Cruise itinerary
14-Night Caribbean Cruise from San Juan
14 nights · Caribbean · 14 ports of call
14-night Caribbean cruise aboard Azamara Journey, departing San Juan and calling at Virgin Gorda, Saint John's, Saint Pierre, Port Elizabeth, Bequia, Saint George's and Scarborough and 7 more.
- Free advisor
- No booking fees
- 10,000+ sailings
At a glance
- Ship
- Azamara Journey
- Cruise line
- Azamara
- Duration
- 14 nights
- Region
- Caribbean · Americas
- 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 Azamara Journey sailing, typically within 24 hours.
Where this voyage takes you
Day-by-day itinerary
- Day1
San Juan
Depart 18:00
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
Virgin Gorda
Arrive 8:00 · Depart 18:00
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
- Day3
Saint John's
Arrive 8:00 · 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
- Day4
Saint Pierre
Arrive 8:00 · Depart 22:00
The capital of Saint-Pierre and Miquelon, a small French archipelago off Newfoundland and the last remnant of France in North America. Its harbour town has pastel houses, French shops and cafés, and a windswept Atlantic setting steeped in fishing and rum-running history.
- French colonial town
- Île aux Marins
- harbour waterfront
- Day5
Port Elizabeth, Bequia
Arrive 8:00 · Depart 20:00
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
- Day6
Saint George's
Arrive 8:00 · Depart 17:00
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
- Day7
Scarborough
Arrive 8:00 · Depart 17:00
- Day8
Bridgetown
Arrive 6:00 · Depart 18:00
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
- Day9
Castries
Arrive 8:00 · 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
Roseau
Arrive 8:00 · Depart 18:00
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
- Day11
Basseterre, Saint Kitts
Arrive 8:00 · Depart 22:00
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
- Day12
Charlestown
Arrive 8:00 · Depart 18:00
- Day13
Philipsburg
Arrive 8:00 · Depart 22:00
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
- Day14
Gustavia
Arrive 8:00 · Depart 17:00
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
- Day15
San Juan
Arrive 7:00
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 2026
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, Virgin Gorda, Saint John's, Saint Pierre, Port Elizabeth, Bequia, Saint George's, Scarborough, Bridgetown, Castries, Roseau, Basseterre, Saint Kitts, Charlestown, Philipsburg and Gustavia.
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.
How long is this cruise?
14 nights aboard Azamara Journey.
When does this itinerary sail?
Upcoming departures include 21 Nov 2026. A NestCruise advisor can confirm current availability.