Hawaii

Question

We want to plan a trip to Hawaii for about 15-20 days thinking of a week on Kauai, similar on Maui and 3-4 days on Oahu. Would like ideas what to do where to go where to stay and getting island to island. For example on Kauai would you suggest mixing staying a few days on North Shore a few on South and some on East.

Answer

A 15-20 day trip to Hawaii sounds like an amazing way to experience the diverse beauty and culture of the islands! With a week on Kauaʻi, a similar amount of time on Maui, and 3-4 days on Oʻahu, you’ll have a wonderful mix of relaxation, adventure, and sightseeing. Here’s an outline of how you could plan your time and stay on each island, along with some ideas on how to get between them:

Kauaʻi (North Shore, South Shore, East Side)

Kauaʻi, known as the "Garden Isle," offers lush landscapes, beautiful beaches, and incredible hiking opportunities. Splitting your stay between the North Shore, South Shore, and East Side of the island is a great way to experience different aspects of the island.

North Shore: This area is known for its dramatic coastline, beautiful beaches (such as Hanalei Bay), and the famous Na Pali Coast. You can stay in the charming town of Hanalei or Princeville for stunning views and access to incredible beaches. The North Shore is also close to the start of the Kalalau Trail, which leads to some of the most scenic parts of the Na Pali Coast.
South Shore: Poipu and Koloa are great areas to explore for sun, surf, and laid-back vibes. This side of the island tends to be sunnier, making it perfect for beach days and exploring the Spouting Horn, Allerton Garden, or hiking the Maha'ulepu Heritage Trail.
East Side (Lihue, Wailua): This area is home to the island’s airport and some great attractions like the Wailua Falls and Fern Grotto. Staying here is convenient for exploring the island and also close to the famous Na ʻAina Kai Botanical Gardens.

Suggested Accommodation: Consider staying in different areas to experience Kauaʻi’s diversity. For example, spend a few nights in Princeville for the North Shore, followed by a stay in Poipu for a more relaxed atmosphere on the South Shore. If you want to be centrally located, Lihue or Wailua are also excellent options.

Maui (West Maui, Upcountry, South Maui)

Maui is perfect for exploring lush rainforests, dramatic coastlines, and world-class beaches. You’ll have plenty of options depending on the experience you want.

West Maui (Lahaina, Kaanapali): Lahaina, an historic whaling town, is full of culture and excellent dining options. The beaches in Kaanapali and Napili are stunning, and you can also explore the resort areas. Don’t miss a sunset cruise or a trip to Front Street for shopping and dining.
Upcountry Maui (Makawao, Kula): For a completely different experience, head up to the cooler climate of Upcountry Maui. Explore the Maui Wine vineyard, take a scenic drive on the Piʻilani Highway, or visit the Maui Ocean Center for an educational experience.
South Maui (Wailea, Kihei): Wailea offers luxury resorts, golf courses, and quiet beaches, while Kihei is a more casual area with plenty of shops and restaurants. Spend a day exploring the beaches, snorkeling at Molokini Crater, or hiking in the Iao Valley.

Suggested Accommodation: Consider staying in West Maui (Lahaina/Kaanapali) for a few nights, then head to South Maui (Wailea/Kihei) for beach days and relaxation. A night or two in Upcountry Maui offers a unique experience of local culture and stunning views.

Oʻahu (Waikīkī, North Shore)

Oʻahu is the hub of Hawaii’s culture, with bustling Honolulu, historic sites, and the world-renowned North Shore.

Waikīkī: Start your Oʻahu visit in Waikīkī, where you’ll find luxury hotels, great dining, shopping, and iconic beaches. Visit Diamond Head for an easy hike with panoramic views or stroll along the beach and check out the Honolulu Zoo or the Waikīkī Aquarium.
North Shore: Take a day trip to Oʻahu’s famous North Shore, known for its epic surf beaches like Waimea Bay and Sunset Beach. The North Shore is also home to food trucks, including the famous Giovanni’s Shrimp Truck, and Haleʻiwa town, which has charming boutiques and restaurants.

Suggested Accommodation: Stay in Waikīkī for the convenience of being close to attractions and dining. For a more local experience, consider booking a stay in Kailua or Lanikai for a more relaxed, residential vibe.

Getting Between Islands:

The easiest way to travel between islands is by flying. Hawaiian Airlines, Southwest Airlines, and Mokulele Airlines offer regular flights between islands. You can typically book these flights for around $40-$100 one way, depending on the timing and season. It’s best to book these flights in advance, especially during peak travel times. Ferry services between some islands (like Maui and Lanai) are also available, though they tend to be less frequent.

Suggested Itinerary Outline:

Days 1-7: Kauaʻi – Stay on the North Shore for a few nights, then explore the South Shore and finish with a stay on the East Side for easy access to the airport.
Days 8-14: Maui – Split your time between West Maui (Lahaina/Kaanapali), South Maui (Wailea/Kihei), and a day trip or overnight in Upcountry Maui.
Days 15-18: Oʻahu – Spend a few days in Waikīkī, exploring the island’s history and culture, then take a day trip to the North Shore for surfing and food trucks.

With a well-paced itinerary, you can experience the best of each island without feeling rushed. Have a great trip, and enjoy the natural beauty and cultural richness that each island offers!

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