Kauai, Maui & Oahu Family Vacation — 11 Days

We have contracts nationwide — request a customized quote for your departure airport and travel dates.

This Kauai, Maui & Oahu family vacation is 10 nights / 11 days for 2 adults and 3 children — 4 nights at Hilton Vacation Club The Point at Poipu, 3 nights at Aston Kaanapali Shores, and 3 nights at Hilton Hawaiian Village Waikiki Beach Resort, with Alaska Airlines from SAN (also quoted from LAX, SEA, SFO, and OAK), inter-island hops, and an SUV on Kauai and Maui.

Sample itinerary below uses June 25 – July 5, 2027. Other dates in the January 15 – August 31, 2027 window are quoted on request. Blackout 12/23/26 – 1/3/27 at Aston Kaanapali Shores.

Itinerary

Sample dates June 25 – July 5, 2027 — 10 nights, 11 days for 2 adults and 3 children. Other dates in the travel window are quoted on request.

Days	Stay	Notes
Day 1	Fly SAN → LIH · The Point at Poipu	Alaska Airlines · 11:50 a.m. – 3:09 p.m. · 6 hr 19 min
Days 1–4	Kauai · The Point at Poipu	2 Bedroom Garden View · Alamo SUV
Day 5	Fly LIH → OGG · Aston Kaanapali Shores	Alaska Airlines · 9:56 a.m. – 10:47 a.m. · 51 min
Days 5–7	Maui · Aston Kaanapali Shores	2 Bedroom Garden View Suite · Hertz SUV
Day 8	Fly OGG → HNL · Hilton Hawaiian Village	Alaska Airlines · 10:11 a.m. – 10:56 a.m. · 45 min
Days 8–10	Oahu · Hilton Hawaiian Village	Tapa Collection Family Room City View
Day 11	Fly HNL → SAN	Alaska Airlines · 12:30 p.m. – 8:55 p.m.

Day 1 — Friday, June 25, 2027 · San Diego to Kauai

Alaska Airlines SAN → LIH

• Leaves Friday, June 25, 2027 · 11:50 a.m. · San Diego (SAN)
• Arrives Friday, June 25, 2027 · 3:09 p.m. · Lihue, Kauai (LIH)
• Travel time: 6 hr 19 min

Check in Hilton Vacation Club The Point at Poipu Kauai — 4 nights, check-out June 29.

• Room 1 — 2 adults, 3 children
• Room type — 2 Bedroom Garden View: 1 king, 2 twins or 1 queen, sofa bed, kitchen, washer/dryer, sleeps 6

Daily resort charge includes basic guest internet, self-parking for 1 car, PressReader, hula and ukulele lessons, games (cornhole, ping pong, Connect 4), barbecue equipment, and a happy-hour discount on drinks and appetizers.

Alamo Standard SUV (taxes included) — pick up Lihue Airport 4:15 p.m. June 25 / drop off Lihue Airport 8:15 a.m. June 29.

Days 2–4 — Kauai at The Point at Poipu

The Point at Poipu sits at the southern tip of Kauai, a half mile from Makahuena Light, the Mahaʻulepu Heritage Trail, and Shipwreck Beach. Snorkel at Poipu Beach, explore Old Koloa Town, Allerton Garden, Spouting Horn, Wailua Falls, the Nā Pali Coast, or Waimea Canyon. Suites have a living area with sofa sleeper, dining nook, full kitchen, washer/dryer, and a garden- or ocean-view balcony. Grill a barbecue dinner and watch the Hawaiian sunset, use the sauna and pool, or work out in the fitness center. The on-site bar and grill serves Hawaiian plates and tropical drinks.

Day 5 — Tuesday, June 29, 2027 · Kauai to Maui

Alaska Airlines LIH → OGG

• Leaves Tuesday, June 29, 2027 · 9:56 a.m. · Lihue, Kauai (LIH)
• Arrives Tuesday, June 29, 2027 · 10:47 a.m. · Kahului, Maui (OGG)
• Travel time: 51 min

Check in Aston Kaanapali Shores — Honokowai / Kaʻanapali Beach. 3 nights, check-out July 2.

• Room 1 — 2 adults, 3 children
• Room type — 2 Bedroom Garden View Suite
• Save 15% off — the discount is already reflected in the rate

Hertz Standard SUV (taxes included) — pick up Kahului Airport 12:00 p.m. June 29 / drop off Kahului Airport 8:30 a.m. July 2.

Blackout dates 12/23/26 – 1/3/27. Hotel-collected estimates: resort fee $25 plus tax per room, per night; rollaway $25 plus tax per room, per night; parking from $11.95 plus tax per vehicle, per day. Fees can change — the hotel confirms current amounts at check-in.

Days 6–7 — Maui at Aston Kaanapali Shores

Ten acres of gardens and waterfalls open onto Kaʻanapali Beach. Cook in the suite kitchen, swim the garden and ocean pools, or eat at The Beach Club Restaurant & Bar. Nearby: Whalers Village, Black Rock, and Kaʻanapali golf.

Day 8 — Friday, July 2, 2027 · Maui to Honolulu

Alaska Airlines OGG → HNL

• Leaves Friday, July 2, 2027 · 10:11 a.m. · Kahului, Maui (OGG)
• Arrives Friday, July 2, 2027 · 10:56 a.m. · Honolulu, Oahu (HNL)
• Travel time: 45 min

Check in Hilton Hawaiian Village Waikiki Beach Resort — 3 nights, check-out July 5.

• Room 1 — 2 adults, 3 children
• Room type — Tapa Collection Family Room City View — Aloha Rate Rollback Promotion

Days 9–10 — Oahu at Hilton Hawaiian Village

Twenty-two acres on Waikiki Beach with Duke Kahanamoku Lagoon, five pools, Friday fireworks, and the Tapa Collection family room as the Oahu base on this itinerary.

Day 11 — Monday, July 5, 2027 · Honolulu to San Diego

Alaska Airlines HNL → SAN

• Leaves Monday, July 5, 2027 · 12:30 p.m. · Honolulu (HNL)
• Arrives Monday, July 5, 2027 · 8:55 p.m. · San Diego (SAN)

What’s included

• 10 nights in family suites and a Tapa Collection family room
• Round-trip West Coast air plus inter-island Alaska flights
• Alamo SUV on Kauai and Hertz SUV on Maui, taxes included
• Daily resort charge at The Point at Poipu as listed above

We have contracts nationwide — request a customized quote for your departure airport and travel dates.