Cruise itinerary
14-Night Caribbean Cruise from San Juan (Puerto Rico)
14 nights · Caribbean · 13 ports of call
14-night Caribbean cruise aboard Emerald Kaia, departing San Juan (Puerto Rico) and calling at Vieques, Saint John Island, Great Harbour, Jost Van Dyke, Philipsburg, Gustavia and Little Bay and 6 more.
- Free advisor
- No booking fees
- 10,000+ sailings
At a glance
- Ship
- Emerald Kaia
- Cruise line
- Emerald Cruises
- Duration
- 14 nights
- Region
- Caribbean · Americas · South America
- Departs
- San Juan (Puerto Rico)
- Returns
- San Juan (Puerto Rico)
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 Emerald Kaia sailing, typically within 24 hours.
Where this voyage takes you
Day-by-day itinerary
- Day1
San Juan (Puerto Rico)
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
Vieques
- Day3
Saint John Island
Great Harbour, Jost Van Dyke
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
- Day4
Great Harbour, Jost Van Dyke
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
- Day5
Philipsburg
The Dutch-side capital of St. Maarten, set behind the long curve of Great Bay. Front Street is wall-to-wall duty-free; a short water taxi or drive reaches the French side's Marigot market and the famous low-flying jets over Maho Beach.
- Great Bay Beach
- Front Street duty-free
- Maho Beach plane-spotting
Gustavia
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
- Day6
Gustavia
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
Little Bay
Saint John's
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
- Day8
Saint John's
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
- Day9
Basseterre, Saint Kitts
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
- Day10
Îles des Saintes
- Day11
Deshaies
- Day12
Gustavia
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
- Day13
Virgin Gorda
One of the British Virgin Islands, a hilly cay in the eastern Caribbean known for The Baths — a beach where giant granite boulders form tidal pools and grottoes. Quiet bays, yacht anchorages and a relaxed, low-key pace define the island.
- The Baths
- Granite boulders
- Spring Bay
- Day14
Norman Island
- Day15
San Juan (Puerto Rico)
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
Upcoming departures
- 20 Nov 2027
- 27 Nov 2027
- 8 Jan 2028
- 15 Jan 2028
- 22 Jan 2028
- 25 Mar 2028
Upcoming sailings of this itinerary — a NestCruise advisor confirms current availability and your fare.
14-Night Caribbean Cruise from San Juan (Puerto Rico) FAQ
Which ports does this cruise visit?
This 14-night Caribbean cruise calls at San Juan (Puerto Rico), Vieques, Saint John Island, Great Harbour, Jost Van Dyke, Philipsburg, Gustavia, Little Bay, Saint John's, Basseterre, Saint Kitts, Îles des Saintes, Deshaies, Virgin Gorda and Norman Island.
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 is a round-trip sailing from San Juan (Puerto Rico).
How long is this cruise?
14 nights aboard Emerald Kaia.
When does this itinerary sail?
Upcoming departures include 20 Nov 2027, 27 Nov 2027, 8 Jan 2028 and 15 Jan 2028. A NestCruise advisor can confirm current availability.