Star Collector: A Lesser Antilles Odyssey

From $6,299 per person

22 days

Ship: Wind Surf

Star Collector: A Lesser Antilles Odyssey
Windstar Cruises

Embrace extraordinary experiences exclusive to small ship cruising during this three-week exploration of the Caribbean&rsquo;s Lesser Antilles island chain. Swim with dolphins during an extended overnight stay in Jost Van Dyke in the British Virgin Islands. Savor African, European, and Indian ingredients and influences in popular Caribbean dishes as you sample spicy regional cuisine in the Fairview Great House on St. Kitts. Tour the Montserrat Volcano Observatory and learn how plant and animal life recover after volcanic eruptions, then see firsthand at the Montserrat National Trust Amerindian Gardens near Little Bay. Float above colorful coral reefs in clear-bottom kayaks as you glide through the pristine blue waters of Les Saintes on Guadeloupe. Hang onto halyards and winch handles as you master sailing a 40-foot racing yacht on scenic Rodney&rsquo;s Bay near Pigeon Island on St. Lucia. Wander the 18<sup>th</sup> century grounds of the childhood home of Empress Josephine, Napoleon&rsquo;s future wife, as you uncover historic French colonial life on Martinique.

Journey Summary

  • Day 1 - Jan. 4, 2026, Sun. - Philipsburg, St. Maarten
  • Day 2 - Jan. 5, 2026, Mon. - Falmouth Harbour
  • Day 3 - Jan. 6, 2026, Tue. - Road Bay
  • Day 4 - Jan. 7, 2026, Wed. - Soper's Hole
  • Day 5 - Jan. 8, 2026, Thu. - Jost Van Dyke, Great Harbour
  • Day 6 - Jan. 9, 2026, Fri. - Virgin Gorda / Prickly Pear, British Virgin Islands
  • Day 7 - Jan. 10, 2026, Sat. - Gustavia
  • Day 8 - Jan. 11, 2026, Sun. - Philipsburg, St. Maarten
  • Day 9 - Jan. 12, 2026, Mon. - Basseterre
  • Day 10 - Jan. 13, 2026, Tue. - Gustavia
  • Day 11 - Jan. 14, 2026, Wed. - St. John's
  • Day 12 - Jan. 15, 2026, Thu. - Les Saintes
  • Day 13 - Jan. 16, 2026, Fri. - Mayreau
  • Day 14 - Jan. 17, 2026, Sat. - Kingstown
  • Day 15 - Jan. 18, 2026, Sun. - Bridgetown
  • Day 16 - Jan. 19, 2026, Mon. - Anse Mitan
  • Day 17 - Jan. 20, 2026, Tue. - Castries
  • Day 18 - Jan. 21, 2026, Wed. - Pigeon Island
  • Day 19 - Jan. 22, 2026, Thu. - Bequia
  • Day 20 - Jan. 23, 2026, Fri. - Mayreau
  • Day 21 - Jan. 24, 2026, Sat. - St. George's
  • Day 22 - Jan. 25, 2026, Sun. - Bridgetown

Itinerary Highlights

Indulge yourself at Windstar&#39;s Signature Beach Party with plenty of Caribbean flavors and spirit to savor and share<br />
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Detailed Itinerary

Day-by-day description of your cruise and cruise activities.

Day 1 - January 04, 2026

Philipsburg, St. Maarten

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 2 - January 05, 2026

Falmouth Harbour

It&rsquo;s said that Antigua has 365 beaches &ndash; one for every day of the year. See how many you can discover as our stay in port stretches into the evening to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.

Day 3 - January 06, 2026

Road Bay

With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean.&nbsp; It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats.&nbsp; Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.

Day 4 - January 07, 2026

Soper's Hole

Arrive at the boardwalk of Pusser&rsquo;s Landing and mingle with other yachtsmen in the utterly charming marina at Soper&rsquo;s Hole. Find a deserted stretch of beach to kick back and ponder this tiny port&rsquo;s rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime romantic sunset Sail Away.&nbsp;

Day 5 - January 08, 2026

Jost Van Dyke, Great Harbour

For an island comprised of a mere eight square miles, it&rsquo;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 &nbsp;Drake Waterway. After all that, you&rsquo;ll be ready for an evening drink on the beach &mdash; where you can admire your Windstar ship aglow in the harbor.

