For more than 40 years, Pleasant Holiday’s has been offering travelers unique Hawaiian tours. Pleasant Holidays has spent the last 40 years building lasting partnerships with major hotel chains, airlines, and resort destinations. All Travel can now pass the Pleasant Holiday vacation savings on to you.
Pleasant offers many options and savings benefits to travelers. Current offers include a $50 resort credit with a 7 night stay at any Starwood resort in Hawaii. Travelers can also enjoy a 10% savings on their vacation for simply booking a Pleasant Holiday Vacation online.
Pleasant Holidays offers Special Interest Vacation Packages
Whether you’re into golf or looking for family activities, Pleasant Holidays has the custom vacation package for you. Here’s just a few of the special interest vacation options available:
Golf
Pleasant Holidays has created some tremendous hotel and golf packages at a number of the finest resorts. Packages include accommodations, rounds of golf, and cart rentals.
Honeymoon
As a honeymoon traveler on a Pleasant Holiday, you and your spouse can receive many special amenities such as a candlelight dinner, complimentary upgrades and more.
Family Vacations
Pleasant Holidays features many vacation packages catering to families, including "kids stay free" offers and specialized activities for kids.
Spa Getaways
Looking to just relax and feel pampered? Pleasant features many exciting and relaxing spa vacation options.
Senior Specials
Seniors over the age of 55 can also enjoy special savings and free upgrades at participating hotels.

Travel Insurance with AIG Travel Guard
We have plans. Lots of them. Why? So you can easily find the one that fits. And with our plans, it’s not just about coverage. It’s about unique services. Lost your bag? We can help track it with Bag Trak®. Or we can cover your losses if it isn’t found. It’s simple. We have the coverage options and assistance services you want for your globetrotting travels. Read More
Travel Restrictions by Sherpa What to know
Future Cruise Credits What to know
If you are holding on tight to your Future Cruise Credits (FCCs) waiting for the perfect time and itinerary to put them back in use, many of them expire soon! Now is a great time to check the status of your FCC with an All-Travel Travel Advisor. Read More
Real ID Deadline Extension
Starting on May 3, 2023 travelers who elect to use a state-issued driver’s license at Transportation Security Administration (TSA) airport checkpoints must ensure that they are Real ID-compliant, which is designated by a star in a circle in the upper right corner of the license. Read More
