The Best Spots for a Hawaii Group Getaway, Whichever Island You Choose

Whether you’re traveling as a multigenerational family or a group of friends, the islands of Hawai‘i truly offer something for all ages and affinities. Here are our top suggestions for where to lead your pack in 2026, including unique experiences and notable lodgings with new looks and amenities. Although we’ve excluded recently flooded or storm-damaged areas, such as North Shore O‘ahu, there’s still plenty of ground to cover with your traveling companions. 


Outrigger Kona Resort and SPA Dining Sunset Picnic
OUTRIGGER Kona Resort and SPA sunset picnic, courtesy of OUTRIGGER.

As the largest island in the state (4,000 square miles and still growing), this geographically diverse destination has been aptly nicknamed the Big Island. Known as the land of fire and ice, this island boasts climate zones and landscapes ranging from arid lava deserts to tropical rainforests and icy alpine peaks. It’s the only place on the planet where you can trek across the world’s largest active volcano, climb to another volcano’s snowy summit and end the day with a swim in the ocean.

Together Time

Lava Lava Beach Club Hawaii
Pop into Lava Lava Beach Club at Anaeho’omalu Bay on the Kohala Coast for toes-in-the-sand lunch or dinner. Photo by Kristin Addicks.

Walk and learn 

The expert guides of Hawai‘i Forest and Trail share fascinating lore on public and private tours to some of the island’s most unique wahi pana (special places), including several that are otherwise inaccessible to visitors. Our favorites include hiking to hidden waterfalls and ziplining through a canopy of trees in Kamehameha’s home turf of North Kohala, and star-gazing on Mauna Kea, stopping en route to hike and lend a hand at the Waikoloa Dry Forest Preserve.

Take a selfie with the king! 

If you’re planning a drive through the town of Hawi, make sure to round off your day of exploring its art galleries, boutiques and restaurants with a visit to the original statue of King Kamehameha I. Once lost at sea, the figure depicts the former leader, who was born on this island and united all the islands into one kingdom in 1810. 

Canoe Fun 

For an ocean excursion, book a cruise for six on Hawaiian Sails’ traditional double-hulled sailing canoe, departing from the Mauna Kea Resort, or let Anelakai Adventures teach your group to outrigger canoe paddle, with optional snorkeling with manta rays, in Keauhou. 

Where to Stay

Outrigger Kona Resort and SPA Nalu Lounge
Relaxing at the OUTRIGGER Kona Resort and SPA Nalu Lounge. Courtesy of OUTRIGGER.

Perched above Keauhou Bay amid historic sites on lava rocks, the OUTRIGGER Kona Resort & Spa provides the best pool playground on the Kona Coast and easy access to ocean adventures, coffee farms and shopping.

What’s new: The $60 million renovation brought a wave of appealing blue tones into the 511 guestrooms and suites, tying into the spectacular ocean views. The resort has leaned into the rich cultural history of the area, with new exhibits and videos in the lobby and a dedicated cultural center. Plus, there’s a lounge with activities like foosball and pool, perfect for family fun, and the new Voyager 47 Club Lounge offers a serene oasis for club-level guests.

Bite delights: Visitors and residents alike are eagerly awaiting the arrival of Duke’s — famed for its original Waikiki location — later this year. In the meantime, guests can enjoy a casual, island-inspired lunch or sunset pūpū (appetizers) at Holua Poolside Bar & Lounge, pick up coffee or wrap to go at Holoholo Cafe & Market, or sit down for breakfast or dinner at Piko, which offers nightly live music and a well-curated wine list as well as breakfast, dinner and all-day Kona coffee and artisan pastries.

Mauna Kea Beach Hotel boasts the best beach on the Kohala Coast for swimming, snorkeling, sunbathing and, come evening, manta ray watching.

What’s new: Grownups can now bask in an adults-only, ocean-view infinity pool, located next to the brand-new fitness center. A destination spa is also scheduled to open this month and will include indoor/outdoor treatment suites, steam rooms, saunas, a vitality pool and meditation areas. All ages can play in the updated family pool, while golfers may tee off on the redesigned Mauna Kea Golf Course. The 252 refreshed guest rooms and suites feature a relaxing aesthetic inspired by the Pacific Rim culture and brightened by Hawaiian art.

