Image credit – Explora Journeys

The second edition of Explora Journeys Caribbean Season 2027 will include two cruise ships scheduled to begin journeys in October 2026, visiting the most diverse island regions around the world and ending their journeys in March 2027. Both Explora I and Explora II will be staffed to provide guests of the Explora Journeys Caribbean Season 2027 Caribbean cruise adventures a variety of activities to view the nature, culture and cuisine of the Caribbean.

Guests will have the opportunity to visit the most diverse islands of the Caribbean including Anguilla, Guadeloupe, Saint Barthélemy, Saint Lucia, Saint Kitts, Grenada and Puerto Rico and combine leisure cruising with active, adventurous land-based activities.

The Caribbean offered by Explora Journeys to their guests is a variety of cultures and personalities in various landscapes and geographies. As guests explore these regions on thisAdventure cruise, they will have the opportunity to discover the true diversity of the Caribbean.The Caribbean will be an excellent destination for all adventure cruisers.

Why This Matters for Travellers

The Caribbean is one of the world’s most popular cruise regions, but its islands offer far more than beaches. Each destination has its own history, cuisine, ecosystems and landscapes, creating opportunities for travellers to experience different sides of the region in one itinerary.

Explora Journeys 2027 season is designed around this diversity, allowing guests to combine relaxation with adventure, wildlife encounters and cultural discovery.

Why Travellers Are Looking Beyond Traditional Caribbean Cruises

• More destination variety: Guests can visit multiple islands with different landscapes and cultures during one journey.
• Nature-focused exploration: Experiences include whale watching, rainforest discovery and marine activities.
• Local cultural connections: Travellers can experience regional food, crafts and traditions.
• Luxury combined with discovery: The voyages blend premium onboard services with immersive excursions.

The programme reflects the growing demand for luxury travel experiences that create lasting memories rather than simply visiting destinations.

What Has Changed in Explora Journeys Caribbean Season 2027?

Explora Journeys will operate its Caribbean season with two ships for the 2026–2027 period, expanding the company’s ability to offer luxury ocean journeys across the region.

Explora I and Explora II will introduce different sailing options, allowing guests to discover Caribbean destinations through extended itineraries.

Explora Journeys Caribbean 2027 Ship Schedule

Ship	Departure Date	Departure Location	Journey Details
Explora I	November 17, 2026	Miami	Begins Caribbean sailings after transatlantic journey from Barcelona
Explora II	October 15, 2026	Québec City	Sails south along the Atlantic coast before reaching San Juan, Puerto Rico, on November 1

Explora II’s arrival marks its debut in the Caribbean region, while Explora I will continue expanding the company’s presence across tropical destinations.

The two-ship deployment creates more opportunities for travellers to experience the Caribbean during the peak winter travel season.

How Explora Journeys Creates a Different Caribbean Experience

Explora Journeys is positioning its Caribbean programme around exploration, combining luxury ocean travel with experiences designed to reveal the character of each destination.

Guests will not only visit islands but also participate in activities connected with nature, local communities and regional traditions.

Signature Caribbean Experiences Available to Guests

• Swimming among the natural sea pools and giant granite formations of The Baths on Virgin Gorda
• Watching humpback whales in their breeding grounds in Samaná Bay
• Exploring Dominica’s ancient rainforest landscapes and hidden waterfalls
• Powerboating along Grenada’s coastline
• Snorkelling at the Underwater Sculpture Park

These experiences showcase the Caribbean’s natural diversity, from volcanic landscapes and marine environments to underwater attractions.

Which Caribbean Destinations Are Included in the 2027 Voyages?

The programme includes a wide selection of Caribbean destinations, offering travellers a combination of well-known islands and unique regional experiences.

Destinations Featured During Explora Journeys Caribbean Season

Destination	Experience Highlights
Little Bay, Anguilla	Peaceful coastal landscapes and island atmosphere
Guadeloupe	French Caribbean culture and natural beauty
Saint Barthélemy	Luxury island experiences
Saint Lucia	Rainforests, landscapes and culinary discoveries
Saint Kitts	Local traditions and craft experiences
Grenada	Coastal adventures and island exploration
Virgin Gorda	The Baths geological formations
Puerto Rico	Historic culture and Caribbean celebrations
Coco Island	Tropical island experiences

The itinerary allows travellers to experience different sides of the Caribbean, from untouched nature to vibrant island communities.

