Oahu, Hawaii
The Oahu Guide

Oahu

Paradise where the Pacific meets the trade winds.

HawaiiRedAwning · Vol. 01
A Field Guide

What Oahu actually feels like.

Eight coastlines on a single island — Waikiki and Diamond Head on the south shore, Lanikai and Kailua on the windward coast, Pipeline and Sunset Beach up north — all reachable within a two-hour drive of wherever you wake up.

From dawn surf to sunset sail

Activities in Oahu

Surf at Waikiki or watch Pipeline, snorkel Hanauma Bay, hike Diamond Head, drive the windward coast — the calendar bends to the tide.

Surfing
01

Surfing

Beginners belong on the south-facing breaks of Waikiki. Intermediate riders head to Cliffs and Bowls. Winter brings the legendary North Shore — to watch, mostly.

Snorkeling at Hanauma Bay
02

Snorkeling at Hanauma Bay

A protected volcanic crater, calm enough for first-timers. Reservations required and the bay is closed Mondays and Tuesdays. Worth every step of the planning.

Hiking Diamond Head
03

Hiking Diamond Head

Ninety minutes round-trip to one of the most photographed views in the Pacific. Reserve in advance, go early, bring water.

04

Sailing & Catamaran Tours

Sunset sails leave from Kewalo Basin and Waikiki nightly. The Lanikai catamaran day trips are quieter and locally beloved.

05

Jet Skiing & Parasailing

Maunalua Bay and Waianae are the main hubs. Most operators include hotel pickup and the rentals are by the hour.

06

Pearl Harbor & USS Arizona

A solemn, essential half-day visit. The ferry to the Arizona Memorial is free; book the boarding pass online weeks ahead.

On Oahu, you can stand in the surf and the city in the same hour. That's the whole island in a sentence.
Travis Peterson, Director of Host Success at RedAwning since 2017
Oahu
Beyond the beach

Things to Do on Oahu

Markets, neighborhoods, the Diamond Head climb, and a North Shore that runs on its own clock.

Beaches & Nature

01 · 6 spots
  • 01

    Diamond Head State Monument

    The 760-foot extinct volcanic crater at the east end of Waikiki — a 1.6-mile out-and-back climb to a panoramic viewpoint. Reservations required for non-Hawaii residents; book on the state park site.

    Address
    Diamond Head Rd & 18th Ave, Honolulu, HI 96815
  • 02

    Lanikai Pillboxes Hike

    Forty-five minutes of switchbacks for the most famous twin-island view in Hawaii. Sunrise hikes are unforgettable; bring a flashlight for the descent.

    Address
    265 Kaelepulu Dr, Kailua, HI 96734
  • 03

    Hanauma Bay Nature Preserve

    A protected snorkel cove inside a volcanic tuff ring — the most reliable reef-fish swimming on Oahu. Reservations required and the bay is closed Mondays and Tuesdays.

    Address
    100 Hanauma Bay Rd, Honolulu, HI 96825
  • 04

    Waimea Bay & Three Tables (North Shore)

    Glassy summer snorkel cove that flips into legendary winter big-wave break. Cliff jumping off the rock, Pupukea tide pools next door, and Ted's Bakery a mile up the road.

    Address
    61-031 Kamehameha Hwy, Haleiwa, HI 96712
  • 05

    Manoa Falls Trail

    An easy 1.6-mile rainforest hike to a 150-foot waterfall behind Manoa Valley — twenty minutes from Waikiki, kid-friendly, and the easiest jungle walk on the island.

    Address
    3860 Manoa Rd, Honolulu, HI 96822
  • 06

    Kualoa Ranch (Jurassic Park Tours)

    A 4,000-acre working ranch on the windward coast — UTV, ATV, horseback, and the famous Hollywood movie-set tours through the valleys you've seen in Jurassic Park.

    Address
    49-560 Kamehameha Hwy, Kaneohe, HI 96744

Culture & History

02 · 5 spots
  • 01

    Pearl Harbor National Memorial

    The USS Arizona Memorial, USS Bowfin submarine, and the Battleship Missouri — plan a half day. Free shuttle tickets for the Arizona book out a week ahead on recreation.gov.

    Address
    1 Arizona Memorial Pl, Honolulu, HI 96818
  • 02

    Bishop Museum

    The state's premier collection of Hawaiian and Polynesian history. Plan two hours minimum — the planetarium adds another forty-five.

