This 14-night Seabourn itinerary loops out and back from Philipsburg, threading 11 ports of call through 9 countries with 2 days at sea to unwind aboard Seabourn Ovation.
Why sail this route
You unpack once and let the ship do the travelling: 9 countries over 14 nights, beginning and ending in Philipsburg, with a new port waiting most mornings instead of airports and hotel check-ins.
The pacing runs to 11 port days and 2 days at sea — time to enjoy the ship between stops.
Good to know
- Best for
- Immersive, slower-paced explorers
- Season
- Winter sailing
- Fly into
- Philipsburg — round-trip
- Pace
- 11 port days · 2 sea days
Day-by-Day Itinerary
Hover a day to find it on the map.
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Day1
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Day2
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Day3
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Day4At SeaA Day at Sea
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Day5
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Day6
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Day7
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Day8
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Day9
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Day10At SeaA Day at Sea
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Day11Montserrat 8:00 AM – 6:00 PMExplore Montserrat
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Day12
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Day13
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Day14
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Day15
The Ship
Your home for all 14 nights aboard Seabourn Ovation — so you unpack once and wake up somewhere new each morning.
About This Cruise
The 14 Night Caribbean Gems In Depth is a 14-night round-trip itinerary aboard Seabourn Ovation. You board and return in Philipsburg, calling at 11 ports across 9 countries along the way.
In sequence the voyage takes in St. Maarten (Philipsburg), British Virgin Islands (Tortola), St. Kitts (Basseterre), Martinique (Les Anses d'Arlet), Grenadines (Bequia), Grenada (St Georges) and 2 more, among others.
Because it's round-trip from Philipsburg, you fly into and out of a single city and unpack just once. Longer hops are crossed on the 2 days at sea, keeping daylight hours for the ports. Sailing dates, cabin availability and fares vary by season — use Check Dates & Prices for live pricing, or call our team to talk through the options.