Bite delights: At sunset, the graceful hula dancer at the Copper Bar may distract you from the generous sushi rolls, local farm-sourced salads, tasty Mediterranean dips and flatbreads, and fresh fish specials. A jazz duo regularly performs at Manta, where Michelin award-winning chef Bryan Nagao transforms staples such as kale salad and macadamia nut-crusted mahimahi into artful showcases of island ingredients. The casual beachside restaurant Hau Tree metamorphosizes nightly into Hau Tree Cantina, offering gourmet, regional Mexican cuisine — very expensive but delicious.


Fairmont Maui Canoe Experience
Fairmont Kea Lani’s Hawaiian Canoe Experience. Photo courtesy of Fairmont Kea Lani.

The second largest island in the state is first in many hearts, reflected by the saying Maui no ka ‘oi, which translates to “Maui is the best.” The long-dormant volcano Haleakala, which has a lunar landscape of colorful cinders at its 10,023-foot summit, is connected to Kahalawai (West Maui Mountains) by a large central plain that formerly hosted sugarcane plantations. Miles of sandy, sunny beaches line the coast of South Maui and West Maui, where Lahaina continues to rebuild from the devastating fires of 2023. A growing number of shops and restaurants have relocated to or reopened in the largely untouched northern end of Lahaina, while its harbor has reopened to daytime tours. 

Together Time

Dawn Patrol 

Book an early-morning summit tour of Haleakala with Skyline Hawaii (consider scheduling this for the day after you arrive to take advantage of your jetlag).  If you’re a DIY traveler, you’ll need to book park reservations 60 days in advance, but know they fill up fast.  For a bit more shut-eye, consider spending your first night in Kahului. If hiking isn’t your thing, schedule a private tour on the Road to Hana in one of Hawaii by Storm’s luxury SUVs. Keep an eye out for the waterfalls and foliage along its long and winding road.

Boat Ride 

Whether you choose a sunset cruise, a morning snorkel or seasonal whale watching,  (December–April), a catamaran excursion is a must. Kai Kanani is the best option in South Maui, with daily trips to Molokini Crater just 3 miles from shore. Sustainable-minded Trilogy is the only company to sail to Lana‘i for snorkeling in Hulupo‘e Marine Reserve, departing from Ma‘alaea Harbor and Ka‘anapali Beach. 

Chocolate Tour 

Indulge in your inner Augustus Gloop and book one of the tasty “Bean to Bar” tours. Open to ages 6 and up, the tours run on Sundays at the Maui Ku‘ia Estate chocolate factory in Lahaina and all proceeds go to local nonprofits

Where to Stay

Kai Kanani - Snorkeling
Kai Kanani Tours offers various snorkeling tours on the Wailea Coast, including Molokini Crater where you can see up to 250 different types of fish.

More than 45 years after the Hyatt Regency Maui Resort and Spa debuted as the state’s first destination resort — pool playground, grand public spaces, spa, exotic wildlife, etc. — at the southern end of Ka‘anapali Beach, it remains a dazzling compound for all ages.

What’s new: The Ohana Pickleball Club, which opened in March, features 12 covered and lighted professional-grade courts for open or reserved play, plus cornhole, bocce ball, table tennis, a pro shop and shaded spaces for private events. The recently concluded multi-year renovation, which added glass balconies to the hotel’s 810 rooms and reconfigured the main pool and sundeck, among other visible updates, also introduced more reef-friendly landscaping practices and a pollinator garden. 

Bite delights: The Hyatt Regency’s celebrated sushi and seafood fusion restaurant Japengo, overlooking the beach, was also expanded as part of the renovations, but you’ll still want to make a reservation when you book your trip. Set on a sunset-facing lagoon with waterfall, Son’z Steakhouse has a more classic dinner menu, with a semi-private dining space ideal for groups of up to 20. The Honolulu Coffee Co. and Waikomo Shave Ice offer a choice of daytime pick-me-ups.

Perched above Polo Beach, Fairmont Kea Lani has long been the state’s only all-suite and villa resort. It is also involved with many environmental and cultural stewardship initiatives such as Waihe‘e Coastal Dunes & Wetlands Refuge — and with good food, too.

What’s new: A major redesign of all 413 one-bedroom suites and 37 two-story villas — perfect for small-group gatherings — and the lobby wrapped up in 2024. The resort’s commitment to reforestation is displayed through its bamboo garden (located in the lobby) and encouragement of guests to sponsor planting of indigenous flora on Haleakalā. The property also plays host to saplings for Treecovery. The handsome new Hale Kukana cultural center provides a window into Native Hawaiian arts and culture; sales of sculptures carved from wood reclaimed after the Lahaina fire benefit ongoing relief programs.

