Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing

From $4,280 per person

20 days

Ship: Wind Surf

Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing
Windstar Cruises

Caribbean beaches, vibrant tropical fish, and savory West Indies cuisine during this 19-day transatlantic crossing. Relax, unwind and refocus with back-to-back spa days throughout your ocean crossing and dine on award-winning meals paired with the company of your new Windstar family. Relive history while sailing aboard a former America's Cup competition sailboat or cook up delicious French meals with a certified chef in Grand Case outside Philipsburg, St. Maarten. Roll out in offroad vehicles for an unrushed day of snorkeling and relaxing on Tortola's secluded beaches. Swim and frolic with dolphins near Jost Van Dyke in the British Virgin Islands. Snorkel above colorful coral and dizzying schools of curious fish prior to your private beach barbeque on Virgin Gorda in the British Virgin Islands. Glide over a sunken ship in a semi-submersible and take in a glowing Caribbean sunset during a catamaran cruise off Gustavia's tropical beaches on St. Barts.

Journey Summary

  • Day 1 - Nov. 18, 2025, Tue. - Lisbon
  • Day 2 - Nov. 19, 2025, Wed. -
  • Day 3 - Nov. 20, 2025, Thu. -
  • Day 4 - Nov. 21, 2025, Fri. -
  • Day 5 - Nov. 22, 2025, Sat. -
  • Day 6 - Nov. 23, 2025, Sun. -
  • Day 7 - Nov. 24, 2025, Mon. -
  • Day 8 - Nov. 25, 2025, Tue. -
  • Day 9 - Nov. 26, 2025, Wed. -
  • Day 10 - Nov. 27, 2025, Thu. -
  • Day 11 - Nov. 28, 2025, Fri. -
  • Day 12 - Nov. 29, 2025, Sat. -
  • Day 13 - Nov. 30, 2025, Sun. -
  • Day 14 - Dec. 1, 2025, Mon. - St. John's
  • Day 15 - Dec. 2, 2025, Tue. - Philipsburg, St. Maarten
  • Day 16 - Dec. 3, 2025, Wed. - Soper's Hole
  • Day 17 - Dec. 4, 2025, Thu. - Jost Van Dyke, Great Harbour
  • Day 18 - Dec. 5, 2025, Fri. - Jost Van Dyke, Great Harbour
  • Day 19 - Dec. 6, 2025, Sat. - Virgin Gorda / Prickly Pear, British Virgin Islands
  • Day 20 - Dec. 7, 2025, Sun. - Gustavia

Detailed Itinerary

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

Day 1 - November 18, 2025

Lisbon

The rhythm of Lisbon invites you to join its captivating dance. This splendid capital city on the banks of the Rio Teja offers a warm welcome and an unparalleled blend of architectural styles. Elegant outdoor cafés line the cobbled sidewalks. Turn-of-the-century funiculars climb the scenic hills. Find the UNESCO sites of the Tower of Belem and the Monastery of the Hieronymites. And, everywhere, the city engages you with its easy style and remarkable charm.

Day 2 - November 19, 2025

Day 3 - November 20, 2025

Day 4 - November 21, 2025

Day 5 - November 22, 2025

Day 6 - November 23, 2025

Day 7 - November 24, 2025

Day 8 - November 25, 2025

Day 9 - November 26, 2025

Day 10 - November 27, 2025

Day 11 - November 28, 2025

Day 12 - November 29, 2025

Day 13 - November 30, 2025

Day 14 - December 01, 2025

St. John's

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.

Day 15 - December 02, 2025

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 16 - December 03, 2025

Soper's Hole

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

Day 17 - December 04, 2025

Jost Van Dyke, Great Harbour

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 18 - December 05, 2025

Jost Van Dyke, Great Harbour

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 19 - December 06, 2025

Virgin Gorda / Prickly Pear, British Virgin Islands

<ul>
<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 20 - December 07, 2025

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.

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Nov 18, 2025

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