Windward Islands Surf & Sunsets
Revel in seven days of surf, sand and sunsets during this leisurely cruise up and down the Caribbean’s Windward Islands. It’s a perfect vacation getaway for anyone craving a quick...
Cruise only — prices from Solo cruise only — from
Ports of Call & Itinerary
7-night voyage departing San Juan (Puerto Rico).
Printable Itinerary (PDF)Route Map
Windward Islands Surf & Sunsets
7 ports plotted · click a marker for details
Day 1
San Juan (Puerto Rico) , Puerto Rico
Sunday, 22/11/2026
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 3
Saint George's , Grenada
Tuesday, 24/11/2026
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
Port Elizabeth, Bequia , Saint Vincent and the Grenadines
Wednesday, 25/11/2026
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 Island , Saint Vincent and the Grenadines
Thursday, 26/11/2026
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
Terre-de-Haut , Guadeloupe
Friday, 27/11/2026
This is the Caribbean as you've always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.
Day 7
Marigot , Saint Martin (French part)
Saturday, 28/11/2026
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 (Puerto Rico) , Puerto Rico
Sunday, 29/11/2026
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.
Room Type & Prices
All prices per person based on double occupancy. Solo traveller prices — single occupancy. Contact our cruise experts for the latest availability and best fares.
Star Ocean View Suite
277 sqft · Up to 2 guests
Balcony Suite
277 sqft · Up to 2 guests
Star Porthole Suite
277 sqft · Up to 2 guests
Ocean View Suite
277 sqft · Up to 2 guests
Star Balcony Suite
277 sqft · Up to 2 guests
Deluxe Suite
468 sqft · Up to 2 guests
Broadmoor Suite/Sea Island Suite
400 sqft · Up to 2 guests
Owner's Suite
575 sqft · Up to 2 guests
Oceanview
| Cabin | Grade | Per Person | Avail. | |
|---|---|---|---|---|
| Star Ocean View Suite · 277 sqft | SS1 | Enquire → |
Star Ocean View Suite · 277 sqft
SS1
Balcony
Suite
| Cabin | Grade | Per Person | Avail. | |
|---|---|---|---|---|
| Star Porthole Suite · 277 sqft | SP | Enquire → | ||
| Ocean View Suite · 277 sqft | S Ocean View Suite (Deck 4, forward) | Enquire → | ||
| S1 Ocean View Suite 1 (Deck 4) | Enquire → | |||
| S2 Ocean View Suite 2 (Deck 5) | Enquire → | |||
| S3 Ocean View Suite 3 (Deck 6) | Enquire → | |||
| Star Balcony Suite (Deck 5) | SBS | Enquire → | ||
| Star Balcony Suite · 277 sqft | SBS1 Star Balcony Suite 1 (Deck 6) | Enquire → | ||
| Deluxe Suite · 468 sqft | DS | Enquire → | ||
| Broadmoor Suite/Sea Island Suite · 400 sqft | CS Classic Suite | Enquire → | ||
| Owner's Suite · 575 sqft | OW Owner's Suite | Enquire → |
Star Porthole Suite · 277 sqft
SP
Ocean View Suite · 277 sqft
S Ocean View Suite (Deck 4, forward)
Ocean View Suite · 277 sqft
S1 Ocean View Suite 1 (Deck 4)
Ocean View Suite · 277 sqft
S2 Ocean View Suite 2 (Deck 5)
Ocean View Suite · 277 sqft
S3 Ocean View Suite 3 (Deck 6)
Star Balcony Suite (Deck 5)
SBS
Star Balcony Suite · 277 sqft
SBS1 Star Balcony Suite 1 (Deck 6)
Deluxe Suite · 468 sqft
DS
Broadmoor Suite/Sea Island Suite · 400 sqft
CS Classic Suite
Owner's Suite · 575 sqft
OW Owner's Suite
More Departures
10 nights
Grand Japan
16/10/2026
From
£5,491
7 nights
Enchanting Greece & the Amalfi Coast
17/10/2026
From
£2,071
14 nights
Star Collector: Ancient to Avant-Garde Mediterranean
17/10/2026
From
£3,989
8 nights
Aegean Sea Odyssey via the Corinth Canal
19/10/2026
From
£3,207
16 nights
Star Collector: Aegean & Bosporus Escapades
19/10/2026
From
£6,021
70 nights
Star Collector: Grand Mediterranean and Latin America Adventure
19/10/2026
From
£18,809
Your Ship
Star Pride
Serving just 312 guests, Star Pride is the perfect size — small enough to offer unique experiences that set Windstar apart from other cruise lines (like our complimentary Signature Beach Party), yet large enough for you to make plenty of new connections on board — all without ever feeling crowded.
