9 Things to Do in Your First Week in Wailea

9 Things to Do in Your First Week in Wailea

  • Chelsea Dimin
  • 12/19/22

Congratulations on your purchase of Wailea real estate!  As veteran Maui real estate agent Chelsea Dimin can tell you, in this beautiful paradise, you’re on your way to having the experience of a lifetime just as she has. After all, this is a vacation that never has to end! Let your first week here be filled with two key objectives: discovering memorable things to do in Wailea, and learning to find your way around like a local. Sure, there’s so much more to see, do, and learn than what you might discover in a week, but remember, you’re on island time now, and that means your first week can take as long as you need it to!

Explore the area

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Take a drive through town and the surrounding areas. As you do so, make a mental note of landmarks and street names to begin familiarizing yourself with the area. Within your neighborhood, walk or bike for a slower pace to take in your surroundings. This will also provide opportunities for chance encounters with your new neighbors as they’re out doing the same.

Meet your neighbors

Hawaii is the Aloha State, and that means you can expect to receive warm, friendly hospitality wherever you go. The people you meet will be genuinely interested in getting to know you, and working from day one to build a great relationship with your neighbors will prove helpful time and again. Your neighbors are likely to extend your first social invites, are your best resource for learning about the community, and are a helpful point of contact for anything your family may need.

Book a scenic tour

Whether by land, air, or sea, Maui is a feast for the senses. A guided tour with a local expert can provide you with stories and fascinating facts and narrate your experiences, making them all the more memorable. Your biggest challenge may lie in deciding which tour to take! Why not try one now and continue to explore Maui further over the weeks and months ahead? Here are some unique options:

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Incredibly, these amazing adventures are only a small sampling of the many ways you can explore and experience Maui.

Relax at the beach

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Feeling those tropical breezes beckoning you to the water’s edge? Don’t ignore their call to spend a perfect morning, evening, or even a whole day at one of the beautiful beaches nearby! Beachgoing will always be the most popular thing to do in Wailea. Snorkel at Ulua Beach, stroll the coastline trail at Wailea Beach, or enjoy the quiet, undeveloped oceanfront of Po’Olenalena Beach. 

Try a local restaurant

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Not far from your Wailea real estate, you’ll find delectable dining options with a variety of restaurants to please any palate. Monkeypod Kitchen showcases the very best of Hawaiian fare. Craving sushi? Morimoto Maui offers unparalleled sushi and other Japanese dishes in a beach house-inspired restaurant. Ka’ana Kitchen prides itself in presenting a variety of farm-to-table dishes family-style in a warm and friendly atmosphere. Enjoy sunset views and a rotating seasonal menu at Humuhumunukunukuapua’a, located at the Grand Wailea.

Book a round of golf

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You can’t help having your best round of golf at Wailea Golf Club, the breathtakingly beautiful, award-winning course at the Wailea Resort. With three courses to choose from, you’ll simply have to try them all to determine which one is your favorite. Is your golf game a little rusty? Schedule some expert instruction from the Wailea Golf Academy.

Locate the services/businesses you’ll frequent regularly

While there’s so much to explore and enjoy, this is also home now, and learning your way around the practical stops of everyday life will help you get settled in more quickly. Locate a grocery store, a pharmacy, a home improvement store, the post office, and other essentials. Ask neighbors for recommendations of physicians, dentists, barbers, mechanics, and other professionals. A personal referral from someone whose perspective you trust will save you considerable stress and headaches, so don’t hesitate to ask locals for their recommendations.

Shop for finishing touches for your new home

No matter your taste in artistic expression, local art galleries will provide you with endless options for statement pieces to complete the decor of your Wailea real estate. You’ll also be investing in local talent and embracing local culture. Wailea Fine Art is a new art gallery located in Wailea Town Center, featuring art from internationally recognized artists. NaPua Gallery showcases a large collection of Chihuly glass among works of various media. Find diverse artwork, jewelry, and resin furniture at the Maui Art Gallery

Find a way to connect with the community

Maui will begin to truly feel like home when you make connections with people you enjoy and become a part of the larger community. Explore affinity groups based on your interests and talents, whether that’s a professional organization, a book club, a hiking group, or more. Maul’s community events calendar is filled with classes, performances, and celebrations. Say “yes!” as often as possible. You’ll meet and mingle with people who share similar interests and begin to feel right at home.

Your relational realtor

Remember that your realtor Chelsea Dimin is here to offer resources and support as you settle into your new life on Maui. Reach out to her if you have questions or need any recommendations and resources along the way.

*Header photo courtesy of Unsplash

Chelsea Dimin

Chelsea Dimin

Realtor® Broker

About The Author

Chelsea Dimin stands at the pinnacle of Maui's luxury real estate, consistently ranking among the top 1% of agents in sales volume. Chelsea specializes in oceanfront property and vacation homes and has over 17 years of expertise in real estate, business development, and advertising sales.

Originally from Milwaukee, Wisconsin, Chelsea holds degrees in Journalism and Spanish from the University of Wisconsin Madison. Her career journey led her to Los Angeles in 2006, honing negotiation skills representing top brands in digital media and advertising sales. In 2010, she joined New York Magazine's digital publication, NYmag.com, as the West Coast Advertising Sales Account Executive. In 2014, Chelsea embraced Maui's allure, obtaining her real estate license and collaborating with a local developer. As a Realtor Salesperson, she played a key role in transforming vacation rental estates into profitable ventures, attracting a global clientele.

Acquiring her Broker license in 2017, Chelsea made history in January 2023, becoming the first female Realtor to list and sell a $32 million dollar home in Makena, as reported by the Wall Street Journal. Today, Chelsea guides buyers in realizing their Maui dream homes. Known for tenacity and creativity, she forges connections, assesses needs, and delivers strategic results. Chelsea's signature is creating opportunities, leveraging a global network for off-market deals and win-win negotiations.

Clients appreciate Chelsea's commitment to staying informed, providing updates on values, market trends, and recommendations. Beyond real estate, Chelsea enjoys an active lifestyle, engaging in surfing, yoga, barre classes, mountain biking, beach runs, jungle hikes, and waterfall adventures with her husband Tim and beloved pitbull, Lulu.

“My mission is to exceed your expectations so that you never hesitate to refer your friends, family or coworkers to me in the future.”

Work With Chelsea

Are you interested in buying or selling a home on Maui? Contact me to tap into my local knowledge and global connections. My mission is to exceed your expectations so that you never hesitate to refer your friends, family or coworkers to me in the future.

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