Cruise itinerary
14-Night Caribbean Cruise from San Juan
14 nights · Caribbean · 10 ports of call
14-night Caribbean cruise aboard Emerald Princess, departing San Juan and calling at St Thomas Island USVI, Philipsburg St Maarten, St Johns Antigua, Castries, Bridgetown and Tortola Island BVI and 3 more.
- Free advisor
- No booking fees
- 10,000+ sailings
At a glance
- Ship
- Emerald Princess
- Cruise line
- Princess Cruises
- Duration
- 14 nights
- Region
- Caribbean
- Departs
- San Juan
- Returns
- San Juan
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 Princess sailing, typically within 24 hours.
Where this voyage takes you
Day-by-day itinerary
- Day1
San Juan
Depart 19:00
The capital of Puerto Rico and a major Caribbean cruise homeport. The walled colonial quarter of Old San Juan keeps blue-cobbled streets, pastel facades and two Spanish fortresses, El Morro and San Cristóbal, guarding the harbour mouth.
- Old San Juan
- El Morro
- Castillo San Cristóbal
- Day2
St Thomas Island USVI
Arrive 08:00 · Depart 17:00
- Day3
Philipsburg St Maarten
Arrive 08:00 · Depart 17:00
- Day4
St Johns Antigua
Arrive 07:00 · Depart 16:00
- Day5
Castries
Arrive 08:00 · Depart 17:00
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
- Day6
Bridgetown
Arrive 07:00 · Depart 21:00
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
- Day7At sea
- Day8
San Juan
Arrive 06:00 · Depart 19:00
The capital of Puerto Rico and a major Caribbean cruise homeport. The walled colonial quarter of Old San Juan keeps blue-cobbled streets, pastel facades and two Spanish fortresses, El Morro and San Cristóbal, guarding the harbour mouth.
- Old San Juan
- El Morro
- Castillo San Cristóbal
- Day9
Tortola Island BVI
Arrive 08:00 · Depart 17:00
The main island of the British Virgin Islands, where steep green hills drop to a yacht-filled harbour at Road Town. It is a noted sailing base in the Caribbean, with quiet bays such as Cane Garden and ferries out to neighbouring Virgin Gorda.
- Road Town
- Cane Garden Bay
- Sailing charters
- Day10
Basseterre St Kitts
Arrive 08:00 · Depart 17:00
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
- Day11
Roseau
Arrive 07:00 · Depart 16:00
The capital of Dominica, a green volcanic island in the eastern Caribbean known as the Nature Isle. The town sits below forested peaks, with the botanic gardens, sulphur springs and the trail to Trafalgar Falls a short drive inland.
- Trafalgar Falls
- Botanic Gardens
- Boiling Lake
- Day12
St Georges Grenada
Arrive 08:00 · Depart 17:00
- Day13
Bridgetown
Arrive 07:00 · Depart 21:00
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
- Day14At sea
- Day15
San Juan
Arrive 06:00
The capital of Puerto Rico and a major Caribbean cruise homeport. The walled colonial quarter of Old San Juan keeps blue-cobbled streets, pastel facades and two Spanish fortresses, El Morro and San Cristóbal, guarding the harbour mouth.
- Old San Juan
- El Morro
- Castillo San Cristóbal
Upcoming departures
- 21 Nov 2027
- 28 Nov 2027
- 5 Dec 2027
- 2 Jan 2028
- 9 Jan 2028
- 16 Jan 2028
- 23 Jan 2028
- 30 Jan 2028
- 6 Feb 2028
- 13 Feb 2028
- 20 Feb 2028
- 27 Feb 2028
Upcoming sailings of this itinerary — a NestCruise advisor confirms current availability and your fare.
14-Night Caribbean Cruise from San Juan FAQ
Which ports does this cruise visit?
This 14-night Caribbean cruise calls at San Juan, St Thomas Island USVI, Philipsburg St Maarten, St Johns Antigua, Castries, Bridgetown, Tortola Island BVI, Basseterre St Kitts, Roseau and St Georges Grenada.
How many days are spent at sea?
2 days are spent at sea; the rest are in port.
Where does this cruise depart from?
It is a round-trip sailing from San Juan.
How long is this cruise?
14 nights aboard Emerald Princess.
When does this itinerary sail?
Upcoming departures include 21 Nov 2027, 28 Nov 2027, 5 Dec 2027 and 2 Jan 2028. A NestCruise advisor can confirm current availability.