Windstar 7 Nights Caribbean Eastern

Windward Islands Surf & Sunsets

Star Pride • Embarkation: San Juan

Voyage Overview

Embark Date 20-Dec-2026
Disembark Date 27-Dec-2026
Duration 7 Nights
Vessel Star Pride

Day-by-Day Itinerary

Day 1: SAN JUAN

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

Day 2: SEAD

SEAD

Day 3: ST GEORGES, GRENADA

Inhale the intoxicating aroma of the "Isle of Spice" 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 4: BEQUIA

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

Day 5: MAYREAU

Mayreau is the smallest inhabited island of St. Vincent and the Grenadines, covering just about 1.5 square miles with a population of only a few hundred people. Tucked between Union Island and the Tobago Cays in the southern Grenadines, it's known for its laid-back, off-the-grid charm—there are no airports, no banks, and only one small village (Old Wall) perched on a hillside.

Day 6: DESHAIES

Situated near the Grand Anse beach, Deshaies has the deepest bay of all the Caribbean coasts with the best natural protection which made it a shelter for pirates of days gone by and is said to still be housing treasures on the Island. Grand Anse beach is one of the most beautiful of the islands with its over half a mile of fine golden sand and coconut palms.

Day 7: MARIGOT BAY

Established around 1689, Marigot is the attractive capital of French St. Martin, with its brightly colored houses, a lively open-air market, secluded beaches, and pretty waterfront promenade. Because of its tax-free status, Marigot is a popular center for duty-free shopping, where all of the world's most prestigious brands can be found.  Originally the area was marshy, and surrounded by mangroves. In the 1970s part of the bay was filled in to extend Marigot into a larger city with a marina. Overlooking Marigot is Fort St. Louis, the largest historical monument in St. Martin with an impressive panoramic view of the bay.

Day 8: SAN JUAN

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

About Star Pride

Star Pride
  • Cruise Line: Windstar
  • Guest Capacity: 3 guests
  • Vessel Type: Ocean Liner / Mega-Cruise Ship
  • IMO Registration: 8707343
Starting From
$3,951
per person / based on double occupancy
Category Estimates
Inside Cabin: Call
Oceanview Cabin: $3,951
Private Balcony: $5,211
Luxury Suite: $4,065
Book Online Now
Prefer Personalized Service?

Speak directly with an expert cruise consultant. We can place a courtesy 48-hour hold with zero obligation.

Call 1-888-883-0460