Continue your journey

14 Day Star Collector: Lovely Leewards

Departure Date
November 8, 2026
Multiple Dates Available
Supplier
Windstar Cruises
Destination
Caribbean
Ship
Star Pride
Multiple

14 Night Alaska CRAZY DEAL!

Choose your departure date

Roundtrip San Juan

Whether you’re passionate about swimming among rarely seen undersea wildlife or the intricate cultures and intertwined European histories of the Windward Islands, this 2-week cruise offers the best combinations of charm, island heritage and natural beauty. Shop unique designer apparel in St. Barts, where you’ll discover a fashionable confluence of high-end brands normally associated with places like Madison Avenue, but displayed in an ambiance that’s anything but intimidating. Master the art of cooking with distinct spices like nutmeg, cloves, and allspice in authentic Caribbean cuisine while taking direction from a highly-skilled native chef in Philipsburg. This Caribbean getaway is the perfect duration for lovers of island life and those who want to spend more time exploring the Windward Islands overlooked by other cruise lines.

$
6497
Oceanview Suite
per person
CAD
$
per person
CAD
$
per person
CAD
$
per person
CAD
Ask About Great Single Pricing

*14 nights in the same stateroom: + $100pp (double occupancy) 

*14 nights in the same stateroom: +$200pp (single occupancy)

*There are only a limited amount of staterooms available on each sailing where moving is not going to be necessary.

Includes:

Your Cruise

  • 14 Day Cruise
  • Taxes

CruisePlus Booking Bonus

  • Onboard Credit - Ask Us!

Windstar Booking Bonus

  • Early Bird All Inclusive Offer: Complimentary All-Inclusive experience, featuring Wi-Fi, unlimited select wine, beer and cocktails, and gratuities, Plus, enjoy an onboard credit of up to $200 per stateroom.
CruisePlus Perks
Priority Access

» Priority check-in

» Priority access to specialty restaurant reservations

» Priority line at the Guest Services desk

» Priority line at the Shore Excursions desk

» Priority access to tenders ashore in select ports

» Priority disembarkation

Premium Dining

» Expanded 24-hour room service breakfast menu

» Pinnacle Class ships: Private dining venue for breakfast and dinner with an expanded menu

» All other ships: Priority seating in the Dining Room for breakfast and dinner with an expanded menu

Exclusive Amenities

» Complimentary stateroom upgrade

» Dedicated concierge service

» Welcome glass of sparkling wine on embarkation day

» Premium bathrobes

» Club Orange keycard

» Exclusive Club Orange tote bag (one per stateroom)

More information

Pricing
Cruise Only
$
6497
Oceanview Suite
per person
CAD
$
per person
CAD
$
per person
CAD
$
per person
CAD
Call for pricing. 1.800.854.9664
Pricing is per person, based on double occupancy and in CAD. Additional terms & conditions apply.
Highlights & Sightseeing

Old San Juan

Explore the colourful cobblestone streets of old San Juan, a UNESCO World Heritage Site and National Historic Site within the U.S. National Park Service.

Shell Beach

The town of Gustavia is close to Shell Beach. The shoreline is covered in millions of shells, as befits the name. It's a terrific location for a quick swim and extensive beach exploration. The Eden Rock resort divides St. Jean's two beaches, making it the ideal place for a leisurely promenade. After that, you can eat lunch while admiring the scenery at one of the many establishments along the glistening dunes. It's common to sunbathe without a to

Itinerary
Day Location Arrive Depart
1 San Juan 7:00 PM
2 At Sea
3 St Georges 9:00 AM 10:00 PM
4 Bequia 8:00 AM 10:00 PM
5 Mayreau 8:00 AM 5:00 PM
6 Les Saintes 10:00 AM 5:00 PM
7 Marigot, St Martin 8:00 AM 3:00 PM
8 San Juan 7:00 AM 7:00 PM
9 Cruz Bay, St John, Virgin Islands (Us) 8:00 AM 6:00 PM
10 Basseterre 8:00 AM 5:00 PM
11 Gustavia 7:00 AM 10:00 PM
12 Philipsburg, St Maarten 8:00 AM 10:00 PM
13 Jost Van Dyke, Great Harbour 9:00 AM 10:00 PM
14 Virgin Gorda / Prickly Pear, British Virgin Islands 8:00 AM 5:00 PM
15 San Juan 7:00 AM
Pricing is per person, in CAD and based on double occupancy. Additional terms & conditions apply.
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 (CAD), 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: Apr 15, 2025

$
6497
Oceanview Suite
per person
CAD
$
6497
Oceanview Suite
per person
CAD
$
per person
CAD
1.800.854.9664
A+ BBB Rating
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