The Roundup

A Hawaiian Vacation for All of Life's Big Occasions

by Jeralyn Gerba
A bride, her friends, and the vast ocean. Photo by Jeralyn Gerba.

It didn't take much island-hopping, mock-wedding crashing, or tiki-tippling for Popupla editorial director Jeralyn Gerba to realize there's pretty much always a good excuse to celebrate in Hawaii.

HAWAIIAN ISLANDS – The aloha spirit is the most hospitable kind. The sun is shining, the palm trees are swaying, the rainbows are doubling down, and the fruit is always fresh from the tree. What more do you need to celebrate? Just the people you love. (Not that it will take too much convincing to get them there with you.)


When You Want: To look like you're trying, but not too hard.
The Island: Maui
The Ho , an affordable and hippie-chic four-room sanctuary that is laid-back, ecofriendly, and a far cry from the golf course resort. Its Lahaina location is known to have a great reef and break wall, making it just the spot for learning to paddleboard and surf.
Go home with: A box of .


When You Want: Enough room for all your girls, the ease of big resort amenities, and the option to effortlessly customize.
The Island:
The Ho  has rooms with half-moon balconies overlooking aqua pool after aqua pool, surrounded by tall palms (great for selfies). The spa, the hotel's main feature, can be booked for private parties. This means you'll spend a whole afternoon getting treatments, relaxing together in a private suite, and snacking on a lovely arrangement of healthy snacks (parfaits, local fruit plates) and fresh juice cocktails.
Send the ladies home with: from the island distillery.

Impressive breakfast spread. Photo courtesy of The Palmwood.


When You Want: To feel grounded.
The Island: Kauai
The Ho is a B&B delight. The secluded guest house, fashioned after the ryokans of Japan, offers simple luxuries, carefully prepared meals, and a rustic breakfast you'll be talking about until the baby comes home.
For the Ride Home: Locally made .


When You Want: Old-fashioned glamour.
The Island: Oahu
The Ho , that iconic palace of pink on the shores of Waikiki. Slip into a rhythm in side-by-side rocking chairs on the lanai overlooking a coconut grove or retreat to your well-appointed room to put on matching, pink-striped Frette bathrobes and relax. In the morning, claim a chaise-for-two around the beautiful circular pool and nap under the pink umbrellas, the sounds of bustling Waikiki Beach in the background.
Keepsake for the two of you: Get the bathrobes! And .

Citrus as decor at a breakfast party at Moana Surfrider. Photo by Jeralyn Gerba.


When You Want: A wow-factor for your wedding guests.
The Island:
The Ho , with its sweeping colonial style and famously fab Waikiki beachfront location. We're talking prime-time views and well-worn tropical luxury. Avoid the crowds and call on the incredible on-site wedding planners to arrange for an intimate Hawaiian blessing at sunrise on the roof and a gorgeous breakfast spread to follow.
Parting Gift: A trio of .


When You Want: Comfort and convenience for the whole family.
The Island: Kauai
The Ho Get everyone to book out the apartment-style hotel rooms at . The large resort is low-density, with plenty of room for a game of freeze tag or catch, swimming, sunbathing, and sporting — without getting in the way of other guests. Rooms have working kitchens and washer/dryers, and dotting the premises are barbecues for dinner as you like it. (There's an on-site grocer, and you can ship or deliver whatever you like in advance of your stay).
Stock the Pantry: Find local specialties the whole family will love, like and bean-to-bar .

Chill out. Photo courtesy of Surfjack.


When You Want: Cannonballs and cocktails at the pool.
The Island: Oahu
The Ho Surfjack Hotel & Swim Club, a soulful little boutique hotel — new to the island — with mid-century modern furniture, local artwork, organic Hawaiian home cooking, and a really cute .
The Snack of Choice: potato chips (shrimp flavor!).

Welcome! Photo by Jeralyn Gerba.


offers nonstop service from several US cities — mostly from the west coast, and there is a 10-hour direct flight from New York's JFK. Their clever and under-the-radar program allows brides and grooms to get discounts for their flights and send fare discounts to their guests.


Popupla Guide to The Big Island