Holland America Line 10-Night Caribbean Cruise w/ Private Island Stop

Save $1,780 on this late-November Atlantic crossing - plus, unlike most ocean-crossing voyages, this itinerary includes stops in France, Spain, Portugal, and Bermuda. This 1-way cruise aboard the Sky Princess departs from Southampton, England, on November 28 with debarkation in Fort Lauderdale, FL. Book this travel deal by September 30; All prices, dates, and booking details were valid at the time of publication. Buy Now at Princess Cruises

This winter cruise from the mainland is $1,000 off. This roundtrip cruise aboard the Ruby Princess departs from San Francisco, CA, on December 18 and includes stops in Hilo, Kona, Kauai, and Honolulu, HI. Book this travel deal by September 30; All prices, dates, and booking details were valid at the time of publication. Buy Now at Princess Cruises

That's the best price we could find for such a cruise this December by $60. This roundtrip cruise aboard the MSC Seaside departs from Miami, FL on December 15 and includes ports of call in Ocean Cay and Nassau, Bahamas; Puerto Plata, Dominican Republic; and San Juan, Puerto Rico. Book this travel deal by September 30; All prices, dates, and booking details were valid at the time of publication. Buy Now at SmartCruiser

Save at least $376 per person on this bit of glacier appreciating. This roundtrip cruise aboard the Norwegian Bliss departs from Seattle, with stops in Juneau, Skagway, Glacier Bay, Ketchikan, and Victoria, British Columbia. Travel dates run through October 3, 2026. All prices, dates, and booking details were valid at the time of publication; book this travel deal by September 23. Buy Now at ShermansTravel