Destinations / Hawaii
Hawaii Travel Guide
Four islands, four very different trips. Pick the island first and the hotel second, and do one or two islands well instead of four in a rush. Here's how they compare, when to go and what to book before you land.
Hawaii
Where I'm sending people now
About 18.7% on top of the room rate, plus resort fees. The state hotel tax went up to 11% in 2026.
April to May and September to October for better rates and fewer crowds. January to March for whales.
Luxury oceanfront resorts usually run $700 to $1,500+ a night before taxes and resort fees. Plan on a rental car unless you're staying in Waikīkī.
Book these before you land: Haleakalā sunrise, Waiʻānapanapa, Diamond Head, Hanauma Bay, Pearl Harbor and Hāʻena. Hurricane season runs June to November, so get travel insurance.
Places in Hawaii
Which one is right for you?
Maui
Great for
Honeymoons, luxury resorts, whale season, scenic drives
Skip it if
You don't want to drive, or you want a big-city feel and nightlife
Kauai
Great for
Hikers, couples, big scenery, a quieter trip
Skip it if
You want nightlife, lots of shopping or guaranteed North Shore sun in winter
Oahu
Great for
First-timers, food lovers, history, families, trips without much driving
Skip it if
Quiet, empty beaches are the whole point of your trip
Big Island
Great for
Adventurous couples and families, snorkelers, volcano and stargazing trips
Skip it if
You want to stay put without driving, or you want a walkable town
Know before you go
Getting there
Honolulu (HNL) is the main gateway, with nonstops to Maui (OGG), Kauai (LIH) and Kona (KOA) mostly from West Coast cities like LAX, SFO, SEA and PDX. International visitors usually connect through HNL or a West Coast hub, and interisland hops on Hawaiian Airlines take 30-50 minutes.
Getting around
Each island is its own trip: there are no ferries between Oahu, Maui, Kauai or the Big Island, so you fly. I'd rent a car on every island except Oahu if you're staying in Waikiki, and book it early because neighbor-island fleets sell out in peak weeks.
Money and tipping
It's all US dollars and cards work everywhere; the state's general excise tax gets added on top of almost everything, including meals and tours. Tip like the mainland US (18-20% at restaurants), and budget for resort fees and parking, which most big resorts charge nightly.
How I'd spend 10 days
Days 1-3 Oahu, Waikiki base, Pearl Harbor, Diamond Head sunrise, a North Shore day
Days 4-7 Maui, Road to Hana or Haleakala sunrise, snorkel Molokini, a slow beach day in Wailea
Days 8-10 Kauai, Na Pali by boat or helicopter, Waimea Canyon, Hanalei Bay
Tip two islands is the sweet spot for 7-8 days; three works best with 10 or more
Hotels I'd book in Hawaii
Things to do in Hawaii
Where to eat in Hawaii
Mama's Fish House
Merriman's Kapalua
Merriman's Poʻipū
JO2
La Mer
Senia
Merriman's Waimea
Brown's Beach House
Where I'm sending people now
Hawaii
Maui, Kauai, Oahu and the Big Island, and how to pick between them.
Italy
Rome and the Amalfi Coast, with the hotels and tours worth booking ahead.
Caribbean
Punta Cana, Turks and Caicos and Puerto Rico, all-inclusive and not.
Hawaii FAQ
Can I do two islands in one trip?
Yes. Inter-island flights are short. With a week, I'd stick to one island; with ten days or more, two islands works well.
Which island should I pick for a first trip?
Maui for a honeymoon or resort time, Oahu if you want Waikīkī, Pearl Harbor and great food without much driving, Kauai for scenery and hiking, and the Big Island for the volcano, snorkeling and stargazing.
How many days do I need?
A week for one island, 10 days or more for two. Every island change costs about half a day between checkout, the airport, the flight and a new rental car.
How do I get between islands?
You fly. There's no ferry between the main islands. Hawaiian Airlines runs most interisland flights, Southwest flies some routes but plans to end that service in spring 2027, and Mokulele flies small planes on a few routes.
What do I need to reserve before I go?
Haleakalā sunrise (60 days out, plus a small release 2 days out), Waiʻānapanapa and Diamond Head (30 days out), Hāʻena on Kauai (30 days out), Hanauma Bay (2 days out) and the USS Arizona Memorial (8 weeks out). Popular slots sell out fast.
How much are hotel taxes in Hawaii?
18.712% in 2026: the 11% state hotel tax, a 3% county tax and 4.712% general excise tax. Resort fees are usually $25 to $55 a night and get taxed too, so look at the total, not the nightly rate.
When is whale season?
Humpbacks are in Hawaii from about November to early May. January to March is the best time to see them, especially off Maui.
What sunscreen can I bring?
Hawaii bans sunscreens with oxybenzone and octinoxate. On Maui only mineral sunscreen (zinc oxide or titanium dioxide) can be sold. Bring mineral and you're fine everywhere.
Do I need travel insurance?
I'd get it. Hurricane season runs June to November, and in 2026 Hurricane Lowell hit Kauai and Hurricane Lala hit the Big Island. Insurance covers the costs that hotels and airlines won't refund.