Paʻia, Maui. Courtesy of Hawaiʻi Tourism Authority. Photo by Tor Johnson.
This story contains affiliate links.
Best known for saying “e komo mai” to honeymooners and families, Maui can also be that rare spot to reclaim solo travel when you don’t have a significant other. Buck the trends. Be a rebel. Revel in Maui’s beauty and local charm—all on your own. Whether you’re healing from a breakup, launching your “Eat, Pray, Love” era on the Valley Isle, or just want to have some vacation autonomy, Maui can be the ultimate spot to reclaim your independence. Extroverts will rejoice in the many ways to meet people on-the-fly, while introverts can lock into the myriad activities Maui has to offer.
Day One: Sun & Sustenance
Morning:
But first… coffee. Visit Island Vibes Café at Napili Villages for an Aloha Latté that features coconut and mac nut flavors to perk you up on your first day. Back up your order with a breakfast burrito or an açai bowl to supercharge you for the day ahead. If you’re feeling adventurous, rent a paddleboard from Napili Bay Kayaks and SUPs right inside the café.
Afternoon:
Grab a towel and some SPF (may we recommend a reef-safe spray so you don’t have to worry about someone else getting your back?). Sun yourself on the shores of Napili Bay and laze in front of Napili Kai, swimming and snorkeling to your heart’s content. Feeling peckish? Grab a snack and a bevy from the Sea House restaurant, just steps away from your beach towel with some of the most iconic views on the westside.
Evening:
Party of one? More like party of fun. Let’s get this solo travel going with a solo dinner at the bar at Monkeypod Kitchen Kā’anapali (a disclaimer, I may see you racing around the floor in my uniform). With live music and friendly staff, there will always be a conversation waiting to happen. Make sure to order the Monkeypod Mai Tai ($18), crowned with their signature Honey-Lilikoi foam. Then treat yourself to the seared ahi with a Maui onion-soy vinaigrette ($49) and their famous strawberry pie ($14)
Monkeypod Kitchen Kāʻanapali strawberry cream pie. Courtesy of Monkeypod Kitchen.
Day Two: Rejuvenation & Revelry
Morning:
You know you brought a spandex fit for some reason. Center yourself with a class at Form Pilates ($38), the latest fitness studio set up in Kā’anapali’s Fairway Shops. With a sleek look and top-of-line equipment, these reformer-based classes offer small class sizes that lends a little extra attention during your workout.
Afternoon:
Take the Kā’anapali Trolley (you deserve it; you did work out after all) or opt for a leisurely stroll down to Kahekili or “Airport” Beach for a midday dip at a spot that locals love. This north Kā’anapali mainstay was nicknamed for the former airport that was built only 30 feet from its shoreline back in 1965.
Shake off the sand, then traipse up to Lāhainā Noon, the Royal Lahaina Resort & Bungalows’ latest modern Hawaiʻi eatery. Snack on some Smoked ʻAhi Dip ($25) or indulge in the Paniolo Beef Smashburger ($28).
Evening:
After a late afternoon nap, grab that cocktail dress or that Reyn Spooner button-up you’ve been dying to rock and head to Lāhainā Healing Center for their weekly salsa classes. Shake it like Shakira, then use your svelte look to score a seat at the bar at Honu Oceanside, a newfound Lāhainā staple that adopted many of the talented culinary and hospitality staff from the beloved Lahaina Grill that was lost in the Maui wildfires. Sip on a Bee’s Knees ($18), get the Dore Style daily catch ($60), and count how many honu (green sea turtles) you see coming up for air below the sunset.
Don’t want to head back to the room just yet? Grab a ride share service and head north to Honokōwai for a nightcap at Pineapple Robot – a local dive that boasts stiff drinks and nightly karaoke with performances that prove the bar’s potency.
Courtesy of Lahaina Noon. Photo by Bixel Creative.
Day Three: Wanderlust
Morning:
Set your alarm a little earlier today for a 4.5-hour snorkel cruise on the Quicksilver’s double-decker catamaran that leaves out of the Māʻalaea harbor. Check in at 8:30 a.m., board the boat, and slap on your snorkel gear. Once you’re in the water, you’ll come across several different species and maybe even see a pod of dolphins on the way out. Remember to bring these essentials: a towel, reef-safe sunscreen, sunglasses, a valid photo ID (in case you’d like to purchase alcoholic beverages after snorkeling) and cash for tipping.
