11-13 Day Kauai and Maui Island Adventure from Hanalei Bay

Day 1: Arrival and Relaxation

Hanalei Bay, Kauai, Hawaii on June 18, 2025

8:00am

Flight from Boston to Kauai

Take an early flight from Boston Logan International Airport to Lihue Airport in Kauai; due to travel time and connections, expect arrival in the early evening.
USD600+, 10h0m+

7:00pm

Check-in Hanalei Bay Hotel

Settle into your hotel in the beautiful Hanalei Bay area, the perfect base for your Kauai exploration.
USD200+, N/A

8:00pm

Dinner at Bar Acuda

Enjoy locally sourced West Coast-influenced Hawaiian cuisine at this popular Hanalei restaurant open until 9:00pm.
USD40-60, 1h30m
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Day 2: North Kauai Exploration

Hanalei Bay, Kauai, Hawaii on June 19, 2025

7:30am

Breakfast at Hanalei Bread Company

Start the day with fresh pastries and Hawaiian coffee at this local bakery open from 7am.
USD10-15, 1h

9:00am

Explore Hanalei Pier and Bay

Enjoy a scenic walk along the iconic Hanalei Pier and relax on the beach, famous for its stunning mountain backdrop and gentle waves.
Free, 2h

12:00pm

Lunch at The Dolphin Restaurant

Savor fresh sushi and seafood specialties in Hanalei, open for lunch starting at 11:30am.
USD25-45, 1h30m

2:00pm

Hike the Kalalau Trail (partial)

Take a moderate 4-mile hike to Hanakapiai Beach to experience breathtaking coastal views; the trailhead is at Ke’e Beach, north of Hanalei, allow 3-4 hours round trip.
Free, 3h30m

6:00pm

Dinner at Postcards Café

Dine at this charming spot offering organic and vegan-friendly dishes from 5pm onwards.
USD30-50, 1h30m
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Day 3: East Kauai Adventure

Hanalei Bay, Kauai, Hawaii on June 20, 2025

7:30am

Breakfast at Hanalei Coffee Roasters

Enjoy locally roasted coffee and healthy breakfast bowls available starting 7am.
USD12-18, 1h

9:00am

Visit Wailua Falls and Opaekaa Falls

Spend the morning visiting these iconic Kauai waterfalls located about an hour south from Hanalei, perfect for easy photo stops and nature appreciation.
Free, 3h

12:30pm

Lunch at Street Burger

Grab a casual gourmet burger and sides in Kapaa, open daily from 11am to 9pm.
USD15-25, 1h

2:00pm

Kayaking the Wailua River

Take a guided kayak tour to explore the lush Wailua River and visit Fern Grotto, tours run from 9am to 3pm, book in advance.
USD60-100, 3h

6:30pm

Dinner at Tahiti Nui

Enjoy traditional Hawaiian dinner and live music at this beloved Kapaa eatery open until 9pm.
USD30-50, 1h30m
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Day 4: Relax and Explore Local Markets

Hanalei Bay, Kauai, Hawaii on June 21, 2025

8:00am

Breakfast at Hanalei Bay Poke Market

Try a poke bowl breakfast, fresh and famous in Kauai, open at 8am.
USD10-15, 1h

10:00am

Visit Hanalei Farmers Market

Explore local vendors offering fresh produce, artisan crafts, and snacks, best visited in the morning before noon.
Free, 2h

12:30pm

Lunch at Nourish Hanalei

Enjoy a healthy and creative menu featuring organic dishes, open from 11am to 9pm.
USD20-35, 1h30m

2:30pm

Beach time at Lumaha’i Beach

Relax or take a swim at this dramatic and lesser crowded beach on Kauai's North Shore.
Free, 3h

6:00pm

Dinner at The Dolphin Restaurant

Return to savor fresh seafood or sushi choices in Hanalei.
USD30-50, 1h30m
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Day 5: South and West Maui Bound

Hanalei Bay to Lahaina, Maui, Hawaii on June 22, 2025

7:00am

Early Breakfast and Check-out

Enjoy a final quick breakfast at your hotel and check out early to catch your inter-island flight.
USD15-25, 1h

9:00am

Flight from Lihue (Kauai) to Kahului (Maui)

A short 40-50 minute flight that will place you in the heart of Maui to start your island adventure.
USD100-150, 50m

10:30am

Drive to Lahaina and Hotel Check-in

Check into your hotel in Lahaina or nearby West Maui resort area, a great base for exploring Maui's west and south coasts.
USD200+, N/A

12:00pm

Lunch at Lahaina Fish Co.

