Ocean Crossings + Ponta Delgada, Azores

From $2,599 per person

15 days

Ship: Wind Surf

Ocean Crossings + Ponta Delgada, Azores
Windstar Cruises

This is a place where dreams really do come true. The place where nothing comes between you and your fondest wishes. Where no schedules intrude, where day-to-day annoyances can’t reach you, where every moment of every hour of every day is yours alone. This is your place – at sea under an open sky – the one place in which you truly can get away from it all. Simply step on board and we’ll take it from there. Meals so delicious they might be sinful are served when, where, and any way you choose. Decadent spa treatments. Lazy hours stretched out on deck. Workouts you’ve been meaning to get around to in the state-of-the-art Fitness Center. Uninterrupted time to spend with new friends or in exquisite solitude. One delightful stop in Ponta Delgada, the Azores Islands en route to Lisbon for an outdoor activity or relaxing on the beach.  Best of all, this is the place and the time to reconnect – with each other, with yourself, with your dreams.

Journey Summary

  • Day 1 - Apr. 4, 2026, Sat. - Philipsburg, St. Maarten
  • Day 2 - Apr. 5, 2026, Sun. -
  • Day 3 - Apr. 6, 2026, Mon. -
  • Day 4 - Apr. 7, 2026, Tue. -
  • Day 5 - Apr. 8, 2026, Wed. -
  • Day 6 - Apr. 9, 2026, Thu. -
  • Day 7 - Apr. 10, 2026, Fri. -
  • Day 8 - Apr. 11, 2026, Sat. -
  • Day 9 - Apr. 12, 2026, Sun. -
  • Day 10 - Apr. 13, 2026, Mon. -
  • Day 11 - Apr. 14, 2026, Tue. - Ponta Delgada
  • Day 12 - Apr. 15, 2026, Wed. -
  • Day 13 - Apr. 16, 2026, Thu. -
  • Day 14 - Apr. 17, 2026, Fri. -
  • Day 15 - Apr. 18, 2026, Sat. - Lisbon

Itinerary Highlights

Drop by the Bridge for an impromptu navigation lesson.

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Detailed Itinerary

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

Day 1 - April 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 - April 05, 2026

Day 3 - April 06, 2026

Day 4 - April 07, 2026

Day 5 - April 08, 2026

Day 6 - April 09, 2026

Day 7 - April 10, 2026

Day 8 - April 11, 2026

Day 9 - April 12, 2026

Day 10 - April 13, 2026

Day 11 - April 14, 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.  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  the Azorean culture.

Day 12 - April 15, 2026

Day 13 - April 16, 2026

Day 14 - April 17, 2026

Day 15 - April 18, 2026

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.

Dates and Prices

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Available dates:

Apr 04, 2026

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