Hawaiian islands trip

Question

First trip to Hawaii… my wife and I want to include the big island, Maui, and Kauai. We’d like to arrive on 9/9 and can stay as long as necessary to hit all of our spots. We’ll take inter-island flights as necessary and will rent cars as needed to get around. To save a little time, we’d like to arrive on one island and depart to head home (Detroit) from another. The order doesn’t matter. We’re in our mid 70s, so a little light hiking would be OK. Looking for best advice on hotels (mid and above), good tours and operators, other good things to do, and anything else helpful.

Activities so far:

Hawaii – Hawaii volcanoes NP, tropical botanical garden, ride down from Mauna Kea (but it can’t be done on bikes– can it be done at sunrise in a tour or by car)?

Maui - Road to Hana (with a night in Hana), Wai’anapanapa SP, helicopter tour, snorkel Molokini Crater, Haleakala NP, best scenic beaches

Kauai - sail the Na Pali coast, Waimea Canyon

Thanks!!

Answer

For a first-time Hawaiian Islands trip covering the Big Island, Maui, and Kauai, a well-paced itinerary that balances sightseeing, light hiking, and relaxing is key, especially considering your preference for comfort in mid-70s. Arriving on one island and departing from another is a smart idea and will save backtracking.

Here’s a suggested approach and recommendations for hotels, tours, and activities:

Big Island (Hawaii)
- Accommodations: Consider the Mauna Lani, Auberge resorts, or Waikoloa Beach Marriott. These offer comfortable mid-to-upper scale amenities and convenient beach access.
- Activities:
  - Hawai’i Volcanoes National Park – allow at least half a day, consider a guided tour for added insight.
  - Tropical Botanical Garden near Hilo – easy walks, shaded paths.
  - Mauna Kea – sunrise tours are available via car or small bus tours; biking down is optional but challenging. Most operators provide stargazing and sunrise from summit accessible via vehicle.
  - Optional: Punalu’u Black Sand Beach, and for light hiking – Pololu Valley lookout trail or Akaka Falls State Park.
Maui
- Accommodations: Wailea area is great for mid- to high-end hotels (Andaz, Four Seasons, Wailea Beach Resort). Kihei or Napili offer smaller boutique hotels or condos.
- Activities:
  - Road to Hana – plan an overnight stay in Hana for a relaxed pace; Wai’anapanapa State Park is a must. Consider a guided van tour if you want to reduce driving stress.
  - Helicopter tour – Blue Hawaiian or Air Maui offer excellent guided flights over the island and waterfalls.
  - Snorkel Molokini Crater – book morning tours for calm waters.
  - Haleakalā National Park – sunrise tours are available; booking a guided sunrise tour is safer and more comfortable than driving alone, especially for early morning ascent.
  - Beaches – Kaanapali, Napili, Wailea Beach are scenic, safe for walking and light swimming; great for relaxation days.
Kauai
- Accommodations: Princeville or Hanalei for North Shore views and resort options; Poipu for sunny South Shore with mid-range resorts.
- Activities:
  - Na Pali Coast – consider a boat tour or catamaran cruise; some offer snorkel options. Helicopter tours also showcase inaccessible areas.
  - Waimea Canyon – easy to moderate trails for light hiking; scenic drive is an alternative if hiking is too strenuous.
  - Other light activities – Wailua River boat tour, Opaekaa Falls lookout, Hanalei Bay beach walks.

Other tips and considerations:

Inter-island flights are frequent via Hawaiian Airlines or Southwest. Book early to secure preferred times.
Rent cars on all islands for flexibility. Consider smaller, fuel-efficient cars for Hana drive and Waimea Canyon roads.
Light hiking is feasible in most parks; carry water, sun protection, and wear comfortable walking shoes.
For a smoother experience, consider guided tours for challenging drives like Road to Hana and Mauna Kea sunrise.
Book popular activities (helicopter tours, Molokini snorkel, Na Pali sail) in advance, especially for September.

Sample island order: arrive Big Island (Hilo/Kona) → fly to Maui → fly to Kauai → depart from Kauai. This minimizes backtracking and keeps travel comfortable.

This plan balances sightseeing, light adventure, and relaxation while allowing you to enjoy mid-to-high end hotels, scenic drives, and the best natural beauty of each island.

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