Winter is one of the best times of year to be in South Maui, and if you are planning a trip between November and March, this guide to things to do in Kihei will help you make the most of it. The weather stays warm and mostly dry on this side of the island, humpback whales return to the channel right off the beach, and the holidays bring a relaxed, local kind of celebration that feels very different from the mainland.
Our Midway Vacations team lives and works here (our Kihei office is at the Kama’ole Shopping Center on South Kihei Road), so these are the same tips we share with our own friends and family when they visit.
Why Kihei Is a Smart Winter Base
Kihei sits on Maui’s leeward (dry) side, which means it gets far less rain than Hana or the North Shore. Winter daytime highs typically sit in the upper 70s to low 80s, with cooler, comfortable evenings. While big winter swells pound the north-facing shores, the south shore is often calmer in winter, which makes it a great base for families, snorkelers and anyone who simply wants an easy beach day.
Kihei is also central. From here, it is a short drive to Wailea, Ma’alaea Harbor, Kahului Airport and the road up to Haleakala. You get a laid-back beach town feel without being far from the rest of the island.
Things to Do in Kihei This Winter
1. Watch for Humpback Whales from Shore
Humpback whale season is the headline act. According to NOAA’s Hawaiian Islands Humpback Whale National Marine Sanctuary, the whales visit Hawaiian waters from November through April, with peak season from January through March. The shallow, protected waters between Maui, Lanai and Kahoolawe are one of their favorite places to breed, calve and nurse, and Kihei looks right out over that channel.
You do not need a boat to see them. Bring binoculars to any beach park along South Kihei Road in the morning, when the water is usually calmest, and watch for blows and breaches. For a closer look, book a whale watch out of Ma’alaea or the Kihei boat ramp. Our full guide to whale watching in Oahu and Maui covers tours, etiquette and what to expect.
Federal rules require boats and people to stay at least 100 yards from humpback whales in Hawaii, so give them their space and let them come to you.
2. Spend Lazy Days at the Kamaole Beach Parks
Kamaole Beach Parks I, II and III are the heart of Kihei beach life. They have soft sand, lifeguards, restrooms, showers and grassy areas for picnics. Mornings are typically calmer for swimming and snorkeling along the rocky points, and afternoons tend to bring more wind. Keawakapu Beach, at the south end of town, is a longer, quieter stretch that is perfect for a sunset walk.
For more ideas up and down the coast, see our guide to South Maui’s best beaches.
3. Snorkel Molokini or Turtle Town
Morning snorkel tours to Molokini Crater and the reef areas south of Wailea run year round, and in winter you may hear whale song underwater or spot whales on the ride out. Book a morning departure for the best conditions and ask the operator about reef-safe sunscreen. Hawaii law bans the sale of sunscreens containing oxybenzone and octinoxate, and mineral options are kinder to the reef.
4. Walk the Kealia Pond Boardwalk
Kealia Pond National Wildlife Refuge, at the north end of Kihei, is a peaceful break from the beach. The coastal boardwalk along North Kihei Road has interpretive signs and views across the wetlands, where you may spot native birds like the Hawaiian stilt (ae’o) and Hawaiian coot (alae ke’oke’o). Winter is a good time for birding, as migratory shorebirds spend the season here too.
5. Catch a Haleakala Sunrise or Sunset
The drive up Haleakala is one of Maui’s signature experiences. Sunrise viewing at the summit requires an advance reservation through Recreation.gov, and spots go quickly in winter. Pack real layers. It can be near freezing at the summit before dawn, even when Kihei is in the 60s. If early mornings are not your thing, sunset does not require the sunrise reservation and is every bit as beautiful.
6. Paddle or Surf at The Cove
Kalama Park and The Cove at the south end of Kihei are known for gentle waves that make them a favorite for beginner surf lessons and stand-up paddleboarding. Several local surf schools operate nearby and provide boards and instruction.
Winter Events Worth Planning Around
Here are a few events on the Maui calendar this season. Dates can change, so always confirm with the organizer before you build your trip around one.
- Made in Maui County Festival (November 6 and 7, 2026): A celebration of locally made food, art, gifts and products at the Maui Arts and Cultural Center in Kahului. Great for holiday shopping that supports local makers.
- Maui Invitational (November 23 to 25, 2026): The well-known college basketball tournament returns to the Lahaina Civic Center in West Maui over Thanksgiving week.
- Thanksgiving (November 26) and the December holidays: Expect busier restaurants and higher demand. Reserve dinners and rental cars early.
- Maui Oceanfront Marathon (January 17, 2027): The course starts at The Shops at Wailea and runs along the South Maui coast, so expect some road impacts in Kihei that morning.
- Great Whale Count (late January 2027): Volunteers count whales from shoreline sites around Maui. It is a fun, community way to take part in whale season.
Holiday Tips for a Smooth Kihei Trip
The weeks around Thanksgiving, Christmas and New Year’s are some of the busiest of the year on Maui. A little planning goes a long way.
- Book early. Holiday weeks and whale season fill up. If your dates are set, lock in your stay and rental car as soon as you can.
- Plan a few meals at home. A condo with a full kitchen makes holiday meals easy, and grocery stores in Kihei carry everything you need for a Hawaii-style Thanksgiving or Christmas dinner.
- Get on the water early. Winds usually pick up after midday, so schedule snorkel and paddle outings for the morning.
- Respect the places you visit. Stay off reefs, keep your distance from turtles and monk seals, and follow posted signs. Maui is still healing from the 2023 wildfires, and visitors who travel with care and support local businesses make a real difference.
Looking for restaurant ideas? Our Things to Do on Maui guide and Maui restaurants page are good places to start.
Where to Stay in Kihei
Midway Vacations manages condos across Kihei, including properties at Maui Banyan across from Kamaole Beach Park II, Kihei Ali’i Kai near Kamaole Beach Park I, Kamaole Sands on South Kihei Road and the oceanfront Maui Sunset. Staying in a condo gives you more room than a hotel, a kitchen for easy breakfasts before an early whale watch, and a lanai to enjoy the evening trade winds.
Because our team is right here in Kihei, you have local help before and during your stay, whether you need a dinner recommendation or a hand with check-in.
Plan Your Winter Escape
From whale watching right off the beach to holiday dinners on your lanai, there is no shortage of things to do in Kihei between now and spring. The trick is to book early, plan your ocean time for the mornings and leave room to simply slow down.
Ready to find your place in the sun? Browse our Maui vacation rentals and book your Kihei stay directly with Midway Vacations. If you have questions about a specific condo or dates, contact our team and we will be happy to help. A hui hou!
