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Maui Itineraries

Since 2012, guests have asked us what to do with their week. These are five plans you can follow from our lanai, and each one starts and ends in Kihei.

Photo: Jonathanking, CC BY-SA 3.0
Photo: Peckphotographyart, CC BY-SA 4.0

01

3 Days in Maui

Three days is not enough Maui — but planned from a Kihei base with zero wasted driving, it is enough to fall permanently in love.

See the day-by-day plan →
Photo: Jonathanking, CC BY-SA 3.0

02

5 Days in Maui

Five days unlocks the big three — the volcano, the Hana road, the west side — and still leaves sand time between them. This is the trip we would book ourselves.

See the day-by-day plan →
Photo: Forest and Kim Starr, CC BY 3.0 US

03

7 Days in Maui

A week is when Maui stops being a checklist and starts being a rhythm — this plan schedules the sights AND the sacred do-nothing day.

See the day-by-day plan →
Photo: Peckphotographyart, CC BY-SA 4.0

04

The Maui Honeymoon

The clichés exist because they work — sunrise above the clouds, champagne at golden hour, a table at Mama's. The trick is sequencing them with room to breathe in between.

See the day-by-day plan →
Photo: Brocken Inaglory, CC BY-SA 3.0

05

Maui With Kids

The secret to Maui with kids is embarrassingly simple: lifeguarded sand in the morning, shade and naps after lunch, shave ice as currency — and one big adventure every OTHER day.

See the day-by-day plan →

The five plans side by side

PlanLengthDay by day
3 Days in Maui3 days
  1. Land soft: Kamaole afternoon, sunset dinner
  2. Haleakala sunrise, upcountry morning, afternoon flat on the sand
  3. Snorkel morning, Wailea golden hour, one great dinner
5 Days in Maui5 days
  1. Arrival: groceries, Kamaole, first sunset
  2. Haleakala sunrise + upcountry, afternoon recovery
  3. The Road to Hana, done right
  4. West side: Kapalua coast, Napili, an evening in Lahaina's north end
  5. Molokini morning, Wailea finale
7 Days in Maui7 days
  1. Arrive, provision, first swim, first sunset
  2. South-shore mastery: snorkel, beaches, Wailea path
  3. Haleakala sunrise + upcountry loop
  4. The Road to Hana (the unhurried version)
  5. The Do-Nothing Day
  6. West side: Kapalua trail, Napili, Nakalele, Lahaina's north end
  7. Molokini finale + the goodbye dinner
The Maui Honeymoon6 days
  1. Arrive, exhale, first sunset barefoot
  2. Beach-hop audition + the Wailea golden hour
  3. Sunrise above the clouds, upcountry lavender, afternoon nap
  4. The do-nothing day (the actual honeymoon)
  5. West-side romance: Kapalua coast, Napili, sunset sail
  6. Turtle Town morning + the Mama's Fish House finale
Maui With Kids6 days
  1. Land, provision, first beach, early night
  2. The perfect Kihei family day (template — you will repeat it)
  3. Turtle day: Maluaka snorkel + whale sanctuary stop
  4. The mountain, kid-sized: crater lookout + upcountry
  5. Boat day OR the Hana sampler (pick by ages)
  6. Free-choice finale + the family goodbye dinner

Why every plan starts in Kihei

Kihei sits in the middle of Maui’s south shore, so the things most guests do more than once are close. Sugar Beach is across the street, the Kamaole beach parks are about ten minutes south, Kealia Pond’s boardwalk is five minutes up North Kihei Road, and the Molokini snorkel boats leave from harbors about ten minutes away.

The big days start from the same door. The Road to Hana begins in Paia, about 45 minutes north; the Kapalua Coastal Trail in West Maui is about 55 minutes; and Haleakala sunrise is an early-morning drive up through Kula. The table above shows which day of each plan takes which drive, so you can swap days around the weather or your reservation dates.

Every plan leaves room for the bookings that sell out: the $1 Haleakala sunrise reservation on recreation.gov, which opens 60 days ahead, and the Wai’anapanapa parking reservation on the Road to Hana. If you only have three days, the 3-day plan skips Hana on purpose; our best time to visit guide helps you pick the week.

Stay With Us

Stay steps from Sugar Beach

Four beachside bungalows in North Kihei, hosted by Megan & Bryan since 2012.