Cruise itinerary
10-Night Caribbean Cruise from San Juan (Puerto Rico)
10 nights · Caribbean · 11 ports of call
10-night Caribbean cruise aboard Silver Shadow, departing San Juan (Puerto Rico) and calling at Great Harbour, Jost Van Dyke, Gustavia, Saint John's, Little Bay, Îles des Saintes and Basseterre, Saint Kitts and 4 more.
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At a glance
- Ship
- Silver Shadow
- Cruise line
- Silversea
- Duration
- 10 nights
- Region
- Caribbean · Americas · South America
- Departs
- San Juan (Puerto Rico)
- Returns
- Bridgetown
How NestCruise works:we're advisor-led, not a booking engine. No fares are listed and there are no booking fees — tell an advisor your dates and party and they price your exact Silver Shadow sailing, typically within 24 hours.
Where this voyage takes you
Day-by-day itinerary
- Day1
San Juan (Puerto Rico)
Depart 19:00
The capital of Puerto Rico and a major Caribbean homeport. Old San Juan's pastel colonial streets sit behind the massive El Morro and San Cristóbal forts, with rum distilleries and the beaches of Condado close to the cruise piers.
- Old San Juan
- El Morro fort
- Condado beaches
- Day2
Great Harbour, Jost Van Dyke
Arrive 08:00 · Depart 18:00
The main anchorage of Jost Van Dyke, smallest of the British Virgin Islands' main islands, in the Caribbean. A laid-back yachting stop, its sheltered bay is fringed by sand and beach bars, with the natural rock pools of the Bubbly Pool a short walk away.
- Bubbly Pool
- White Bay
- beach bars
- Day3
Gustavia
Arrive 08:00 · Depart 23:00
The harbour capital of St. Barthélemy, a chic French island in the Caribbean. Yachts crowd the small port below red-roofed hills, with designer boutiques along the quay and quiet coves and beaches scattered around the rugged coast.
- Shell Beach
- Designer boutiques
- Gustavia harbour
- Day4
Saint John's
Arrive 08:00 · Depart 19:00
The capital of Antigua, set around a deep natural harbour in the eastern Caribbean. The island is known for its many sandy beaches and for Nelson's Dockyard, a restored Georgian naval base on the south coast that is now a World Heritage site.
- Nelson's Dockyard
- Dickenson Bay
- Shirley Heights
- Day5
Little Bay
Arrive 08:00 · Depart 18:00
- Day6
Îles des Saintes
Arrive 08:00 · Depart 18:00
- Day7
Basseterre, Saint Kitts
Arrive 08:00 · Depart 18:00
The capital of St. Kitts, set below the green slopes of a volcanic Caribbean island. Its colonial centre circles The Circus and Independence Square, while the hilltop fortress of Brimstone Hill and a scenic railway lie out along the coast.
- Brimstone Hill Fortress
- The Circus
- Scenic railway
- Day8
Trois-Ilets
Arrive 08:00 · Depart 18:00
- Day9
Castries
Arrive 08:00 · Depart 18:00
The capital of St. Lucia, tucked into a sheltered harbour on the island's northwest coast. Beyond the market town rise the rainforested interior and the iconic twin Piton peaks further south along the volcanic coastline.
- The Pitons
- Central market
- Pigeon Island
- Day10
Saint George's
Arrive 08:00 · Depart 18:00
The capital of Grenada in the eastern Caribbean, set around a horseshoe harbour ringed by red-roofed houses. Known as the Spice Isle for its nutmeg, the island offers Grand Anse beach, hillside Fort George and rainforest waterfalls inland.
- Grand Anse Beach
- Fort George
- Nutmeg plantations
- Day11
Bridgetown
Arrive 07:00
The capital of Barbados on the island's southwest coast, a long-standing Caribbean cruise port. Its colonial centre and Garrison Savannah are UNESCO-listed, with the white sand of Carlisle Bay and turtle-filled waters close to the harbour.
- Carlisle Bay
- Garrison Savannah
- Rum distilleries
Upcoming departures
- 10 Jan 2027
- 6 Feb 2027
Upcoming sailings of this itinerary — a NestCruise advisor confirms current availability and your fare.
10-Night Caribbean Cruise from San Juan (Puerto Rico) FAQ
Which ports does this cruise visit?
This 10-night Caribbean cruise calls at San Juan (Puerto Rico), Great Harbour, Jost Van Dyke, Gustavia, Saint John's, Little Bay, Îles des Saintes, Basseterre, Saint Kitts, Trois-Ilets, Castries, Saint George's and Bridgetown.
How many days are spent at sea?
This is a port-intensive itinerary with no full days at sea.
Where does this cruise depart from?
It departs from San Juan (Puerto Rico) and ends in Bridgetown.
How long is this cruise?
10 nights aboard Silver Shadow.
When does this itinerary sail?
Upcoming departures include 10 Jan 2027 and 6 Feb 2027. A NestCruise advisor can confirm current availability.