Bite delights: An upscale celebration of Maui’s culinary diversity, which has roots in the plantation era, the recently reimagined Ko Restaurant  also showcases the island’s abundant produce and proteins, appealing to residents and visitors alike. The new lobby bar Pilina serves superb sushi and sashimi all day, starting at lunchtime; at dinner, your group can grill their own Hawaiian ahi, A-5 Wagyu beef, king salmon, pork belly, local venison and tofu on a hot rock, too.  


Moana Surfrider Moana Lani Spa
Up to eight people can book the Moana Lani Spa at the Moana Surfrider. Photo courtesy of Moana Surfrider.

Nicknamed “The Gathering Place,” O‘ahu was popularized in the 20th century by surfing icon Duke Kahanamoku, Matson Line cruises and the “Hawaii Calls” radio program. Today, the island draws visitors to its notable sites like Waikiki Beach, Le’ahi (particularly at sunrise), the Pearl Harbor National Memorial and the edutainment-oriented Polynesian Cultural Center. If you’re planning a visit, make sure to also explore the islands’ two royal palaces, excellent museums, trendy bars and restaurants in Chinatown, and the Honolulu Zoo (great for kids).

Together Time

Spa Time 

For some beachside bliss and bonding, head to the Moana Lani Spa in the 125-year-old Moana Surfrider, a Westin Resort and the grande dame of Waikiki. The Celebration Soiree is a particular group favorite!

Chase Dinosaurs 

Sprawling across several valleys on the lush windward side, guests of Kualoa Ranch can book all-age private excursions which show off the property’s scenery, along with its natural and cultural history (including screen time in “Jurassic Park”). Choose your mode of transportation from horseback, zipline, UTVs (for one driver and up to five passengers), e-bike, catamaran and open-air “jungle vehicles” (think wooden benches on a pickup truck.)

Where to Stay

Outrigger Reef Waikiki Beach Resort - Cultural Center
Courtesy of OUTRIGGER Reef Waikiki Beach Resort.

The family-friendly OUTRIGGER Reef Waikiki Beach Resort celebrates Hawaiian culture with easy access to Waikiki’s many shops, restaurants and entertainment options.

What’s new: Since its $80 million makeover in 2022 that included all 658 rooms and public spaces, the hotel has put finishing touches on its penthouse suites—ideal for groups, with large lanais overlooking Waikiki Beach—and the luxurious Voyager 47 Lounge, which Club Rooms have access to for all-day food and drink. The new oceanfront Kahawai Chapel, opened in 2025, is a casually elegant, multi-room space ideal for intimate weddings and vow renewals.

Bite delights: You won’t want to miss Peter Merriman’s Monkeypod Kitchen, the famed farm-to-table chef’s only restaurant in Waikiki, the only one serving breakfast and the only one where waves may splash on the window next to you — it’s that close to the water. Next to the renovated pool deck,  Kani Ka Pila Grille serves hearty island/American fare with a nightly side of live Hawaiian music, often with spontaneous hula from local patrons.  

The Four Seasons Resort O‘ahu at Ko Olina, next to Disney’s better-known Aulani resort on the sunny southwest corner of Oahu, is its own magic kingdom — a refined oasis with the island’s best day spa, unique cultural activities, fine dining and the complimentary Kids for All Seasons program for ages 5 to 12.

What’s new: The largest Four Seasons club lounge in the world is both homey and luxurious. Plan your day over a hot breakfast, rustle up snacks and drinks mid-afternoon, pop in for pre-dinner drinks at the bar or simply share conversation anytime with the friendly concierge and staff. The relaunched five | one | six rooftop bar is an island-style,  rooftop speakeasy behind the pink door of Room 516, open just for a few magical hours around sunset.

Bite delights: Michael Mina’s Fish House, which has expanded seating just above the beach, excels at seafood with Asian touches (chili miso glazed black cod, yum), while the casual Waterman Bar, which serves guests by the ‘Ohana (family) Pool and on the beach, makes a mean grilled fish sandwich and smashburger. The earthy yet elegant Italian cuisine of Noe pairs well with date night. For breakfast, grab a malasada and cafe latte at the Hokule‘a coffee bar, or go all out with the lavish buffet at La Hiki. 


Father & Son Playing in the Main Pool
Fun for days at Koloa Landing Resort’s pools. Courtsey of Koloa Landing Resrot at Poipu.

