EXCLUSIVE OFFER

7-night Windward Islands Surf & Sunsets Cruise

Roundtrip San Juan

Voyage Overview

Embarkation
San Juan
Disembarkation
San Juan
Destination Highlight

San Juan, Puerto Rico, is an old city of cobblestone streets, colonial architecture and shaded courtyards. It reflects its Spanish past in such famous fortresses as El Morro and San Cristobal. San Juan is also a modern world capital -- a cosmopolitan metropolis of wide boulevards, lively cafes and highly regarded shops and galleries. San Juan is two unique destinations -- and you'll be fascinated by them both.

About the Ship
Star Pride is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach.
Carrying only 312 guests, Star Pride still tucks into small ports like Sanary-sur-Mer and Seville or narrow waterways like the Corinth and Keil Canal. We can’t wait to welcome you on board for your next 180 degree from ordinary adventure!

Daily Itinerary
Mar 27, 2028 - San Juan

San Juan, Puerto Rico, is an old city of cobblestone streets, colonial architecture and shaded courtyards. It reflects its Spanish past in such famous fortresses as El Morro and San Cristobal. San Juan is also a modern world capital -- a cosmopolitan metropolis of wide boulevards, lively cafes and highly regarded shops and galleries. San Juan is two unique destinations -- and you'll be fascinated by them both.

Mar 28, 2028 - At Sea
Mar 29, 2028 - St. George's, Grenada

A lively blend of French and English cultures, St. George's has steep hills to climb, spectacular views to photograph and a rum distillery to tour. St George's has one of the prettiest harbour settings in the Caribbean. Tourist infrastructure is still generally small-scale and locally owned and offers a good balance between comfort and price, making Grenada a great getaway for those who want to avoid the resort experience.

Mar 30, 2028 - Bequia, Grenadines

See the whole panoply of tropic splendor, lagoons, white sand, coral reefs and the island of Bequia and the stunning approach to St. Vincent and its rugged grandeur.

Mar 31, 2028 - Mayreau, Grenadines

Tossed like a tiny emerald among the Grenadines' 100 islands is Mayreau. In this idyllic spot there are no cars, just one tiny village and one resort, hidden away in the palms.

Apr 01, 2028 - Iles des Saintes

Pastoral and far off the beaten track, the Saintes are a cluster of eight islands off the southern coast of Guadeloupe. In Bourg, the charming hamlet on Terre-de-Haut, the largest isle, you can wander peaceful streets past small houses, then follow the narrow road out of town through fields and hills to a sweeping strand of secluded beach.

Apr 02, 2028 - Marigot, St. Martin

Marigot is the French side of the magnificent island of St. Martin. Its amenities provide for one of the most exhilarating experiences in the Caribbean. Sailing buffs can join in a real race on a pair of multi-million dollar America's Cup Yachts, for a 12-meter "mini-regatta."

Apr 03, 2028 - San Juan

San Juan, Puerto Rico, is an old city of cobblestone streets, colonial architecture and shaded courtyards. It reflects its Spanish past in such famous fortresses as El Morro and San Cristobal. San Juan is also a modern world capital -- a cosmopolitan metropolis of wide boulevards, lively cafes and highly regarded shops and galleries. San Juan is two unique destinations -- and you'll be fascinated by them both.

Stateroom Options

Owner's Suite
Owner's Suite (Cat OW)
$9,376

Classic Suite
Classic Suite (Cat CS)
$7,626

Deluxe Suite
Deluxe Suite (Cat DS)
$5,876

Guarantee Stateroom
Guarantee Stateroom (Cat Y)
$2,411

With this selection, you are guaranteed to receive a stateroom within a selected category, anywhere on the ship. However, the actual room assignment and location on the ship may be determined at any time after your reservation has been completed and paid in full up to the day of sailing.

Star Balcony Suite
Star Balcony Suite (Cat SBS1)
$4,126

These Suites are 277 square feet (26 square meters) Star Balcony Suites with 3rd berths — 530, 532, 533, 626, 628, 629.
All accommodations feature:
- Queen Size Bed with Luxurious Linens
- Waffle Weave Robe and Slippers
- Flat Screen TV with DVD player
- Fully-Stocked Mini Bar/Refrigerator
- Safe
- Direct Dial Phone
- L’Occitane Bath Amenities
- Wi-Fi (internet cards can be purchased at reception)
- Fresh Flowers
- Fresh Fruit
- Granite vanity with magnifying mirror
- Walk-in closet and ample drawer space
- Bathroom with granite countertop, full-size tub, and shower
- Hair Dryers and 110/220 outlets





