Gems of the Leeward Islands
 
San Juan to San Juan
Fri Mar 27, 2026 - Mon Apr 6, 2026,
 10 days
 on Star Seeker
VIEW ALL DATES
Starting from $3,999 USD
ADD TO
WISH LIST
REMOVE
FROM
WISH LIST

ITINERARY AND SHORE EXCURSIONS

The best on land brought to you by the best at sea. Get to the heart of local cultures with Windstar shore excursions. You don't want to just dip a toe in local culture, you want to dive into the deep end, and that's exactly what Windstar shore excursions are designed to do. All of our excursion are created to provide authentic local experience - the kind travelers like you are looking for. And with more than 2,500 excursions to choose from, you can experience your destination in whatever way is most meaningful to you. Whether you're an outdoor enthusiast, a foodie, a history buff, or someone who loves to get to know the faces behind the many places we travel.

Date
Port
Arrive
Depart
Watersports
Platform
Shore
Excursions
Expand
Fri Mar 27
San Juan
Arrive:
Depart:7:00 PM
Watersports Platform: 
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.
Sat Mar 28
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Sun Mar 29
St. John's
Arrive:9:00 AM
Depart:6:00 PM
Watersports Platform: 
8 Available
+_
St. John’s is a city of Old World charm and elegance which lingers in the varied architecture of Georgian, Victorian, Vernacular, Romantic and International flavors.  The picturesque seafront where tiny, colorful boats are moored, the cheerful wooden buildings carefully refurbished to retain their original features, the vibrant Market Street offering vegetables, fruit and fish and the duty-free Heritage Quay shopping area provide a delightful atmosphere to captivate you.  Sites to see include St. John’s Cathedral with its white Baroque towers, the Botanical Garden, St. John’s Antigua Lighthouse, and Fort James.
8 Shore Excursions Available
+
_
St. Johns, Beach EscapeBeach | Essentials Collection
Duration4 Hours
Activity LevelEasy
$79
VIEW DETAILS
St. Johns, Concierge Collection, Birds Nest Eco Tour with Snorkeling and Caribbean LunchBeach | Concierge Collection | Dining | Sightseeing | Wildlife
Duration5.5 Hours
Activity LevelModerate-Strenuous
$269
VIEW DETAILS
St Johns, Concierge Collection, Jet Ski AdventureBeach | Boating | Essentials Collection | Sightseeing
Duration1.75 Hours
Activity LevelModerate-Strenuous
$379
VIEW DETAILS
St. Johns, Open Course Canopy Challenge Outdoors | Wildlife | Sightseeing | Essentials Collection
Duration4 Hours
Activity LevelStrenuous
$139
VIEW DETAILS
St. Johns: Presidents TourEssentials Collection | Sightseeing
Duration3 Hours
Activity LevelEasy
$109
VIEW DETAILS
St. Johns, Segway Fort Conqueror Outdoors | Sightseeing | Refreshments | Beach | Essentials Collection
Duration3 Hours
Activity LevelModerate-Strenuous
$159
VIEW DETAILS
St. Johns, Spectacular Antigua Sightseeing | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$79
VIEW DETAILS
St Johns, Swim with the StingraysEssentials Collection | Refreshments | Watersports
Duration3 Hours
Activity LevelModerate
$109
VIEW DETAILS
Mon Mar 30
Les Saintes
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
8 Available
+_
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.