    Address
    1525 Bernice St, Honolulu, HI 96817
  • 03

    Iolani Palace

    The only royal palace on US soil — guided and self-led tours of the 1882 home of Hawaii's last monarchs. A short, surprising visit downtown.

    Address
    364 S King St, Honolulu, HI 96813
  • 04

    Polynesian Cultural Center

    A full-day experience on the windward side — hula, fire-knife dancing, canoe rides, luau dinner. Touristy in the best way.

    Address
    55-370 Kamehameha Hwy, Laie, HI 96762
  • 05

    Honolulu Museum of Art

    A serene downtown museum with a quiet courtyard café — Pacific Asian and contemporary collections, and a film series in the Doris Duke Theatre. Free entry on first Wednesdays.

    Address
    900 S Beretania St, Honolulu, HI 96814

Markets, Neighborhoods & Family

03 · 5 spots
  • 01

    KCC Saturday Farmers Market

    Saturday mornings at Kapiolani Community College — mochi, malasadas, fresh ahi, and a hundred other reasons to skip hotel breakfast.

    Address
    4303 Diamond Head Rd, Honolulu, HI 96816
  • 02

    Kakaako & Honolulu Murals

    A self-guided walking tour through the warehouse district's POW! WOW! murals. Pair it with coffee at Arvo and lunch at Highway Inn.

    Address
    Cooke St & Auahi St, Honolulu, HI 96814
  • 03

    Haleiwa Town (North Shore)

    A surf-town main street with gallery storefronts, shave-ice institutions (Matsumoto's), and the slowest twenty minutes on the North Shore. Park once, walk it.

    Address
    Haleiwa, HI 96712
  • 04

    Honolulu Zoo & Waikiki Aquarium

    Two compact, kid-easy attractions on the Diamond Head end of Waikiki — a forty-two-acre zoo and a small but thoughtful aquarium with monk seals and reef tanks.

    Address
    151 Kapahulu Ave, Honolulu, HI 96815
  • 05

    North Shore Food Trucks

    Giovanni's, Big Wave Shrimp, Macky's — the Kahuku and Haleiwa shrimp-truck tour is a half-day in itself. Bring an appetite and napkins.

    Address
    Kamehameha Hwy, Kahuku, HI 96731

Adventure & Watersports

04 · 2 spots
  • 01

    Surfing Lessons at Waikiki

    The gentlest learn-to-surf waves in the world break right off Kuhio and Queens. Two-hour group lessons with a Waikiki Beach Boys outfit get most beginners up by the end of the session.

    Address
    Kuhio Beach, Waikiki, Honolulu, HI 96815
  • 02

    Snorkeling at Sharks Cove (North Shore)

    A sheltered tide-pool reef across from Foodland Pupukea — the best beach snorkel on the island in summer. Water shoes are non-negotiable.

    Address
    59-727 Kamehameha Hwy, Haleiwa, HI 96712
The dining guide

Where to Eat on Oahu

An island where a $5 plate lunch and a $200 omakase share the same lanai breeze.

Upscale

01 · 7 spots
  • 01

    Orchids at Halekulani

    Open-air oceanfront dining at the legendary Halekulani — Diamond Head views, Sunday brunch as Honolulu institution, and a Pacific-Rim seafood menu that has set the bar for fifty years.

    Address
    2199 Kalia Rd, Honolulu, HI 96815
  • 02

    Senia

    Chinatown tasting menu and à la carte from chef Chris Kajioka — global techniques, Hawaiian ingredients, and a chef's-counter seat that fills weeks out. The James Beard nominee Honolulu locals book first.

    Address
    75 N King St, Honolulu, HI 96817
  • 03

    Alan Wong's Honolulu

    The dining room that put Hawaii Regional Cuisine on the map — three decades of refined island flavors, a five-course tasting menu, and Honolulu's most quietly accomplished kitchen.

    Address
    1857 S King St 3rd Floor, Honolulu, HI 96826
  • 04

    Roy's Waikiki

    Roy Yamaguchi's flagship — Pacific-Rim plates, the famous Misoyaki butterfish, and an oceanside lanai a short walk from the Royal Hawaiian. A celebration spot that's been polished for thirty years.

    Address
    226 Lewers St, Honolulu, HI 96815
  • 05

    La Vie

    Eighth-floor French-American tasting menus at the Ritz-Carlton Residences — Diamond Head views, a quiet room, and one of the most refined wine programs on Oahu.