Star Balcony Suite
Star Balcony Suite (Cat SBS)
$3,846

These Suites are 277 square feet (26 square meters) Star Balcony Suites with 3rd berths — 530, 532, 533, 626, 628, 629.
All accommodations feature:
- Queen Size Bed with Luxurious Linens
- Waffle Weave Robe and Slippers
- Flat Screen TV with DVD player
- Fully-Stocked Mini Bar/Refrigerator
- Safe
- Direct Dial Phone
- L’Occitane Bath Amenities
- Wi-Fi (internet cards can be purchased at reception)
- Fresh Flowers
- Fresh Fruit
- Granite vanity with magnifying mirror
- Walk-in closet and ample drawer space
- Bathroom with granite countertop, full-size tub, and shower
- Hair Dryers and 110/220 outlets




Balcony Suite
Balcony Suite (Cat BS1)
$3,986

Balcony Suite
Balcony Suite (Cat BS)
$3,776

Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.  All accommodations feature:
- Queen Size Bed with Luxurious Linens
- Waffle Weave Robe and Slippers
- Flat Screen TV with DVD player
- Fully-Stocked Mini Bar/Refrigerator
- Safe
- Direct Dial Phone
- L’Occitane Bath Amenities
- Wi-Fi (internet cards can be purchased at reception)
- Fresh Flowers
- Fresh Fruit
- Granite vanity with magnifying mirror
- Walk-in closet and ample drawer space
- Bathroom with granite countertop, full-size tub, and shower
- Hair Dryers and 110/220 outlets
 

Star Ocean View Suite
Star Ocean View Suite (Cat SS1)
$2,726

Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers. Star Ocean View Suites with 3rd berths — 430, 432, 433.

All accommodations feature:
- Queen Size Bed with Luxurious Linens
- Waffle Weave Robe and Slippers
- Flat Screen TV with DVD player
- Fully-Stocked Mini Bar/Refrigerator
- Safe
- Direct Dial Phone
- L’Occitane Bath Amenities
- Wi-Fi (internet cards can be purchased at reception)
- Fresh Flowers
- Fresh Fruit
- Granite vanity with magnifying mirror
- Walk-in closet and ample drawer space
- Bathroom with granite countertop, full-size tub, and shower
- Hair Dryers and 110/220 outlets

Ocean View Suite 3
Ocean View Suite 3 (Cat S3)
$2,936

Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
All accommodations feature:
- Queen Size Bed with Luxurious Linens
- Waffle Weave Robe and Slippers
- Flat Screen TV with DVD player
- Fully-Stocked Mini Bar/Refrigerator
- Safe
- Direct Dial Phone
- L’Occitane Bath Amenities
- Wi-Fi (internet cards can be purchased at reception)
- Fresh Flowers
- Fresh Fruit
- Granite vanity with magnifying mirror
- Walk-in closet and ample drawer space
- Bathroom with granite countertop, full-size tub, and shower
- Hair Dryers and 110/220 outlets

Ocean View Suite 2
Ocean View Suite 2 (Cat S2)
$2,796

Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
All accommodations feature:
- Queen Size Bed with Luxurious Linens
- Waffle Weave Robe and Slippers
- Flat Screen TV with DVD player
- Fully-Stocked Mini Bar/Refrigerator
- Safe
- Direct Dial Phone
- L’Occitane Bath Amenities
- Wi-Fi (internet cards can be purchased at reception)
- Fresh Flowers
- Fresh Fruit
- Granite vanity with magnifying mirror
- Walk-in closet and ample drawer space
- Bathroom with granite countertop, full-size tub, and shower
- Hair Dryers and 110/220 outlets

Ocean View Suite 1
Ocean View Suite 1 (Cat S1)
$2,621

Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
All accommodations feature:
- Queen Size Bed with Luxurious Linens
- Waffle Weave Robe and Slippers
- Flat Screen TV with DVD player
- Fully-Stocked Mini Bar/Refrigerator
- Safe
- Direct Dial Phone
- L’Occitane Bath Amenities
- Wi-Fi (internet cards can be purchased at reception)
- Fresh Flowers
- Fresh Fruit
- Granite vanity with magnifying mirror
- Walk-in closet and ample drawer space
- Bathroom with granite countertop, full-size tub, and shower
- Hair Dryers and 110/220 outlets

