16 Best Caribbean Cruise Deals for Solo Travelers in 2026

12. Windstar Cruises' Intimate Sailing Adventures

Windstar Cruises offers solo travelers a unique sailing experience that combines the romance of traditional sailing with modern luxury amenities, visiting smaller Caribbean ports and hidden gems that larger cruise ships cannot access. Their 2026 Caribbean program features seven to 10-night voyages aboard their elegant sailing yachts and all-suite ships, with solo rates starting at $1,899 per person and reduced single supplements on select stateroom categories during promotional booking periods. The cruise line's intimate ship size, accommodating between 148 and 342 guests, creates a