NOVEMBER 19 DEPARTURE · FIVE TRAVELERS

A little
island time.

Two ways to Hawaii. A few nights at Four Seasons. Plenty of room to unwind.

Explore the two options

ALOHA
THANKSGIVING ’26WAILEA COAST · MAUI

2 adults + 1 senior + two 5-year-oldsSFO departure · Nov 19Four Seasons · at least 2 nights

ON THE MENU

Two ways to get away

Plan updated Sep 18, 2026

01 / TWO ISLANDS

Maui + Big Island

Four nights at Four Seasons Maui, then two nights on the Big Island. Fly home from Kona on November 25.

Nov 19Arrive MauiNov 23Island hopNov 25Fly home

02 / SLOW IT DOWN

Five nights on Maui

Two nights at Four Seasons, then three at a more affordable stay. One island and fewer travel days.

Nov 19SFO → MauiNov 21Change hotelsNov 24Fly home

OPTION 1 · DEPART NOV 19

A little of both islands

Four Seasons · Nov 19–23

4 nights · Sep 18, 2026

Garden-View Room · king2 rooms · 600 sq ft per room$1,358 per room / night$10,8644 nights · before taxDeluxe Garden-View Room2 rooms · 600 sq ft per room · king$1,433 per room / night$11,4644 nights · before taxDeluxe Garden-View Executive Suite1 suite · 840 sq ft + lanai · king + sofabed$2,450 per suite / nightAll five together · pending hotel approval$9,8004 nights · before tax

Estimates include the $55 nightly fee per unit. Two-room totals double a single-room quote; availability and the second room’s rate need confirmation. The suite quote is for 2 adults + 2 children; any extra-adult charge is additional. Amex rates may differ and upgrades are subject to availability.

A living room and everyone together

Preferred arrangement to discuss with the hotel: 2 adults + 1 child in the king bed, and 1 adult + 1 child on the sofabed.

Call to confirm approval for 3 adults + 2 children, sofabed size and any additional charge. The published limit is 3 adults, or 2 adults + 2 children.

NOV 19–23 · 4 NIGHTS

Four Seasons Maui

Garden-View Room · king · 2 rooms. Request connecting rooms.

NOV 23–25 · 2 NIGHTS

Big Island Airbnb

Fly OGG → KOA on Nov 23. Southwest 1:35–2:15 pm, $345 for five. Look for an Airbnb around Kona or Waikoloa.

WED, NOV 25 · FLY HOME

Kona → San Francisco

1:04 pm departure · 8:20 pm arrival, same day.

Return date

The original six-night sketch.

Choose the earlier SFO arrivalUnited 1:04–8:20 pm: $2,641 for five. Alaska 4:51–11:59 pm: $1,291. Checked Sep 18.

VALUE PICK

Maui only, Nov 19–24

Flights total $3,667 for five with the 2:05 pm outbound and 11:46 am return. Budget about $4,712 before tax for the first two Four Seasons nights in two rooms, then price the other three nights.

IF YOU WANT BOTH ISLANDS

Four nights together on Maui

The Deluxe Garden-View Executive Suite is about $9,800 before tax for Nov 19–23, saving $1,064 versus two Garden-View king rooms. It adds a living room and keeps everyone together if the hotel approves five guests; any extra-adult fee reduces that saving.