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Welcome to Dream Vacations, a lifestyle column on travelling to amazing destinations with practical advice and my revelations about locales from years of personal experience. Heading to Hawaii for many is the dream of a lifetime, while for others, it’s a yearly excursion that excites them the twentieth time as much as it did the first. So, whether you are a first-timer or consistent vacationer to Maui, Hawaii, let this example itinerary be your guide.

The Family and Casual Vacationer guide – this itinerary is meant for those with families or who expect to visit Maui and Hawaii more than once. There is simply no way you could do everything in seven days, so look for future 14-day itinerary to Maui to follow up on your next visit.

Day 1 – Arrival

If you can, book a direct flight to Kahului Airport in Maui, the main airport (code OGG) and get the most out of your vacation. Flying from Chicago west to Los Angeles, you can do in a direct flight (recommended), but most cities east of Chicago will require a layover on the west coast. Flights from the west coast of the U.S. are between five to six hours, so plan you will arrive in Maui from an early morning flight in the early afternoon, just perfect for check-in at most hotels and resorts.

The Westin Ka’anapali Ocean Resort Villas is less than an hour from the airport so that you could be checked in and ready to relax quickly. I’d recommend getting to the resort, getting checked in and then heading to get stocked up on groceries for the week. Near the Westin, there is a Safeway only six minutes away, but there are sure to be grocery stores near your resort. Spend the rest of the evening, settling in, talking to the concierge to book your events below and learning what activities are available on-site at your resort. An evening swim at the beach, enjoying your first Hawaiian sunset is an unforgettable experience.

Day 2 – Haleakala Experience

I like to day trip the second day of a vacation. You and your party are still excited to be on vacation and are ‘raring’ to go. The Haleakala National Park is home to the Haleakala crater, a dormant volcano that overlooks several beautiful landscapes. It is quite popular to be at the summit for sunrise, but you are now required to reserve in advance for personal or rental vehicles on top of the park entrance fee, as it is one of the most popular Maui attractions. Mark Twain described it as “the most sublime spectacle I have ever witnessed.”

The drive from Ka’anapali is about two hours but adjust for traffic and crowds and leaving 2.5-3 hours early is not unheard of to catch the sunrise. If you are not a morning person, seeing a sunset and the star-scape from the summit is almost as stunning. Plan ahead, bring some snacks and drinks for a day at the park. Enjoy a hike or horseback riding through a changing landscape, from volcanic desert to tropical rainforest. Get a preview here.

Day 3 – Snorkel with the Family

It’s time to relax with a day at the beach; it is a vacation after all. However, instead of just spending an entire day lazing at the beach, be sure to get into the water and snorkel with the entire family. Even young swimmers will enjoy the amazingly clear water, colorful fish species and even the corals that can be seen near your Ka’anapali resort. Refer to our article “How to Snorkel Hawaii Like a Pro” to learn more about snorkelling in Hawaii. No need to go further than your front door from the Westin Ka’anapali, as the Ka’anapali Beach is world renown. Even just strolling down it’s beauty and taking in the sights is worth it.

Not sure you can spend a full day at the beach? The afternoon during full sun is a great time to enjoy some resort activities such as Lei-making, tye-dye shirt making or spending some time at the Westin’s world-class spa for adults in your party. Attending a Luau tonight would also help round out your cultural experiences. Using Westin’s concierge services and activity planner is a great idea.

Day 4 – Island Hopping Day-Trip

I don’t recommend day tripping to the larger islands, like some blogs suggest, because they require more than a day to explore. If you love Hawaii, you will visit all the main spots over time. Instead, try a day-trip to nearby Lanai. Lanai is one of the least populated of the large islands, and 97% privately owned but offers you amazing sights, great snorkelling, Lanai City and Mount Lana’ihale, the island’s dormant volcano as well as three golf courses. You can catch a convenient ferry from Maui to Lanai return with ease.

Day 5 – The Road to Hana

One of the most famous U.S. road trips is the ‘Road to Hana.’ This road trip is not for the inexperienced driver, as there are places where the road hugs the mountains with sheer drop-offs, tight turns, and during peak tourist times, traffic can get heavy. If you are a nervous driver, you may be better off taking a tour. The drive to Hana is 2.5 hours, so a full day to Hana will include at least five hours of driving. As the road is not a true highway, it’s best to be back to your resort before dark. Starting your trip about 30 minutes before sunrise will give you the best amount of time to enjoy sights, turn-offs, mountain stream swimming and some light shopping in Hana. Here are some of the best places to stop. Doing Hana in one day will require you to choose three to four stops.  Lastly, this trip is to see unspoilt and wild Hawaii, be sure to be fully stocked on food and beverages and fuel.

Day 6 – Resort Day

After two days away from your home away from home, it’s time to relax again. Here are few at-home suggestions for a truly relaxing day:

  • Stroll the Ka’anapali Beach, go for a dip
  • Get a massage
  • Lounge by the resort pool
  • Visit the local shops in your area for some retail therapy
  • Head out on the local trails for an invigorating hike

Day 7 – Lahaina!

The closest town to Ka’anapali is Lahaina and was the capital of the Hawaiian Kingdom from 1820 to 1845. Steeped in history and local tradition, Lahaina also offers the most attractions to visitors, including restaurants, beaches, Luaus and shopping. Go for the day to enjoy a wide range of activities with some of the most unique including:

  1. Mermaid Adventures
  2. Paddleboarding
  3. Joining a Glass Blowing Class
  4. Maui Sunset Dinner Cruise
  5. Banyan Tree Photo Op

Day 8 – Time to Say Goodbye

Sadly, it’s time to go, but not before you take one last dip in the beautiful waters of the Pacific Ocean. Get up early to enjoy the sunrise and soak in the beauty of Maui one last time.

The Westin Ka’anapali Ocean Resort Villas or our other Maui resorts are perfect for providing you with an idyllic vacation! We have availability, so call us today. Be sure to sign up for our newsletter for a future feature of a 14-day Itinerary for Maui!

Tags: Westin Kaanapali, Maui, Hawaii, 7-day itinerary, beach vacation, family vacation, water sports