Cruise itinerary
21-Night Caribbean Cruise from Philipsburg
21 nights · Caribbean · 16 ports of call
21-night Caribbean cruise aboard Emerald Sakara, departing Philipsburg and calling at Basseterre, Saint Kitts, Anguilla, Virgin Gorda, Gustavia, Charlestown and Saint John's and 9 more.
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- No booking fees
- 10,000+ sailings
At a glance
- Ship
- Emerald Sakara
- Cruise line
- Emerald Cruises
- Duration
- 21 nights
- Region
- Caribbean · Americas · South America
- Departs
- Philipsburg
- 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 Emerald Sakara sailing, typically within 24 hours.
Where this voyage takes you
Day-by-day itinerary
- Day1
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
- Day2
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
- Day3
Anguilla
- Day4
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
- Day5
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
- 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
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
- Day8
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
- Day9
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
- Day10
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
- Day11
Charlestown
- Day12
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
- Day13
Îles des Saintes
- Day14
Soufrière
- Day15
Bridgetown
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
- Day16
Bridgetown
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
Speightstown
- Day17
Kingstown
The capital of St. Vincent and the Grenadines, set in a deep bay on the island's southwest coast in the eastern Caribbean. A working harbour town backed by steep green ridges, it has a colourful market, an old hilltop fort and botanic gardens dating to the 1760s.
- Botanic Gardens
- Fort Charlotte
- Kingstown Market
Port Elizabeth, Bequia
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
- Day18
Port Elizabeth, Bequia
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
Mayreau Island
- Day19
Mayreau Island
Union Island
- Day20
Union Island
- Day21
Union Island
Tobago Cays
- Day22
Bridgetown
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
- 5 Feb 2028
Upcoming sailings of this itinerary — a NestCruise advisor confirms current availability and your fare.
21-Night Caribbean Cruise from Philipsburg FAQ
Which ports does this cruise visit?
This 21-night Caribbean cruise calls at Philipsburg, Basseterre, Saint Kitts, Anguilla, Virgin Gorda, Gustavia, Charlestown, Saint John's, Îles des Saintes, Soufrière, Bridgetown, Speightstown, Kingstown, Port Elizabeth, Bequia, Mayreau Island, Union Island and Tobago Cays.
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 departs from Philipsburg and ends in Bridgetown.
How long is this cruise?
21 nights aboard Emerald Sakara.
When does this itinerary sail?
Upcoming departures include 5 Feb 2028. A NestCruise advisor can confirm current availability.