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...
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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
Monday, 20/12/2027
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
Basseterre, Saint Kitts , Saint Kitts and Nevis
Wednesday, 22/12/2027
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 4
Gustavia , Saint Barthélemy
Thursday, 23/12/2027
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 5
Philipsburg , Sint Maarten (Dutch part)
Friday, 24/12/2027
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
Saturday, 25/12/2027
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
Monday, 27/12/2027
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
Wednesday, 29/12/2027
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
Thursday, 30/12/2027
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
Friday, 31/12/2027
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
Terre-de-Haut , Guadeloupe
Saturday, 01/01/2028
This is the Caribbean as you've always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.
Day 14
Marigot , Saint Martin (French part)
Sunday, 02/01/2028
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
Monday, 03/01/2028
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 Porthole Suite
277 sqft · Up to 2 guests
Ocean View Suite
277 sqft · Up to 2 guests
Ocean View Suite 1
277 sqft · Up to 2 guests
Star Ocean View Suite 1
277 sqft · Up to 2 guests
Ocean View Suite 2
277 sqft · Up to 2 guests
Ocean View Suite 3
277 sqft · Up to 2 guests
Balcony Suite
277 sqft · Up to 2 guests
Star Balcony Suite
277 sqft · Up to 2 guests
Balcony Suite 1
277 sqft · Up to 2 guests
Star Balcony Suite 1
277 sqft · Up to 2 guests
Deluxe Suite
468 sqft · Up to 2 guests
Broadmoor Suite/Sea Island Suite
400–530 sqft · Up to 2 guests
Owner's Suite
575 sqft · Up to 2 guests
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 → | ||
| Ocean View Suite 1 · 277 sqft | S1 Ocean View Suite 1 (Deck 4) | Enquire → | ||
| Star Ocean View Suite 1 · 277 sqft | SS1 Star Ocean View Suite | Enquire → | ||
| Ocean View Suite 2 · 277 sqft | S2 Ocean View Suite 2 (Deck 5) | Enquire → | ||
| Ocean View Suite 3 · 277 sqft | S3 Ocean View Suite 3 (Deck 6) | Enquire → | ||
| Balcony Suite · 277 sqft | BS Balcony Suite (Deck 5) | Enquire → | ||
| Star Balcony Suite · 277 sqft | SBS Star Balcony Suite (Deck 5) | Enquire → | ||
| Balcony Suite 1 · 277 sqft | BS1 Balcony Suite 1 (Deck 6) | Enquire → | ||
| Star Balcony Suite 1 · 277 sqft | SBS1 Star Balcony Suite 1 (Deck 6) | Enquire → | ||
| Deluxe Suite · 468 sqft | DS | Enquire → | ||
| Broadmoor Suite/Sea Island Suite · 400–530 sqft | CS Classic Suite | Enquire → | ||
| Owner's Suite · 575 sqft | OW | Enquire → |
Star Porthole Suite · 277 sqft
SP
Ocean View Suite · 277 sqft
S Ocean View Suite (Deck 4, forward)
Ocean View Suite 1 · 277 sqft
S1 Ocean View Suite 1 (Deck 4)
Star Ocean View Suite 1 · 277 sqft
SS1 Star Ocean View Suite
Ocean View Suite 2 · 277 sqft
S2 Ocean View Suite 2 (Deck 5)
Ocean View Suite 3 · 277 sqft
S3 Ocean View Suite 3 (Deck 6)
Balcony Suite · 277 sqft
BS Balcony Suite (Deck 5)
Star Balcony Suite · 277 sqft
SBS Star Balcony Suite (Deck 5)
Balcony Suite 1 · 277 sqft
BS1 Balcony Suite 1 (Deck 6)
Star Balcony Suite 1 · 277 sqft
SBS1 Star Balcony Suite 1 (Deck 6)
Deluxe Suite · 468 sqft
DS
Broadmoor Suite/Sea Island Suite · 400–530 sqft
CS Classic Suite
Owner's Suite · 575 sqft
OW
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Your Ship
Star Legend
Serving just 312 guests, Star Legend is the perfect size — small enough to offer unique experiences that set Windstar apart from other cruise lines (think crossing the Corinth Canal), yet large enough for you to make plenty of new connections on board — all without ever feeling crowded.
