Cruise itinerary
11-Night Caribbean Cruise from Miami, Florida
11 nights · Caribbean · 8 ports of call
11-night Caribbean cruise aboard Silver Shadow, departing Miami, Florida and calling at At Sea, San Juan (Puerto Rico), Saint John Island, Gustavia, Basseterre, Saint Kitts and Little Bay and 1 more.
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At a glance
- Ship
- Silver Shadow
- Cruise line
- Silversea
- Duration
- 11 nights
- Region
- Caribbean · Americas · South America
- Departs
- Miami, Florida
- Returns
- Miami, Florida
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
Miami, Florida
Depart 18:00
The cruise capital of the world — Miami sends more ships to sea than any port on earth. Most sailings board mid-afternoon, leaving the morning for South Beach, Little Havana or the Wynwood murals before you cast off.
- South Beach
- Little Havana
- Wynwood murals
- Day2
At Sea
- Day3
At Sea
- Day4
San Juan (Puerto Rico)
Arrive 09:00 · 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
- Day5
Saint John Island
Arrive 08:00 · Depart 18:00
- Day6
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
- 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
Little Bay
Arrive 08:00 · Depart 17:00
- Day9
Great Harbour, Jost Van Dyke
Arrive 08:00 · Depart 14:00
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
- Day10
At Sea
- Day11
At Sea
- Day12
Miami, Florida
Arrive 07:00
The cruise capital of the world — Miami sends more ships to sea than any port on earth. Most sailings board mid-afternoon, leaving the morning for South Beach, Little Havana or the Wynwood murals before you cast off.
- South Beach
- Little Havana
- Wynwood murals
Upcoming departures
- 7 Nov 2026
Upcoming sailings of this itinerary — a NestCruise advisor confirms current availability and your fare.
11-Night Caribbean Cruise from Miami, Florida FAQ
Which ports does this cruise visit?
This 11-night Caribbean cruise calls at Miami, Florida, At Sea, San Juan (Puerto Rico), Saint John Island, Gustavia, Basseterre, Saint Kitts, Little Bay and Great Harbour, Jost Van Dyke.
How many days are spent at sea?
4 days are spent at sea; the rest are in port.
Where does this cruise depart from?
It is a round-trip sailing from Miami, Florida.
How long is this cruise?
11 nights aboard Silver Shadow.
When does this itinerary sail?
Upcoming departures include 7 Nov 2026. A NestCruise advisor can confirm current availability.