Why Food and Local Traditions Are Becoming Central to Luxury Cruises

Luxury travellers are increasingly searching for authentic experiences connected with local identity. Explora Journeys’ Caribbean season includes culinary and craft-focused activities designed to introduce guests to regional flavours and traditions.

Caribbean Culinary and Cultural Experiences

• Beachside lobster lunch experiences
• Creating a bespoke rum blend in Saint Kitts
• Working with a master chocolatier in Saint Lucia
• Local craft experiences across island destinations

These activities allow guests to connect with the Caribbean through food, craftsmanship and personal interactions.

What Travellers Should Know Before Booking

Travellers considering an Explora Journeys Caribbean voyage should understand the seasonal schedule, destinations and experience style before booking.

The programme is designed for guests seeking a combination of luxury, relaxation and active exploration.

Before Booking an Explora Caribbean Voyage

• Check sailing dates: The season operates from mid-October 2026 through March 2027.
• Review ship schedules: Explora I and Explora II offer different departure options.
• Compare itineraries: Destination lists and experiences may vary by voyage.
• Consider activities: Some excursions involve swimming, hiking, boating and outdoor exploration.
• Plan for seasonal events: Holiday sailings include Thanksgiving, Christmas and New Year celebrations.

Travellers should review individual itineraries carefully to select the voyage that best matches their interests.

Festive Caribbean Voyages Add Holiday Celebrations at Sea

The 2027 Caribbean season will include special celebrations during Thanksgiving, Christmas and New Year, creating a tropical alternative for travellers seeking holiday experiences.

The ships will become venues for gatherings, celebrations and seasonal events while sailing through Caribbean waters.

Holiday Highlights During the Season

• Thanksgiving celebrations beneath tropical skies
• Christmas festivities onboard
• New Year celebrations surrounded by Caribbean scenery
• Fireworks over San Juan for guests aboard Explora III

The New Year’s Eve celebration aboard Explora III will offer guests the opportunity to welcome the year with fireworks over San Juan, Puerto Rico, creating a memorable setting against the city skyline.

Industry Impact: Luxury Caribbean Cruising Enters a New Experience Era

The Caribbean cruise market continues to evolve as travellers increasingly seek personalised and meaningful journeys.

Luxury cruise operators are moving beyond traditional port visits by developing experiences focused on nature, culture, food and local communities.

Trends Shaping Luxury Caribbean Travel

• Growing demand for immersive experiences
• Increased interest in local culture and cuisine
• Expansion of premium yacht-style cruising
• Rising popularity of adventure-based luxury holidays

Explora Journeys’ Caribbean expansion reflects how the cruise industry is adapting to travellers who want both comfort and discovery.

Frequently Asked Questions

When does Explora Journeys Caribbean Season 2027 begin?

The Caribbean season begins in mid-October 2026 and continues through March 2027.

Which ships will operate the Caribbean programme?

Explora I and Explora II will operate the seasonal Caribbean voyages.

Which destinations are included?

The programme includes destinations such as Anguilla, Guadeloupe, Saint Barthélemy, Saint Lucia, Saint Kitts, Grenada, Virgin Gorda and Puerto Rico.

What activities are available during the voyages?

Guests can enjoy whale watching, rainforest exploration, snorkelling, boating, cultural experiences and culinary activities.

Will Explora Journeys offer Christmas and New Year cruises?

Yes. The season includes Thanksgiving, Christmas and New Year celebrations onboard.

Closing Update

The Explora Journeys Caribbean Season 2027 provides a luxury opportunity to visit several regions of the Caribbean to experience the varied wildlife, food, and islands, and to enjoy events and festivals.

With Explora I and Explora II, vacationers will travel beyond typical island travel and resorts to coastal cities and areas of the Caribbean. Luxury travel now means island journeys packed with experiences and unforgettable connections. This program offers guests the opportunity to travel to all corners of the world to experience distinction.