If you’re planning a Hawaii island hopping itinerary but want to make the long flight from the Midwest easier, this 10-day travel guide is the perfect solution. By adding a stop in San Francisco on the way home, you can break up travel time, reduce jet lag, and turn your return journey into an unforgettable part of the trip.
This 10-day Hawaii itinerary includes three of the most popular islands—Oahu, Maui, and Big Island—combining bucket-list adventures, luxury stays, and budget-friendly travel tips.
🌴 Days 1–2: Oahu (Honolulu + North Shore)
Start your trip in Honolulu, one of the best places to visit in Hawaii for first-time travelers. With a mix of history, beaches, and vibrant city life, Oahu is the perfect introduction to the islands.
Best Things to Do in Oahu:
- Visit Pearl Harbor (reserve tickets in advance)
- Hike Diamond Head for panoramic views of Waikiki
- Rent a car and explore the North Shore (surf beaches, food trucks, and local culture)
Where to Stay in Waikiki:
- OUTRIGGER Reef Waikiki Beach Resort – beachfront, walkable, and ideal for a first stay in Hawaii
🌺 Days 3–5: Maui (Adventure + Relaxation)
Next, fly to Maui, known for its stunning coastline, luxury resorts, and unforgettable excursions.
Best Things to Do in Maui:
- Drive the famous Road to Hana
- Take a helicopter tour over waterfalls and volcanic landscapes
- Go night snorkeling with sea turtles
- Relax at the beach or pool in Wailea
Where We Stayed (Highly Recommend):
- Fairmont Kea Lani – all-suite luxury, incredible pools, beachfront location, and one of the best stays of the trip
🌋 Days 6–7: Big Island (Volcanoes + Budget-Friendly Balance)
The Big Island offers a completely different experience—perfect for travelers who want a mix of adventure and affordability.
Best Things to Do on the Big Island:
- Visit Hawaii Volcanoes National Park
- Spend a beach day or relax by the pool
Where to Stay (Budget-Friendly Option):
- VRBO: Oceanfront condo with AC, WiFi, and parking
→ A great way to save money while still enjoying ocean views and extra space
Money-Saving Travel Tips:
- Use a ResortPass at OUTRIGGER Kona Resort and Spa
→ Enjoy resort pools and amenities without booking a full stay - Buy groceries for breakfast and lunch
→ One of the easiest ways to cut down on food costs in Hawaii
Other Big Island Hotels:
- Four Seasons Resort Hualalai
- Fairmont Orchid
- Royal Kona Resort
🌉 Days 8–9: San Francisco Stopover
Adding a stop in San Francisco is one of the best travel hacks when flying home from Hawaii.
Best Things to Do in San Francisco:
- Take a food tour through Chinatown and North Beach (Little Italy)
- Explore the city via a retro VW van tour
- Visit Alcatraz Island
Where to Stay:
- Staypineapple, An Elegant Hotel, Union Square – we stayed here on points but would not recommend
Better Hotel Options:
- Fairmont San Francisco
- Hotel Zephyr
- The Westin St. Francis San Francisco on Union Square
✈️ Hawaii Travel Tips & Logistics
- Fly from the Midwest to Honolulu and return via San Francisco
- Book inter-island flights in advance (they’re short and affordable)
- Rent cars in Maui and the Big Island for flexibility
- Reserve popular activities early (Pearl Harbor and Alcatraz sell out fast)
💡 Why This Hawaii Itinerary Works
This 10-day Hawaii island hopping itinerary gives you:
- The culture and energy of Oahu
- The luxury and scenery of Maui
- The unique landscapes of the Big Island
- And a city experience in San Francisco
It also balances luxury travel with budget-friendly tips, combining high-end resorts with smart savings like VRBO stays, groceries, and day passes.
