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Two-Week Ultimate Hawaii Adventure in May 2025

Viewed by 152 travelers

Day 1: Oahu Arrival & Exploration

Honolulu, Oahu, Hawaii on May 1, 2025

8:00am

Breakfast at Koko Head Cafe

Enjoy a creative brunch with local Hawaiian twists like cornflake french toast in this popular Honolulu eatery open from 7:30am to 3pm.
USD25, 1h0m

10:00am

Visit Pearl Harbor National Memorial

Explore the historic USS Arizona Memorial and learn about WWII history. The site is open from 7:00am to 5:00pm; reservations recommended.
USD0, 2h0m

1:00pm

Lunch at Helena's Hawaiian Food

Taste authentic Hawaiian plates like Kalua pig and poi at this beloved local spot open 10am to 3pm, closed Sundays.
USD20, 1h0m

3:00pm

Relax at Waikiki Beach

Unwind on world-famous white sands, swim, or try beginner surfing at Waikiki; best enjoyed in the afternoon.
Free, 2h0m

6:30pm

Dinner at Roy's Hawaii Kai

Dine on upscale Hawaiian fusion dishes featuring fresh seafood. Restaurant hours 5pm to 9pm.
USD50, 1h30m
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Day 2: North Shore Adventure

North Shore, Oahu, Hawaii on May 2, 2025

7:30am

Breakfast at Ted's Bakery

Try their famous chocolate haupia pie and hearty breakfast plates. Open from 7am to 7pm.
USD15, 1h0m

9:00am

Explore Waimea Valley

Walk through beautiful botanical gardens to a waterfall where you can swim. Open 9am to 5pm, entrance fee required.
USD20, 2h30m

12:00pm

Lunch at Giovanni's Shrimp Truck

Famous for garlic shrimp plates served from 10am to 5pm; casual and must-try local food truck experience.
USD18, 1h0m

1:30pm

Visit Banzai Pipeline Beach

Watch world-class surfers tackle huge waves; explore the beach and surrounding shops.
Free, 1h0m

3:00pm

Shopping and exploring Haleiwa Town

Browse local boutiques and art galleries in this charming historic town.
Varies, 1h30m

6:30pm

Dinner at Haleiwa Joe's Seafood Grill

Enjoy fresh seafood and Hawaiian specialties with sunset views. Open 5pm to 9pm.
USD40, 1h30m
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Day 3: Fly to Maui & Explore West Maui

Lahaina, Maui, Hawaii on May 3, 2025

7:00am

Breakfast at Gazebo Restaurant

Known for pancakes and local comfort food with ocean views. Opens at 7am, arrive early.
USD20, 1h0m

9:00am

Flight to Maui (OGG Airport)

Take a short flight from Honolulu to Kahului Airport, approx. 40 minutes.
USD100, 1h30m

11:00am

Check-in and explore Lahaina Historic Town

Stroll along Front Street to see art galleries, shops, and the famous Banyan Tree.
Free, 2h0m

1:00pm

Lunch at Down the Hatch

Casual dining with fresh fish tacos and island fare, open 11:30am to 9pm.
USD22, 1h0m

3:00pm

Relax at Kaanapali Beach

Spend the afternoon swimming and snorkeling at this beautiful beach.
Free, 2h0m

6:30pm

Dinner at Leilani's on the Beach

Enjoy upscale island cuisine and sunset views on the beach; open till 9pm.
USD45, 1h30m
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Day 4: Road to Hana & Waterfalls

Hana, Maui, Hawaii on May 4, 2025

6:00am

Early Breakfast at Paia Bay Coffee

Grab quick, fresh coffee and pastries before heading out; open from 6am.
USD10, 0h30m

6:30am

Drive Road to Hana

Scenic drive with multiple stops for waterfalls and hiking such as Twin Falls and Wai'anapanapa State Park. Plan for a full day, the trip takes 10-12 hours roundtrip.
USD0, 10h0m

12:30pm

Lunch picnic at Wai'anapanapa State Park

Enjoy packed lunch surrounded by black sand beaches and lava tubes.
USD0, 1h0m

6:30pm

Dinner at Mama's Fish House (Reserve ahead)

Renowned fine dining specializing in fresh island seafood near Hana, open 5pm to 9pm.
USD60, 1h30m
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Day 5: Haleakalā Sunrise & Upcountry

Haleakalā National Park, Maui, Hawaii on May 5, 2025

3:30am

Haleakalā National Park Sunrise Tour

Witness breathtaking sunrise above the clouds; park opens at 3am for sunrise visitors. Dress warmly.
USD30, 3h0m

7:00am

Breakfast at Kula Lodge

Breakfast with stunning views of the island, open from 7am.
USD20, 1h0m

9:00am

Visit Surfing Goat Dairy Farm

Tour the farm and meet goats, taste local cheese. Open 9am to 4pm.
USD15, 1h0m

12:00pm

Lunch at Hali'imaile General Store

Enjoy creative island cuisine in an old plantation store; open 11am to 3pm.
USD30, 1h0m

2:00pm

Explore Makawao Town

Visit this charming paniolo (cowboy) town with galleries and boutiques.
Free, 1h30m

6:00pm

Dinner at Flatbread Company, Paia

Relaxed spot with wood-fired pizzas and organic ingredients open till 9pm.
USD25, 1h0m
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Day 6: Big Island Volcano Day

Hilo and Volcanoes National Park, Big Island, Hawaii on May 6, 2025

7:00am

Flight to Hilo, Big Island

Fly from Maui to Hilo, approx 40 minutes flight.
USD120, 1h30m

9:00am

Breakfast at Ken's House of Pancakes

Popular local breakfast with a variety of pancakes and classic dishes, open 24 hours.
USD15, 1h0m

