EDIT: Due to the tragic fires in Lahaina in 2023, making a move to Maui this year is not recommended. Tourism is needed and vacation rentals are a great option, but it’s an important time to leave the long-term housing available for island residents who have been displaced.

Are you considering a big move or an extended stay in the Hawaiian Islands? While I initially planned for a 6-month adventure in Maui, I've gathered not just memories but also invaluable insights that could help anyone looking to make Hawaii their new home or a long-term getaway. Here's an updated and expanded guide based on my experiences, now tailored for those eyeing the Aloha State as their next chapter.

Why Maui and Beyond?

Our journey began with a dream to escape the dreadful Canadian winter, aiming for a month or two but quickly realizing that to truly immerse ourselves in Hawaiian culture and the island lifestyle, a longer stay was necessary. The Hawaiian Islands offer a diverse range of experiences, from the urban appeal of Oahu, home to the bustling North Shore and historic Pearl Harbor, to the Big Island's natural wonders like active volcanoes and the expansive Hawaii Volcanoes National Park.

An extended journey to Hawaii, specifically Maui, turned out to be an AMAZING experience that went beyond mere vacationing to embracing a whole new lifestyle.

Deciding on Maui and the Real Estate Revelation

The initial stage of planning our stay in Maui was eye-opening, particularly when it came to accommodations. The sheer cost of monthly rentals was staggering, often exceeding $10,000, and that's not even considering the premium condo hotels and vacation rentals, where prices soared to around $10,000 per week. This discovery prompted a creative approach to our living situation, leading to the realization that a 6-month lease could bypass the short-term rental market, granting us access to residential properties not zoned for vacation rentals—a critical insight for anyone considering a move to the Hawaiian Islands.

Transforming Plans into a Super Extended Vacation

Our decision to turn our extended vacation into a 6-month residency from December to May was driven by the allure of the islands and the practicalities of real estate in Hawaii. This decision not only allowed us to immerse ourselves in the island lifestyle but also to navigate the high cost of living, which is a well-known challenge in the state of Hawaii, especially for new residents.

Top Things to Know for Your Big Move

1. Childcare is Crucial

Maui's reputation as a kid-friendly destination was a major draw for us, given its safe, predator-free environment and abundance of activities. However, the need for reliable childcare to allow for adult adventures became apparent. Utilizing Care.com proved invaluable in finding trustworthy babysitters, highlighting the importance of community resources for families making a similar move.

Childcare can be a Gateway to Cultural Immersion and Community Engagement:

Maui's allure as a kid-friendly paradise is well-known, drawing families with its promise of safety, natural beauty, and a plethora of activities suitable for all ages. The island's environment, free from large predators and rich in educational outdoor experiences, presents an idyllic backdrop for childhood exploration. From the serene beaches perfect for building sandcastles to the lush trails inviting adventurous hikes, the opportunities for family fun are endless.

However, the transition to island life, especially for new residents, brings to the forefront the necessity of reliable childcare. This need is not merely about finding someone to watch over the children but about ensuring they're engaged, learning, and experiencing the best of what Maui has to offer in a safe and nurturing setting. For us, leveraging Care.com was more than a logistical solution; it was a bridge to the local community, enabling us to connect with experienced caregivers who shared our values and understood the unique cultural context of Hawaii.

The Role of Childcare in Hawaiian Cultural Integration

Finding the right babysitter or childcare provider opened up new avenues for our children to learn about Hawaiian culture and traditions firsthand. Engaging with local caretakers allowed our kids to hear the Hawaiian language, participate in traditional games, and even taste the diverse flavors of the island's cuisine, enriching their understanding and appreciation of their new home. This immersion is crucial for families seeking not just to live in Hawaii but to become a part of its vibrant tapestry.

Community Resources and Support Systems

The process also highlighted the importance of community resources and support systems for families. Maui's welcoming spirit is evident in its plethora of family-oriented services, activities, and educational programs, from public parks and community centers offering keiki (child) yoga classes to local libraries hosting storytelling sessions that weave Hawaiian legends and folklore. These resources are invaluable for families looking to settle and thrive on the island, providing a support network that fosters both integration and independence.

A Balancing Act: Adventure and Responsibility

For parents, having reliable childcare did more than just free up time for adult adventures—it allowed us to pursue our interests and responsibilities knowing our children were in safe hands, experiencing the best of Maui's educational and cultural offerings. Whether it was tackling a challenging hike, exploring the underwater wonders through snorkeling, or simply enjoying a quiet dinner, these moments of adult leisure were made possible by the trust we placed in our childcare providers.

