Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

Two-Week Ultimate Hawaii Adventure Itinerary for October

Viewed by 124 travelers

Day 1: Arrival and Beach Relaxation

Honolulu, Oahu, Hawaii on October 1, 2025

8:00am

Breakfast at Koko Head Cafe

Enjoy an innovative brunch at this popular spot that opens at 7am, known for its Hawaiian twists on classic breakfast fare like Cornflake French Toast.
USD30, 1h0m

10:00am

Waikiki Beach

Relax or surf at the iconic Waikiki Beach. This beachfront is perfect for warming up to Hawaii’s ocean and atmosphere.
Free, 3h0m

1:00pm

Lunch at Helena's Hawaiian Food

Savor traditional Hawaiian dishes such as Kalua pig and Lomi salmon in this local favorite open from 11am to 3pm, offering authentic island flavors.
USD25, 1h0m

2:30pm

Iolani Palace Tour

Explore the historic royal palace of Hawaii, open daily from 9am-4pm, to learn about Hawaiian monarchy and culture.
USD20, 1h0m

5:00pm

Sunset at Diamond Head State Monument

Hike to the summit for breathtaking sunset views over Honolulu. The park is open until 6pm; hiking takes about 1.5 hours roundtrip.
USD5, 1h30m

7:30pm

Dinner at Alan Wong’s Honolulu

Dine on upscale Hawaiian regional cuisine in a refined setting; reservations recommended as it closes by 9:30pm.
USD70, 1h30m
Find Hotels in Honolulu

Day 2: Cultural Sites and Shopping

Honolulu, Oahu, Hawaii on October 2, 2025

7:30am

Breakfast at Leonard's Bakery

Try the famous malasadas (Portuguese doughnuts) at this iconic bakery open from 6:30am to 9pm.
USD10, 0h30m

9:00am

Pearl Harbor National Memorial

Visit this historic WWII site, including the USS Arizona Memorial. Open from 7am to 5pm; timed tickets recommended for entry.
Free, 2h30m

12:00pm

Lunch at Nico’s Pier 38

Enjoy fresh seafood by the water, known for poke and fish and chips, open daily from 10am to 9pm.
USD30, 1h0m

1:30pm

Bishop Museum

Explore Hawaiian history and culture through exhibits. Open daily 9am-5pm.
USD25, 2h0m

4:00pm

Shopping at Ala Moana Center

Visit the largest open-air shopping mall with diverse stores and eateries. Open 9:30am-9pm.
Free, 2h0m

7:00pm

Dinner at Roy’s Hawaii Kai

Experience Hawaiian fusion cuisine in a family-friendly setting; open daily until 9pm.
USD50, 1h30m
Find Hotels in Honolulu

Day 3: Travel to Maui and Scenic Drive

Maui, Hawaii on October 3, 2025

7:00am

Breakfast at Highway Inn

Sample traditional Hawaiian breakfast dishes before your trip; open daily at 7am.
USD20, 0h45m

9:00am

Flight from Oahu to Maui

Short flight (approx. 45 minutes) from Honolulu to Kahului Airport in Maui.
USD100, 1h0m

11:00am

Drive the Road to Hana

Experience the legendary scenic coastal drive with waterfalls, beaches, and rainforests. Start mid-morning to have daylight for stops.
Free, 6h0m

5:00pm

Check-in at accommodation in Hana

Settle in and relax after the long drive.
Varies, N/A

7:00pm

Dinner at Hana Ranch Restaurant

Enjoy fresh, locally sourced Hawaiian fare available until 8:30pm.
USD40, 1h0m
Find Hotels in Maui

Day 4: Hana Exploration and Beaches

Hana, Maui, Hawaii on October 4, 2025

7:30am

Breakfast at Accommodation or local cafe

Start the day with a local breakfast option to fuel your exploration.
USD15, 0h45m

9:00am

Wainapanapa State Park

Explore the park's famous black sand beach, sea caves, and coastal trails open from 7am to 7pm.
USD5, 2h30m

12:00pm

Lunch at Hana Fresh

Enjoy fresh, casual food made with regional ingredients; open until 3pm.
USD20, 1h0m

1:30pm

Relax at Hamoa Beach

Spend a peaceful afternoon on one of Maui’s most beautiful beaches, great for swimming and sunbathing.
Free, 3h0m

5:00pm

Return towards central Maui

Drive back to central Maui area, prepare for next day activities.
Free, 2h0m

7:30pm

Dinner at Mama’s Fish House

Reserve well in advance for this renowned seafood restaurant open until 9pm, celebrated for ocean views and fresh fish.
USD75, 1h30m
Find Hotels in Hana

