This food & wine itinerary reshuffles the schedule around food & wine activities — local cuisine, wine tastings, and food tours. Mostly low-effort and walkable, with a mix of self-guided and guided activities. Includes 7 must-see landmarks across Oahu and Maui and Big Island.
Highlights: Haleakala Sunrise Experience, Hawai'i Volcanoes National Park, Road to Hana Scenic Drive, Road to Hana Scenic Drive, Mama's Fish House
This 14-day Hawaii itinerary is built around food and drink experiences — 20 activities focus on local cuisine, markets, cooking classes, and tastings across Oahu, Maui, and Big Island.
Your Route — ordered to minimize backtracking
25+ activities scored and ranked · route optimized across 3 cities
Day-by-Day Schedule — heavy and light days alternate so you don’t burn out
Oahu
OahuWatch world-class surfers at Pipeline, explore Haleiwa, and grab shave ice at Matsumoto's
Year-round. Nov-Feb for big wave season and surf competitions. Summer has calmer water for swimming. Matsumoto's open daily.Experience an authentic Hawaiian feast with hula, fire dancing, and kalua pig under the stars
$120 Verified Mar 2026 Year-round; book ahead for Friday and Saturday shows. 📍 MapWaikiki / Kailua
Sample Hawaii's iconic raw fish dish at the island's top poke shops from Waikiki to the North Shore
$15 Verified Mar 2026 Year-round; fresh ahi tuna is always available. 📍 MapEat fresh ahi poke with rice and tamari at Honolulu's best poke shops — Hawaii's naturally gluten-free power bowl
$16 Year-round 📍 MapWaikiki / Kailua
Feast on garlic butter shrimp from legendary roadside food trucks in Kahuku and Haleiwa
$18 Verified Mar 2026 Year-round; arrive before noon to avoid long lines. 📍 MapDine at Peace Café, Honolulu's fully vegan comfort-food restaurant with a creative Asian-fusion menu
$18 Year-roundWaikiki / Kailua
Browse the KCC Saturday Farmers Market for fresh tropical fruit, GF baked goods, and local honey at Diamond Head
$20 Saturdays only, 7:30–11am 📍 MapOrder a GF plate lunch — grilled teriyaki chicken, two scoops of rice, and macaroni salad — at a Honolulu lunch spot
$13 Year-round 📍 MapWaikiki / Kailua
Eat a plant-based deli lunch at Down to Earth, Hawaii's largest vegan and organic grocery chain
$14 Year-roundTaste Hawaii's fusion cuisine on a guided food walk through Honolulu's best local neighborhoods
$65 Verified Mar 2026 Year-round. Walk-based tours are more comfortable in cooler morning hours.Waikiki / Kailua
Try Hawaii's signature dish in plant-based form — vegan poke bowls with watermelon tuna or tofu
$16 Year-roundLearn to make poke, coconut shrimp, and mochi in a chef's Diamond Head home kitchen
$149 Verified Mar 2026 Year-round. Book at least 2 weeks ahead. Available on Airbnb Experiences and hawaiianstylecookingclass.com. Book this tour →Waikiki / Kailua
Maui
MauiSample loco moco, kalbi ribs, and acai bowls at Maui's best roadside food trucks
$15 Verified Mar 2026 Year-round; some trucks close Sundays. 📍 MapDine on fresh-caught Hawaiian fish at Maui's most iconic oceanfront restaurant in Paia
$125 Verified Mar 2026 Year-round; lunch and dinner service daily. 📍 MapWailea / Lahaina / Kihei
Explore Maui's cool highland country — lavender farms, a historic winery, and the cowboy town of Makawao.
Year-round. Cooler and rainier than coast — bring a light jacket. Lavender farm open Fri-Mon only.
Drive the famous winding coastal road past waterfalls and rainforests
$30 Verified Mar 2026 Best May-Oct 📍 MapWailea / Lahaina / Kihei
Roast, brew, and taste Maui-grown coffee on a guided farm tour in Upcountry's misty Waipoli forest.
$139 Verified Mar 2026 Mon-Fri year-round. Reservation required. Tours start at 8:30am. Book this tour →Drive the legendary 64-mile coastal highway through rainforests, waterfalls, and black sand beaches.
Year-round but drier months (Apr-Oct) offer better road conditions. Winter rains can cause rockslides and closures.Wailea / Lahaina / Kihei
Watch sunrise above the clouds from a dormant volcano summit
$30 Verified Mar 2026 Open year-round; sunrise reservations required 3-7am, book 60 days ahead 📍 MapRelax at world-class beaches — snorkel Kapalua Bay, bodysurf Big Beach, or sunbathe at Wailea.
Year-round. Summer (Apr-Oct) has calmer waters; winter brings bigger surf and whale sightings from shore.Wailea / Lahaina / Kihei
Big Island
Big IslandTour a working Kona coffee farm and taste freshly roasted single-origin beans from the slopes of Hualalai
Year-round; harvest season (Aug-Jan) is most interesting. 📍 Map
Explore Kona's waterfront with Hulihee Palace, Pu'uhonua o Honaunau, and coffee country
Year-round. Kona Coffee harvest season (Aug-Jan) adds extra farm activity.Kona / Hilo
Browse 200+ vendors selling tropical fruits, fresh poke, leis, and local crafts in downtown Hilo
Year-round; Wednesdays and Saturdays are full-scale market days. 📍 MapSee the entire Big Island in one guided day: volcanoes, waterfalls, black sand, and coffee
$239 Verified Mar 2026 Year-round; drier months offer better volcano and waterfall conditions. Book at least a few days ahead. Book this tour →Kona / Hilo
Explore Kilauea's craters, lava tubes, and Chain of Craters Road at this UNESCO World Heritage Site
$30 Verified Mar 2026 Open year-round 24/7. Drier months (Apr-Oct) best for hiking. Evening visits may reveal lava glow at Halema'uma'u. Construction project may affect some summit trails.Kona / Hilo
Check out of your hotel, grab a final breakfast, and head to the airport. Safe travels from Big Island!
Where You’ll Stay
Estimated total: $1,912–$2,868
Trip Budget Estimate
Estimates based on listed activity prices and hotel rates. Actual costs vary by season, availability, and personal spending.
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