A Reflection on Family Life in Maui

In reflection, the emphasis on childcare is a testament to Maui's family-centric culture, where the well-being and development of children are seen as a community responsibility. Our experience is a reminder to those considering a move to the Hawaiian Islands of the importance of building a network of support that includes trusted childcare providers. This network not only ensures the safety and happiness of children but also deepens the family's connection to the island, making the transition to Hawaiian life a truly enriching experience for all members of the family.

2. Renting a place is a bit tricky when you’re not on the island.

Before you look at rentals, check out Home Exchange. You may be able to find someone in Maui who is looking to take a trip to your location. Arranging a home exchange is a low cost option that is worth exploring!

Maui is an expensive destination, especially for Canadians with the currency conversion.  Just think about the logistics of shipping products to the middle of the Pacific Ocean and then you start to appreciate why everything costs a pretty penny. Get familiar with the geography and join some move to Maui Facebook groups to get the inside scoop. Ask questions and make sure you feel completely comfortable before signing a lease. I decided to secure a rental before arriving for a few reasons:

• I didn’t want the stress of finding a place to live with two small kids in tow.

• The cost of two weeks in a hotel was more than what I wanted to pay per month in rent.

• We were only intending to stay for just under 6 months. Every day we stayed in a hotel meant we were extending the date on our lease and therefore overpaying on our rental agreement (i.e. if we didn’t move in until Dec. 15th we would have the unit until June 15th even though we were leaving May 15th).

• Rentals come and go very quickly, and I wasn’t confident as a first timer to Maui about finding something suitable under pressure.

To make all this happen you do need to be willing to rent a place sight unseen. Make sure you get a virtual tour, but you won’t get to go in person. If you have any connections on the island, getting a friend to look on your behalf is a great idea! I didn’t know anyone locally so I had to collect all the information I had available and make the best decision. It worked out, but it was a scary process! Securing housing from afar presented its challenges, notably in an expensive market like Maui's. The strategy of securing a rental before arriving, despite the need to potentially rent sight unseen, alleviated the stress of house-hunting with children in tow. This approach, coupled with the insights gained from local Facebook groups, was essential in navigating the island's real estate landscape.

The Virtual Hunt: Navigating Maui's Real Estate from Afar

The housing search without the ability to physically inspect properties necessitated a reliance on virtual tours, online listings, and the candid feedback from local residents and real estate professionals. This virtual approach, while daunting, offered a unique opportunity to explore Maui's diverse neighborhoods and housing options from the comfort of our current home. High-quality photos, virtual walkthroughs, and detailed descriptions became invaluable resources, enabling us to envision our potential new homes and weigh the pros and cons from a distance.

Leveraging Local Knowledge Through Social Media

The decision to engage with local Facebook groups and forums was a game-changer in our housing search. These platforms provided a wealth of local knowledge, from insights into the nuances of different neighborhoods to tips on navigating Maui's rental market. The firsthand experiences shared by members of these groups were particularly enlightening, offering a glimpse into the realities of living in various parts of the island, the average cost of utilities, and even the best schools and community amenities. This local wisdom, generously shared by long-time residents and recent transplants alike, was instrumental in guiding our decisions and setting realistic expectations.

The Importance of a Flexible and Open Mindset

Approaching the housing search with flexibility was crucial, especially when considering the possibility of renting a property sight unseen. Understanding that compromises might be necessary, whether in terms of location, size, or amenities, helped us remain open to a range of possibilities. This openness also allowed us to quickly adapt our search strategy based on availability and our evolving understanding of what we truly valued in a potential home.

Building Trust and Verifying Details

In a market where scams can occur, building trust with landlords and property managers was paramount. This meant asking for additional verification of property details, seeking out reviews or testimonials from previous tenants, and, when possible, enlisting the help of local contacts to perform a preliminary check of the property. These steps, though time-consuming, were vital in ensuring that our leap of faith into a new home was as secure as possible.

A Proactive Approach to Paperwork and Agreements

Securing a rental from afar also meant navigating the complexities of lease agreements without the benefit of face-to-face negotiations. We became proactive in seeking clarity on lease terms, understanding the local laws regarding rentals, and ensuring that all agreements were thoroughly reviewed and understood before signing. This diligence was not just about protecting our interests but also about building a solid foundation for our new life in Maui.

Reflections on the Process

Looking back, the process of securing housing from a distance was a testament to the power of community, the importance of technology in bridging geographical gaps, and the need for patience and persistence. While the journey was fraught with challenges, it was also an invaluable lesson in the importance of trust—trust in the information gathered, in the new community we were joining, and in our own instincts as we made one of the most significant decisions in our move to Maui. This experience, steeped in uncertainty but guided by research and community support, was a crucial first step in our transition to life in the Hawaiian Islands, laying the groundwork for the adventures that lay ahead.