Day 5: Haleakalā National Park

Maui, Hawaii on October 5, 2025

3:30am

Haleakalā Sunrise Tour

Drive early to view the famous sunrise above the clouds at Haleakalā summit. Park opens 2 hours before sunrise; entry fee applies.
USD30, 4h0m

8:00am

Breakfast at Kula Lodge

Late breakfast with stunning views in upcountry Maui; open from 7am.
USD25, 1h0m

10:00am

Explore Haleakalā crater and trails

Hike or drive scenic routes in the park to see volcanic landscapes and native flora.
Included in entry fee, 3h0m

1:30pm

Lunch at T Komoda Store & Bakery

Taste freshly baked treats and local snacks at this specialty bakery; open until 3pm.
USD15, 1h0m

3:00pm

Return to hotel for rest

Take an afternoon break from exploration.
Free, 2h0m

6:30pm

Dinner at Leoda’s Kitchen and Pie Shop

Enjoy hearty meals and delicious pies in a casual atmosphere; open till 8pm.
USD30, 1h30m
Find Hotels in Maui

Day 6: Flight to Big Island - Volcano Adventure

Hilo, Big Island, Hawaii on October 6, 2025

7:00am

Breakfast at Kihei Caffe

Start day with popular breakfast fare in Kihei before flying out; open from 6am.
USD20, 0h45m

9:00am

Flight from Maui to Hilo, Big Island

Approximate 45-minute flight landing at Hilo International Airport.
USD120, 1h0m

11:00am

Visit Hawaii Volcanoes National Park

Explore volcanic landscapes, lava tubes, and visitor centers. Park open 24 hours, Visitor Center 8am-5pm.
USD30, 4h0m

3:30pm

Check in hotel in Hilo

Settle in with rest before evening activities.
Varies, N/A

6:00pm

Dinner at Hilo Bay Cafe

Upscale dining featuring locally sourced ingredients and ocean views, open daily till 9pm.
USD50, 1h30m

8:00pm

Night lava viewing (if active)

Check local conditions for lava glow viewing spots within the park; viewing is best after dark.
Included in park fee, 2h0m
Find Hotels in Hilo

Day 7: Waterfalls & Botanical Gardens

Hilo, Big Island, Hawaii on October 7, 2025

8:00am

Breakfast at Ken’s House of Pancakes

Enjoy hearty breakfast classics open 24/7, perfect before a day of exploring.
USD15, 0h45m

9:30am

Rainbow Falls State Park

Visit this 80-foot waterfall just outside Hilo, free to access and perfect for photos.
Free, 1h0m

11:00am

Liliuokalani Gardens

Stroll this beautiful Japanese garden in Hilo town, open daily during daylight hours.
Free, 1h0m

12:30pm

Lunch at Cafe Pesto

Popular restaurant offering Hawaiian and Italian-inspired dishes, open from 11am to 9pm.
USD30, 1h0m

2:00pm

Panaewa Rainforest Zoo & Gardens

Small zoo with exotic animals and botanical collections, open 8am-5pm with free admission.
Free, 1h30m

4:00pm

Afternoon free time or beach visit

Relax or explore nearby beaches like Carlsmith Beach Park.
Free, 2h0m

7:00pm

Dinner at Moon and Turtle

A trendy spot specializing in fresh, local seafood and innovative dishes, open till 9pm.
USD45, 1h30m
Find Hotels in Hilo

Day 8: South Kona Coffee and Culture

Captain Cook, Big Island, Hawaii on October 8, 2025

7:30am

Breakfast at Hawaiian Style Cafe

Start with hearty, island-style breakfast options in nearby Kealakekua; open at 7am.
USD20, 0h45m

9:00am

Visit Kona Coffee Living History Farm

Tour a working coffee farm to learn about Kona coffee production; open 9am-4pm, closed on Saturdays.
USD10, 1h30m

11:00am

South Kona Coffee and Tea plantations tour

Take a self-guided drive around local plantations and tasting rooms.
Varies, 2h0m

1:30pm

Lunch at Umekes Fishmarket Bar & Grill

Enjoy fresh poke and seafood, open daily for lunch from 11am to 3pm.
USD25, 1h0m

3:00pm

Pu’uhonua O Honaunau National Historical Park

Explore this sacred place of refuge highlighting Hawaiian culture; open 7:45am to 5pm.
USD20, 2h0m

6:30pm

Dinner at Kona Brewing Company

Casual dining with craft beers and pizza; open till 9pm.
USD30, 1h30m
Find Hotels in Captain Cook

