Hawaii’s story stretches from Polynesian wayfinding to the Hawaiian Kingdom and statehood, leaving a living legacy in mele (song), hula, and food. Across its islands, you’ll read lava in the landforms, hear trade winds in the palms, and learn why the ocean is both pantry and pathway. This itinerary highlights Oahu, the Big Island, and Maui—each with a distinct personality and a sweep of adventures perfect for sightseeing.

Expect big contrasts: urban Honolulu’s surf and street food, Kona’s coffee farms and volcanic badlands, and Maui’s high-up crater and reef-bright coastlines. You’ll hike ridge trails, snorkel over turtles, and, if timing aligns, spot humpbacks on their winter migration. We’ve woven cultural touchpoints and local small businesses throughout—go hungry and curious.

Practical notes: Island-hopping is easiest by short flights, with early-morning departures to maximize your days. Reserve park entries (like Haleakalā sunrise and Waiʻānapanapa Black Sand Beach) in advance, and travel with reef-safe sunscreen. Respect kapu (sacred) places and stay off closed trails; when in doubt, ask. Now lace up: it’s time to explore.

Honolulu (Oahu)

Oahu blends surf-town aloha with a capital-city pulse. Waikiki’s crescent beach has drawn swimmers since the days of Hawaiian royalty, while the Koʻolau mountains rise like green cathedrals behind the skyline. Come for the beaches and stay for the plate lunches, shave ice, and the story-rich sites that shaped the Pacific.

Days 1–5: Iconic Honolulu, Windward Lookouts, and the North Shore

• Waikiki and Diamond Head: Ease in with a morning swim at Waikiki, then hike Lēʻahi (Diamond Head) for a WWII-era bunker and sweeping views. Go early for cooler temps; entry requires a timed reservation.
• Honolulu culture circuit: Learn Hawaiʻi’s history at the Bishop Museum and browse contemporary island art at the Honolulu Museum of Art. Stroll Kakaʻako for murals that turn warehouses into open-air galleries.
• Windward coast drive: Circle to Nuʻuanu Pali Lookout for trade-wind drama, then continue to Kailua/Lanikai for powdery sand. If you like stair-climbers, the Koko Crater Railway Trail is a quad-burning prize.
• North Shore day: Watch waves at Banzai Pipeline and Waimea Bay (winter surf is serious—observe from shore), wander Haleʻiwa’s boutiques, and end with sunset at Shark’s Cove tide pools (calmest in summer).

Adventurous and sightseeing-friendly tours (Oahu):

• Oahu: Pearl Harbor USS Arizona Memorial

  

  Powerful, essential history with time at the visitor center exhibits. A fitting counterpoint to beach days.

• Waikiki: Turtle Canyon Snorkel

  

  Short boat ride, clear water, and frequent honu (Hawaiian green sea turtles). Bring a rash guard and reef-safe sunscreen.

• Oahu Shark Dive

  

  A North Shore cage dive with silky blue views—thrilling yet secure, and a marine-biology lesson in motion.

Eat and drink (local favorites):

• Breakfast/coffee: ARVO (Aussie-style toast and flat whites), Leonard’s Bakery (hot malasadas all day), Island Vintage Coffee (100% Kona brews, acai bowls).
• Lunch: Marukame Udon (hand-pulled noodles under $15), Ono Seafood (classic shoyu and spicy ahi poke), Rainbow Drive-In (plate lunch icon since 1961).
• Dinner: Helena’s Hawaiian Food (pipikaula short ribs; family-run since 1946), The Pig & the Lady (modern Vietnamese-Hawaiian in Chinatown), Side Street Inn (hearty local-style sharing plates).
• Sweet treats: Waiola Shave Ice (ultra-fine shave), Pipeline Bakeshop (malasada holes and haupia fillings).

Where to stay (Oahu): For budget-value near the action, compare condos and studios on VRBO Honolulu or deals on Hotels.com Honolulu. Splurge options: Halekulani Hotel (elegant oceanfront); great mid-range style: The Surfjack Hotel & Swim Club; family paradise with pools and lagoon: Aulani, A Disney Resort & Spa.

