First time to Hawaii for 4 adults

Question

We want to split our stay but have no clue which island to stay on. Resort style with swim up bar etc is ideal for part of the trip and even happy with a condo style with 2 bedrooms near a resort would be ideal. We want to enjoy pure relaxing and beach activities along with shopping. We also want to explore and sightsee waterfalls and landscapes with history etc. we are planning on visiting in aug/SEP for approx 10 days. Any ideas would be great!

Answer

Aloha! Hawaii is an amazing destination, and choosing the right islands for your trip will depend on what you want to do and the type of experience you're looking for. Based on your preferences for resort-style accommodations with a swim-up bar, condo-style options, beach activities, shopping, and sightseeing, I would recommend splitting your stay between two islands: Oahu and Maui. Both islands offer a mix of relaxation, adventure, and cultural experiences. Here’s a detailed breakdown of each island and some of the best options for you:

Oahu (Honolulu / Waikiki): Oahu is perfect for those who want a lively mix of resort amenities, shopping, dining, and cultural sights. Waikiki is where you’ll find a large selection of resorts with swim-up bars, beautiful beaches, and plenty of options for relaxation. It's also a major hub for shopping, with high-end stores and local boutiques. Here are some great options:

Ala Moana Hotel & Resort: This is a luxury hotel in Waikiki with fantastic amenities, including a pool with a swim-up bar. The resort is close to the beach, shopping malls (like Ala Moana Center), and local dining.
Hilton Hawaiian Village: Located in Waikiki, this resort offers multiple pools, a swim-up bar, and a private beach. It's a large resort with plenty of dining and activity options, perfect for relaxing and enjoying the beach.
Waikiki Beach Marriott Resort: Another great resort with oceanfront views, a swim-up bar, and direct access to Waikiki Beach. It’s ideal for both relaxation and easy access to shops and restaurants.
Condo Option: You can also look for condos near Waikiki, such as at the Waikiki Banyan or Ilikai Hotel & Luxury Suites, which offer condo-style accommodations with kitchenettes and access to resort amenities.

Oahu is also home to numerous sightseeing opportunities, including:

Visit Pearl Harbor to learn about the history of World War II.
Explore Diamond Head for a short, scenic hike with panoramic views of Waikiki.
Relax at Hanauma Bay, one of the best snorkeling spots on the island.
Tour Iolani Palace and experience Hawaii’s royal history.

Maui (Kaanapali / Wailea): Maui is a beautiful island for a more laid-back, scenic experience with plenty of beaches, waterfalls, and natural landscapes. It’s also known for its luxury resorts and condo-style accommodations, so it’s perfect for unwinding in a beautiful setting while still having opportunities for adventure.

Kaanapali Beach Resort: A beautiful area with upscale resorts and condo options. You can find accommodations with great amenities, such as the Westin Maui Resort & Spa or the Hyatt Regency Maui Resort & Spa, both offering swim-up bars, pools, and great beach access.
Wailea Beach Resort: This is another fantastic area on Maui with resorts like The Four Seasons and Grand Wailea, which have gorgeous pools, ocean views, and excellent dining options.
Condo Option: Consider staying in condo-style accommodations at places like The Whaler on Kaanapali Beach, which offers a more home-like atmosphere but still close to resort amenities.

Maui also offers breathtaking scenery and activities for sightseeing and nature lovers:

Drive the Road to Hana for stunning waterfalls, lush landscapes, and hiking trails.
Hike to Waimoku Falls or visit Seven Sacred Pools in Kipahulu.
Explore Haleakalā National Park and watch the sunrise at the top of the volcano.
Visit Makena Beach for beautiful white sand beaches and snorkeling.

Suggestions for the best 10-day itinerary: A great option would be to spend 5 days in Oahu and 5 days in Maui.

Days 1-5 (Oahu): Spend your first 5 days in Oahu relaxing on Waikiki Beach, exploring Pearl Harbor, hiking Diamond Head, and shopping in Honolulu.
Days 6-10 (Maui): Then fly to Maui for 5 days of adventure on the Road to Hana, hiking in Haleakalā National Park, and enjoying the beach resorts in Wailea or Kaanapali. Make sure to spend some time at the luxurious resorts for relaxation, and maybe try a luau for a fun cultural experience.

Both Oahu and Maui offer a perfect balance of resort amenities, beach relaxation, shopping, and natural beauty. You’ll get the best of both worlds—Oahu for its city and cultural sights, and Maui for its outdoor adventures and laid-back charm.

Happy travels and enjoy your Hawaii vacation!