8 Shore Excursions Available
+
_
Les Saintes, Blue Escape Kayaking *Boating | Essentials Collection | Outdoors | Sightseeing | Refreshments
Duration2 Hours
Activity LevelModerate
$149
VIEW DETAILS
Les Saintes, Sample Culinary Treasures of GuadeloupeBeach | Concierge Collection | Culture | Dining
Duration3 Hours
Activity LevelEasy-Moderate
$209
VIEW DETAILS
Les Saintes, Explore Terra de Haut by FootCulture | Essentials Collection | Refreshments | Walking
Duration1.25 Hours
Activity LevelModerate
$109
VIEW DETAILS
Les Saintes, Sailing the BayBoating | Concierge Collection | Refreshments
Duration3 Hours
Activity LevelModerate
$199
VIEW DETAILS
Les Saintes, Historic Tastes & Treasures of Fort NapoleonCulture | Essentials Collection | Sightseeing | Refreshments
Duration2.5 Hours
Activity LevelModerate
$129
VIEW DETAILS
Les Saintes, Terre de Haut Panoramic TourEssentials Collection | Sightseeing
Duration Hour
Activity LevelEasy
$119
VIEW DETAILS
Les Saintes, Snorkel Experience in Les Saintes *Boating | Essentials Collection | Refreshments | Snorkeling | Wildlife
Duration2 Hours
Activity LevelStrenuous
$119
VIEW DETAILS
Les Saintes, Relax & Snorkel *Beach | Boating | Essentials Collection | Refreshments | Snorkeling
Duration3 Hours
Activity LevelModerate-Strenuous
$169
VIEW DETAILS
Tue Mar 31
Pigeon Island
Arrive:8:00 AM
Depart:10:00 PM
Watersports Platform: 
12 Available
+_
The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.
12 Shore Excursions Available
+
_
Pigeon Island, Concierge Collection: Full Day Private Car & Guide Sightseeing | Concierge Collection
Duration8 Hours
Activity LevelEasy
$699
VIEW DETAILS
Pigeon Island, Concierge Collection: Full Day Private Van & Guide Sightseeing | Concierge Collection
Duration8 Hours
Activity LevelEasy
$899
VIEW DETAILS
Pigeon Island, Aerial Tram Park Wildlife | Refreshments | Walking | Sightseeing | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$155
VIEW DETAILS
Pigeon Island, Catamaran Cruise to the PitonsBeach | Boating | Essentials Collection | Sightseeing | Refreshments | UNESCO
Duration5 Hours
Activity LevelEasy
$149
VIEW DETAILS
Pigeon Island, St. Lucian Walking Food TourCulture | Essentials Collection | Sightseeing | Refreshments | Walking
Duration3.5 Hours
Activity LevelEasy-Moderate
$179
VIEW DETAILS
Pigeon Island, Mt. Pimard Nature Trail & HikeEssentials Collection | Hiking | Sightseeing
Duration2.5 Hours
Activity LevelModerate
$109
VIEW DETAILS
Pigeon Island, Panoramic St. LuciaSightseeing | Refreshments
Duration3 Hours
Activity LevelEasy
$55
VIEW DETAILS
Pigeon Island, Discover Sailing Boating | Essentials Collection
Duration3 Hours
Activity LevelModerate-Strenuous
$129
VIEW DETAILS
Pigeon Island, Off Road Segway Adventure Outdoors | Refreshments | Sightseeing | Essentials Collection
Duration3 Hours
Activity LevelModerate-Strenuous
$149
VIEW DETAILS
Pigeon Island, Rainforest Canopy Zip Line Adventure Wildlife | Refreshments | Sightseeing | Essentials Collection
Duration4.5 Hours
Activity LevelStrenuous
$119
VIEW DETAILS
Pigeon Island, Concierge Collection: Half Day Private Car & Guide Sightseeing | Concierge Collection
Duration4 Hours
Activity LevelEasy
$399
VIEW DETAILS
Pigeon Island, Concierge Collection: Half Day Private Van & Guide Sightseeing | Concierge Collection
Duration4 Hours
Activity LevelEasy
$499
VIEW DETAILS
Wed Apr 1
St. George's
Arrive:11:00 AM
Depart:6:00 PM
Watersports Platform: 
10 Available
+_
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.
