How do I get there?

Hawaii is much further away than some may think from the east coast. It is even further away than many European destinations, so be prepared for some long flights. We initially flew on Alaska Airlines from Columbus to Seattle directly and ended the trip with an overnight stay in Seattle. The following morning, we departed on Alaska Airlines to Kahului Airport. I recommend breaking it up since most flights are red-eyes due to the 6-hour change. In total, flight time was around 11 hours.

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What is the weather like? When is the best time to visit?

We planned our trip in mid-June, and the weather was perfect. Depending on where you stay, the weather can vary drastically across the island. The northern part of Maui is much more tropical and wet, and the southern part is more of a drier desert. The temperatures didn't fluctuate much and consistently averaged 80 and sunny. With the trade winds across the island, you get a nice breeze. 

Maui is a great place to visit year-round. Certain months are busier and more expensive than others, but it is bustling with tourists constantly. Their "rainy" season typically runs from November to March, with the most popular timeframe from April to September. If you want to see humpback whales, their peak migration months are January to March.

Where should I stay?

During our 8-night stay, we stayed in a couple of different towns. We booked an Airbnb just North of Lahaina for the first five nights, closer to Kaanapali. It was around a 45-minute drive from the airport. The studio was on the 8th floor and had an excellent lanai view where we watched turtles swim around the reef below and the fantastic sunsets. We rented a car for this portion of our stay since the Airbnb offered free parking, and we wanted to explore. A few things were within walking distance, but I'd recommend a car for any stay longer than two nights.

For the final 3-nights, we splurged on a room at the Four Seasons in Wailea. It was around 30 minutes from the airport. We learned that this hotel was the first Four Seasons hotel ever built; how cool! Upon arrival, the breathtaking views and abundance of activities offered blew us away. We spent many hours at the adults-only pool, participating in snorkeling and playing pickleball. The adult-only pool had a swim-up bar, a fantastic view, and exceptional poolside service. If you go without kids, reserve your chairs early because they go fast! We took our coffee every morning and walked the path in front of the resort for a little morning movement before breakfast. One thing to note is the complimentary outrigger canoe excursion. It books up super-fast, so I'd recommend booking in advance. 

How do you get additional perks at the Four Seasons?

We booked our stay through a travel partner. She has partnerships with several luxury hotels worldwide, and booking through her offered perks like a room upgrade (subject to availability). In addition, we received a complimentary full island breakfast at Duo every morning and a $125 daily resort credit. Lastly, we had an additional $100 one-time credit during our stay. These perks gave us $475 in resort credit and daily breakfast. If you work with her, you'll get guaranteed access to exclusive perks and amenities that elevate your luxury vacation. We booked our stay online for the Four Seasons, and she was able to add it to our reservation with our confirmation number. We even received a special delivery on our first evening of chocolate-covered strawberries and a bottle of champagne as an early anniversary celebration. Since the cost of living on the island is significantly higher, these perks offered some financial relief to enjoy our stay. I recommend reaching out to see her other luxury hotel partnerships! 

How was the Four Seasons room?

We booked the mountainside room since we predominately use our room to sleep. Since we booked through Jetset & travel, we knew we would get a complimentary upgrade to the garden view room. Upon check-in, we were upgraded again to the deluxe garden-view room! This room had a small ocean view and a private lanai overlooking a meticulously maintained garden.  The spacious room offered nice touches like outdoor patio furniture, music in the bathroom, and luxurious bathrobes. The bed had high-quality linens and pillows, and housekeeping came around twice daily. It was one of the most thoughtful rooms, from the design to the extra space.

Should I island hop?

Since Hawaii is so far away, 6 hours from the Pacific coast, exploring multiple islands in one trip is popular. We decided against that since we wanted to spend less time traveling and more time exploring. If we were to return to Hawaii, we would check out Hawai'i or O'ahu. 

What should I do?

We love to have a combination of relaxation and activity for our vacations. While staying near Lahaina, we went to several different beaches to snorkel. Luckily, the Airbnb we stayed at provided all beach necessities, from snorkel gear to beach chairs and towels. Below is a list of some activities we did when visiting Kaanapali.