    Address
    383 Kalaimoku St, Honolulu, HI 96815
  • 06

    53 By the Sea

    A Kakaako landmark with floor-to-ceiling Diamond Head and harbor views — a Mediterranean-inflected menu, a 7,000-bottle cellar, and the showstopper Honolulu sunset reservation.

    Address
    53 Ahui St, Honolulu, HI 96813
  • 07

    Sushi Ginza Onodera

    Edomae omakase from the Tokyo and New York Onodera group — fish flown daily from Toyosu Market, a twelve-seat counter, the most serious sushi reservation on the island.

    Address
    1108 Auahi St #160, Honolulu, HI 96814

Family-friendly

02 · 7 spots
  • 01

    Helena's Hawaiian Food

    James Beard America's Classic award-winning Kalihi institution — kalua pig, pipikaula short ribs, lomi salmon, and the most authentic Hawaiian plate lunch on the island.

    Address
    1240 N School St, Honolulu, HI 96817
  • 02

    Rainbow Drive-In

    The plate-lunch spot you've seen on every Hawaii travel show — loco moco, mixed plates, and a mid-century counter that hasn't changed in sixty years. Cheap, fast, beloved.

    Address
    3308 Kanaina Ave, Honolulu, HI 96815
  • 03

    Giovanni's Shrimp Truck

    The original North Shore shrimp truck, scrawled with two decades of guest signatures. Garlic shrimp, hot-and-spicy, lemon-butter — order all three and eat standing up.

    Address
    66-472 Kamehameha Hwy, Haleiwa, HI 96712
  • 04

    Ted's Bakery

    Roadside North Shore bakery famous for the chocolate-haupia cream pie. Plate lunches, breakfast sandwiches, and the surfer-and-shave-ice line that wraps around the parking lot.

    Address
    59-024 Kamehameha Hwy, Sunset Beach, HI 96712
  • 05

    Leonard's Bakery

    Honolulu's malasada landmark since 1952 — Portuguese fried-dough pastries served warm in paper bags. Get a half-dozen for the rental, eat them on the lanai.

    Address
    933 Kapahulu Ave, Honolulu, HI 96816
  • 06

    Duke's Waikiki

    Beachfront classic on the Outrigger Waikiki sand — the Hula Pie is non-negotiable, the live music runs nightly, and the kids' menu means everyone's happy at sunset.

    Address
    2335 Kalakaua Ave, Honolulu, HI 96815
  • 07

    Eggs 'n Things

    Pancakes piled with whipped cream, omelets, and the breakfast-all-day formula that has earned three Waikiki locations. Easy with kids, fast even on a holiday.

    Address
    343 Saratoga Rd, Honolulu, HI 96815

International

03 · 7 spots
  • 01

    Sushi Sasabune (Japanese)

    An omakase-only counter where the chef tells you what to order and the rice is the star. No menu, no substitutions, no regrets — Honolulu's most disciplined sushi night.

    Address
    1419 S King St, Honolulu, HI 96814
  • 02

    Marukame Udon (Japanese)

    Hand-cut udon, tempura by the piece, and a line out the door on Kuhio that moves shockingly fast. The cheapest, fastest, most comforting bowl in Waikiki.

    Address
    2310 Kuhio Ave, Honolulu, HI 96815
  • 03

    Tonkatsu Ginza Bairin (Japanese)

    A century-old Tokyo tonkatsu house's first US outpost — panko-crusted pork cutlets, house-ground sesame, and a tidy Beach Walk room. A reliable rainy-day Waikiki lunch.

    Address
    255 Beach Walk, Honolulu, HI 96815
  • 04

    Side Street Inn (Local-Korean fusion)

    The chef hangout — fried pork chops, kimchi-fried-rice, and karaoke-bar energy. Big plates built for sharing and a beer list a block long.

    Address
    1225 Hopaka St, Honolulu, HI 96814
  • 05

    Lucky Belly (Asian/Ramen)

    Chinatown ramen joint — Belly Bowl with pork three ways, fried rice, and a late-night menu that runs past midnight on weekends. A favorite of the city's chefs.

    Address
    50 N Hotel St, Honolulu, HI 96817
  • 06

    Mei Sum Dim Sum (Chinese)

    Chinatown dim sum in the cart-rolling tradition — har gow, char siu bao, turnip cake, and a packed dining room every weekend morning. Cash-friendly, family-loud.

    Address
    1170 Nuuanu Ave, Honolulu, HI 96817
  • 07

    Bac Nam (Vietnamese)

    Family-run pho and Vietnamese plates that locals have packed for thirty years — rare-beef pho, lemongrass chicken, and a homey, no-frills room.

