., so check the current hours before you go. The light at that hour is soft and golden, and the view of the coast from 3,600 feet is unbeatable. Bring a jacket — the temperature drops fast once the sun goes down.
If you’re short on time, skip La Perouse Bay and spend the full day at the beach. The lava fields are unique, but they require a 45-minute drive each way from Kihei, and the exposure is unshaded.
Day 6: Last Morning on the Beach
Your last day is a short one. The goal is to squeeze in one more beach session before heading to the airport.
Pick your favorite beach from the week and go early. The South Shore beaches are quietest between 7:00 a.m. and 9:00 a.m., and the water is glassy. This is the moment to take a last swim, collect a few shells, and soak in the view.
Grab a coffee and pastry at a local cafe in Kihei before heading to OGG. The drive to the airport takes about 45 minutes from Kihei and 30 minutes from Wailea. Factor in rental car return time and security — Kahului Airport can get busy mid-morning, especially on weekends.
Getting Around South Maui and Upcountry
Transportation is the biggest practical consideration for this itinerary. The South Shore and Upcountry are connected by a single road — Highway 37 — which winds up the mountain from Kihei. The drive is straightforward but winding in places, and the elevation gain is noticeable.
| Route | Drive Time | Road Conditions | Tip |
|---|---|---|---|
| Kihei → Makawao | 30 min | Paved, two-lane, winding | Take Highway 37 — avoid narrow back roads |
| Kihei → Haleakala Summit | 1 hr 45 min | Paved, steep, switchbacks | Check brake condition before descending |
| Kihei → Ma’alaea Harbor | 15 min | Flat, straight, light traffic | Arrive 30 min before tour departure |
| Kihei → OGG Airport | 45 min | Highway, moderate traffic | Allow extra time during morning rush |
If you’re still weighing which side of the island to sleep on, this interactive map of the island’s hotels and rentals makes it easier to compare options against the beach or the trailhead. Kihei offers more budget-friendly condos and shorter drives to Upcountry, while Wailea has resort amenities and quieter beaches.
Rental car companies on Maui have gotten stricter about off-road driving. If you take a car down a rough dirt road (like the back side of Haleakala), the insurance may not cover the damage. Stick to paved roads for this itinerary.
Before You Go: Maui Upcountry and South Shore Questions Answered
Do I need a 4WD for Upcountry?
No. All the stops in this itinerary are on paved, well-maintained roads. A standard sedan works fine. The road to Ali’i Kula Lavender Farm is narrow but paved, and the Haleakala summit road is fully paved all the way to the top.
Can I do Upcountry and the Road to Hana in the same trip?
You can, but it’s tight. The Road to Hana takes a full day, and the drive is exhausting. If you want to add it, swap Day 5 for a Hana loop and skip La Perouse Bay. Just know that Hana pulls you away from the South Shore for a full day, which breaks the balance of this itinerary.
What’s the worst time of year for this itinerary?
December through February brings more rain to Upcountry, and the summit of Haleakala can see snow. The South Shore stays drier, but the higher surf can make swimming less safe. If you’re visiting in winter, check the ocean conditions daily and be flexible with beach plans.
Is the South Shore good for beginner snorkelers?
Yes. The South Shore has the calmest conditions on the island, especially in the morning. Molokini Crater is sheltered, and the beach entries at Kamaole and Makena are gradual. Avoid swimming near the lava rock points at La Perouse Bay — the current can pick up suddenly.
What’s the biggest downside of basing in South Maui?
The drive to Upcountry is 30–60 minutes each way, and you’ll do it three times in this itinerary. If you’re prone to motion sickness, the winding roads might be an issue. Consider staying in a central location like Kahului if you want to reduce drive times, but you’ll lose the easy beach access.
Upcountry and South Shore, Balanced
Most Maui itineraries ask you to choose between the beach towns and the high country. This one doesn’t. By alternating days between the two, you get the full range of what the island offers — snorkeling in the morning, farm visits in the afternoon, and a sunset that changes depending on which side of the mountain you’re on. If you’re interested in other ways to structure a Hawaii trip, designing your Hawaii trip around the North Shore offers a completely different angle worth considering.
References
Hawaii Guide. “6-Day Maui Itinerary: East Maui Coast, West Maui, Haleakala & Upcountry, South Maui, Central & North Maui.” Hawaii Guide, 2024. ↗
Ribbon Rock Maui. “Upcountry Maui Itinerary: How to Spend a Perfect Day in Upcountry Maui.” Ribbon Rock Maui, 2024. ↗
Discovering Hidden Gems. “The Ultimate Maui 6 Day Itinerary — 6 Days in Maui.” Discovering Hidden Gems, 2024. ↗
If this itinerary clicked with you, the family Hawaii itinerary that keeps everyone happy and sane covers similar ground with more kid-tested stops, and the wellness-focused Hawaii itinerary for mind and body reset takes a slower, restorative approach to the same regions. Both pair well with the pacing laid out here.
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