Classic Vacations 2026 Anniversary Sweepstakes

Live — ends in 115 days

Prize	Grand prize winners can score a 9-night Italy getaway (Rome, Florence, Venice) or luxury overwater bungalow stays in Bora Bora and Moorea, plus Costa Rica resort packages with Visa gift cards, across three destination-themed drawings.
Winners	9
Ends	October 31, 2026 at Europe winners drawn by 6/30/26; Tahiti & Costa Rica winners drawn by 10/31/26 (11:59:59 PM PT for spotlight periods)
Entry	Unlimited No limit on entries earned via new eligible FIT/FIT Group bookings during each Spotlight Period; advisor must also reach a sales minimum and score 100% on the destination quiz during its quiz window to qualify for the drawing
Open to	18+ · 50 US + DC
Sponsor	Classic Vacations, LLC

Enter on the sponsor's site → Official rules

Classic Vacations 2026 Anniversary Sweepstakes is an unlimited-entry sweepstakes from Classic Vacations, LLC. Grand prize winners can score a 9-night Italy getaway (Rome, Florence, Venice) or luxury overwater bungalow stays in Bora Bora and Moorea, plus Costa Rica resort packages with Visa gift cards, across three destination-themed drawings. There's no limit on entries. It runs through October 31, 2026. No purchase is necessary — entry is free on the sponsor's own site, and the official rules linked above have the full eligibility details.

Details extracted from the official rules; last verified July 8, 2026 at 3:01 AM.