• Kapalua Coastal Trail has excellent views and is a straightforward trail!
• Back Rock Beach – There is a volcanic rock edge with a reef below. It's a great place to snorkel or cliff jump.
• Kapalua Bay Beach – This was a super popular beach and gets busy quickly! Make sure you get there early to get a spot in the free public parking area. There are great reefs to snorkel and several restaurants nearby.
• Snorkeling – We snorkeled pretty much every beach we went to. Reef fish are abundant in addition to the Hawaiian Green Sea Turtles. The turtles are a protective species, so you must keep your distance – no touching!
• Honolua Bay – This is a snorkel bay. The beach is rocky, so it is not a place you would lay out for the day. There is also a lot less parking than other beaches. We saw some neat reef fish and our first barracuda!
• Whalers Village is a great place to walk around and shop. Monkeypod, Leilani's on the beach, and Hula Grill are nearby if you want a bite. If you want to keep exploring, there is a walkway near the beach.
• Road to Hana is an all-day excursion worth it for a first-timer. Please read the "Do I recommend the Road to Hana" for more details below.
• Watch the sunset! They will take your breath away!!

Do I recommend the Road to Hana?

The short answer is yes. With that in mind, this question has a couple of caveats. If you are traveling with small children, want to avoid being in the car all day, or feel uncomfortable with narrow, windy roads, this would not be the trip for you. We started this trip from the island's east side, adding an hour to our travel. It is an adventure of a lifetime, and if you are okay with the caveats I listed above, the Road to Hana is a great tourist attraction. We used the Shaka app and purchased the classic Hana guide. It was entertaining and informative, and I recommend it. Cell service can be spotty, but the app still operates offline. 

Another recommendation would be to plan this day. Specific stops on the tour require reservations, like the famous Waiʻānapanapa State Park, otherwise known as the black sands beach. Reservations are open up to 30 days in advance. We weren't aware of this before our trip, so we got stuck with the earliest available time slot, requiring us to begin our journey at 4:30 am. To avoid this, book online here.

One of the other most popular spots is close to the end, Waimoku Falls, via Pipiwai Trail. The National Park does require a $30 vehicle entry fee. The Pipiwai Trail is a 4-mile round trip moderately strenuous hike. It takes around an average of 2 hours to complete. There are a lot of uneven stone steps and tree roots to be cautious of. Waimoku Falls is the tallest single-drop waterfall on Maui, measuring around 400 feet. It is worth the hike! 

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Should I rent a car?

We rented a car via Turo for our first 5-nights while staying in our Airbnb. Since we knew we wanted to do the Road to Hana and further explore the island, we decided to rent a car for a portion of our trip. We dropped the car off at the airport before heading to the Four Seasons. The resort charges $50/night for parking, and we decided we wouldn't utilize it with the hotel offering a complimentary car service to all of Wailea. If you're staying at a resort, a rental car may not be necessary, depending on the duration of your stay and the amenities provided.

Where should I eat/drink?

Below is a list of all the places we explored during our 8-night stay. I recommend making reservations a month in advance because times go quickly. We only booked a week before our trip, and the available times were around 8 pm. We also enjoyed a few happy hours, Mala Ocean Tavern and Monkeypod being two of our favorites.

• Monkeypod – Happy hour and dinner 10/10 We were told to order the banana cream pie, and unfortunately it's so popular it was sold out!
• Duke's Beach House – Ambiance and service were good, but the food was sub-par 6/10
• Sergio's Cantina – Close to our Airbnb and offered an excellent Taco Tuesday deal
• Sea House Restaurant – Happy hour with a pretty bay view
• Mala Ocean Tavern – Happy hour was fantastic! We went twice during our 5-nights near Lahaina.
• Maui Brewing Co – A few located around the island. The drinks were good, but we never ordered food.
• Hale Mo'olelo is in the Westin resort. Our meal was good but nothing special.
• Bad ass coffee – Great iced vanilla lattes!
• Island Vibes café – Breakfast burritos were giant and filling—great bite to eat near Kapalua Bay Beach.
• Spago – On-site at the Four Seasons and sat at one of the best tables. The service was fantastic, but fine dining.
• Ferraro's – On-site at the Four Seasons and offered a more casual ambiance than the others. Ferraro's is outside, and we secured a reservation during sunset. We shared the calamari, and each ordered the tagliatelle alla Bolognese made from scratch. This is a must try!

What do I pack?

The vibe is island casual. I'd recommend anything lightweight and even a little jacket, as the winds can be strong and chilly once the sun sets. I wish I had packed more athleisurewear for exploration and walks than resort wear, but it depends on what you plan to do during your trip! Some fine dining restaurants may require a specific dress code, but casual wear is usually acceptable.

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