Takeoff to the Caribbean and discover even more ways to save on an island escape. From white-sand beaches and turquoise waters to lush landscapes, vibrant culture, and exceptional resorts, the Caribbean offers something for every style of getaway.
Explore participating properties across Anguilla, Antigua, The Bahamas, the British Virgin Islands, Cayman Islands, Curaçao, the Dominican Republic, Grenada, Jamaica, St. Kitts, St. Lucia, St. Martin, and more.
This collection features $200 instant savings on 4-night stays at participating properties.
Booking Window: 9/9/26 – 10/31/26
Travel Window: 9/9/26 – 3/31/27
Offer is subject to availability and may be changed or canceled at any time. If the booking credit, booking window, or travel window differs from the above, it will be noted below. Blackout dates apply.
4 nights from $4,209 per person based on double occupancy
4 nights from $4,939 per person based on double occupancy
4 nights from $7,789 per person based on double occupancy
Travel window: 1/1/27 – 3/31/27
4 nights from $3,299 per person based on double occupancy
4 nights from $3,019 per person based on double occupancy
4 nights from $829 per person based on double occupancy
4 nights from $1,009 per person based on double occupancy
4 nights from $2,309 per person based on double occupancy
4 nights from $1,739 per person based on double occupancy
Travel window: 1/1/27 – 3/31/27
4 nights from $3,249 per person based on double occupancy
4 nights from $1,749 per person based on double occupancy
4 nights from $5,119 per person based on double occupancy
4 nights from $1,039 per person based on double occupancy
4 nights from $1,209 per person based on double occupancy
4 nights from $1,089 per person based on double occupancy
4 nights from $4,219 per person based on double occupancy
4 nights from $879 per person based on double occupancy
4 nights from $1,599 per person based on double occupancy
4 nights from $2,509 per person based on double occupancy
4 nights from $1,099 per person based on double occupancy
4 nights from $2,049 per person based on double occupancy
4 nights from $5,619 per person based on double occupancy
4 nights from $1,169 based on double occupancy
4 nights from $929 per person based on double occupancy
Travel window: 1/1/27 – 3/31/27
4 nights from $3,999 per person based on double occupancy
4 nights from $2,299 per person based on double occupancy
4 nights from $859 per person based on double occupancy
4 nights from $1,569 per person based on double occupancy
4 nights from $1,739 per person based on double occupancy
4 nights from $2,009 per person based on double occupancy
4 nights from $1,019 per person based on double occupancy
4 nights from $889 per person based on double occupancy
4 nights from $979 per person based on double occupancy
4 nights from $639 per person based on double occupancy
4 nights from $959 per person based on double occupancy
4 nights from $969 per person based on double occupancy
4 nights from $949 per person based on double occupancy
4 nights from $1,209 per person based on double occupancy
4 nights from $879 per person based on double occupancy
4 nights from $1,089 per person based on double occupancy
4 nights from $1,029 per person based on double occupancy
4 nights from $1,899 per person based on double occupancy
4 nights from $2,599 per person based on double occupancy
4 nights from $2,279 per person based on double occupancy
4 nights from $1,719 per person based on double occupancy
4 nights from $1,359 per person based on double occupancy
4 nights from $1,779 per person based on double occupancy
4 nights from $899 per person based on double occupancy
4 nights from $1,399 per person based on double occupancy
4 nights from $2,179 per person based on double occupancy
BOOK ONLINE NOW OR CALL +1 (800) 221-3949
Classic Vacations offers customers access to vacation packages, which are provided by separate and independent vendors of travel services. Classic Vacations does not operate, control, or otherwise provide the services of the independent travel vendors. Offers are valid on new bookings only and cannot be applied to existing reservations. Prices shown are per person, land-only, based on double occupancy, and do not include optional excursions or other optional items unless expressly stated otherwise. Obvious errors and misprints are not binding. Offers are subject to availability at the time of booking and may be modified, replaced, or discontinued without prior notice. Prices are subject to change until full payment is received. Blackout dates, minimum night stays, air booking requirements, seasonal surcharges, resort fees (if applicable), and other restrictions may apply. Customers are responsible for purchasing travel insurance. Some offers may require the purchase of Classic Vacations’ Travel Smart Plan or a travel waiver for eligibility. Customers are responsible for paying any cancellation fees. Offers are not valid for Group Travel unless explicitly stated. Booking and travel dates may vary by offer. Additional promotions and alternative departure dates may be available, potentially resulting in different pricing or hotel inclusions. Customers are responsible for all applicable taxes and fees associated with a booking, including those associated with complimentary nights at hotels, where applicable. For properties where Classic Vacations offers dynamic pricing rates, prices are subject to change based on market conditions and external factors beyond Classic Vacations’ control. Additional terms and conditions may apply to specific offers. Please refer to the individual offer details for full terms. California Seller of Travel # 2079429. Registration as a seller of travel does not constitute approval by the State of California.
