Suggested 5 day itinerary for Hawaii

Which Island to Visit? Maui

Where to book? Book flights + hotel + car at

Total days needed? 7 (1 day to fly in and 1 day to fly back)

Where to stay? for 3 star recommend Napili Surf Beach Resort. For 4-5 star recommend Hyatt Regency or another 4 star property along Kaanapali Beach (Westin, Marriot, Sheraton etc.)

Where not to stay? Napili Shores by Outrigger. Not a disaster but Napili Surf Beach Resort is right next to it and more updated with same price.

What car to rent? Full size car like Hyundai Sonata. We had 4 pieces of baggage (3 carry-on sized, 1 bigger), 2 bagpacks, 1 stroller, 1 carseat for baby and it fit in the Sonata. There is Costco Gas near airport to fill up the tank before returning the car.

Where to rent beach gear? Boss Frog. They have locations all over Maui including Napili, Lahaina, Kihei. You can drop off your gear at any of their locations, not necessarily the one from where you picked it up.

Where to buy groceries? You can buy some on the day you land at the Costco near the airport. On other days there is a good grocery store called Napili Market in the nearby Napili Plaza if you are staying at the Napili Surf Beach Resort. There is also a Safeway in Lahaina.

Day 1 – Lahaina, Front St. Beware of many shops selling discount tickets to helicopter tours and other activities. They will require you to attend some seminar where they will try to sell you some condo or property in Hawaii. Just stay clear of them. Be prepared to pay $7/hr parking.

Day 2 – Maui Ocean Center and adjacent Harbor Shops at Maalaea Harbor. Eat at Seascape and coffee at Hula Cookies in Harbor Shops. You can buy ocean center tickets online at to get some discount.

Day 3 – Snorkel at Molokini Island. Book at Blue Water Rafting. Rent a wet suit from Boss Frog before going to snorkel. Blue Water Rafting will not provide any wet suit. Eat at Choice Health Bar in Lahaina. Have coffee on the way back at the Coffee Store in Napili Plaza.

Day 4 – Helicopter tour of Hana Rainforest. Book at Maverick Helicopters. I think Maverick is the only operator who does a landing at the Hana Rainforest so you can explore it on foot. Eat at AA Roots in Napili Plaza.

Day 5 – Boogie boarding at the beach. Check out Whaler’s Village and while there buy some cookies at Honolulu Cookies (ask them to validate parking) and spend evening watching Drums of the Pacific Maui at Hyatt Regency. Take some warm jacket as it will get about 10-12 degrees cooler in the night and you might want to have it. Hyatt Regency has valet parking for $5 which is worth it IMO.

Total Distance Covered by car: 300 miles

Further Notes:

  • Be prepared for strong winds.
  • You may rent a beach package from Maui Vacation Equipment including a Coleman tent, baby toys, a cooler and 2 Tommy Bahama Chairs for one week. You pay them in advance and they deliver the gear to your room before you check in at the hotel. They also pick it up and the delivery is included in the price. We did so but didn’t end up using it so YMMV (your mileage may vary).
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