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Profits in Paradise: How to Sell Hawaii Vacations – Pleasant Holidays

 Written By Steven Hattem, Senior Director of Sales, Pleasant Holidays



The world is filled with beautiful places to visit. What makes Hawaii different? The magic of the Aloha Spirit that infuses the islands. It greets you the moment you board you flight and lingers with you long after you return home.


Hawaii travel has been at the core of Pleasant Holidays’ product line since the company began selling vacation travel packages more than 55 years ago. Now one of the largest agent-focused travel companies in the United States, Pleasant Holidays has sold more than 10 million vacations since 1959, turning its passion for these tropical islands into a profitable business enterprise for itself and the travel agent partners it serves.


Top 5 Reasons to Sell Hawaii Vacation Packages

  1. Profitable – on everyone’s Bucket List of places to visit within their lifetime, Hawaii is always in demand and offers  ample opportunity for agents to  increase their income with commissionable resorts, cruises and activities; and Groups Incentive programs
  1. Convenient – no passport required for U.S. citizens
  1. Accessible – convenient flights on all major carriers from gateways nationwide
  1. Accommodating – a full range of hotels and resorts, from luxurious five-star spa resorts with all the amenities to family-friendly condos with room for everyone to budget-friendly two-star hotels offering a comfortable home base from which to explore
  1. Idyllic – with year-round temperatures that average around 80 degrees, it’s the land of endless summer and endless natural beauty any time of year


An Island for Every Traveler

People know Hawaii for its glistening beaches, epic surfing, hidden waterfalls, legendary luaus and glistening palm trees dancing in the island breeze. And while you can find these iconic items on each of the main vacation islands, each individual island offers an ambiance and experience that is unique. Once you know the unique qualities of each island, it’s easy to match the perfect one to your clients’ personal preferences and travel styles.



This is where the action is! The most popular and populated of Hawaii’s islands, Oahu is No. 1 for visitor arrivals and for good reason: it’s as convenient as it is captivating. You’ll find the most flights, a wide range of hotels and resorts, and an endless list of sights and attractions to explore, all working together to make a vacation on this island fun, fabulous and affordable. Bustling Waikiki is world renowned for its famous beach, and strolling along its iconic golden sands is a must-do for every visitor. But that’s just the beginning of what this vibrant city has to offer. Travelers can immerse themselves in the customs, culture and history of the islands at the Polynesian Cultural Center, pay homage to the brave men and women who paid the ultimate sacrifice at the USS Arizona Memorial at Pearl Harbor (which commemorates the 75th anniversary of the attacks this December), and hike to the top of Diamond Head to take in the breathtaking view. You’ll want to tell your clients to venture up to North Shore to watch the surfers test their skill against the legendary waves and to spend some quiet time snorkeling in the crystal-clear waters of Hanauma Bay. Waikiki’s active nightlife invites travelers to indulge their palate at a variety of celebrity chef owned restaurants that tempt them with culinary fusion dishes that are both exotic and familiar at the same time.



Maui has earned a well-deserved reputation for romance and its pampering spa resorts keep it a popular honeymoon destination—but it is truly so much more. From the lush waterfalls of the Iao Valley to the tranquil beaches of Ka‘anapali and Wailea to the unforgettable Road to Hāna, travelers find breathtaking natural beauty at every turn that inspires all ages. The challenging links at Kapalua are the standing favorite of the PGA tour for its annual season opener, offering championship play and spectacular vistas. Be sure to recommend your clients watch the sunrise from the slopes of Haleakala for an experience they will never forget.



Known as the Island of Adventure, this is the place for active travelers and nature lovers. Larger than all of the other islands combined, it offers 11 of the world’s 13 climate zones, ranging from the snow-capped mountains of Mauna Loa and Mauna Kea to the black-sands of Punalu‘u Beach.  A visit to Hawaii Volcanoes National Park is not to be missed!



Are your clients looking to venture a little off the beaten path to a quieter island? This is the one to recommend. Travelers can experience the expansive grandeur of Waimea Canyon (aptly named the Grand Canyon of Hawaii), kayak up the Wailua River, surf the waters of Hanalei Bay, swim with sea turtles in Poipu and indulge in a pampering spa treatment at a luxury spa resort. A cruise along the Napali Coast is a true must!



These are the islands for the seasoned Hawaii traveler who simply wants to get away from it all. Secluded Lana‘i features luxurious resort hideaways and championship golf. Moloka‘i embodies the essence of Hawaii with few cars, no traffic lights and endless opportunities to discover the natural beauty of the island.


Cruising the Hawaiian Islands

If your clients are looking to sample more than one island or prefer the carefree convenience of all-inclusive-style travel, then a Hawaiian cruise is an excellent option. Norwegian Cruise Line (NCL) features a seven-night itinerary aboard the newly refreshed Pride of America that sails year-round each Saturday from Honolulu and includes accommodations, onboard meals, nightly entertainment and more. The only cruise sailing to all four of the most popular Hawaiian Islands (Oahu, Maui, Kauai and Hawaii Island), voyages feature more than 100 hours of port time to explore.


