Star Collector: Lovely Leewards

Nov 8, 2026 — Nov 22, 2026

Starting from

See more routes around Caribbean

SAN JUAN → SAN JUAN

14 Nights on Star Pride

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.

1
NOV 08, 2026
San Juan
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
8

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.

San Juan: Old San Juan Natl Historic Parks Walking Tour with Transfer to Airport

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate-Strenuous
Price
$159

Time
8:30 AM
Duration
4 Hours
Activity Level
N/A
Price
$729

San Juan, Concierge Collection: Half Day Private SUV with Guide

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$829

San Juan: Rainforest Eco Wonder Tour with Transfer to Windstar Hotel

Time
8:30 AM
Duration
5 Hours
Activity Level
Moderate-Strenuous
Price
$199

San Juan: Rainforest Eco Wonder Tour with Transfer to Airport

Time
8:30 AM
Duration
5 Hours
Activity Level
Moderate-Strenuous
Price
$199

San Juan, Bacardi Rum Tour & Tasting- With Transfer to Windstar Hotel

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$289

San Juan, Bacardi Rum Tour & Tasting- With Transfer to Airport

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$289

San Juan: Old San Juan Natl Historic Parks Walking Tour with Transfer to Windstar Hotel

Time
8:30 AM
Duration
3.25 Hours
Activity Level
Moderate-Strenuous
Price
$159
2
NOV 09, 2026
AT SEA
3
NOV 10, 2026
St. George's
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
10

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.

St. Georges, Fort Frederick Rainforest & Waterfall

Time
9:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$99

St. Georges, Powerboat & Snorkeling at the Statues Park *

Time
9:30 AM
Duration
2 Hours
Activity Level
Moderate-Strenuous
Price
$119

St. Georges, Discover Scuba

Time
9:30 AM
Duration
4.5 Hours
Activity Level
Moderate
Price
$279

St. Georges, Clear Bottom Kayaking

Time
9:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$89

St Georges, Spice of Our Lives

Time
9:30 AM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$69

St. Georges, Izzie's Great House Discovery

Time
9:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$119

St. Georges, The Best of Grenada

Time
9:30 AM
Duration
7.5 Hours
Activity Level
Easy
Price
$169

St. Georges, Certified One-Tank Dive

Time
9:30 AM
Duration
3.5 Hours
Activity Level
Moderate-Strenuous
Price
$215

St. Georges, Sailing Cruise to the Statue Park

Time
9:30 AM
Duration
3.5 Hours
Activity Level
Moderate-Strenuous
Price
$99

St. Georges, Certified Two-Tank Dive

Time
9:30 AM
Duration
4.25 Hours
Activity Level
Moderate-Strenuous
Price
$319
4
NOV 11, 2026
Bequia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
6

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.

Bequia, Mustique Magic with Lunch

Time
9:30 AM
Duration
6 Hours
Activity Level
Moderate
Price
$269

Bequia Snorkel Adventure

Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$119

Bequia Highlights

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy-Moderate
Price
$89

Bequia, Taste of Bequia

Time
10:00 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$149

Bequia, Concierge Collection: Rum Tasting at Firefly Plantation

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$169

Bequia, Bequia Fort & Lower Beach Getaway *

Time
8:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$99
5
NOV 12, 2026
Mayreau
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
1

With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you're on your own private island. Saline Bay is a delightful anchorage that separates the Caribbean from the Atlantic - and a perfect place to play with some of the toys from the Watersports Platform.

Mayreau, Grenadines Island Escape

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$89
6
NOV 13, 2026
Les Saintes
ARRIVE
10:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
8

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.

Les Saintes, Blue Escape Kayaking *

Time
10:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$149

Les Saintes, Snorkel Experience in Les Saintes *

Time
10:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$119

Les Saintes, Sailing the Bay

Time
10:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$249

Les Saintes, Explore Terra de Haut by Foot

Time
10:30 AM
Duration
1.25 Hours
Activity Level
Moderate
Price
$109

Les Saintes, Terre de Haut Panoramic Tour

Time
10:30 AM
Duration
1 Hours
Activity Level
Easy
Price
$119

Les Saintes, Historic Tastes & Treasures of Fort Napoleon

Time
10:30 AM
Duration
2.5 Hours
Activity Level
Moderate
Price
$129

Les Saintes, Sample Culinary Treasures of Guadeloupe

Time
10:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$209

Les Saintes, Relax & Snorkel *

Time
10:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$179
7
NOV 14, 2026
Marigot, St. Martin
ARRIVE
8:00 AM
DEPART
3:00 PM
MARINA
NO
SHORE EXCURSIONS
4

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.

