Star Collector: Lovely Leewards
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...
Cruise only — prices from Solo cruise only — from
Ports of Call & Itinerary
14-night voyage departing San Juan (Puerto Rico).
Printable Itinerary (PDF)Route Map
Star Collector: Lovely Leewards
12 ports plotted · click a marker for details
Day 1
San Juan (Puerto Rico) , Puerto Rico
Sunday, 29/11/2026
The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.
Day 3
Gustavia , Saint Barthélemy
Tuesday, 01/12/2026
Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.
Day 4
Basseterre, Saint Kitts , Saint Kitts and Nevis
Wednesday, 02/12/2026
With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.
Day 5
Philipsburg , Sint Maarten (Dutch part)
Thursday, 03/12/2026
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
Day 6
Great Harbour, Jost Van Dyke , British Virgin Islands
Friday, 04/12/2026
For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you'll be ready for an evening drink on the beach - where you can admire your Windstar ship aglow in the harbor.
Day 8
San Juan (Puerto Rico) , Puerto Rico
Sunday, 06/12/2026
The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.
Day 10
Saint George's , Grenada
Tuesday, 08/12/2026
Inhale the intoxicating aroma of the "Isle of Spice" as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.
Day 11
Port Elizabeth, Bequia , Saint Vincent and the Grenadines
Wednesday, 09/12/2026
The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia's whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island's famed model boat builders at work on their miniature masterpieces.
Day 12
Mayreau Island , Saint Vincent and the Grenadines
Thursday, 10/12/2026
Mayreau is the smallest inhabited island of St. Vincent and the Grenadines, covering just about 1.5 square miles with a population of only a few hundred people. Tucked between Union Island and the Tobago Cays in the southern Grenadines, it's known for its laid-back, off-the-grid charm—there are no airports, no banks, and only one small village (Old Wall) perched on a hillside.
Day 13
Deshaies , Guadeloupe
Friday, 11/12/2026
Situated near the Grand Anse beach, Deshaies has the deepest bay of all the Caribbean coasts with the best natural protection which made it a shelter for pirates of days gone by and is said to still be housing treasures on the Island. Grand Anse beach is one of the most beautiful of the islands with its over half a mile of fine golden sand and coconut palms.
Day 14
Marigot , Saint Martin (French part)
Saturday, 12/12/2026
Established around 1689, Marigot is the attractive capital of French St. Martin, with its brightly colored houses, a lively open-air market, secluded beaches, and pretty waterfront promenade. Because of its tax-free status, Marigot is a popular center for duty-free shopping, where all of the world's most prestigious brands can be found. Originally the area was marshy, and surrounded by mangroves. In the 1970s part of the bay was filled in to extend Marigot into a larger city with a marina. Overlooking Marigot is Fort St. Louis, the largest historical monument in St. Martin with an impressive panoramic view of the bay.
Day 15
San Juan (Puerto Rico) , Puerto Rico
Sunday, 13/12/2026
The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.
Room Type & Prices
All prices per person based on double occupancy. Solo traveller prices — single occupancy. Contact our cruise experts for the latest availability and best fares.
Star Ocean View Suite
277 sqft · Up to 2 guests
Balcony Suite
277 sqft · Up to 2 guests
Star Porthole Suite
277 sqft · Up to 2 guests
Ocean View Suite
277 sqft · Up to 2 guests
Star Balcony Suite
277 sqft · Up to 2 guests
Deluxe Suite
468 sqft · Up to 2 guests
Broadmoor Suite/Sea Island Suite
400 sqft · Up to 2 guests
Owner's Suite
575 sqft · Up to 2 guests
Oceanview
| Cabin | Grade | Per Person | Avail. | |
|---|---|---|---|---|
| Star Ocean View Suite · 277 sqft | SS1 | Enquire → |
Star Ocean View Suite · 277 sqft
SS1
Balcony
Suite
| Cabin | Grade | Per Person | Avail. | |
|---|---|---|---|---|
| Star Porthole Suite · 277 sqft | SP | Enquire → | ||
| Ocean View Suite · 277 sqft | S Ocean View Suite (Deck 4, forward) | Enquire → | ||
| S1 Ocean View Suite 1 (Deck 4) | Enquire → | |||
| S2 Ocean View Suite 2 (Deck 5) | Enquire → | |||
| S3 Ocean View Suite 3 (Deck 6) | Enquire → | |||
| Star Balcony Suite (Deck 5) | SBS | Enquire → | ||
| Star Balcony Suite · 277 sqft | SBS1 Star Balcony Suite 1 (Deck 6) | Enquire → | ||
| Deluxe Suite · 468 sqft | DS | Enquire → | ||
| Broadmoor Suite/Sea Island Suite · 400 sqft | CS Classic Suite | Enquire → | ||
| Owner's Suite · 575 sqft | OW Owner's Suite | Enquire → |
Star Porthole Suite · 277 sqft
SP
Ocean View Suite · 277 sqft
S Ocean View Suite (Deck 4, forward)
Ocean View Suite · 277 sqft
S1 Ocean View Suite 1 (Deck 4)
Ocean View Suite · 277 sqft
S2 Ocean View Suite 2 (Deck 5)
Ocean View Suite · 277 sqft
S3 Ocean View Suite 3 (Deck 6)
Star Balcony Suite (Deck 5)
SBS
Star Balcony Suite · 277 sqft
SBS1 Star Balcony Suite 1 (Deck 6)
Deluxe Suite · 468 sqft
DS
Broadmoor Suite/Sea Island Suite · 400 sqft
CS Classic Suite
Owner's Suite · 575 sqft
OW Owner's Suite
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Your Ship
Star Pride
Serving just 312 guests, Star Pride is the perfect size — small enough to offer unique experiences that set Windstar apart from other cruise lines (like our complimentary Signature Beach Party), yet large enough for you to make plenty of new connections on board — all without ever feeling crowded.
