Wind Surf Caribbean Cruise From Philipsburg - January 4, 2026

55 Night Star Collector: Grand Caribbean Adventure

Caribbean round trip cruise departs from Philipsburg on Sunday January 4, 2026. The 55 day cruise ends with the arrival of Wind Surf back in Philipsburg on Saturday February 28, 2026. The Presidents Day holiday (February 16, 2026) is during the cruise.

Ports of Call

January 11, 2026

Philipsburg, St. Maarten

Philipsburg is the capital of the Dutch side of the island of St. Maarten (aka Sint Maarten). The island is an extremely popular spot for visits by cruises to the eastern Caribbean. It's about 175 miles east of Puerto Rico and 1,220 miles southeast of Miami.

More Philipsburg cruises...

January 12, 2026

Basseterre, Saint Kitts

Bassetterre is on the Caribbean island of St. Kitts and is the capital city of Saint Kitts and Nevis. The islands are on the east side of the Caribbean, about 200 miles southeast of Puerto Rico and 1,300 miles southeast of Miami.

More Basseterre cruises...

January 20, 2026

Castries, St. Lucia

Castries is the capital of St. Lucia and is located on the northwest side of the island. St. Lucia is on the eastern edge of the Caribbean, between the islands of Martinique and St. Vincent.

More Castries cruises...

January 24, 2026

St Georges, Grenada

Grenada is at the southern end of the string of islands that form the eastern edge of the Caribbean Sea. It's less than 100 miles north of Venezuela and 1,500 miles southeast of Miami.

More St Georges cruises...

January 30, 2026

Kralendijk, Bonaire

Kralendijk is port town on the west side of the Dutch island of Bonaire. Bonaire is at the southern side of the Caribbean, less than 60 miles off the coast of Venezuela and about 1200 miles southeast of Miami.

More Kralendijk cruises...

January 31, 2026

Willemstad, Curacao

Willemstad is the capital of Curacao, at the southern edge of the Caribbean, less than 50 miles from the northern coast of Venezuela.

More Willemstad cruises...

February 8, 2026

Colon, Panama

Colon is a port city on the Caribbean end of the Panama Canal. Due to the geographic orientation of Panama, this is actually the west end of the canal.

More Colon cruises...

February 14, 2026

Roatan, Honduras

Roatan is a tourist destination island located about 40 miles north of the mainland coast of Honduras. It is a popular stop on western Caribbean cruises that travel along the coasts of Mexico, Belize, Honduras and Costa Rica.

More Roatan cruises...

February 16, 2026

Costa Maya, Mexico

Costa Maya is a resort area on the Caribbean coast of Mexico's Yucatan peninsula. Popular cruise excursions from here include visits to Mayan ruins.

More Costa Maya cruises...

February 17, 2026

Cozumel, Mexico

Cozumel is the most popular stop for western Caribbean tours out of US ports such as Galveston, New Orleans and Tampa. It's an island about 11 miles off the mainland.

More Cozumel cruises...

February 24, 2026