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Maui Real Estate Resources

The Maui Real Estate Blog

January 2023 Calendar of Events

We here at the Sayles Team hope you had a wonderful holiday season and want to wish you and yours the best in health and wealth in 2023! January is the month with some of Maui’s most popular reoccurring events. There’s an intimate music festival featuring some of Country’s biggest stars here in Wailea. A luau benefit oceanfront in Lahaina. Comedy and symphonic performances at the MACC. But perhaps January’s biggest draw takes place every first weekend of the year. With frigid conditions and temperatures bracing much of the mainland, midwinter is the perfect time for a PGA Tour sanctioned golf tournament!

Sentry Tournament of Champions

Even though Maui’s golf courses are enjoyed year round, there is just one PGA sanctioned golf tournament on Maui. Founded in 1953, the Sentry Tournament of Champions is about to celebrate its 25th anniversary being held at the legendary Plantation Course in Kapalua.

This 4 day nationally televised event flaunts our island’s natural beauty and winter warmth. Making many mainland golfers day dream, images of swinging sterling shots in their favorite pair of golf shorts. The forecast looks to be mostly sunny, in the low 80s and winds hovering around the 5-15 mph range. Just perfect.

See a current list of Kapalua homes for sale

And of course the unique format, highlighted by the fact that its qualified field is selected from the best of the best, makes for a star-studded affair. Each January the tourney features 40 players who either won a PGA Tour event or finished in the top 30 in the final FedExCup standings in the past year. 

The field has included golf greats such as Tiger Woods, Vijay Singh, Justin Leonard, Ernie Els, Davis Love III and many more. Just recently the 2023 Sentry Tournament of Champions announced Keegan Bradley, Patrick Cantlay, Hideki Matsuyama and Jon Rahm are all set to return to Maui.

First Tee Hawaii and Sentry Tournament of Champions Free Junior Golf Event

The Sentry Tournament of Champions, in conjunction with First Tee – Hawaii, will host a fun and interactive event for Junior golfers of all skill levels. Hosted by Golf Channel and NBC commentator and Hawaii’s own Mark Rolfing, this event is complimentary and open to kids of all ages.

In addition to instruction by PGA Professionals and First Tee – Hawaii coaches, there will be contests, prizes, shave ice and entertainment. All you have to do is RSVP online here! When: Monday January 2nd, event lasts from 2PM-4PM. Where: Kaanapali Golf Courses Driving Range, 2290 Kaanapali Pkwy, Lahaina, 96761.

2023 Annual Juried Exhibition

This prestigious exhibition gives visitors an opportunity to view current work by local artists in all media. The Hawai’i State Foundation on Culture & the Arts recognizes this exhibition each year through its Art in Public Places Program.

With renowned guest jurors offering a different perspective for a unique show each year, this exhibition offers an opportunity to view current work of local and mainland artists in all media. Ceramics, printmaking, sculpture, photography, painting, drawing, jewelry, digital media, fiber, wood, mixed media and all other creative explorations are welcome! With no theme, this exhibition challenges artists to submit their best work created within the past two years. The exhibit lasts for just over a month, so here are the important dates and details to note:


January 13 – February 17

Artwork Receiving Day: Tuesday, January 3rd from 9am-4pm.

Online Registration: December 27 – January 3

Opening Reception: Friday, January 13 / 5-7pm

In-Person Juror Walkthrough: Friday, January 13 / 4-5pm

Where: Hui No’eau Visual Arts Center, 2841 Baldwin Avenue, Makawao

2023 Maui Songwriters Festival

Lukas Nelson performing at the 2019 Maui Songwriters Festival

The Maui Songwriters Festival is already now in its 6th year, hard to believe! Started by BMI in 2015, this multi day showcase brings some of the worlds’ best Singer-Songwriters, Producers and Composers. From the streets of Nashville to beachfront at The Grand Wailea. A highly sought after ticket year after year, these Country music powerhouses perform their #1 songs while sharing the stories behind their origins in a series of intimate to larger scale acoustic shows.

Featuring Maui’s own Derick Sebastian, Lukas Nelson and Lily Meola, accompanied by a who’s who of contemporary songwriters and performers: Chris Young, Randy Houser, Natalie Grant, Mitchell Tenpenny, Kameron Marlowe, Meghan Patrick, Bernie Herms, Madeline Edwards, Ella Langley, JT Harding, and hosted by Emcee Storme Warren as well as CMT Host, Carissa Culiner. A list of shows and details below, starting with the:

Heaven Hill Distillery Dinner

Set within the Grand Wailea Resort’s beautiful Chapel Garden, experience Heaven Hill’s collection of rare and fine whiskeys, expertly paired with crafted creations by Grand Wailea’s culinary team. Featuring kiawe smoked brisket, tako al pastor, dry-aged duck, and decadent desserts. When: January 15th, music goes from 6PM-8PM. Where: Chapel & Chapel Gardens, Grand Wailea. Tickets are $150 each, and available online here.

‘Live at the Botero Lounge’

Enjoy a Complimentary Acoustic Show at the newly re-imagined Botero Lounge in the Grand Wailea Lobby to Kick off the 2023 Maui Songwriters Festival with Ella Langley, Lily Meola, Meghan Patrick, and JT Harding. Beverages and bites available for purchase. When: Sunday, Jan 15, music from 8pm – 10pm. Where: Botero Lounge, Grand Wailea

Grand Wailea Botero Lounge Lobby Bar

‘How I Wrote That Song’ 

An Evening with Award Winning Singer & Songwriters sharing the origin stories and performing their songs on the Seaside Chapel Lawn with ​Randy Houser, Kameron Marlowe, Madeline Edwards, and Lukas Nelson.