Enjoy fresh oceanfront dining specializing in local fish and island flavors, open from 11am.
USD25-45, 1h30m

2:00pm

Explore Front Street in Lahaina

Stroll along Lahaina’s historic Front Street with shops, galleries, and cultural sites.
Free, 2h

6:30pm

Dinner at Kimo's

Dine on local seafood and bistecca dishes in this popular oceanfront restaurant open until 9pm.
USD40-60, 1h30m
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Day 6: West Maui Beaches and Snorkeling

Lahaina, Maui, Hawaii on June 23, 2025

7:30am

Breakfast at Gazebo Restaurant

Enjoy famous pancakes and island classics at this popular spot open from 7am; arrive early to avoid wait times.
USD10-20, 1h

9:00am

Snorkeling at Napili Bay

Spend the morning snorkeling in crystal-clear waters abundant with marine life at this family-friendly beach.
Free, 3h

12:30pm

Lunch at Sea House Restaurant

Relax with ocean views and fresh seafood at this nearby lunch spot, open daily from 11am.
USD20-40, 1h30m

2:30pm

Visit Honolua Bay

Explore this marine preserve known for snorkeling and scenic hiking, access depends on weather conditions.
Free, 2h

6:00pm

Dinner at Merriman's Kapalua

Enjoy farm-to-table dining with sunset views at this top-rated restaurant, reservation recommended.
USD50-80, 2h
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Day 7: Road to Hana Day Trip

Lahaina / Hana, Maui, Hawaii on June 24, 2025

6:00am

Early Breakfast and Departure

Start early with breakfast from your hotel or packed snacks, to get an early start on the famous Road to Hana drive.
USD15-25, 1h

7:00am

Road to Hana Scenic Drive

Enjoy a full day exploring waterfalls, beaches, and rainforest along this iconic drive, including stops at Twin Falls, Wainapanapa State Park, and Hana Town.
Free - Park fees USD5-10, 8h

4:00pm

Return to Lahaina

Drive back in the late afternoon to your hotel for dinner and rest.
Free, 2h

7:00pm

Dinner at Lahaina Grill

Recharge with fine dining featuring island cuisine and seafood, reservation recommended.
USD50-70, 1h30m
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Day 8: Upcountry Maui and Iao Valley

Makawao / Iao Valley, Maui, Hawaii on June 25, 2025

8:00am

Breakfast at Komoda Store & Bakery

Start your day with popular sweet and savory baked goods in Makawao, open from 6am.
USD10-15, 1h

9:30am

Explore Iao Valley State Park

Visit the stunning Iao Needle and lush valley trails; park is open 7am-7pm, no fee required.
Free, 2h

12:00pm

Lunch at Hali’imaile General Store

Dine on elevated Hawaiian dishes in a historic plantation setting, open from 11am.
USD30-50, 1h30m

2:00pm

Explore Makawao Town Galleries

Visit art galleries and boutiques highlighting local crafts and artists in this charming upcountry town.
Free, 2h

6:00pm

Dinner at Monkeypod Kitchen

Enjoy island-inspired cuisine with live music in Wailea, open until 10pm.
USD40-60, 1h30m
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Day 9: Snorkeling and Beach Day

Wailea / South Maui, Hawaii on June 26, 2025

8:00am

Breakfast at Kihei Caffe

Enjoy hearty breakfast favorites open from 6am, ideal before a beach day.
USD10-20, 1h

9:30am

Snorkeling at Molokini Crater

Take a morning boat tour to Molokini, a partially submerged volcanic crater with vibrant coral reefs; tours depart from Maalaea Harbor starting at 7am.
USD100-150, 4h

2:00pm

Relax at Big Beach (Makena State Park)

Spend a relaxing afternoon on one of Maui's largest and most beautiful sandy beaches.
Free, 3h

6:30pm

Dinner at Monkeypod Kitchen

Return for fresh, locally sourced dinner fare with an emphasis on sustainability.
USD40-60, 1h30m
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Day 10: Departure

Kahului, Maui to Boston, USA on June 27, 2025

7:00am

Breakfast and Check-out

Final breakfast at your hotel followed by check-out preparation.
USD15-25, 1h

9:00am

Drive to Kahului Airport

Head to airport for your flight departing Maui for Boston with connection(s) via Los Angeles or San Francisco.
USD50 (car rental drop-off), 45m

11:30am

Flight from Maui to Boston

Long haul return flight with one or two stops, departing mid-morning to arrive Boston by late evening or next day.
USD600+, 10h+
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