Afternoon:
Take a drive through central Maui up to the north shore in the historic town of Pa’ia. With plantation-era storefronts, galleries, and restaurants, this is a charming hamlet with hippie sensibilities. Stock up on the supplements you forgot at home and some natural bites at Mana Foods, Maui’s consummate health food store.
Take a drive up Baldwin Avenue to Makawao for some retail therapy and a stick donut – a legendary pull-apart glazed donut on a skewer from Komoda’s Bakery. Come early, they sell out fast. Stop by Tribe Maui for a collection of retro styled beach and streetwear for both men and women, with shops on both Makawao Ave. and Baldwin Ave.
Evening:
Swing by the nearby neighborhood of Pukalani for Maui’s foodie haven, Marlow. This café and pizerria-plus stuns with its execution and flavors. Have a glass of Italian Frappato while you revel in the braised octopus and Neapolitan-style pizza. If it’s a weekend, make a pit stop on your way back to the other side and stop down in Pa’ia to catch a DJ set at Belle Surf Café & Lounge.
Courtesy of Marlow.
Day Four: Adventure & History
Morning:
Giddyup. It’s time to saddle up for a horseback ride through lush valleys onward to the Maui coastline with Circle M Ranch. Meet up at the corral in Wailuku at 8:45 a.m. for a 9:00 a.m. departure, where you’ll be guided by paniolo (cowboys) through stunning vistas all on your sturdy steed.
Afternoon:
Head to the Maui Plantation Center in Waikapu for a quaint, lakeside lunch at The Mill House run by Café O Lei. Try the Calamansi Honey Sour ($15) to whet your appetite, then order the Café O Lei Crab Club ($21) for post-ride satisfaction. Walk it off and stroll the grounds to shop for local crafts or take a 40-minute tour by tram ($25) to explore the agricultural history of Maui.
Take a short 10-minute drive to the heart of historic Wailuku town for some quirky shopping. Hit up Market Street and Wailuku Coffee Co. to grab a third-wave coffee, or matcha, then walk a few stores down to peruse the vast inventory of Request Music, which has been serving the discerning listener since 1990 with the best vinyl, CD and cassette collections on island.
Evening:
Take your shopping haul to impress your friends back home and stop by Esters Fair Prospect on Main Street for a tropical tipple made by their highly skilled bar staff. Feeling iconic? Try the Mai Tai with their house rum blend ($14). Feeling contrarian? Try the smoky yet sweet Til Dawn with mezcal, coconut, orgeat, and lime ($15). There’s also bar snacks, like ceviche with local marlin ($16) and guacamole ($12) to tide you over.
If it happens to be the first Friday of the month, you’re in luck. Wailuku’s monthly First Fridays event buzzes with energy from the local community and shops and galleries offer an open house. While strolling the main drag, grab a pic under the marquee of the historic ‘Iao Theatre. Better yet, see a play there. Think musicals like “Rocky Horror Picture Show” and “Grease” or one-off performances like their experimental “One Night Only” run of original, local material.
Esters Fair Prospect. Photo by Sarah Burchard
Day Five: Relaxation
Morning:
Today, we rest. And by rest, we mean shop and dine til you drop on top of a massage table for some end-of-vacation indulgence. Give yourself a break from your action-packed solo travel schedule and simply relax. Head to Whaler’s Village in Kā’anapali for a wide variety of shopping from local brands, such as ALOHA Collection, luxury brands like Louis Vuitton and beauty behemoths like Sephora.
Afternoon:
After some retail therapy, sway your way to Hula Grill’s Barefoot Bar, where you can kick off your slippers and wiggle your toes in the sand as you listen to local musicians play Hawaiʻi classics. After lunch, take the Kā’anapali boardwalk north to the Sheraton Maui Resort and Spa and check in for your appointment at the Spa at Black Rock, where massages range from $85 to $295 with the option of indoor treatment rooms or an outdoor lanai and oceanfront cabana.
Evening:
For your Valley Isle farewell, make your way to Merriman’s in Kapalua for a happy hour—and sunset—that is not to be missed. Running from 4:00p.m. to 5:00p.m. at the Point Lounge and the main bar, get discounted epicurean delights from the mind of renown Hawaiʻi Regional Cuisine chef Peter Merriman. Try the Kalua Pork & Sweet Onion Quesadilla ($15) paired with the No Ka Oi cocktail featuring Ocean Vodka, Lilikoʻi, and Thai Basil ($14). If you’re feeling lucky, stay for a full dinner. You never know who might pick up your tab…
Napili Bay. Courtesy of Hawaiʻi Tourism Authority. Phot by Mathieu Duchier.
