Escape the Canadian Winter in Style with Explora Journeys’ Luxe Caribbean Winter Sailings

As temperatures drop and Canadians search for sunny vacations, Explora Journeys is offering sun-soaked escapes designed for travellers craving warmth, culture and slow-paced luxury. This season, EXPLORA I has returned to the Caribbean with a collection of curated journeys that pair boutique-hotel elegance at sea with curated, immersive island experiences—perfect for those seeking elevated winter travel inspiration.

Below is a snapshot of the upcoming winter sailings, ranging from week-long island voyages to extended, multi-week explorations. Each itinerary blends lesser-travelled ports, laid-back luxury and Explora Journeys’ signature “Ocean State of Mind” philosophy.

Canadians can enjoy a special limited-time offer, “The Exclusive Invitation – Festive Edition” with up to 35% savings and a reduced deposit of just 5% available through January 4, 2026. This offer is applicable to all suite grades and most Journey Collections*.

Featured Winter Escapes:

A Journey from Sparkling Cityscapes to Tranquil Island Escapes
EXPLORA I — Miami to San Juan, Feb. 12–20
An idyllic blend of Miami’s urban energy and the peaceful rhythms of the Caribbean’s most scenic islands.

An Extended Journey through Caribbean Echoes, Balmy Breezes & Emerald Landscapes
EXPLORA I — Miami to San Juan, Feb. 12–Mar. 2
A 19-night itinerary perfect for travellers wanting to fully immerse themselves in Caribbean culture, island-hopping through lush landscapes and warm coastal havens.

A Journey into Historic Charm & Tropical Bliss
EXPLORA I — San Juan to San Juan, Feb. 20–Mar. 2
A roundtrip journey from Puerto Rico featuring a balance of heritage-rich ports and postcard-perfect beaches.

An Extended Journey into Tropical Utopia, Coral Wonders & Blissful Beaches
EXPLORA I — San Juan to Miami, Feb. 20–Mar. 9
A sweeping tropical escape that highlights the Caribbean’s clearest waters, vibrant coral ecosystems and serene island retreats.

A Journey into Tropical Utopia & Art Deco Flair
EXPLORA I — San Juan to Miami, Mar. 2–9
This itinerary mixes Caribbean tranquility with the style and sophistication of the Art Deco district in Miami.

These sailings offer rich storytelling potential for audiences from winter travel trends and luxury cruise experiences to Caribbean destination highlights and the rising demand for extended and immersive voyages.