3. Location Matters, but Flexibility is Key

You really need to drive everywhere on Maui. Our condo is across the street from the beach, but we still drive to the beach since the driveway is long and uphill and it’s tiring for us and our kids to haul our beach gear down. That sounds lazy, but it’s just practical! We save our energy and drive to the beach and it’s perfect. Also, you will want to explore LOTS of beaches. The beaches on Maui are each unique and good for different activities, so depending on what you like to do (and you may not know that until you get here) you will be driving to different beaches.

Kihei is the best spot for a long tourist visit like this (3-6 months). The weather is hot, dry, and sunny. Kihei is really central and it’s easy to get into town (Kahului) for access to the mall, walmart, target and the airport. It’s a short drive to the Maui Ocean Centre, and all the amenities you need are right there (grocery, walk-in clinics, pharmacy, gym, playgrounds, community pool). Kihei also has excellent beaches and you can get anywhere on the island (except Hana) within an hour.

4. Navigating Housing Amenities: Rent Fully Furnished!

The quest for a fully furnished rental highlighted the realities of Hawaii's real estate market. While our partially furnished condo necessitated initial extra spending, it also offered us the chance to personalize our space, reflecting the compromise and adaptation required when settling into a new home in Hawaii.

5. Leveraging the Local Buy/Sell Economy

The vibrant buy/sell market on Maui, especially through platforms like Facebook Marketplace and Craigslist, was awesome for furnishing our home and living sustainably on the island. This aspect of island life is a testament to the resourcefulness needed when adjusting to Hawaii's cost of living. We bought a vehicle and sold it again before we left for exactly what we paid. Talk about an affordable rental car!

6. People will want to come to visit you!! Make sure you consider your space.

I really wasn’t sure if any of our family would make the trip to the middle of the pacific ocean to visit us….but it turns out if you are able to offer free accommodation, they will certainly come!!  Maui is an expensive place to vacation with hotels costing at least $500 USD/night.  A free room means suddenly that vacation in paradise is affordable!  We were able to host guests in our 3 bedroom condo by giving up our master suite and bunking with the kids in the other two bedrooms. It was totally fine, and definitely worth it to be able to share this beautiful place with our family.  If that’s not your style (don’t worry I didn’t think it was my style either until I did it), just consider renting a place with a guest room.

The ability to host family and friends, turning our condo into a welcoming space for visitors, was a joy. But it was also a BIT TIGHT at times! This experience definitely taught me to consider guest/ hosting space when choosing a rental, as sharing the beauty of the islands with loved ones can enrich your stay, and I mean, you really can’t people away when you move to Maui!

7. The Essentials of Island Transportation: You will need a car! Buying vs. Renting

 I thought this one over long and hard! I decided to buy a vehicle and it was definitely the right call. The DMV is a breeze in Maui, and the process to buy and sell a vehicle is quite simple. As long as you don’t sell the car for more than what you bought it for you won’t have any issues. We were able to buy two vehicles and sell them both at the same price we paid, minus $500. It was an experiment, but it worked out WAY better than paying $2000 or more per month to rent a vehicle! We rented a vehicle for the first two weeks and started looking for a used car once we were on the island. Buy something with good re-sale that is in good condition. The last thing you want to deal with on your 6 months in paradise is car trouble!

Through this journey, the lessons learned extended far beyond the logistics of moving and settling in. They encompassed the deeper aspects of embracing a new community, understanding the unique blend of cultures that define the Hawaiian Islands, and the importance of approaching this significant life change with flexibility, respect, and an open heart. From navigating the complexities of the real estate market to integrating into the local lifestyle, the adventure of moving to Hawaii is as much about finding a new home as it is about discovering a new way of living—one that is in harmony with the islands' natural beauty, culture, and spirit.

If you decide to rent a car, make sure to check out the rates through UnderCoverTourist.Com, they can save you a ton of $$!

Embracing the Hawaiian Lifestyle

Living in Hawaii is about more than just enjoying the warm weather; it's about integrating into a community with a strong sense of identity and respect for the natural beauty and native Hawaiians' culture. Hawaiian culture is vibrant, deeply rooted in tradition, and welcoming to those who approach it with openness and respect. From learning a few phrases in the Hawaiian language to understanding the significance of places like Pearl Harbor, every bit helps in making a meaningful connection to your new home.

Education and Community Life

For families, the quality of public schools can vary greatly across the different islands and communities. Hawaii offers a mix of public and private schools, so researching the best fit for your family is essential. Community life in Hawaii is rich with opportunities for outdoor activities, making it a great place for families and individuals who love nature. From surfing on the North Shore to exploring the unique ecosystems of Hawaii's national parks, the islands offer endless adventures.

