Star Collector: Spectacular Transatlantic Journey: Caribbean to the Azores

From $4,194 per person

22 days

Ship: Wind Surf

Map featuring the Caribbean and Azores, highlighting key travel destinations along the transatlantic route.
Windstar Cruises logo

Relax on the beaches of the Caribbean before you begin your ocean crossing of the Atlantic Ocean towards Portugal. Sample some of the best rum punch in the Caribbean in Road Bay, then head off to the British Virgin Islands, where you can walk along Stroll Pusser’s Landing, the lovely boardwalk of Soper’s Hole on Tortola. Snorkel among the sponges and angelfish in Jost Van Dyke’s Sandy Spit or take a speed boat to Little Bay, Anguilla’s smallest and most private beach to swim. When you dock in Virgin Gorda join an excursion to The Baths, an array of caves with shallow pools created by large boulders. The historic town of Gustavia, the capital city on the island of St. Barthelemy, is where you can explore the 17th-century Fort Gustaf known for its lighthouse and cannons.  Disconnect as you begin the journey across the Atlantic Ocean. Indulge in breakfast in bed while you lounge in your robe all morning before heading to the spa for a massage and a facial; pop into the Open Bridge for an impromptu navigation lesson; make new friends over pre-dinner cocktails as you savor every moment of the exquisite cuisine created by the onboard chefs; and watch the sunset every night before experiencing more stars in the sky than you ever imagined. Wander the charming port of Ponta Delgada, Azores with its medieval fort and look for the art on the jetty, before heading to your final destination– Lisbon.

Journey Summary

  • Day 1 - Mar. 28, 2026, Sat. - Philipsburg, St. Maarten
  • Day 2 - Mar. 29, 2026, Sun. - St. John's
  • Day 3 - Mar. 30, 2026, Mon. - Road Bay
  • Day 4 - Mar. 31, 2026, Tue. - Soper's Hole
  • Day 5 - Apr. 1, 2026, Wed. - Jost Van Dyke, Great Harbour
  • Day 6 - Apr. 2, 2026, Thu. - Jost Van Dyke, Great Harbour
  • Day 7 - Apr. 3, 2026, Fri. - Virgin Gorda / Prickly Pear, British Virgin Islands
  • Day 8 - Apr. 4, 2026, Sat. - Gustavia
  • Day 9 - Apr. 5, 2026, Sun. - Philipsburg, St. Maarten
  • Day 10 - Apr. 6, 2026, Mon. -
  • Day 11 - Apr. 7, 2026, Tue. -
  • Day 12 - Apr. 8, 2026, Wed. -
  • Day 13 - Apr. 9, 2026, Thu. -
  • Day 14 - Apr. 10, 2026, Fri. -
  • Day 15 - Apr. 11, 2026, Sat. -
  • Day 16 - Apr. 12, 2026, Sun. -
  • Day 17 - Apr. 13, 2026, Mon. -
  • Day 18 - Apr. 14, 2026, Tue. -
  • Day 19 - Apr. 15, 2026, Wed. - Ponta Delgada
  • Day 20 - Apr. 16, 2026, Thu. -
  • Day 21 - Apr. 17, 2026, Fri. -
  • Day 22 - Apr. 18, 2026, Sat. -

Detailed Itinerary

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

Day 1 - March 28, 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 - March 29, 2026

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 3 - March 30, 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.  It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats.  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 - March 31, 2026

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 5 - April 01, 2026

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 6 - April 02, 2026

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 7 - April 03, 2026

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>
&nbsp;<br />
<strong>Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.</strong>

Day 8 - April 04, 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 9 - April 05, 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 10 - April 06, 2026

Day 11 - April 07, 2026

Day 12 - April 08, 2026

Day 13 - April 09, 2026

Day 14 - April 10, 2026

Day 15 - April 11, 2026

Day 16 - April 12, 2026

Day 17 - April 13, 2026

Day 18 - April 14, 2026

Day 19 - April 15, 2026

Ponta Delgada

Ponta Delgada is the capital of São Miguel Island, gateway to the crater lakes and volcano of Sete Cidades and to the Azores Archipelago of Portugal. There is much to do here including horseback riding, golfing, and inviting beaches with volcanic sand, tidal pools and inviting surfing or body boarding.&nbsp; Sites to see include the impressive, 3-arched city gates and the Gothic-style Church of St. Sebastian near the harbor, the Hermitage of Our Lady of Peace Temple, the quirky street art and the Carlos Machado Museum with a variety of artifacts of&nbsp; the Azorean culture.

Day 20 - April 16, 2026

Day 21 - April 17, 2026

Day 22 - April 18, 2026

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Mar 28, 2026

Ship

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The Wind Surf sailing through clear blue waters, showcasing its iconic tall sails against a bright sky.
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