14 Day Caribbean Explorations

Star Collector!

14 Day Caribbean Explorations

Departure Date
January 7, 2023
Multiple Dates Available
Windstar Cruises
Wind Surf

Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.

What's Included?

Your Cruise

  • 14 Day Caribbean Explorations cruise
  • Taxes

CruisePlus Bonus

  • $150 US per person Onboard Credit

Windstar Booking Bonus

  • $300 US per person Onboard Credit
  • Free Laundry
  • All meals in all venues, at all times
  • Non-alcoholic beverages
  • Welcome cocktail
  • And More!
Cruise Only
Oceanview 5099pp
Pricing is per person, in USD and based on double occupancy. Additional terms & conditions apply.

Highlights & Sightseeing


Day Location Arrive Depart
1 St. Maarten 7:00 PM
2 Falmouth Harbour 8:00 AM 10:00 PM
3 At Sea
4 Soper'S Hole 8:00 AM 6:00 PM
4 Jost Van Dyke, Great Harbour 7:00 PM 11:59 PM
5 Jost Van Dyke, Great Harbour 3:00 PM
5 Virgin Gorda 6:00 PM 11:59 PM
6 Virgin Gorda 5:00 PM
7 Gustavia 8:00 AM 10:00 PM
8 St. Maarten 6:00 AM 7:00 PM
9 Charlestown 8:00 AM 5:00 PM
10 Roseau 8:00 AM 5:00 PM
11 Pigeon Island 8:00 AM 5:00 PM
12 Les Saintes 8:00 AM 5:00 PM
13 Gustavia 8:00 AM 10:00 PM
14 Basseterre 8:00 AM 9:00 PM
15 St. Maarten 6:00 AM
Itinerary information may change anytime without notice and may not be reflected on this page.

Travel Insurance

For your protection, we strongly recommend that you purchase trip cancellation and medical insurance through Manulife.

However, no representation or description of the protection made by CruisePlus Management Ltd to you, constitutes a binding assurance or promise about the protection. We (CruisePlus) are not an insurance company and we do not have the responsibility for ensuring adherence to the insurance terms & conditions, submission, payment or adjustment of claims.

We strongly suggest you read through the insurance information provided upon purchase and email us with any questions.

Covid-19 is considered a known event and exclusions apply for most, if not all policies.

Terms & conditions

New bookings only. Fares are per person in the currency noted (USD), based on double occupancy, are capacity controlled, subject to availability at the time of booking and may be withdrawn without notice. Optional supplier charges may apply and are not included. Amenities, if offered, are available for the first two in a stateroom only & based on double occupancy unless specifically stated otherwise.

Hotel inventory is capacity controlled, and this offer may be pulled at any time without notice; Future Cruise Credits may not be combinable or be only partially combinable with advertised promotion; cruise line insurance may not be available to purchase on advertised offer.

Please note, this website may not reflect changes to offers in real time. Therefore, it is important you contact us in order to receive to a quote.

CruisePlus reserves the right to correct any human or electronic errors throughout the website at anytime. Before you book, be aware of Covid-19 restrictions and clearly understand insurance terms and conditions.

Offer Last Updated: Sep 23, 2022

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