The Economic Reality

The dream of living in Hawaii comes with its set of economic considerations. The high cost of living, driven by the islands' isolation and the high demand for housing, affects everything from the price of groceries to real estate. However, the good news is that Hawaii offers a variety of job opportunities, especially in tourism, healthcare, education, and technology. Understanding the local economy, including the average price of a one-bedroom apartment, consumer goods, and the average income, is crucial for planning your move.

8. Making the Move: Logistics and Adjustments

Moving to Hawaii is no small feat, especially if you're coming from the continental United States or further afield like Canada. Shipping household goods via a shipping container, finding a reliable moving company, and adjusting to the island's laid-back pace can take some getting used to. The concept of "island time" can be a culture shock for newcomers, but it's also part of the charm that makes Hawaii such a unique place to live.

As we embarked on our journey to find a new home in the Hawaiian Islands, our search wasn't limited to just Maui. The allure of living in a tropical paradise prompted us to consider other islands as well, each with its unique charm and challenges. This exploration was about finding the right balance between our dream lifestyle and the practicalities of daily life in one of the most beautiful yet most expensive states in the U.S.

We chose Maui, but I did a lot of research to help me decide which island was the best fit for you. Maybe these descriptions will help you too!

The Island of Oahu: Urban Living in a Tropical Setting

The Island of Oahu, with its vibrant mix of urban and natural landscapes, was a strong contender. Known for its bustling city life, Honolulu offered the convenience of public transportation, a rarity in the more rural Hawaiian Islands. The cultural and economic heart of Hawaii, Oahu presented a dynamic community with diverse job opportunities, which was appealing considering the unemployment rate and the importance of securing stable employment in the island's economy. However, the high housing prices and the prospect of island fever in a densely populated area made us pause. Oahu's laid-back lifestyle juxtaposed with its urban hustle made it a popular destination, yet we wondered if the hustle and bustle might be too reminiscent of our previous life in San Francisco.

The Big Island of Hawaii: Diverse Landscapes and Laid-back Living

Hawaii Island, or the Big Island, captivated us with its vast landscapes, from the snowy peaks of Mauna Loa to the lush rainforests and the volcanic deserts. The Big Island's size meant more opportunities to find a small home in a less crowded setting, promising a stronger sense of community and a more laid-back lifestyle. The island's natural beauty, including the chance to live near palm trees, sea turtles, and an active volcano, underscored the unique daily life awaiting Hawaii residents. Yet, the variability in housing costs across its vast square miles made financial planning a crucial first step.

Considering the Smaller Islands: Seeking Solitude and Community

The allure of smaller islands, like Kauai and Molokai, offered a glimpse into a quieter, more secluded life. These islands promised a tropical island experience far removed from the high costs and fast pace of the major islands. The strong sense of community, the abundance of fresh fruit, and the opportunity to embrace a lifestyle centered around nature were compelling. Yet, concerns about the limited job opportunities, the potential for island fever in such secluded settings, and the logistics of accessing medical and educational facilities put these options into perspective.

Evaluating Our Options: Lifestyle, Costs, and Community

Throughout our exploration, several important factors emerged as decisive in choosing our new home. The warm climate, tropical lifestyle, and the dream of living in such a beautiful place were balanced against the reality of the national average for housing prices, the daily life adjustments required, and the need for a community that reflected our values and lifestyle aspirations. The comparison highlighted the diversity of the Hawaiian Islands, from the urban appeal of Oahu and the expansive natural beauty of the Big Island to the intimate communities of the smaller islands.

In the end, our decision to move to Maui was influenced by a combination of factors, including the island's manageable size, the balance between natural beauty and community resources, and the potential for a laid-back lifestyle that still offered access to essential amenities. The whole process, from considering each island's unique attributes to weighing the practicalities of housing prices, and cultural integration, was a journey in itself. It reinforced our desire for a change that wasn't just about a new location but about embracing a new way of life—a life where the dress code includes Hawaiian shirts, the diet includes plate lunch, and the scenery is a daily reminder of the tropical paradise we now call home.

Conclusion: The Aloha State Awaits

Our 6-month stay in Maui was nothing short of epic, filled with learning experiences, breathtaking natural beauty, and a deep appreciation for the Hawaiian islands and their people. If you're considering a move or an extended stay in Hawaii, my best advice is to do thorough research, connect with local communities online, and visit in person if possible. Whether it's the vibrant streets of Urban Honolulu, the serene beaches of Maui, or the rugged landscapes of the Big Island, Hawaii offers a diverse range of experiences for those willing to embrace its challenges and rewards.

Remember, moving to Hawaii is not just about finding a new home but also about embracing a new way of life. The aloha spirit is real, and with some planning, flexibility, and openness to new experiences, the Hawaiian Islands can offer an incredible backdrop to your next adventure.

In health & good travels,

Jen

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