When: January 16th, doors open at 7:30PM, show starts 8PM and goes until 10PM. Where: Chapel and Gardens, Grand Wailea. Tickets to the GA are $100 and available online here.

There is also a VIP Package that includes:

  • VIP ticket price includes VIP event, and VIP seating at main show at Chapel Lawn and (1) drink ticket
  • 5:30pm – 6:30pm: Mix & mingle! Wine-Spirit Tasting & Chef Bites Experience in the Chapel Garden
  • 6:30-7:30: Live in the Chapel performance with Natalie Grant & Bernie Herms
  • Preferred front-row seating at the main show

A front-row experience featuring 9x Grammy Nominee Natalie Grant and 2017 Grammy Winner, Bernie Herms, as they perform. Featuring Emcee, Storme Warren. The VIP experience starts at 5:30 with an hour mix and mingle in the gardens, private show starts at 6:30. Tickets to this package are $200 and available online here.

Chris Young & Famous Friends

The ‘Finale’ show will be held at the Molokini Garden, ocean side at Grand Wailea. Enjoy this acoustic show highlighting Songwriters that are also Award Winning Artists with numerous #1’s. Featuring: Chris Young, Mitchell Tenpenny along with Randy Houser, Kameron Marlowe, Madeline Edwards, Meghan Patrick, Ella Langley, Lukas Nelson, and Lily Meola.

During the show Storme will auction off an autographed by all singer-songwriters and other Maui celebrities ukulele with 100% of the proceeds going to the Boys & Girls Club of Maui. Beverages and Bites available for purchase.

When: Tuesday, Jan 17, doors open at 6PM and pre-show starts at 6:30pm. Where: Molokini Garden, Grand Wailea. GA tickets are $125 and available online here. There is also a VIP ticket that includes priority front seating at the tables and one drink ticket. VIP is $175 and available online here.

Lewis Black: Off the Rails

Known as the King of Rant, Lewis Black uses his trademark style of comedic yelling and animated finger-pointing to skewer anything and anyone that gets under his skin. His comedic brilliance lies in his ability to make people laugh at the absurdities of life, with topics that include current events, social media, politics and anything else that exposes the hypocrisy and madness he sees in the world. Receiving critical acclaim as a stand-up, actor and author, Black has performed for audiences throughout Europe, New Zealand, Canada and the United States.

Since 2014 Lewis Black has done over 400 live streaming shows, called The Rant is Due, at the end of each of his standup performances. Adding his own unique style, Lewis delivers audience-written Rants which have been submitted from the fans at his show and throughout the world. These rants are now available on Lewis Black’s podcast, Rant Cast.

When: January 29, 2023, show from 7:30PM-9:30PM. Where: Castle Theater, Maui Arts & Cultural Center. Tickets are tiered starting at $35, $45, $55, $75 (plus applicable fees), available online here.

Buy Back the Beach (21st Annual)

The Hawaii Island Land Trust proudly presents the 21st annual Buy Back the Beach benefit lūʻau hosted by Old Lāhainā Lūʻau, an island style pā‘ina under the stars! Join us for an fun-filled evening with incredible live entertainment by the Old Lāhainā Lūʻau Entertainers and featured entertainment by our island’s newest super-duo: Eric Gilliom and Vince Esquire; a live and silent auction; and many reasons to celebrate land conservation on Maui.

Your participation in this event directly supports HILT’s mission to protect and steward the lands that sustain Hawai‘i and enables HILT to effectively meet land conservation needs on Maui and the rest of the State. When: Saturday, January 28, 2023, event hours are 5:00 PM 9:00 PM. Where: Old Lahaina Luau 1251 Front Street Lahaina, HI, 96761. Individual tickets are $275, sponsorship tables range from $2,750 to $10,000, and are available online here.

Maui Pops Orchestra – Broadway Pops

Maui Pops Orchestra’s annual sell-out Broadway Pops concert features the vocal talents of Nikki Renée Daniels & Jeff Kready in songs of Rodgers & Hammerstein, Stephen Sondheim, Andrew Lloyd Webber and more. Both with extensive credits on Broadway, television and in concert halls, this engaging couple will bring you the excitement of the Broadway stage!

They join Music Director James Durham and the Maui Pops Orchestra in a celebration of familiar and family-friendly music from Broadway and beyond. For more details, check out the Maui Pops Concert page here.

When: January 22, show hours are 3PM-5:30PM. Where: Castle Theater, Maui Arts & Cultural Center. Tickets are tiered: $22, $35, $50, $60 (plus applicable fees). Available online only here. As a reminder, the MACC Box Office windows are not open except for day of show, opening three hours prior to show time for sales and will call pickup. Season discount and student rates available.

Contact a Maui Real Estate Specialist

Hanging out with good friend Eric Gilliom after his weekly set at the Four Seasons Lobby Lounge.

Beyond being a trusted advisor in the real estate market, your REALTOR should be a professional who recognizes their role in supporting your wealth building and wealth preservation. Helping to magnify wealth is one of the core values of The Sayles Team; a set of guiding principles for how we serve our clients at the highest level. As experts in the field, we are constantly learning and providing guidance about making the wisest choices for the future. If someone you care about needs guidance or recommendations, please share our contact information and we would be honored to help them! If you would like to receive our in-depth market update or would like an evaluation of your property’s value we would love to hear from you.


Dano Sayles R(B)


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