This May, we celebrate YOU—the heart and soul of the travel industry. Your creativity, passion, and grit are what bring the world within reach for so many. At Classic, we are endlessly grateful for your partnership and dedication. As we kick off a month filled with recognition, rewards, and inspiration, know this: your work changes lives. Let’s make this your most empowering season yet.

Melissa Kreuger

Chief Executive Officer, Classic Vacations

The Sweepstakes

THE MORE YOU BOOK, THE MORE CHANCES TO WIN

Every new eligible FIT or FIT Group booking to Hawaii or Europe between
May 1 – 31, 2025 earns you another entry to win prizes in the
Classic Love Travel Advisors Sweepstakes.

Grand Prize image

Grand Prize

6 nights in Hawaii + air + car (Oahu & Kauai)

The Whole Mahalo

One lucky Travel Advisor will win an unforgettable 6-night getaway to Hawaii, including stays on both Oahu and Kauai, complete with flights and car rental:

  • 3 nights at The Ritz-Carlton Residences, Oahu – Turtle Bay
    Ocean view room, daily buffet breakfast for two, and parking included.

  • 3 nights at 1 Hotel Hanalei Bay, Kauai
    Ocean view room, daily buffet breakfast for two, resort and parking fees included.

  • Roundtrip Airfare for Two
    Courtesy of United Airlines — from major U.S. gateways to Hawaii. Travel must be completed by May 31, 2026.

    6-Day Intermediate Car Rental, courtesy of Alamo
    Provided by Alamo, perfect for exploring Hawaii at your own pace.

This dream Hawaiian adventure celebrates your passion and dedication as a Travel Advisor.

Travel must be completed by May 31, 2026. See official rules for complete details.

first Place

5 nights in Italy

Rome & Florence, Italy

A captivating journey through Italy’s historic and artistic capitals:

  • 2 nights in Rome
    Premium double room at Anantara Palazzo Naiadi Rome Hotel, breakfast and VAT included.

  • 3 nights in Florence
    Prestige room with Calzaiuoli view at Hotel Calzaiuoli, breakfast and VAT included.

Travel must be completed by April 30, 2026.  
See official rules for complete details.

second Place

4 nights in Greece

Athens & Santorini, Greece

A magical Mediterranean escape to two of Greece’s most iconic destinations:

  • 2 nights in Athens
    Superior double room at Athens Capital Hotel – MGallery Collection, breakfast and VAT included.

  • 2 nights in Santorini
    Dorian Suite at Vedema Resort, a Luxury Collection Hotel, breakfast and VAT included.

Travel must be completed by May 15, 2026.
See official rules for complete details.

third Place

3 nights in Spain

Seville, Spain

Unwind in the rich culture and charm of southern Spain with:

  • 3 nights in Seville
    Deluxe double room at Hotel Alfonso XIII, a Luxury Collection Hotel, breakfast and VAT included.

Travel must be completed by December 20, 2025. See official rules for complete details.

More Prizes

3 $100 Gift Cards

Thank you to the prize sponsors.

NO PURCHASE NECESSARY. Enter by May 31, 2025. Open to legal residents of the eligible territory who are of legal age at time of entry. One (1) prize per winner to be awarded. Potential winner notification: by June 6, 2025 Odds of winning depend on the number of eligible entries received. Qualified advisors may enter online, through the Classic Contact Center, or by mail. Void where prohibited. Restrictions apply. See Official Rules. Sponsor: Classic Vacations® 

Classic Vacations CST# 2079429-20.

Classic Vacations began as a Hawaii specialist and has grown by listening to travel advisors every step of the way. Guided by advisor insight, Classic has expanded destinations, introduced Groups, and developed tools and events to empower advisors in crafting extraordinary vacations.

1978

The starting point: timeless island escapes, luxury resorts, and cultural experiences that continue to inspire unforgettable client vacations.

Big Island  |  Kauai  |  Lanai  |  Maui  |  O’ahu

1996

Expanded to meet demand for iconic cities, cultural tours, and curated itineraries across Europe’s most beloved destinations.

Austria  |  Belgium  |  Croatia  |  Czech Republic  |  Denmark  |  England  |  France  |  Germany  |  Greece  |  Hungary  |  Iceland  |  Ireland  |  Italy  |  Malta  |  Monaco  |  Montenegro  |  Netherlands  |  Portugal  |  Scotland  |  Slovenia  |  Spain  |  Sweden  |  Switzerland  |  Turkey

1988

Added for tropical luxury, private islands, and all-inclusive escapes — an advisor favorite for romance, groups, and celebrations.

Anguilla  |  Antigua  |  Aruba  |  Bahamas  |  Barbados  |  Bermuda  |  British Virgin Islands  |  Cayman Islands  |  Curacao  |  Dominica  |  Dominican Republic  |  Grenada  |  Jamaica  |  Puerto Rico  |  Saint Eustatius  |  Saint Lucia  |  St. Barthelemy  |  St. Kitts and Nevis  |  St. Martin  |  St. Vincent and The Grenadines  |  Turks and Caicos  |  U.S. Virgin Islands

1999

Introduced with luxury beachfront resorts and all-inclusive options, perfect for weddings, groups, and seamless sun-soaked getaways.

Baja California  |  Cancun  |  Cozumel  |  Huatulco  |  Los Cabos  |  Merida  |  Mexico City  |  Nuevo Vallarta  |  Puerto Vallarta  |  Punta Mita  |  Riviera Cancun  |  Riviera Maya  |  Riviera Nayarit  |  San Miguel de Allende  |  Sinaloa  |  Tamarindo  |  Todos Santos

2006

Overwater bungalows and romantic escapes in French Polynesia, answering advisor demand for once-in-a-lifetime travel experiences.

Bora Bora  |  Moorea  |  Papeete  |  Rangiroa  |  Tahaa  |  Tikehau

2018

Classic’s first immersive event brings travel advisors together to learn, connect, and grow — fostering community and sparking new ideas that inspire business growth, strengthen industry partnerships, and create even more unforgettable experiences for your clients.

Learn More

2019

Brought onboard for culinary exploration, ancient traditions, and vibrant cities — all curated for enriching, memorable travel.

Hakone  |  Kyoto  |  Osaka  |  Tokyo

2022

Save the Date LIVE connects travel advisors with top destination wedding partners, offering dedicated education, valuable networking, and trusted resources to help grow destination wedding business and create unforgettable celebrations for every couple.

Learn More

2024

The latest addition: safaris, coastal retreats, and luxury lodges for life-changing adventures across Africa’s diverse landscapes.

Botswana  |  Egypt  |  Kenya  |  Masai  |  Mombasa  |  Morocco  |  Nairobi  |  Republic of Seychelles  |  Rwanda  |  South Africa  |  Tanzania  |  Zambia  |  Zimbabwe

Explore the Milestones