Explore the Enchantment of Hawaii: Hills, Beaches, and Historical Wonders

Day 1: Arrival in Honolulu

Honolulu, Hawaii on June 8, 2025

3:00PM

Check into Hotel

Settle into your hotel and get refreshed for your adventure. The hotels on Waikiki Beach offer excellent views and proximity to attractions.
USD200, 1 hour

5:00PM

Waikiki Beach

Stroll along the beautiful beach, enjoy the sunset, and immerse yourself in the vibrant local atmosphere.
Free, 2 hours

7:30PM

Duke's Waikiki for Dinner

A lively beachfront bar and restaurant, try their famous Hula Pie and fresh fish tacos. Open until 10:00 PM.
USD40, 1.5 hours
View Hotel Availability

Day 2: Beach Day in Oahu

Oahu, Hawaii on June 9, 2025

8:00AM

Breakfast at Eggs 'n Things

Famous for their pancakes and hearty breakfast options, open from 7:00 AM. Start your day right!
USD20, 1 hour

9:30AM

Kailua Beach

A stunning beach known for its clear waters and soft sand, perfect for swimming and sunbathing.
Free, 3 hours

1:00PM

Lunch at Buzz's Lanikai

A local favorite featuring fresh seafood and picturesque views, open until 3:00 PM. Don’t miss their fish sandwiches!
USD25, 1.5 hours

3:00PM

Lanikai Pillbox Hike

A moderate hike that offers breathtaking views of the beach and ocean; the best time to hike is in the afternoon.
Free, 2 hours

6:00PM

Dinner at The Beach House

Enjoy oceanfront dining with local specialties like Mahi Mahi. Reservations are recommended as they close at 9:00 PM.
USD50, 2 hours
View Hotel Availability

Day 3: Hiking and History

Diamond Head, Hawaii on June 10, 2025

7:00AM

Breakfast at Leonard's Bakery

Start your day with their famous malasadas. The bakery opens early, at 5:30 AM, so you can enjoy a tasty treat before the hike.
USD10, 1 hour

8:00AM

Diamond Head State Monument

Hike to the crater's summit for a panoramic view of Waikiki and the Pacific Ocean. The park opens at 6:00 AM, so arrive early.
USD5, 2 hours

11:00AM

Explore Local Shops

Browse boutique shops and find unique souvenirs in the Waikiki area. A perfect way to experience local culture.
Free, 2 hours

1:00PM

Lunch at Hula Grill Waikiki

A great place to enjoy local flavors and fresh catches from the ocean. Open until 3:00 PM.
USD30, 1.5 hours

3:00PM

Visit Iolani Palace

The only royal palace on U.S. soil; a historical site that provides insight into Hawaii's monarchy. It closes at 5:00 PM, so go early.
USD27, 2 hours

6:00PM

Dinner at Roy's Waikiki

Enjoy a fine dining experience with a blend of Hawaiian and Asian cuisine. Reservations are highly recommended, and they close at 10:00 PM.
USD70, 2 hours
View Hotel Availability

Day 4: Historical Exploration

Pearl Harbor, Hawaii on June 11, 2025

7:00AM

Breakfast at Kimo's

Known for its generous portions and coastal views, this restaurant opens at 8:00 AM. Try their signature pancakes!
USD15, 1 hour

8:30AM

Pearl Harbor National Memorial

Visit the solemn historical sites that commemorate the courage of the military and civilians during WWII. Ensure you arrive early as reservations are recommended.
USD1, 3 hours

12:00PM

Lunch at L&L Hawaiian Barbecue

Enjoy a taste of Hawaii’s local plate lunch with a variety of options. Open until 8:00 PM, ideal for a casual meal.
USD15, 1 hour

1:30PM

USS Arizona Memorial

Part of the Pearl Harbor site; take a boat ride to this memorial which honors those lost during the attack. Make sure to check the schedule for boat times.
Free, 1.5 hours

3:30PM

Return to Hotel and Relax

Head back to your hotel for some downtime before an evening adventure. Unwind and recharge before dinner.
Free, 2 hours

6:00PM

Dinner at Side Street Inn

Famous for local comfort food and a relaxed atmosphere. Check out their crispy pork and fried rice, open until 11:00 PM.
USD40, 2 hours
View Hotel Availability

Day 5: Island Hopping to Maui

Maui, Hawaii on June 12, 2025

7:00AM

Breakfast at Mama's Fish House

Start your day with beachfront dining at this iconic restaurant known for fresh seafood and beautiful presentations. Opens at 7:00 AM.
USD50, 1.5 hours

9:00AM

Travel to Maui

Catch a morning flight to Maui; enjoy the scenic view during the short trip. Book tickets in advance.
USD80, 4 hours including travel time and check-in

1:00PM

Lunch at Paia Fish Market

A casual eatery known for fresh fish tacos and local vibe. Open until 8:00 PM, perfect for visitors.
USD25, 1 hour

2:30PM

Explore Haleakalā National Park

Visit the park to experience its unique landscapes and natural beauty. Open until 7:00 PM, great for hikes.
USD30, 3 hours

6:00PM

Dinner at The Mill House

Enjoy farm-to-table dining that highlights local ingredients and flavors. Reservations are recommended, and they close at 9:00 PM.
USD60, 2 hours
View Hotel Availability

Day 6: Nature and Adventure

Maui, Hawaii on June 13, 2025

8:00AM

Breakfast at Crater Café

Enjoy breakfast at this cafe located in Haleakalā National Park, open from 7:00 AM. Take a breath of fresh air before your adventures.
USD15, 1 hour

9:00AM

Snorkeling at Molokini Crater

Discover the vibrant marine life in the clear waters around Molokini; book a tour in advance. Tours generally last 4 hours.
USD100, 4 hours

1:00PM

Lunch at The Seafood Bar & Grill

Savor a seafood lunch with views of the ocean, open until 10:00 PM. Their poke bowls are highly recommended!
USD30, 1.5 hours

2:30PM

Relax at Kaanapali Beach

Unwind on one of the island's best beaches, known for its soft sand and excellent swimming conditions.
Free, 3 hours

6:00PM

Dinner at Fleetwood's on Front St

A must-visit for visitors; enjoy a casual upscale atmosphere with live music and local dishes. Reservations suggested, last seating at 9:00 PM.
USD70, 2 hours
View Hotel Availability

Day 7: Return to Honolulu

Honolulu, Hawaii on June 14, 2025

8:00AM

Breakfast at Hula Grill

Start your day off right with beautiful beachfront views and a hearty breakfast, popular among visitors and locals alike. Opens at 7:00 AM.
USD20, 1 hour

9:30AM

Flight back to Honolulu

Ensure to check in early for your flight back to Honolulu. Enjoy your last views of Maui during your flight.
USD80, 2 hours including travel time

12:00PM

Lunch at Helena's Hawaiian Food

Serving traditional Hawaiian plate lunches, this restaurant is a must-try! Open until 8:00 PM.
USD20, 1.5 hours

2:00PM

Last-minute Shopping

Pick up any last-minute souvenirs at the International Marketplace or local shops before heading to the airport.
Free, 2 hours

5:00PM

Depart from Honolulu

Head to the airport for your departure flight; reflect on a week filled with adventure!
Free, N/A
View Hotel Availability