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Island Hopper Hawaii Vacation Packages
Two Islands, One Unforgettable Trip
Maximize your Hawaiʻi vacation by exploring from mauka to makai—and from island to island. Our Island Hopper packages give you the best of multiple islands in one seamless, locally crafted itinerary. From flights to hotels and tours, every detail is handled for you by experts who live here.
Prices from $999.00 per person (not including airfare)**
Start Planning Your Island-Hopping Escape
Each pairing offers something distinct. Let this guide help you choose the right combo for your travel style.
Oʻahu + KauaʻI
- Waikīkī fun and Pearl Harbor in Oʻoahu
- Nā Pali Coast, Hanalei, and tranquil scenery on Kauaʻi
- Perfect for beach lovers and laid-back explorers
Oʻahu + Maui
- Iconic landmarks and vibrant nightlife in Oʻahu
- Road to Hāna, waterfalls, and romantic beaches in Maui
- Great for couples or first-time visitors who want balance
Which Island Fits Your Style?
Maui + Big Island
- Lush drives and sunset beaches in Maui
- Volcanoes, black sand, and coffee farms on Big Island
- Ideal for adventure-seekers
Oʻahu + Big Island
- Oʻahu's iconic sites and surf culture
- Big Island's epic landscapes and local heritage
- A great balance of history and nature
Oʻahu + KauaʻI
- Waikīkī fun and Pearl Harbor in Oʻoahu
- Nā Pali Coast, Hanalei, and tranquil scenery on Kauaʻi
- Perfect for beach lovers and laid-back explorers
Oʻahu + Maui
- Iconic landmarks and vibrant nightlife in Oʻahu
- Road to Hāna, waterfalls, and romantic beaches in Maui
- Great for couples or first-time visitors who want balance
Maui + Big Island
- Lush drives and sunset beaches in Maui
- Volcanoes, black sand, and coffee farms on Big Island
- Ideal for adventure-seekers
Oʻahu + Big Island
- Oʻahu's iconic sites and surf culture
- Big Island's epic landscapes and local heritage
- A great balance of history and nature
Create Your Island Hopper Experience
Choose from our curated multi-island packages or build a combo that matches your vision. All Island Hopper itineraries include inter-island flights, accommodations on each island, guided tours, and private airport transportation—plus full support from local planners who live right here in Hawaiʻi.
What a Week of Island Hopping Could Look Like
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Day 1: Aloha Arrival
Touch down in Oʻahu, receive your lei greeting, and kick off your journey with an oceanfront dinner.
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Day 2: Oʻoahu Discovery
Explore Pearl Harbor, Diamond Head, or the North Shore with a local guide.
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Day 3: Island Hop to Maui
Take a short flight to Maui and enjoy a scenic drive to your resort.
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Day 4: Maui Exploration
Tour the Road to Hāna or snorkel at Molokini Crater—you decide.
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Day 5: Free Day + Optional Upgrade
Relax at the resort or book a spa day, sunset cruise, or zipline adventure.
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Day 6: Cultural Experience
Enjoy a traditional Hawaiian lūʻau or local storytelling event.
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Day 7: Final Adventure
Go for one last hike or beach morning before heading home.
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Day 8: Depart with Aloha
Take off with unforgettable memories and stories to share.
Top-Rated All-Inclusive Packages
Oʻahu
Honeymoon Package
Private island tours, Jeep rental, beach setup, and luxury resort options.
Maui Super Saver Package
Affordable flights, curated food tours, and upgraded hotel deals.
Kauaʻi Family Adventure
Kid-friendly hikes, waterfall picnics, and beach days with local guides.
Big Island All-Inclusive Adventure
Volcano tours, Kona coffee tastings, and cultural exploration.
Use Our Trip Planner Tool to Start Building Your Hawaiian Vacation
Your package’s total price is based on what you choose—let us help you plan it right.
Custom Hawaii Vacation Packages Built by Local Experts
Design your ideal multi-island itinerary with help from our planning team. Choose a pre-built Island Hopper combo or start fresh with a custom trip. Whether it’s a honeymoon, family celebration, or solo adventure, we’ll handle every detail so you can relax and explore.
Call us at 1.800.843.8771 or submit your info to begin planning your custom Island Hopper experience.
Fill Out the Trip
Planning Form
Call us or fill out our trip planner to start. We'll listen to what matters most and guide you through your options.
We Craft Your
Custom Vacation
Based on your preferences and budget, we'll build a personalized itinerary using our deep local connections and expertise.
Review, Approve,
and Pay Later
You'll receive a full plan in writing to review-no pressure. Pay when you're ready, starting at just $50 down per person for a land package.
Need help choosing the right all-inclusive package, hotel, or activity? Our local experts are here to guide you.
Island Hopper FAQ
You can choose two, three, or even all four major islands—whatever fits your timeline and wishlist.