Offbeat Honolulu and the Islands: 5 Days
Five days is where this trip earns its first inter-island flight: three nights on Oahu to clear Diamond Head, Hanauma Bay, and Pearl Harbor, then a 35-minute hop to Maui for one compressed but genuine taste of a neighbor island. It’s a tighter add-on than the 7-day version , which gives Maui two full nights instead of one.
| Day | Focus | Distance/flight time from Waikiki |
|---|---|---|
| 1 | Arrival, domestic gateway logistics, Waikiki settle-in | 20-30 min drive (HNL to Waikiki) |
| 2 | Pearl Harbor, downtown Honolulu and Iolani Palace | 20-25 min drive |
| 3 | Diamond Head, Hanauma Bay | 10 min drive; 20-30 min drive |
| 4 | Fly to Maui, settle in Kahului or Kihei | 35 min flight (HNL-OGG) |
| 5 | Maui morning, fly home direct, departure | 35 min flight (OGG-HNL or direct) |
Book these before you go:
- Pearl Harbor’s free USS Arizona ticket opens 56 days out: reserve on recreation.gov
- Diamond Head opens a 30-day window: book on gostateparks.hawaii.gov
- Hanauma Bay opens only 2 days ahead at 7am Hawaii time, closed Monday and Tuesday: check dates on hanaumabayhawaii.org
- Compare Waikiki hotel rates on Booking.com for the Oahu nights
- Check Maui lodging on Booking.com before the inter-island flight
Day 1: Arrival and the domestic reality check
No passport, no customs, USD throughout: a REAL ID check at security is the only thing this flight requires that a mainland domestic trip wouldn’t. Treat it as a travel day; the shortest mainland nonstops still run 5 to 6 hours. TheBus routes 20 or 303 reach Waikiki in 45-60 minutes for a $3 fare, or a rideshare in about half that for $35-50.
Day 2: Pearl Harbor and downtown Honolulu
Arrive at Pearl Harbor an hour ahead of your reserved USS Arizona Memorial slot; the program runs 45 minutes, and visitor center parking is a separate $7. In the afternoon, Iolani Palace downtown runs about $28 self-led or $34 docent-led, the only royal palace on US soil.
Day 3: Diamond Head and Hanauma Bay
Diamond Head’s 0.8-mile trail is steep, 1.5-2 hours round trip, last entry 4:30pm, a 10-minute drive from Waikiki. Follow it with an afternoon at Hanauma Bay, a 20-30 minute drive southeast, unless your slot falls on the Monday or Tuesday closure.
Day 4: Fly to Maui
Hawaiian Airlines and Southwest both run this route often; the flight itself is about 35 minutes, though airport time on both ends easily doubles the door-to-door total. Land at Kahului (OGG), pick up a rental car (worth it here, unlike Waikiki), and settle into Kihei or Wailea for the afternoon. This is a short add-on by design; a longer Maui stay belongs to its own trip, not this one.
Day 5: Maui morning, then home
Spend the morning on whichever single Maui highlight matters most, a short stretch of the Road to Hana or a Wailea beach morning, then head to Kahului for a direct flight home rather than routing back through Honolulu first. A guided Maui day tour is worth booking if a full day of driving on your only Maui day sounds like the wrong trade.
For the version that gives Maui two full nights instead of a rushed one, see the 6-day itinerary ; the full guide covers Kauai and the Big Island as alternate add-ons with their own flight times.