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Cruises with an overnight in Gustavia

21 cruises in our feed stay the night docked in Gustavia — dine ashore, catch the evening, and sail at dawn. Each overnight is drawn from the line's published day-by-day schedule; your advisor confirms the exact port times for your departure date.

21 sailings
An Extended Journey of Maritime Soul & Island ZestCaribbean

Explora Journeys

14 nights: San Juan, the Caribbean

Aboard EXPLORA III

Round-trip from Miami

Overnight in GustaviaRare itinerary
Oct 2026Next 25 Oct 2026
An Extended Journey into Island Delights, Hidden Coves & Chic CoastlinesCaribbean

Explora Journeys

14 nights: San Juan, the Caribbean

Aboard EXPLORA III

Round-trip from San Juan

Overnight in GustaviaRare itinerary
Nov 2026Next 1 Nov 2026
A Journey into Caribbean Exploration & Island DelightsCaribbean

Explora Journeys

7 nights: San Juan, the Caribbean

Aboard EXPLORA III

San Juan → Miami

Overnight in GustaviaRare itinerary
Nov 2026Next 1 Nov 2026
An Extended Journey of Island Calm & Coastal RetreatsCaribbean

Explora Journeys

14 nights: San Juan, the Caribbean

Aboard EXPLORA I

Round-trip from Miami

Overnight in GustaviaRare itinerary
Dec 2026Next 13 Dec 2026
An Extended Journey into Island Bliss & Lively CelebrationsCaribbean

Explora Journeys

15 nights: San Juan, the Caribbean

Aboard EXPLORA I

Round-trip from San Juan

Overnight in GustaviaRare itinerary
Dec 2026Next 20 Dec 2026
A Journey of Caribbean Celebrations & Island WondersCaribbean

Explora Journeys

7 nights: San Juan, the Caribbean

Aboard EXPLORA I

San Juan → Miami

Overnight in GustaviaRare itinerary
Dec 2026Next 20 Dec 2026
An Extended Journey through Azure Horizons & Elegant IslesCaribbean

Explora Journeys

14 nights: San Juan, the Caribbean

Aboard EXPLORA III

Round-trip from Miami

Overnight in GustaviaRare itinerary
Feb 2027Next 28 Feb 2027
An Extended Journey from Ocean Calm to Vibrant CultureCaribbean

Explora Journeys

14 nights: San Juan, the Caribbean

Aboard EXPLORA III

San Juan → Bridgetown

Overnight in GustaviaRare itinerary
Mar 2027Next 7 Mar 2027
A Journey into Tropical Marvels & Enchanting Coastal DiscoveryCaribbean

Explora Journeys

7 nights: San Juan, the Caribbean

Aboard EXPLORA III

San Juan → Miami

Overnight in GustaviaRare itinerary
Mar 2027Next 7 Mar 2027
An Extended Journey from Sophisticated Harbours to Sun-Soaked HorizonsCaribbean

Explora Journeys

The Caribbean loop

Aboard EXPLORA III

Round-trip from Miami

Overnight in GustaviaRare itinerary
Mar 2027Next 14 Mar 2027
An Extended Journey of Endless Beauty & Historic TreasuresCaribbean

Explora Journeys

15 nights: San Juan, the Caribbean

Aboard EXPLORA III

Bridgetown → San Juan

Overnight in GustaviaRare itinerary
Mar 2027Next 21 Mar 2027
A Journey of Tranquil Harbours, Stunning Peaks & Caribbean CharmCaribbean

Explora Journeys

8 nights in the Caribbean

Aboard EXPLORA III

Bridgetown → Miami

Overnight in GustaviaRare itinerary
Mar 2027Next 21 Mar 2027
An Extended Journey from Vibrant Shores to Spectacular SceneryCaribbean

Explora Journeys

14 nights: San Juan, the Caribbean

Aboard EXPLORA III

Round-trip from Miami

Overnight in GustaviaRare itinerary
Mar 2027Next 29 Mar 2027
A Grand Journey through Balmy Shores & Enchanting Nature to Panama’s WondersCaribbean

Explora Journeys

17 nights: San Juan, the Caribbean

Aboard EXPLORA III

San Juan → Panama City

Overnight in GustaviaRare itinerary
Apr 2027Next 5 Apr 2027
A Journey through Balmy Shores & Stirring SceneryCaribbean

Explora Journeys

7 nights: San Juan, the Caribbean

Aboard EXPLORA III

San Juan → Miami

Overnight in GustaviaRare itinerary
Apr 2027Next 5 Apr 2027
Discover the Pearls of the CaribbeanCaribbean

Emerald Cruises

14 nights in the Caribbean

Aboard Emerald Sakara

Bridgetown → Philipsburg

Overnight in Virgin Gorda
Nov 2027 – Mar 2028Next 13 Nov 2027 · 5 more
Cruising the Leeward IslandsCaribbean

Emerald Cruises

The Caribbean loop

Aboard Emerald Sakara

Round-trip from Philipsburg

Overnight in Virgin Gorda
Nov 2027 – Apr 2028Next 20 Nov 2027 · 6 more
Colours of the Caribbean: Antigua to San JuanCaribbean

Emerald Cruises

9 nights: San Juan, the Caribbean

Aboard Emerald Kaia

Saint John's → San Juan

Overnight in GustaviaRare itinerary
Dec 2027Next 11 Dec 2027
West Indies Island HoppingCaribbean

Emerald Cruises

7 nights: San Juan, the Caribbean

Aboard Emerald Kaia

Round-trip from San Juan

Overnight in GustaviaRare itinerary
Dec 2027 – Nov 2028Next 20 Dec 2027 · 2 more
Epic Voyage: Barbados to Sint MaartenCaribbean

Emerald Cruises

21 nights in the Caribbean

Aboard Emerald Sakara

Bridgetown → Philipsburg

Overnight in BridgetownRare itinerary
Sails monthly, Jan 2028 – Feb 2028
Epic Voyage: Sint Maarten to BarbadosCaribbean

Emerald Cruises

21 nights in the Caribbean

Aboard Emerald Sakara

Philipsburg → Bridgetown

Overnight in Virgin GordaRare itinerary
Feb 2028Next 5 Feb 2028