Day 9: Flight to Kauai and Relax

Lihue, Kauai, Hawaii on October 9, 2025

7:00am

Breakfast at Pineapple’s Island Fresh Cuisine

Enjoy fresh island-inspired breakfast in Kona area before flying out; open from 7am.
USD20, 0h45m

9:00am

Flight from Big Island to Kauai

Connecting flights via Honolulu or direct flights to Lihue Airport, approx. 1-2h travel time.
USD150, 2h0m

11:30am

Check in hotel in Lihue

Settle in and prepare for afternoon activities.
Varies, N/A

1:00pm

Lunch at Duke’s Kauai

Beachfront dining with Hawaiian comfort food, open 11am to 9pm.
USD30, 1h0m

2:30pm

Relax at Kalapaki Beach

Spend the afternoon enjoying this accessible beach near Lihue perfect for swimming and sunbathing.
Free, 3h0m

6:30pm

Dinner at The Fish Express

Casual spot known for fresh poke bowls and seafood; open till 7pm.
USD25, 1h0m
Find Hotels in Lihue

Day 10: Napali Coast Tour

Kauai, Hawaii on October 10, 2025

6:30am

Early Breakfast at hotel or local cafe

Fuel up early before the active day ahead.
USD15, 0h30m

7:30am

Napali Coast Boat Tour

Depart from Port Allen or Hanalei. Tours run in the morning until early afternoon to view the stunning sea cliffs and marine life; check company schedules in advance.
USD150, 5h0m

1:30pm

Lunch in Hanalei Town

Casual eateries serving fresh local fare, open early afternoon.
USD25, 1h0m

3:00pm

Explore Hanalei Bay and Pier

Relax and take photos at this iconic, beautiful bay with ample shops and cafes nearby.
Free, 2h0m

6:00pm

Dinner at Bar Acuda

Upscale farm-to-table dining in Hanalei open until 9pm; reservations recommended.
USD60, 1h30m
Find Hotels in Kauai

Day 11: Waimea Canyon and Kokee State Park

Kauai, Hawaii on October 11, 2025

7:00am

Breakfast at Kalaheo Cafe & Coffee Company

Start with fresh coffee and breakfast sandwiches; good stop on the way to Waimea Canyon.
USD15, 0h30m

8:00am

Drive to Waimea Canyon State Park

Known as the 'Grand Canyon of the Pacific,' enjoy lookout points and short hikes with majestic views; park open 6am-6pm.
USD5, 3h0m

11:30am

Drive to Koke'e State Park for hiking

Continue exploring lush trails with cooler weather and native forests, park also open 6am-6pm.
Included in park fee, 3h0m

3:00pm

Lunch at Koke'e Lodge

Late lunch with casual dining options in the park open until 3pm - prepare to time accordingly or pack lunch.
USD20, 1h0m

5:00pm

Return to hotel

Relax after a day of nature exploration.
Free, 1h0m

7:00pm

Dinner at Red Salt

Fine dining in Poipu featuring Asian-Pacific cuisine, open till 9pm.
USD60, 1h30m
Find Hotels in Kauai

Day 12: Beach Day and Departure Prep

Kauai, Hawaii on October 12, 2025

8:00am

Breakfast at The Greenery Cafe

Enjoy fresh smoothies and healthy breakfast fare to start your last full day.
USD20, 0h45m

9:00am

Relax at Poipu Beach Park

Spend your morning swimming, snorkeling, or simply soaking in Kauai’s best beach; ideal for families and open all day.
Free, 4h0m

1:00pm

Lunch at Brennecke's Beach Broiler

Casual beachside dining with seafood and grills, perfect for a laid-back meal; open until 2pm.
USD25, 1h0m

2:30pm

Pack & Rest

Prepare for departure with time to rest at your hotel.
Free, 3h0m

7:00pm

Farewell Dinner at Plantation Gardens

Dine in a tropical garden setting with Hawaiian fusion cuisine; open till 9pm and perfect for a memorable last evening.
USD60, 1h30m
Find Hotels in Kauai

Day 13: Departure Day

Lihue, Kauai, Hawaii on October 13, 2025

7:00am

Breakfast at hotel

Enjoy a relaxing breakfast before your travel day.
Included, 0h45m

9:00am

Check out and transfer to Lihue Airport

Head to the airport for your departure flight home or next destination.
Varies, N/A
Find Hotels in Lihue
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version

More About Hawaii for 2 weeks

Best Hawaii Travel Deals
Travel Deals
Itinerary created by AI-assisted, human-reviewed

Plan Your Hawaii for 2 weeks Trip

Cost Estimator
Estimate your trip budget
Packing List
Get a custom checklist
Weather Expert
Check weather & best time to go