Continue Your Journey

14 Night Lovely Leewards

Departure Date
November 22, 2026
Multiple Dates Available
Supplier
Windstar Cruises
Destination
Caribbean
Ship
Star Pride
Multiple

14 Night Alaska CRAZY DEAL!

Choose your departure date

Spend two unforgettable weeks exploring the Caribbean's most captivating islands, cultures and coastal beauty.

Whether you’re passionate about swimming among undersea wildlife or the intricate cultures and intertwined European histories of the Leeward 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. Stare in wonder at the glow from miniscule bioluminescent organisms stirred by your kayak paddle during a tour of the Fajardo Bio Bay nature reserve near San Juan. 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.

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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 Night Lovely Leewards Cruise
  • Taxes

CruisePlus Booking Bonus

  • $250 US per person Onboard Credit

Windstar Inclusions

  • Included STATEROOM / SUITE AMENITIES:
    • Suites are all queen beds
    • Complimentary fresh fruit basket
    • Cotton waffle robes
    • L’Occitane en Provence bath toiletries
    • Lighted make-up mirror and hair dryer
    • Personal safe
    • Direct-dial ship-to-shore telephones (additional charge)
    • Beverage mini-bar refrigerator (additional charge)
    • Satellite flat screen TV/DVD with movies, TV, News, and Music options
    • Individually controlled temperature dial
    • Nightly turn-down service
  • Included SHIPBOARD DINING & RECEPTIONS:
    • Breakfast, lunch & dinner served daily
    • Open single seating dining for all meals
    • World-class gourmet cuisine served in Amphora Restaurant
    • Indoor/Outdoor Veranda Cafe serving breakfast & lunch
    • Al fresco dining in Candles
    • Alternative dining at Stella Bistro (Wind Surf Only)
    • 24-hour complimentary room service
    • Afternoon snacks daily, except on embarkation day
    • Captain’s Welcome Aboard cocktail reception
    • Deck BBQ under the stars (itinerary and weather dependent, may not be feasible on cruises embarking/debarking in US waters)
  • Included SHIPBOARD SERVICES & AMENITIES:
    • Complimentary soft beverages including: bottled water, sparkling water, sodas, fresh juices, fruit smoothies, tea, coffee, cappuccinos, lattes, mochas and espresso
    • Outdoor swimming pool and Jacuzzi
    • Gym equipment: Cybex weights system, assorted free weights, two treadmills, two bikes, workout mats and benches
    • Aft sports platform (marina), equipment includes complimentary snorkel gear, paddleboards, 1-2 person kayaks, and water mats
    • Bridge open to all guests while ship is sailing
  • Included SHIPBOARD ENTERTAINMENT:
    • Live music in lounge
    • Local entertainment (subject to itinerary/availability)
    • Library stocked with DVDs, CDs, books, and board games

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
Call for pricing. 1.800.854.9664
Pricing is per person, based on double occupancy and in CAD. Additional terms & conditions apply.
Star Balcony Suite Balcony Suite Oceanview Suite
Cruise Only 9242 9098 7262
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.

Castries

Castries, a thriving harbour city, serves as the nation's capital. For fruits, vegetables, and handicrafts, shoppers throng Castries Market and the city's numerous boutiques. In the Derek Walcott Square, which bears the poet from St. Lucia's name who won the Nobel Prize, tourists may unwind while admiring murals created by a local artist within the Cathedral of the Immaculate Conception. Visitors can take in expansive views from Morne Fortune (Hill of Good Luck), the site of a conflict between the French and English for sovereignty of the island.

Itinerary
Day Date Port Arrival Departure Marina Day
1 Nov 22, 2026 San Juan Embark 1:00 PM 7:00 PM No
2 Nov 23, 2026 At Sea
3 Nov 24, 2026 St. George's 9:00 AM 10:00 PM No
4 Nov 25, 2026 Bequia 8:00 AM 10:00 PM Yes
5 Nov 26, 2026 Mayreau 8:00 AM 5:00 PM No
6 Nov 27, 2026 Les Saintes 10:00 AM 5:00 PM Yes
7 Nov 28, 2026 Marigot, St. Martin 8:00 AM 3:00 PM No
8 Nov 29, 2026 San Juan 7:00 AM 7:00 PM No
9 Nov 30, 2026 Cruz Bay, St. John, U.S. Virgin Islands 8:00 AM 6:00 PM No
10 Dec 1, 2026 Gustavia 8:00 AM 10:00 PM Yes
11 Dec 2, 2026 Basseterre 8:00 AM 5:00 PM No
12 Dec 3, 2026 Philipsburg, St. Maarten 8:00 AM 10:00 PM No
13 Dec 4, 2026 Jost Van Dyke, Great Harbour 9:00 AM 10:00 PM Yes
14 Dec 5, 2026 Virgin Gorda / Prickly Pear, British Virgin Islands 8:00 AM 5:00 PM No
15 Dec 6, 2026 San Juan 7:00 AM Disembark 8:00 AM No
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.

Please note that travel suppliers reserve the right to change policies and dates at any time without notice.

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: July 20, 2026

$
7262
S1 Oceanview Suite
per person
CAD
$
per person
CAD
$
per person
CAD
1.800.854.9664
A+ BBB Rating
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