This 14-night Seabourn itinerary links Bridgetown to Jost Van Dyke, threading 8 ports of call through 7 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: 7 countries over 14 nights, starting in Bridgetown and finishing in Jost Van Dyke, with a new port waiting most mornings instead of airports and hotel check-ins.
The pacing runs to 8 port days and 2 days at sea — time to enjoy the ship between stops.
Good to know
- Best for
- Repositioning & bucket-list cruisers
- Season
- Winter sailing
- Route
- Bridgetown → Jost Van Dyke
- Pace
- 8 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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Day3At SeaA Day at Sea
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Day4Montserrat 8:00 AM – 6:00 PMExplore Montserrat
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Day5Montserrat 8:00 AM – 9:00 PMExplore Montserrat
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Day6
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Day7
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Day8
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Day9
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Day10
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Day11At SeaA Day at Sea
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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 Yacht Explorer is a 14-night one-way itinerary aboard Seabourn Ovation. You board in Bridgetown and disembark in Jost Van Dyke, calling at 8 ports across 7 countries along the way.
In sequence the voyage takes in Barbados (Bridgetown), St Lucia (Castries), St. Kitts (Basseterre), British Virgin Islands (Jost Van Dyke, Jost Van Dyke), St. Maarten (Philipsburg), St. Kitts (Basseterre) and 2 more.
As a one-way sailing you'll fly into Bridgetown and home from Jost Van Dyke, so it's worth checking the two gateways before you book. 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.