10:30am

Explore Hawaii Volcanoes National Park

Visit Kīlauea volcano, hike trails, see lava tubes and steam vents; park is open 24 hours but visitors center hours 8am to 5pm.
USD30, 4h0m

3:00pm

Visit Akaka Falls State Park

Short walk to spectacular 442 ft waterfall surrounded by tropical vegetation; open 8am to 5pm.
USD5, 1h0m

5:00pm

Dinner at Hilo Bay Cafe

Contemporary Hawaiian dishes with ocean views, open till 9pm.
USD40, 1h30m
Find Hotels in Hilo and Volcanoes National Park

Day 7: Coffee & Beaches Big Island

Kona, Big Island, Hawaii on May 7, 2025

7:30am

Breakfast at Kona Coffee & Tea

Great coffee and light breakfast options with laid-back ambiance, open 7am to 4pm.
USD12, 1h0m

9:00am

Tour a Kona Coffee Farm

Learn about Kona coffee and sample fresh brews. Most farms open 9am to 5pm; reservations recommended.
USD20, 2h0m

12:00pm

Lunch at Umekes Fishmarket Bar & Grill

Fresh poke bowls and seafood dishes in Kona town, open 11am to 9pm.
USD25, 1h0m

1:30pm

Relax at Hapuna Beach State Park

One of the island’s best sandy beaches, perfect for swimming and sunbathing.
USD5, 3h0m

6:30pm

Dinner at Merriman's Kona

Fine dining focused on farm-to-table Hawaiian cuisine; open 5:30pm to 9pm.
USD60, 1h30m
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Day 8: Fly to Kauai & Beach Day

Lihue and Poipu, Kauai, Hawaii on May 8, 2025

7:00am

Flight to Lihue, Kauai

Fly from Kona to Kauai, about 1 hour flight.
USD130, 1h30m

9:00am

Breakfast at Kalaheo Cafe & Coffee Co.

Fresh, casual breakfast with good coffee, open from 7am.
USD15, 1h0m

10:30am

Relax at Poipu Beach Park

Family-friendly beach with great snorkeling and chances to spot sea turtles.
Free, 3h0m

2:00pm

Lunch at Brennecke's Beach Broiler

Casual beachside dining offering fresh seafood and island flavors, open 11am to 9pm.
USD30, 1h0m

4:00pm

Visit Spouting Horn

Watch ocean water spout through lava tubes creating natural geysers; open all day.
Free, 1h0m

6:30pm

Dinner at Merriman’s Poipu

Enjoy elegant island dishes with sunset ocean views; open 5:30pm to 9pm.
USD55, 1h30m
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Day 9: Napali Coast & Hiking

Napali Coast, Kauai, Hawaii on May 9, 2025

6:00am

Breakfast to go from Little Fish Coffee

Grab quick coffee and sandwiches before early hiking; open from 6am.
USD12, 0h30m

6:30am

Kalalau Trail Hike (Partial)

Hike the first 5 miles of the famous Napali Coast trail to Hanakapiai Beach; allow 4-6 hours round trip. Permits required for full hike, partial requires none.
USD0, 5h0m

12:00pm

Lunch Picnic on the Trail

Pack a lunch to enjoy on the beach or shaded areas along the hike.
USD0, 1h0m

3:30pm

Return to Kauai South Shore

Relax and refresh after a long hike.
USD0, 1h30m

6:30pm

Dinner at The Beach House Restaurant

Dine with stunning ocean views offering Pacific Rim cuisine; open 5pm to 9pm.
USD60, 1h30m
Find Hotels in Napali Coast

Day 10: Waimea Canyon & Relax

Waimea Canyon, Kauai, Hawaii on May 10, 2025

7:30am

Breakfast at Kountry Kitchen

Down-home Hawaiian breakfast favorites; open from 6am.
USD15, 1h0m

9:00am

Drive to Waimea Canyon State Park

Explore the ‘Grand Canyon of the Pacific’ with scenic lookouts and hiking trails.
USD5, 4h0m

1:00pm

Lunch at Shrimp Station

Local shrimp plates in Waimea; open 10am to 6pm.
USD18, 1h0m

3:00pm

Relax at Hanalei Bay

Spend peaceful afternoon at this breathtaking beach on the north shore.
Free, 3h0m

7:00pm

Dinner at Bar Acuda

Contemporary small plates with fresh local ingredients in Hanalei, open until 9pm.
USD45, 1h30m
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Day 11: Kauai Culture & Departure Prep

Lihue, Kauai, Hawaii on May 11, 2025

8:00am

Breakfast at Java Kai

Hip café offering excellent coffee and breakfast fare, open from 7am.
USD15, 1h0m

9:30am

Visit Kauai Museum

Learn about the island’s history, culture, and natural environment; open 10am to 4pm.
USD12, 2h0m

12:00pm

Lunch at Mark’s Place Tacos

Casual Mexican spot with island flair, open 11:30am to 8pm.
USD18, 1h0m

2:00pm

Relax at Lihue Wailua River State Park

Explore the river area with short hikes or kayak rental, open daylight hours.
USD0, 2h0m

6:00pm

Dinner at Duke’s Kauai

Island-inspired cuisine with beachfront views in Lihue; open until 9pm.
USD45, 1h30m
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Day 12: Departure or Optional Extensions

Lihue, Kauai, Hawaii on May 12, 2025

8:00am

Breakfast at Kalapaki Joe’s

Enjoy final Hawaiian breakfast with ocean views, open from 7am.
USD20, 1h0m

10:00am

Last minute shopping at Kauai Community Market

Browse local crafts and fresh produce, open Saturdays 8am to 12pm.
Varies, 1h0m

12:00pm

Airport transfer and departure

Head to Lihue Airport for your flight home or further travel plans.
USD0, N/A
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