Pleasant Holidays is one of the largest tour operators in the U.S., offering vacation packages, flights, hotels, cruises, car rentals, travel protection and related travel services to the world’s most popular destinations including Hawaii, Caribbean, Mexico, Europe, Australia , New Zealand, Central America, Las Vegas, Orlando, New York, Canada, Fiji, Cook Islands, Tahiti, Bora Bora and French Polynesia.

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Pleasant Holidays operates a portfolio of four brands serving the leisure and corporate incentive travel markets, including family, multi-generation and luxury customers:


Exceptional all-in-one vacation packages that include flights, hotel stays, activities and more. Pleasant Holidays provides travelers with the best travel deals and packages to destinations including Hawaii, Mexico, Tahiti, Caribbean, Los Cabos, Dominican Republic, Central America, Europe, the United States and more.

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The St Regis Bora Bora Resort

Four Seasons Resort Maui at Wailea


Planning a family reunion, sports event, friends’ getaway or destination wedding? Pleasant Holidays has the experience and negotiating power to make group travel a success, and within budget. Our group specialists arrange transportation, hotel accommodations, and coordinate all the details – meetings, activities, trip extensions and more. When it comes to group travel deals, discover the Pleasant difference.

Plan a Group Trip

As the luxury brand of Pleasant Holidays, JourneseSM embodies the promise of an exquisite journey, unique experiences with exceptional travel made seamless and effortless with experienced destination specialists.

Let's Plan Your Trip


Four Seasons Resort Maui at Wailea

The Pleasant Weddings Travel Desk helps you find the perfect destination, plan your wedding, and book your guests all with complete flexibility and provides travel packages to meet budgets and special requests.

Plan Your Wedding


The Westin Maui Resort & Spa, Kaanapali
Beach, location and unrivaled amenities make this resort the ultimate Hawaiian getaway. Situated on the spectacular Ka’anapali Beach, this resort offers guests an astonishing range of amenities to relax and recharge. Indulge at the Heavenly Spa® by Westin, relax in a beach cabana or unwind at the resort’s 87,000 square foot aquatic playground.

EXCLUSIVE Vacation Amenities at The Westin Maui Resort & Spa
Buy one activity, get one activity FREE!
For travel through 12/15/17. Book by 6/4/17
Vacations Include:
• Exclusive room rate
• Daily breakfast buffet for two
• 15% savings on spa treatments

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Nick CabugosPleasant Holidays