Getting there + between islands: Fly into Honolulu (HNL). Use Trip.com flights or Kiwi.com to compare fares; West Coast–HNL is ~5–6 hours, often $350–$700 round-trip depending on season.

Oahu → Big Island (Day 6 morning): HNL to Kona (KOA) flights take ~50 minutes, commonly $60–$140 one-way on Trip.com or Kiwi.com. Pick up a rental car—distances are long on the Big Island.

Kailua-Kona (Big Island)

On Hawaiʻi Island, lava built the world anew—black flows, cinder cones, and cloud-topped volcanoes. Kona adds fragrant coffee orchards and snorkeling bays so clear you’ll forget the clock. Base on the leeward (dry) coast and plan a full-day volcano loop to understand the island’s heartbeat.

Days 6–10: Coffee Belt, Snorkel Bays, and Volcanoes National Park

• Kealakekua Bay and Puʻuhonua o Hōnaunau: Snorkel electric-blue reefs at Two Step, then visit the Place of Refuge to learn about ancient Hawaiian law and sanctuary. Go early for light and calmer seas.
• Volcanoes National Park day trip: It’s ~2.5 hours each way from Kona. Hike Crater Rim trails, feel steam vents, and peer into Kīlauea’s caldera. Check current eruption status before you go; lava activity varies.
• Pololū Valley and Kohala: Drive north for windswept cliffs and a switchback trail to a black-sand beach. Cap it with Waimea’s paniolo (cowboy) history and a hearty local dinner.
• Stargazing: Clear nights on Saddle Road can be spectacular—pack warm layers and pull off only at designated turnouts. Respect Maunakea’s cultural significance and road advisories.

Bucket-list tours (Big Island):

• Big Island: Manta Ray Night Snorkeling Adventure in Kailua-Kona

  

  Glide above manta “ballets” under lights—an otherworldly, safe, guided experience you’ll recount for years.

• Big Island: Captain Cook Snorkel On A Power Catamaran With Lunch

  

  Easy boat access to Kealakekua’s marine sanctuary, with reef time and coastal lava arches along the way.

Eat and drink (Kona coast):

• Breakfast/coffee: Kona Coffee & Tea (estate brews and ocean-view patio), Island Lava Java (cinnamon rolls and sunrise seating), HiCO (creative vegan-friendly pastries and cold brew).
• Lunch: Umekes Fishmarket Bar & Grill (poke flights and kalbi ribs), Foster’s Kitchen (scratch-made local plates), Herbivores (plant-based bowls near the pier).
• Dinner: Kai Eat+Drink (waterfront casual), Rebel Kitchen (Kealakekua; elevated comfort food), Kona Brewing Co. Pub (island ales, pizzas, and mac-nut pesto).
• Treats: Scandinavian Shave Ice (old-school syrups, add ice cream), Gypsea Gelato (lilikoi and coconut flavors).

Where to stay (Kailua-Kona): Stretch your budget with a kitchenette condo via VRBO Kailua-Kona or deals on Hotels.com Kailua-Kona. Look in Kailua Village for walkability or Keauhou/Captain Cook for quieter, better-value stays.

Big Island → Maui (Day 11 morning): KOA to Kahului (OGG) is ~40 minutes, usually $60–$140 one-way via Trip.com or Kiwi.com. Rent a car; Maui sights are spread out.

Maui (Kihei/Wailea)

Maui is about edges and in-betweens: the moonlike summit of Haleakalā above, coral gardens below, and the jungle-threaded Hāna Highway in between. Post-2023 wildfires, please respect closures in and around Lahaina and support local businesses elsewhere on the island.