For a small-ship experience, Un-Cruise Adventures offers seasonal seven-night Hawaii sailings with a flexible itinerary that traverses the leeward side of the islands, visiting Molokai, Lanai, Maui and Hawaii Island. These voyages combine the upscale comforts of a boutique yacht cruise with a seemingly endless array of included activities and cultural experiences.


Pleasant Holidays offers everything agents need to book a complete cruise vacation on both cruise lines, including flights on all major airlines from cities nationwide, pre- and post-cruise hotel stays, onboard accommodations, informative excursions and tours, travel protection coverage, port transfers and more, offering one-stop-shop convenience and competitive commissions for travel agents.


Enhancing Activities 

Whichever island is the right fit for your clients, be sure to enhance their vacation experience by booking commissionable activities in advance. Pleasant Holidays’ Pleasant Activities brand offers hundreds of exciting tours and excursions that are as memorable as Hawaii itself. Popular favorites include the USS Arizona Memorial & USS Missouri Tour, Polynesian Cultural Center, luau, sunset dinner cruises, snorkel adventures, Atlantis submarine excursions and flightseeing tours. What are the latest new trends in tours? Eco-adventures like hiking and ziplining, and private tour options ideal for honeymoon couples, destination wedding groups and more.


Travel agents should be aware that the most popular tours can sell out in advance, especially during peak travel times such as the December holiday season and summer vacation months. However features real-time rates and availability with guaranteed reservations, so you can book your clients’ must-see excursions along with the other components of their Hawaii vacation package to ensure their Hawaii vacation is everything it should be and more.


Niche Markets

For travel agents who specialize, Hawaii offers options for every niche market.


Family – Truly a destination for all ages, Hawaii is ideal for family vacations, especially multi-generational gatherings. You’ll find a wide range of accommodations to suit your clients’ family travel needs, including spacious condos with the comforts of home. In addition, many resorts offer complimentary cultural activities such as lei making and ukulele lessons open to all ages, and supervised children’s programs, known as Keiki Clubs, where kids can create memories that last a lifetime.


Luxury – Hawaii’s magnificent spa resorts are world renown, offering elegant accommodations, impeccable service, rejuvenating spa treatments, immersive wellness experiences, world-class golf courses and more. Pleasant Holidays’ luxury brand Journese℠ is well-versed in the needs of this niche market and the luxury agents who serve it. Their knowledgeable Destination Specialists work one-on-one with you to handcraft exquisite journeys and ensure each step of the process is truly seamless—for you and your most discerning luxury travel clients.


Honeymoons—Hawaii hotels have a very romantic heart, offering special amenities for honeymooners, including intimate beachfront dining, luxurious couple’s spa treatments, floral arrangements, champagne breakfast in bed and more to ensure that your client’s honeymoon is a dream come true.


Destination Weddings – Hawaii is one of the most popular choices for destination weddings in the United States. While it is not the only state in the union where same-sex marriage is legal, it is arguably the most beautiful and most welcoming, extending its signature Aloha Spirit to LGBT couples and their families and friends.


Groups Travel – Whether the group size in 10, 100, 1,000 or more, Hawaii has the perfect resort that can accommodate its individual needs, including accommodations, meeting space, special event menus, team building, sightseeing and more. Pleasant Holidays’ group travel specialists provide personal assistance and advice, and exclusive incentives for you and your clients.


Why Book Hawaii with Pleasant Holidays


Experience You Can Trust – Named Best Tour Operator Hawaii for 12 consecutive years


One-Stop-Shop Convenience – we offer everything you need to book a memorable vacation in one convenient location, including:

  • Air
  • Hotels and Resorts
  • Cruises
  • Car rentals
  • Activities
  • Travel Protection Plans
  • Wedding Travel
  • Honeymoons
  • Group Travel


Exceptional Customer Service for Travel Agents and Their Clients

  • Nationwide team of Business Development Managers focused on growing your business
  • Call Centers staffed with destination specialists
  • In-destination customer service available 24/7


Increase Agent Commission Income

  • Earn higher commission selling vacation packages and cruises
  • Service fees may be added to increase commission income
  • Commission Protection included with purchase of travel protection plan
  • Exclusive agent incentives and more offered throughout the year


Get More

  • TRIP Travel Agent Reward Program for personal travel, including Premier Tier with added benefits
  • Annual educational FAM trips
  • Online training, including live webinars and on-demand TRACK courses
  • Extensive Agent Resource Centers with customizable materials, including printed brochures
  • Elite Experience incentive trip for top selling agents and guests


Exclusive Offers that Cannot be Booked Anywhere Else

  • Reduced Room Rates
  • Guaranteed Availability
  • FREE Car Rentals or Car Rental Upgrades
  • FREE Breakfast
  • Spa Treatments
  • And more!


Brand Portfolio

  • Pleasant Holidays® – leading provider of leisure travel packages and cruises for more than 55 years
  • Journese – Curators of Fine Travelluxury vacations with concierge-level service
  • Air by Pleasant® – the leading international air consolidator, add your own commission on First and Business Class fares offering substantial savings
  • Pleasant Activitiescommissionable activities, excursions and tours on Oahu, Maui, Kauai and Hawaii Island



Only available through Pleasant Holidays