Ocean View Suite
Ocean View Suite (Cat S)
$2,516

Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
All accommodations feature:
- Queen Size Bed with Luxurious Linens
- Waffle Weave Robe and Slippers
- Flat Screen TV with DVD player
- Fully-Stocked Mini Bar/Refrigerator
- Safe
- Direct Dial Phone
- L’Occitane Bath Amenities
- Wi-Fi (internet cards can be purchased at reception)
- Fresh Flowers
- Fresh Fruit
- Granite vanity with magnifying mirror
- Walk-in closet and ample drawer space
- Bathroom with granite countertop, full-size tub, and shower
- Hair Dryers and 110/220 outlets

Star Porthole Suite
Star Porthole Suite (Cat SP)
$2,411

These Suites are 277 square feet (26 square meters). Note these Suites have Porthole window.
All accommodations feature:
- Queen Size Bed with Luxurious Linens
- Waffle Weave Robe and Slippers
- Flat Screen TV with DVD player
- Fully-Stocked Mini Bar/Refrigerator
- Safe
- Direct Dial Phone
- L’Occitane Bath Amenities
- Wi-Fi (internet cards can be purchased at reception)
- Fresh Flowers
- Fresh Fruit
- Granite vanity with magnifying mirror
- Walk-in closet and ample drawer space
- Bathroom with granite countertop, full-size tub, and shower
- Hair Dryers and 110/220 outlets

Included Amenities

Exclusive Bonus:
  • $300 Per Couple Shipboard Credit

Note: Amenities may not be combinable with fares shown. Additional restrictions apply.

  • 7-night Cruise
  • Meals
  • Entertainment

Additional Departure Dates for This Itinerary

Select an upcoming departure below to view availability or lock in exclusive Signature Travel Network perks.

Nov 08, 2026
7-night Windward Islands Surf & Sunsets Cruise
7 Nights • Star Pride • Roundtrip San Juan
Nov 22, 2026
7-night Windward Islands Surf & Sunsets Cruise
7 Nights • Star Pride • Roundtrip San Juan
Dec 06, 2026
7-night Windward Islands Surf & Sunsets Cruise
7 Nights • Star Pride • Roundtrip San Juan
Dec 20, 2026
7-night Windward Islands Surf & Sunsets Cruise
7 Nights • Star Pride • Roundtrip San Juan
Jan 03, 2027
7-night Windward Islands Surf & Sunsets Cruise
7 Nights • Star Pride • Roundtrip San Juan
Signature PerksSpecial Rate

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Looking for a specific departure date or custom package? Call 1 (888) 883-0460 Browse All Live Windstar Cruises Sailings →
Starting From
$2,411
Rates are cruise only, per person, based on double occupancy and include government fees/taxes. Optional transfers and airfare (unless otherwise stated) additional for all guests.

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The Vincent Vacations Advantage
Signature Travel Network Member
  • Best Price Guarantee: Exact same price or lower than booking directly with the cruise line.
  • Signature Exclusive Perks: Up to $500 Onboard Spending Credit, Specialty Dining & Welcome Wine on qualifying voyages.
  • Dedicated Certified Specialist: Direct advisor phone line, stateroom selection advice & automated price monitoring.
  • Zero Agency Fees: 100% complimentary white-glove planning & VIP booking service.
Already booked direct within 30-60 days? Transfer for free & claim up to $500 bonus OBC →
Trip Summary
Ship Name Star Pride
Departure Date March 27, 2028
Duration 7 Nights
Offer ID 1690880
Ship Facts
Built 1988
Guests 312
Crew 150
Call Vincent Vacations: 1 (888) 883-0460

Offer Highlights

  • Duration: 7 Nights
  • Supplier: Roundtrip San Juan
  • Destination: Roundtrip San Juan
  • Starting Rate: $2411

Frequently Asked Questions

Prices are per person, based on double occupancy and include government fees and taxes. Optional airfare and transfers additional.All fares are quoted in US Dollars.

You can book this offer directly through Vincent Vacations by clicking the 'Request a Free Quote' button or calling our travel agency at 1 (888) 883-0460 to speak with a travel specialist.

Verified Guest Reviews

4.8 out of 5
Based on verified reviews for Roundtrip San Juan

Satisfied Traveler
Recent Guest
"Booking this trip through Vincent Vacations was incredibly seamless. The vacation arrangements by Roundtrip San Juan were top notch!"

Prices are per person, based on double occupancy and include government fees and taxes. Optional airfare and transfers additional.

All fares are quoted in US Dollars.