Nicknamed the “Garden Isle,” the fourth largest Hawaiian island is also  the westernmost and geographically oldest of the main archipelago. Formed by the volcanoes Kawaikini and Wai‘ale‘ale about 5 million years ago, half of Kauai’s coastline has eroded into gorgeous sandy beaches and numerous small rivers. Highlights include the 25 miles of Napali Coast with 4,000-foot dramatic sea cliffs and the mile-long Waimea Canyon, striped with mineral-rich layers of russet, rose and brown ochre. Kaua‘i remains proud of its multiethnic plantation and ranching heritage, as well as its history as the only Hawaiian island not conquered by King Kamehameha.

Together Time

See Turtles 

View breathtaking cliffs from covered VIP seating and go for a snorkel off the Lady Kailani, Kauai Sea Tours’ first luxury catamaran offering Napali Coast tours. Space is limited to 49 people on a yacht that could accommodate three times as many. This third-generation family-owned company is also one of the few permitted to make seasonal beach landings via Zodiac rafts. If you want to paddle your own canoe, so to speak, Outfitters Kauai can arrange private tours for kayaking, ziplining and stand-up paddle boarding that can include access to otherwise off-limits cinematic scenery.

History Ride 

All ages can take a ride in the beautifully restored mahogany cars of  Kauai Plantation Railway through Kilohana Plantation’s working farm. The lunch tour includes an alpaca encounter, a walk through the plantation’s tropical fruit orchard and native forest, and feeding farm animals. Grownups can learn to make a mai tai at Koloa Rum Company’s tasting room at Kilohana Plantation, too.

Where to Stay

Koloa Landing Resort's Main Pool (Waterslides)
Koloa Landing Resort’s Main Pool (Waterslides)

The three-tiered, 13,000-square-foot main pool of Koloa Landing Resort at Po‘ipu, the island’s largest,has won over many families, along with the convenience of full kitchens, laundry and living rooms in its condo-style villas, within walking distance of Po’ipu’s shops and shoreline.

What’s new: The Spa at Koloa Landing’s updated menu incorporates Kaua‘i-inspired ingredients, such as noni, seaweed, mango and papaya, in various treatments. It also offers the only ofuro (Japanese soaking tub) experience on Kaua‘i, which includes making your own aromatherapy blend before soaking in the all-copper tub and enjoying a massage customized to your liking, too.

Bite delights: Executive Chef Sam Choy helped design not only the island-American menu of the all-day poolside restaurant Holoholo — including his signature dish poke, of course — but also spearheaded the resort’s annual Kaua‘i Poke Festival. The sixth annual edition next month includes a multicourse, celebrity chef Poke Masters’ Table on June 19 and a live competition with pro and amateur chefs’ creations incorporating 1,000 pounds of ahi, live music and a demonstration by Choy on June 20. 

Kauai Sea Tours
Honu (sea turtles) can be seen at many beaches, but Kaua’i’s snorkeling tours take you to truly unforgettable, picture-perfect locations.

A leafy compound of 59 restored plantation-era cottages on 43 oceanfront acres, moderately priced Waimea Plantation Cottages offers room for kids to play and for grownups to relax — perhaps after a full day exploring nearby Waimea Canyon, the forest trails of Koke‘e or the 17-mile beach at Polihale State Park.

What’s new: Take a self-guided tour of the beautiful tropical trees on the property, from spreading monkeypods to fragrant plumeria and hala (pandanus), whose long, sturdy leaves provide the material for traditional Hawaiian weaving, among other uses. The four recently designated Premier Cottages are ideal for groups of six to 10 guests, including the oceanfront five-bedroom, four-and-a-half-bath Manager’s House, which also offers a formal dining room and large lanai. Check out the Hawai‘i Nei special offer for smaller cottages through Dec. 17, 2026, including 26 percent off regular rates and a $26 Cottage Store credit.

Bite delights: Chicken in a Barrel BBQ has four of its casual restaurants on Kaua‘i, popular for plates of savory chicken, ribs, pulled beef and pork, but the Waimea branch is the only one to serve breakfast (pancakes, loco moco, egg burritos, etc.) It’s also one of two (besides the original in Coconut Marketplace in Kapa‘a) to have a “beer wall”: self-serve taps of draft beer, payable by the ounce. Vegetarians can order customizable pizzas, salads and veggie spring rolls. 

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