Our 6-Day Maui Itinerary: A Slow, Romantic Week in Wailea

Last Updated on October 28, 2026 by Lauren Belzer Sanford

Sometimes when life hits you like a ton of bricks, you have to crawl out from under them and go on a vacation.

In June 2022 I was laid off and started the hunt for a new role. Anyone who’s been there knows the job search is a full-time job in itself, and after months of interviews, I needed a break. Max and I had both been to Maui with our families growing up, but never together. He had flexible PTO and my calendar was suddenly wide open, so we planned it about a month out, and on November 1, 2022, we were on our way.

A warning before we begin: this was a relaxation trip. We spent most of our time at the beach and the pool, sipping cocktails, trying wonderful restaurants, and taking it slow. When you spend on a resort, you want to enjoy it. Here’s our 6-day Maui itinerary.

Update: We went back to Maui in late spring for our first wedding anniversary and stayed at the same resort. Everything from that trip, including the new Olakino pool experience, is in my guide to where to stay in Maui.

This 6-day Maui itinerary is built for a slow, romantic trip on the south shore: base yourself at Wailea Beach Resort, spend two or three days between the pools and Ulua and Wailea beaches, book one sunset sail to Molokini Crater, rent a car for a single day trip up the west side and to the black sand beach at Oneʻuli, and save a celebratory dinner for Spago at the Four Seasons and Nick’s Fishmarket at the Fairmont Kea Lani.

Day 1: Arrival & Pool Day

If you’ve flown to the Hawaiian islands from the West Coast, you know it takes a while. We flew out of LAX, and the best part is the “time travel.” We took off around 8 a.m. Pacific, spent about five and a half hours in the air, and landed close to 11 a.m., so it hardly felt like we’d lost the day. Search flights to Kahului (OGG) on Expedia.

From the Kahului airport (OGG), we took an Uber to Wailea Beach Resort. One thing it does that I wish every hotel would: an arrival lounge for guests who land before check-in. We were greeted with fresh POG juice, changed into our swimsuits, and went straight to the pool while the front desk held our bags. We spent the afternoon getting to know the property, wandering and taking in the views. If you’d like to stay where we did, the links below book a room at Wailea Beach Resort.

Once we’d checked in and freshened up, we walked down the beach to the Four Seasons Resort Maui early for a drink with a view before dinner at Spago. Spago was our favorite restaurant of the trip and maybe one of our favorites ever. If it’s on the menu, order the seafood red Thai coconut curry; it’s incredible. More of our favorite meals are in my guide to the best restaurants in Maui.

Day 2: Resort Day

On our first full day, we barely left the resort until dinner. Breakfast was at Humble Market Kitchin by Roy Yamaguchi, with both a buffet and à la carte. Whichever you choose, order the coconut macadamia nut pancakes with haupia cream, toasted coconut, and brûléed pineapple. And don’t skip the fresh tropical juices.

We spent nearly the whole day at the Maluhia Pool, the resort’s adults-only infinity pool. You can rent a cabana, but since we kept hopping between the pool and the beach, we simply went out around breakfast to claim chairs and never had trouble. The resort was building its Olakino Wellness Experience while we were there; we finally tried it on our second trip, and my honest take is in my Maui hotel guide. Visiting in early November meant we weren’t competing with many people anywhere on the resort.

In the afternoon we wandered down to Ulua Beach for a dip. It’s a smaller beach, so it stayed calm and uncrowded, and it became our favorite.

After a day of mai tais and mojitos, we walked up the hill for dinner at Matteo’s Osteria. A tip: the resort has a shuttle within Wailea, and I’d use it. The walk is farther than it looks on the map, and it’s all uphill.

Day 3: Beach Day

The next morning we slept in as much as the time change allowed, then grabbed coffee and breakfast at Whale’s Tale on the property.

We spent the first half of the day on Wailea Beach. Resort loungers need to be reserved early (we forgot), so we laid out our towels and enjoyed the sand and warm water. It’s shared by a few resorts and livelier than Ulua, so after a while we headed back to the Maluhia Pool for the rest of the afternoon.

After a refresh, we called the resort shuttle (lesson learned) up to Monkeypod Kitchen for an early dinner. We only planned on appetizers, but we befriended the bartender and a few people at the bar and stayed for far more than the famous mai tais. Don’t miss the seared ahi. We took the shuttle back and spent the evening walking the beach path.

Day 4: Pool Day & Sunset Sail

After breakfast, we walked the Wailea Beach Path south to where the hotels give way to residences. The viewpoints were stunning, especially looking up the hill, and the best surprise was the cats in the bushes along the way; one even came out to say hello.

We spent most of the day at the family-friendly ʻOhi Pools, which were still peaceful in November, and went back to Ulua for a while because we’d loved it so much.

That evening was our sunset sail with Kai Kanani, which we’d booked through the hotel concierge on our first day. Most boats leave from farther north, but Kai Kanani beach-loads just south of Wailea and arranged pickup and drop-off at our resort. The crew was wonderful (great service, delicious small bites, drinks), and they took us out to Molokini Crater. The sunset from the water was stunning, and aside from getting a little wet loading and unloading on the beach, it was perfect.

Since we’d only had small bites on the boat, we grabbed dinner at Humble Market Kitchin. I was so sleepy from my Dramamine that I nearly dozed off at the table, so we called it an early night.

Day 5: A West-Side Day Trip & the Black Sand Beach

On our last full day, we grabbed coffee at the resort’s Starbucks and picked up a Turo rental in Kihei for the day. (Prefer a traditional rental? Book a car at Kahului (OGG).)

We drove up to Lahaina, found street parking, and wandered the shops along the water. We had lunch at Paia Fish Market and shopped around Lahaina Town, where I found my all-time favorite pale yellow sweatshirt (I still wear it constantly).

Much of what we saw and enjoyed in Lahaina was lost in the August 2023 wildfires. If you’d like to support Paia Fish Market, you can visit its other locations in Paʻia and Kihei on Maui, and on Oʻahu.

On the way back, we stopped in Kihei at Lava Java Coffee Roasters, right next to Paia Fish Market’s Kihei location, for an afternoon pick-me-up. With a little time before returning the car, we drove south to Oneʻuli Beach (also called Naupaka Beach) to see the black sand. It was busy, so we parked along the road and walked in, but it was so worth seeing.

Back at the resort, we took sunset photos and had drinks at KAPA Bar & Grill, using the welcome-drink coupons from check-in that we’d forgotten until our last night (a farewell drink instead). We’d both been to luaus with our families, so we skipped one this trip, but we strolled past the resort’s Te Au Moana Luau and caught a glimpse. If it’s your first time, the Feast at Mōkapu at the Andaz is one of the best on the island.

Our final dinner was at Nick’s Fishmarket Maui at the Fairmont Kea Lani. We took the shuttle down early for a drink at the bar, then sat looking out across the property to the ocean, with a warm breeze, a wonderfully energetic server, and a delicious meal. The perfect end to the trip. We strolled the grounds afterward, then rode back for a nightcap at our resort.

Day 6: Shopping & Departure

Our flight wasn’t until the afternoon, so we went up to The Shops at Wailea for coffee and last-minute shopping (Honolulu Cookie Company, plus a home store where I first spotted a market bag I loved). Then we said “a hui hou kākou” to this beautiful island and headed to the airport.

We loved Maui so much that we went back, and you can read about that trip in my Maui hotel guide.