Marigot, French Creole Cooking Class

Time
8:30 AM
Duration
5 Hours
Activity Level
Easy-Moderate
Price
$319

Marigot, Beach Day at KKO With Lunch

Time
8:30 AM
Duration
5 Hours
Activity Level
Easy
Price
$259

Marigot, Rhum and Rhythm

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$299

Marigot, French and Dutch Island Discovery

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$99

Star Pride

number of decks
6 Decks
yacht length
522 ft (159 meters)
yacht crew size
200 Crew Members
yacht guest capacity
312 Guests

Staterooms

Room Size 575 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 468 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 400 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities
Expand all

Available Dates

Date Yacht
Starting from
Actions
Nov 15 (Sun) – Nov 29 (Sun), 2026November 15 (Sun) – November 29 (Sun), 2026Star Pride$5,893
Nov 22 (Sun) – Dec 6 (Sun), 2026November 22 (Sun) – December 6 (Sun), 2026Star Pride$5,193
Nov 29 (Sun) – Dec 13 (Sun), 2026November 29 (Sun) – December 13 (Sun), 2026Star Pride$5,393
Dec 6 (Sun) – Dec 20 (Sun), 2026December 6 (Sun) – December 20 (Sun), 2026Star Pride$5,493
Dec 13 (Sun) – Dec 27 (Sun), 2026December 13 (Sun) – December 27 (Sun), 2026Star Pride$5,593
Dec 20 (Sun) – Jan 3 (Sun), 2027December 20 (Sun) – January 3 (Sun), 2027Star Pride$6,793
Dec 27 (Sun) – Jan 10 (Sun), 2027December 27 (Sun) – January 10 (Sun), 2027Star Pride$7,393
Jan 3 (Sun) – Jan 17 (Sun), 2027January 3 (Sun) – January 17 (Sun), 2027Star Pride$7,293
Nov 1 (Mon) – Nov 15 (Mon), 2027November 1 (Mon) – November 15 (Mon), 2027Star Pride$4,593
Nov 8 (Mon) – Nov 22 (Mon), 2027November 8 (Mon) – November 22 (Mon), 2027Star Pride$4,593
Nov 15 (Mon) – Nov 29 (Mon), 2027November 15 (Mon) – November 29 (Mon), 2027Star Pride$4,593
Dec 20 (Mon) – Jan 3 (Mon), 2028December 20 (Mon) – January 3 (Mon), 2028Star Legend$5,193
Dec 27 (Mon) – Jan 10 (Mon), 2028December 27 (Mon) – January 10 (Mon), 2028Star Legend$4,993
Jan 3 (Mon) – Jan 17 (Mon), 2028January 3 (Mon) – January 17 (Mon), 2028Star Legend$4,893
Jan 10 (Mon) – Jan 24 (Mon), 2028January 10 (Mon) – January 24 (Mon), 2028Star Legend$4,893
Jan 17 (Mon) – Jan 31 (Mon), 2028January 17 (Mon) – January 31 (Mon), 2028Star Legend$4,893
Jan 24 (Mon) – Feb 7 (Mon), 2028January 24 (Mon) – February 7 (Mon), 2028Star Legend$4,893
Jan 31 (Mon) – Feb 14 (Mon), 2028January 31 (Mon) – February 14 (Mon), 2028Star Legend$4,893
Feb 7 (Mon) – Feb 21 (Mon), 2028February 7 (Mon) – February 21 (Mon), 2028Star Legend$4,893
Feb 14 (Mon) – Feb 28 (Mon), 2028February 14 (Mon) – February 28 (Mon), 2028Star Legend$4,893
Mar 13 (Mon) – Mar 27 (Mon), 2028March 13 (Mon) – March 27 (Mon), 2028Star Pride$4,893
Mar 20 (Mon) – Apr 3 (Mon), 2028March 20 (Mon) – April 3 (Mon), 2028Star Pride$4,893