10 Shore Excursions Available
+
_
St. Georges, Certified One-Tank Dive Outdoors | Wildlife | Refreshments | Boating | Essentials Collection
Duration3.5 Hours
Activity LevelStrenuous
$209
VIEW DETAILS
St. Georges, Certified Two-Tank Dive Outdoors | Wildlife | Refreshments | Boating | Essentials Collection
Duration4.25 Hours
Activity LevelStrenuous
$309
VIEW DETAILS
St. Georges, Clear Bottom Kayaking Watersports | Outdoors | Wildlife | Refreshments | Boating | Essentials Collection
Duration3 Hours
Activity LevelModerate
$89
VIEW DETAILS
Concierge Collection: Farm to Table Homestead Cooking Tour (Easy-Moderate)Concierge Collection | Culture | Dining
Duration3.5 Hours
Activity LevelEasy-Moderate
$139
VIEW DETAILS
St. Georges, Discover Scuba Outdoors | Watersports | Essentials Collection
Duration4.5 Hours
Activity LevelStrenuous
$279
VIEW DETAILS
St. Georges, Powerboat & Snorkeling at the Statues Park *Boating | Essentials Collection | Sightseeing | Snorkeling
Duration2 Hours
Activity LevelModerate-Strenuous
$119
VIEW DETAILS
St. Georges, Adventure River Tubing Watersports | Wildlife | refreshment | Essentials Collection
Duration3 Hours
Activity LevelModerate
$69
VIEW DETAILS
St. Georges, Sailing Cruise to the Statue ParkBoating | Essentials Collection | Refreshments | Snorkeling
Duration3.5 Hours
Activity LevelModerate-Strenuous
$89
VIEW DETAILS
St Georges, Spice of Our LivesCulture | Essentials Collection | Sightseeing | Refreshments
Duration4 Hours
Activity LevelEasy-Moderate
$69
VIEW DETAILS
St. Georges, Izzie's Great House DiscoveryCulture | Dining | Essentials Collection
Duration3 Hours
Activity LevelEasy-Moderate
$119
VIEW DETAILS
Thu Apr 2
AT SEA
Arrive:
Depart:
Watersports Platform: 
Fri Apr 3
Gustavia
Arrive:8:00 AM
Depart:10:00 PM
Watersports Platform: 
2 Available
+_
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.
2 Shore Excursions Available
+
_
St Barts, Concierge Collection: St. Barthelemy Beach DayBeach | Concierge Collection | Dining
Duration6 Hours
Activity LevelEasy-Moderate
$499
VIEW DETAILS
St. Barts, Concierge Collection: Sunset CruiseBoating | Concierge Collection | Sightseeing | Refreshments
Duration1.5 Hours
Activity LevelEasy-Moderate
$199
VIEW DETAILS
Sat Apr 4
Jost Van Dyke, Great Harbour
Arrive:8:00 AM
Depart:11:59 PM
Watersports Platform: 
3 Available
+_
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.
3 Shore Excursions Available
+
_
Jost Van Dyke, Catamaran Cruise and BeachBeach | Boating | Essentials Collection | Snorkeling
Duration4.5 Hours
Activity LevelModerate-Strenuous
$259
VIEW DETAILS
Jost Van Dyke: Tortola Rib Boat TourBoating | Essentials Collection | Sightseeing | Refreshments | Watersports
Duration4 Hours
Activity LevelModerate
$199
VIEW DETAILS
Jost Van Dyke, Sail and SnorkelBoating | Essentials Collection | Sightseeing | Refreshments | Watersports
Duration4 Hours
Activity LevelModerate-Strenuous
$159
VIEW DETAILS
Sun Apr 5
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
2 Available
+_
The  beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns
2 Shore Excursions Available
+
_
Virgin Gorda: Highlights & Bath TourBeach | Boating | Essentials Collection | Walking
Duration4 Hours
Activity LevelStrenuous
$89
VIEW DETAILS
Virgin Gorda: Snorkel AdventureBoating | Essentials Collection | Refreshments | Snorkeling
Duration2.75 Hours
Activity LevelModerate-Strenuous
$239
VIEW DETAILS
Mon Apr 6
San Juan
Arrive:7:00 AM
Depart:
Watersports Platform: 
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.