Cruise itinerary
14-Night Caribbean Cruise from Philipsburg
14 nights · Caribbean · 11 ports of call
14-night Caribbean cruise aboard Seabourn Ovation, departing Philipsburg and calling at Tortola, Basseterre, Saint Kitts, Les Anses d'Arlet, Bequia Island, St George's, Grenada and Bridgetown and 4 more.
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- No booking fees
- 10,000+ sailings
At a glance
- Ship
- Seabourn Ovation
- Cruise line
- Seabourn
- Duration
- 14 nights
- Region
- Caribbean
- Departs
- Philipsburg
- Returns
- Philipsburg
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 Seabourn Ovation sailing, typically within 24 hours.
Where this voyage takes you
Day-by-day itinerary
- Day1
Philipsburg
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
- Day2
Tortola
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
- Day3
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
- Day4At sea
- Day5
Les Anses d'Arlet
Arrive 08:00 · Depart 18:00
- Day6
Bequia Island
Arrive 08:00 · Depart 17:00
- Day7
St George's, Grenada
Arrive 08:00 · Depart 18:00
- Day8
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
- Day9
Castries
Arrive 08:00 · 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
- Day10At sea
- Day11
Montserrat
Arrive 08:00 · Depart 18:00
- Day12
Antigua
Arrive 08:00 · Depart 21:00
- Day13
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
- Day14
Jost Van Dyke Island BVI
Arrive 08:00 · Depart 18:00
- Day15
Philipsburg
Arrive 07:00
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
Upcoming departures
- 5 Feb 2028
- 19 Feb 2028
- 4 Mar 2028
Upcoming sailings of this itinerary — a NestCruise advisor confirms current availability and your fare.
14-Night Caribbean Cruise from Philipsburg FAQ
Which ports does this cruise visit?
This 14-night Caribbean cruise calls at Philipsburg, Tortola, Basseterre, Saint Kitts, Les Anses d'Arlet, Bequia Island, St George's, Grenada, Bridgetown, Castries, Montserrat, Antigua and Jost Van Dyke Island BVI.
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 Philipsburg.
How long is this cruise?
14 nights aboard Seabourn Ovation.
When does this itinerary sail?
Upcoming departures include 5 Feb 2028, 19 Feb 2028 and 4 Mar 2028. A NestCruise advisor can confirm current availability.