Celebrate in style as Classic Vacations marks its remarkable 45th anniversary! For nearly half a century, Classic Vacations has been synonymous with crafting unforgettable travel experiences that seamlessly blend luxury and adventure. With a rich legacy of curating the finest destinations, superb accommodations, and personalized itineraries, Classic Vacations continues to be the preferred choice for travelers seeking exceptional vacations.

Join us in raising a toast to Classic Vacations and embark on your next extraordinary journey with confidence and excitement. Here's to another 45 years of excellence!


45 years of history.

The story of Classic Vacations began in 1978 when a group of passionate travel enthusiasts came together with a shared vision: to transform the way people experience the world. Founded with a deep love for exploration and a commitment to providing unparalleled travel experiences, Classic Vacations started its journey in the enchanting landscapes of Hawaii. This humble beginning laid the cornerstone for a travel company that would go on to redefine luxury and adventure.

Over the years, Classic Vacations has expanded its horizons, traversing continents, and introducing travelers to new cultures, stunning landscapes, and unforgettable adventures. With a dedication to exceptional service and a passion for uncovering hidden gems, Classic Vacations has evolved into a trusted name in the world of travel, consistently delivering dreams and memories to travelers worldwide.


Classic Hawaii was Founded

Step back in time

to the roots of Classic Vacations. In 1978, Classic Hawaii was born, laying the foundation for decades of wanderlust and exploration.




From the romantic streets of Paris to the historic ruins of Rome, Classic Vacations opened new doors to the Old World's timeless treasures.


Caribbean & Bermuda

Island paradises beckoned as Classic Vacations extended its reach to the turquoise waters of the Caribbean and the pink-sand beaches of Bermuda.


Mexico, Tahiti,

Asia and more

From the vibrant streets of Mexico to the tranquil beauty of Tahiti and the mysteries of Asia, Classic Vacation's portfolio of escapes knew no bounds.


45 years of excellence

As we reach this extraordinary milestone, Classic Vacations remains committed to enduring excellence and creating memories that last a lifetime.


45 years of partnership.

AIrline spotlight


Hyatt Inclusive Collection

Hyatt Inclusive Collection

Marriott bonvoy

Caribbean & Latin America

Hyatt Inclusive Collection

Exclusive Giveaways

Enter to Win Amazing prizes

Weekly giveaways

Win marvelous prizes and join the Classic Vacations family in celebrating 45 years of luxury, discovery, and unforgettable experiences.

Stay tuned for more surprises, travel inspiration, and exclusive offers as we embark on our next incredible journey together. Let’s cheers to another 45 years of extraordinary travel with Classic Vacations!

Congratulations to our winners

Week 1: Champagne

Jackie Gomez

Ceera Machotka

Pamela Prindle Fierro

Cami Bartlett

Tahryn Nicastro

Week 2: Travel Steamer

Ann Marie Patt

Alexisa Humphrey

Meg Thompson

Lauren Doyle

Stephanie Trombley

Week 3: Sunscreen Set

Erika Wells

Sydney Nieveen

Susan green

Alisha Berry

Nerissa Zoller Swarthout

Week 4: Chocolate

Erika Wells

Cari Hicks

Week 5: carry-on Bag

Charmaine Falvey

Kara David

Kerry Brown

Carissa Rhule

Amy Freyder

Sand Texture Background

Week 6: Aloha Box

Rosemary Wynn

Tamara Evans

Erica Huerta

Wendy Sandridge

Nicole Andujar

Week 7: William Sonoma

Sandy Ewing

Marnie Constance

Liane Covelli

Week 8: Luggage set

Dixie Cote

Getaway giveaways

Get ready for the journey of a lifetime in grand style with a series of Getaway Giveaways! While we're keeping the details of our Grand Prize Giveaway under wraps for now, we're excited to reveal that these Getaway Giveaways are your ticket to unforgettable adventures. As part of our anniversary festivities, travel advisors have the opportunity to win fantastic prizes, making this milestone year even more special.

Grand Prize Giveaway


ROME | Florence | Venice

How can you win this fantastic prize? It's easy! See all those gorgeous Featured Partners above? All you have to do is book with at least 1 of our participating partners from now through December 31, 2023 for travel through December 20th, 2024. That's your golden ticket to enter to win the Grand Prize Giveaway. Booking must have deposit on file in order to qualify. One winner will be selected at the end of the booking window.

Book with our participating partners today.

Your next adventure awaits, and it starts with Classic Vacations! More information and prize details coming soon!

Getaway Giveaways | Cayman Islands

Cayman Islands

Home of Stingray CIty

Pack your bags and prepare for a journey like no other as Classic Vacations kicks off its 45th Anniversary celebration with a grand prize that will leave you in awe! Travel advisors, here's your chance to win an unforgettable trip for two to the pristine Cayman Islands. The lucky winners will enjoy a 3-night stay at The Westin Grand Cayman Seven Mile Beach Resort & Spa, complete with daily buffet breakfast for two, and two round-trip air tickets. But the adventure doesn't end there – you'll also experience the magic of Stingray City with an exciting excursion for two.

To enter and have your shot at this incredible getaway, all you need to do is book one of our participating Classic Preferred properties in the Cayman Islands from now through 12/31/23, with travel dates through 12/20/24. Get ready for an extraordinary journey that marks our 45th year of crafting memorable travel experiences with Classic Vacations!

Classic Vacations



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