Maui & Oahu Vacation Package: 9 Days Sheraton Maui & OUTRIGGER Waikiki Beachcomber

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This Maui and Oahu vacation package starts on Kaʻanapali Beach at Sheraton Maui Resort & Spa, then hops to Honolulu for three nights at OUTRIGGER Waikiki Beachcomber Hotel — ocean-view rooms on both islands, a full-size car on Maui with taxes included, and West Coast air. Sample stay dates below are January 10–18, 2027. Book any dates inside the travel window.

Suggested 9-Day Family Itinerary

Sample dates: January 10–18, 2027 (5 nights Maui + 3 nights Waikiki). Other dates inside the travel window can be quoted.

• Day 1 — January 10, Arrive Maui (OGG): Land at Kahului, pick up the full-size car, and drive to Kaʻanapali Beach. Check in at Sheraton Maui Resort & Spa (Oceanview Room Two Doubles). Walk Black Rock and watch sunset from the lanai.
• Day 2 — January 11, Black Rock & pool day: Snorkel Puʻu Kekaʻa, then spend the afternoon in the lagoon pool and keiki pool. Use the $100 daily dining credit for lunch or dinner on property.
• Day 3 — January 12, Kaʻanapali & Lahaina: Resort shuttle to Whalers Village or a scenic drive into Lahaina for shave ice, shopping, and dinner.
• Day 4 — January 13, West Maui outing: Drive toward Kapalua or Napili, or book a family snorkel sail. Return for the nightly torch lighting and cliff dive at Black Rock.
• Day 5 — January 14, Maui beach day: Last full day at Sheraton Maui — beach, spa, or cultural activities. Pack for the morning island hop.
• Day 6 — January 15, Maui to Honolulu: Return the full-size car at Kahului Airport. Inter-island flight OGG to HNL, then transfer to OUTRIGGER Waikiki Beachcomber Hotel. Check in to an Ocean View room with two double beds.
• Day 7 — January 16, Kualoa Ranch Secret Island: Use the included Kualoa Ranch Secret Island Full Day Experience — buy one, get one free. Afternoon back in Waikiki for dinner and a beach walk.
• Day 8 — January 17, Waikiki: Sleep in, swim, shop Kalākaua Avenue, or take the kids to the Honolulu Zoo or Waikiki Aquarium — all an easy walk or short ride from the Beachcomber.
• Day 9 — January 18, Departure: Check out of the Beachcomber and depart Honolulu (HNL).

Oceanview Room Two Doubles — Sheraton Maui Resort & Spa

Featured Maui room for 2 adults and 2 children — an Oceanview Room with two doubles and a private lanai on Kaʻanapali Beach at Black Rock.

• Location: Kaʻanapali Beach, Maui
• Check-in January 10, 2027 · check-out January 15, 2027 (5 nights)
• Oceanview Room Two Doubles
• $100 dining credit per room, per night
• Resort fees waived
• Every Sheraton Maui room has a private lanai

Sheraton parking is extra and paid at the hotel (self-park or valet; rates change). Ask Theresa to confirm current parking when you book.

Ocean View, 2 Double Beds — OUTRIGGER Waikiki Beachcomber Hotel

Featured Oahu room for 2 adults and 2 children in the heart of Waikiki — an Ocean View guest room with two double beds at OUTRIGGER Waikiki Beachcomber Hotel.

• Location: Waikiki, Honolulu, Oahu
• Check-in January 15, 2027 · check-out January 18, 2027 (3 nights)
• Ocean View — 2 double beds
• Kids stay free — no extra guest charge for children under 18 using existing beds in a paying adult’s room
• Save up to 35% (already in the package rate) plus Kualoa Ranch Secret Island Full Day Experience buy-one-get-one-free

Kualoa Ranch Secret Island Full Day Experience

This package includes a buy one, get one free ticket to Kualoa Ranch’s Secret Island — a private beach on Kaneohe Bay reached by boat. The full-day experience typically runs about 9:30 am to 4:00 pm.

What’s included with your Secret Island ticket:

• Boat ride across Kaneohe Bay to a private beach
• Kayaks, stand-up paddleboards, and a Hawaiian canoe
• Beach volleyball, table tennis, horseshoes, and cornhole
• Hammocks (first-come)
• Box lunch and bottled water
• Showers and changing rooms

Bring a towel, reef-safe sunscreen, swimsuit, and water shoes. Glass is not allowed. Children 17 and under must be with an adult.