Day 6 - January 09, 2026

Virgin Gorda / Prickly Pear, British Virgin Islands

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<li><strong>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. Although uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called &ldquo;The Baths,&rdquo; which form huge underground pools and caverns.</strong></li>
</ul>
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<strong>Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.</strong>

Day 7 - January 10, 2026

Gustavia

Affectionately known as St. Barts, the Caribbean&rsquo;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&rsquo;s signature ti punch as kite surfers fly by.

Day 8 - January 11, 2026

Philipsburg, St. Maarten

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 9 - January 12, 2026

Basseterre

With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean&rsquo;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 10 - January 13, 2026

Gustavia

Affectionately known as St. Barts, the Caribbean&rsquo;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&rsquo;s signature ti punch as kite surfers fly by.

Day 11 - January 14, 2026

St. John's

St. John&rsquo;s is a city of Old World charm and elegance which lingers in the varied architecture of Georgian, Victorian, Vernacular, Romantic and International flavors.&nbsp; 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.&nbsp; Sites to see include St. John&rsquo;s Cathedral with its white Baroque towers, the Botanical Garden, St. John&rsquo;s Antigua Lighthouse, and Fort James.

Day 12 - January 15, 2026

Les Saintes

This is the Caribbean as you&rsquo;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 13 - January 16, 2026

Mayreau

With fewer than 300 inhabitants and miles of secluded beaches, it&#39;s easy to feel as if you&#39;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.

Day 14 - January 17, 2026

Kingstown

Charming Kingstown, the capital and main commercial center of St. Vincent &amp; the Grenadines is known for its churches, cobblestone streets, colonial buildings and the St. Vincent Botanical Gardens, founded in 1765. &nbsp;Steep hills surround the town, with Fort Charlotte sitting high on a ridge north of the city, offering panoramic views of Kingstown and the surrounding islands. &nbsp;Other sites to see include St. George&rsquo;s Anglican Cathedral, an 1820s structure adorned with stained glass windows, St. Mary&rsquo;s Catholic Cathedral, built in 1823, with its lovely Gothic spires and Romanesque columns and arches.

Day 15 - January 18, 2026

Bridgetown

Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you&rsquo;ll find historic sugar plantations and the fairyland magic of Harrison&rsquo;s Cave.

Day 16 - January 19, 2026

Anse Mitan

Martinique offers a delightful and distinctive blend of French and Caribbean influences, with a bounty of historical sites, museums and a wide array of excellent shopping. Be sure to take a tour of the beautiful Jardin de Balata Botanical Gardens with exotic plants from around the world and a treetop walkway affording mountain views.

Day 17 - January 20, 2026

Castries

The capital and largest city of St. Lucia is a bustling port where shoppers flock.&nbsp; Most of the city&rsquo;s historic buildings were destroyed in major fires between 1785 and 1948 but you&rsquo;ll see the beautiful, scenic backdrop of Morne Fortune (elev. 2,795 ft.) and the bustling harbor.&nbsp; Visit the Castries Market for handicrafts, fruits and vegetables, see the murals painted by a local artist and housed in the Cathedral of the Immaculate Conception, and check out one of the many restaurants or Derek Walcott Square.

Day 18 - January 21, 2026

Pigeon Island

The UNESCO site Pitons&rsquo; 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.

Day 19 - January 22, 2026

Bequia

The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia&rsquo;s whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island&rsquo;s famed model boat builders at work on their miniature masterpieces.

Day 20 - January 23, 2026

Mayreau

With fewer than 300 inhabitants and miles of secluded beaches, it&#39;s easy to feel as if you&#39;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.

Day 21 - January 24, 2026

St. George's

Inhale the intoxicating aroma of the &ldquo;Isle of Spice&rdquo; 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 22 - January 25, 2026

Bridgetown

Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you&rsquo;ll find historic sugar plantations and the fairyland magic of Harrison&rsquo;s Cave.

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Jan 04, 2026

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