Days 11–15: Haleakalā, Snorkel Reefs, and the Road to Hāna

• Haleakalā summit: Sunrise requires a reservation; sunset is equally jaw-dropping and easier on sleep. Hike Sliding Sands for cinder-cone hues if weather cooperates—bring layers; it’s cold up top.
• South Maui snorkeling and beaches: Explore ʻĀhihi-Kīnaʻu Natural Area (no-touch tide pools and reefs) and Wailea’s crescent beaches. Early mornings mean clearer water and calmer wind.
• Road to Hāna: A full-day, curvy epic—waterfalls at Twin Falls (small fee), banana bread at Keʻanae Peninsula, and Waiʻānapanapa’s black sand (timed entry required). Turn back before dark for safety.
• ʻĪao Valley and Wailuku: Short, lush walk to the ʻĪao Needle viewpoint, then browse Wailuku’s new cafes and mom-and-pop shops.

Top-value tours (Maui):

• Maui Afternoon Snorkel Aboard Malolo to Molokini or Coral Gardens

  

  Great timing for late risers; picks the day’s best site (Molokini or Coral Gardens) for clear water and ample reef life.

• Maui Pineapple Farm Tour in Haliimaile

  

  See how Maui’s spiky icon grows, taste just-cut fruit, and hear plantation-era stories in Upcountry’s cool air.

• From Maalaea: Whale Watching Tour Aboard the Quicksilver

  

  Seasonal (roughly Dec–Apr). Naturalists narrate breaching, pec slaps, and mother-calf pairs in the Maui Nui sanctuary.

Eat and drink (South and Central Maui):

• Breakfast/coffee: Kihei Caffe (hefty banana mac-nut pancakes), Akamai Coffee (strong espressos, local roasts), Sugar Beach Bake Shop (lilikoi bars and flaky croissants).
• Lunch: South Maui Fish Company (truck; daily-catch plates and poke), Tin Roof (Kahului; chef-driven, budget-friendly bowls), Like Poke? (truck; generous fresh poke).
• Dinner: Monkeypod Kitchen (lively, great happy hour, kiawe-fired pizzas), Isana (sushi and Korean plates), Nalu’s South Shore Grill (live music, island comfort food).
• Treats: Ululani’s Hawaiian Shave Ice (silky ice, house syrups), Tasaka Guri-Guri pop-ups (old-school sherbet if you spot them).

Where to stay (Maui): For best value and beach access, scan VRBO Kihei and Hotels.com Kihei. Specific options: value-friendly Maui Seaside Hotel (near airport, central for day trips), oceanfront villa-style The Westin Ka'anapali Ocean Resort Villas (note: respect any area guidance), and the splurge-worthy Four Seasons Resort Maui at Wailea.

Budget tips for a 35/100 spend—without missing the magic

• Stay smart: Condos with kitchenettes in Kihei, Kailua-Kona, and Waikiki cut costs (breakfasts + some dinners in). Check VRBO Honolulu, VRBO Kailua-Kona, and VRBO Kihei.
• Eat like a local: Plate lunches, food trucks, and grocery-store poke (Foodland, KTA) keep meals under $15–$20 while tasting authentically island.
• Free sights shine: Beaches, sunrise hikes, scenic drives, and sunset shows are priceless. Save splurges for a few high-impact tours (manta rays! Pearl Harbor!).
• Book flights early: Lock in inter-island fares on Trip.com or Kiwi.com; aim for morning flights to maximize beach time.

Suggested 15-day flow (multi-day blocks)

• Days 1–5 (Oahu): Waikiki swims, Diamond Head, Honolulu museums, Windward lookouts, North Shore day, plus Turtle Canyon snorkel and Pearl Harbor tour.
• Days 6–10 (Big Island): Kealakekua/Two Step snorkel, Place of Refuge, full-day Volcanoes National Park loop, Kohala cliffs at Pololū, manta ray night snorkel.
• Days 11–15 (Maui): Haleakalā summit hike/sunset, ʻĀhihi-Kīnaʻu reefs, Road to Hāna with Waiʻānapanapa reservation, ʻĪao Valley, and an afternoon Molokini/Coral Gardens snorkel. Seasonal whale watch if visiting winter.

Fifteen days in Hawaiʻi lets you taste three islands’ personalities—urban beach energy, lava-forged landscapes, and reef-ringed calm. With smart budgeting, you’ll still catch the big-ticket thrills: turtles, mantas, craters, and history that stays with you long after the lei fades.