Cruise itinerary
14-Night Caribbean Cruise from San Juan (Puerto Rico)
14 nights · Caribbean · 12 ports of call
14-night Caribbean cruise aboard EXPLORA III, departing San Juan (Puerto Rico) and calling at Philipsburg, Gustavia, Basseterre, Saint Kitts, At Sea, Grand Turk Island and Miami, Florida and 5 more.
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- No booking fees
- 10,000+ sailings
At a glance
- Ship
- EXPLORA III
- Cruise line
- Explora Journeys
- Duration
- 14 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 EXPLORA III sailing, typically within 24 hours.
Where this voyage takes you
Day-by-day itinerary
- Day1
San Juan (Puerto Rico)
Depart 18:00
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
Philipsburg
Arrive 09:00 · Depart 21:00
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
- Day3
Gustavia
Arrive 09:00
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
Gustavia
Depart 01:00
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
Basseterre, Saint 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
- Day5
At Sea
- Day6
Grand Turk Island
Arrive 09:00 · Depart 18:00
A small, low-lying island in the Turks and Caicos, a British territory in the Atlantic. Its cruise centre opens onto a long white-sand beach and clear reef water, with a historic lighthouse standing at the island's northern point.
- White-sand beach
- Coral reef
- Historic lighthouse
- Day7
At Sea
- Day8
Miami, Florida
Arrive 08:00 · Depart 17:00
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
- Day9
At Sea
- Day10
Providenciales
Arrive 09:00 · Depart 18:00
- Day11
At Sea
- Day12
Saint John's
Arrive 08:00 · Depart 18:00
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
- Day13
Roseau
Arrive 09:00 · Depart 17:00
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
- Day14
Port Elizabeth, Bequia
Arrive 08:00 · Depart 18:00
The main town of Bequia, a small island in the Grenadines reached only by sea. It sits on Admiralty Bay, a yacht-favoured harbour, and keeps a quiet seafaring tradition of boatbuilding and a beach walk along the shore to Princess Margaret Beach.
- Admiralty Bay
- Princess Margaret Beach
- Model-boat building
- Day15
Bridgetown
Arrive 08:00
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
- 7 Mar 2027
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), Philipsburg, Gustavia, Basseterre, Saint Kitts, At Sea, Grand Turk Island, Miami, Florida, Providenciales, Saint John's, Roseau, Port Elizabeth, Bequia and Bridgetown.
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 departs from San Juan (Puerto Rico) and ends in Bridgetown.
How long is this cruise?
14 nights aboard EXPLORA III.
When does this itinerary sail?
Upcoming departures include 7 Mar 2027. A NestCruise advisor can confirm current availability.