    Address
    1117 S King St, Honolulu, HI 96814
Before you book

Trip Planning, Answered

Best season, where to stay (Waikiki, Kailua, Haleiwa), the rental car question, and what an Oahu week actually costs.

When is the best time to visit Oahu?
Oahu's weather is excellent year-round, but the shoulder seasons — April through early June and September through early October — offer the best mix of weather, lower prices, and fewer crowds. Winter (mid-November through March) brings legendary North Shore surf, whale watching, and slightly more rain on the windward side, plus peak hotel rates. Summer (June–August) is dry, hot, and busy.
What's the closest airport to Oahu?
Daniel K. Inouye International Airport (HNL) in Honolulu is the only major airport on Oahu and the main hub for all Hawaiian island travel. From HNL it's about 20 minutes to Waikiki, 40 minutes to Ko Olina on the leeward coast, and roughly an hour to the North Shore. Direct flights connect Oahu with most West Coast cities and several mainland hubs.
How long should I stay in Oahu?
Seven days is the sweet spot for a first visit — enough time to explore Waikiki, the North Shore, the windward coast, and the south shore without long daily drives. Five days works for a focused trip; eight to ten days lets you slow down and add day trips. Three to four days feels rushed once island traffic and drive times are factored in.
Do I need a car in Oahu?
A rental car is recommended for most trips, especially if you're staying outside Waikiki or want to visit the North Shore, Hanauma Bay, or the windward coast. Visitors based in Waikiki who plan to stick to the south shore can manage with TheBus, ride-shares, and tours — but expect waiting time. Traffic in and out of Honolulu is real; plan around rush hours.
What's the weather like in Oahu?
Oahu is warm and tropical year-round, averaging 80°F in winter and 85–88°F in summer. Trade winds keep the air pleasant most days. Winter (November–March) brings more rain to the windward (east) side, but showers are usually brief. Hurricanes are historically rare. The water temperature stays in the upper 70s F all year — every day is a swim day.
Is Oahu good for families?
Yes. Oahu is one of the most family-friendly Hawaiian islands, with calm-water beaches like Lanikai and Waikiki for younger kids, snorkeling at Hanauma Bay, and family-focused experiences at the Polynesian Cultural Center, Bishop Museum, and Waikiki Aquarium. Many of our Oahu rentals include beach gear (snorkels, paddleboards, beach chairs) at no extra cost.
Where should I stay in Oahu?
Most first-time visitors stay in Waikiki for the convenience — walkable beach, restaurants, and a 20-minute drive from the airport. The North Shore (Haleiwa, Pupukea, Sunset Beach) suits travelers who want surf-town quiet; book early, especially November through February. Ko Olina on the leeward coast has the calmest swimming water and the most resort-style amenities. The windward side (Kailua, Lanikai) is the local favorite for postcard beaches with fewer crowds. Most RedAwning Oahu guests split their stay between Waikiki and one other coast.
How much does an Oahu vacation rental cost?
Oahu vacation rental nightly rates typically range from about $150 for a Waikiki studio to $300–$600 for a two- or three-bedroom condo, and $700+ for beachfront homes on the North Shore or Ko Olina. Rates are highest mid-December through early January, around spring break, and during major surf events on the North Shore. Shoulder seasons (April–early June and September–early October) are usually 20–30% cheaper than peak.
Are pets allowed in Oahu vacation rentals?
Hawaii has strict pet import rules — bringing a pet without a 5-day quarantine waiver requires advance documentation — so pet-friendly Oahu rentals are less common than on the mainland. RedAwning's Oahu inventory does include pet-friendly homes; filter for "Pets OK" when browsing. Service animals are welcome under federal law and exempt from the standard pet policy.
Is the North Shore or Waikiki better for first-time Oahu visitors?
Most first-time visitors are happiest in Waikiki — it's the most central base, walkable to dining and the beach, and a short drive to Pearl Harbor, Diamond Head, and Hanauma Bay. The North Shore is best on a return trip or for travelers explicitly seeking surf culture, slower mornings, and food trucks over restaurants. Many guests do five nights in Waikiki and two on the North Shore for the contrast.
The next chapter

Stay in Oahu, on us.

Every property in our Oahu collection is hand-checked, hand-photographed, and backed by twenty-four-hour concierge support. The guide is the warm-up. The home is the trip.

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