EXCLUSIVE OFFER

14-night Star Collector: Lovely Leewards 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 13, 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 14, 2028 - At Sea
Mar 15, 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 16, 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 17, 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.

Mar 18, 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.

Mar 19, 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."

Mar 20, 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 21, 2028 - Cruz Bay, St. John
Mar 22, 2028 - Basseterre, St. Kitts

Basseterre, St. Kitts’ capital, still shows signs of colonial architecture. However, its setting against the emerald green hills ensures a distinct Caribbean ambiance. Many travelers agree Basseterre is one of the prettiest of the Caribbean’s small capitals.

Mar 23, 2028 - Gustavia

There was never any hope of lucrative sugar plantations in St.Barths. It was too dry, too steep, too rocky, and, finally, too small. Unsuitable for agriculture, the island was never coveted as a prize during the colonial wars of the 18th century. The place had a serviceable harbor, and this allowed the town that grew around it, Gustavia, to play a key role in that intermittent conflict, a role that was to presage much of its future. Overflowing warehouses surrounded a harbor packed with ships from many nations, and a mercantile and architectural tradition was established that has lingered to the present day. Today, Gustavia has adjusted itself to satisfy the increasing number of visiting tourists. Restaurants, boutiques, and gift shops now line streets once busy with merchants, merchant seamen, and adventurers.

Mar 24, 2028 - St. Maarten (Philipsburg)

The island of St. Martin is divided between French St. Martin in the north and Dutch St. Maarten in the south. Although the cultural flow transcends any borders, each side manages to retain its own distinct flavor. This 37-square-mile island promises beautiful vistas, first-rate water sports and stunning beaches. Philipsburg is the capital of Dutch St. Maarten. Its two main streets, Frontstreet and Backstreet, are bustling thoroughfares lined with shops and restaurants.

Mar 25, 2028 - Jost Van Dyke

Jost Van Dyke boasts several lovely beaches and picturesque Great Harbour, with its beach-side West Indian village. Jost is very popular with sailors and has several famous watering holes on its southern shore, including Foxy's Tamarind Bar.

Mar 26, 2028 - Virgin Gorda

Enjoy the fabulous underwater world of the British Virgin Islands. For those who wish to get wet and enjoy the thrill of viewing coral formation and other marine life without diving, you can take a professionally guided snorkel tour of the famous Norman Island underwater sea caves and the Indian Reef. Cruise along Sir Francis Drake Channel to Spanish Town, Virgin Gorda. Or take a short drive to the baths at Spring Bay for swimming, snorkeling and sunning amid the mammoth boulders and sea caves for which the area is well known. The only viewing gear you need are your eyes!

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.

Stateroom Options

Owner's Suite
Owner's Suite (Cat OW)
$15,214

Classic Suite
Classic Suite (Cat CS)
$12,414

Deluxe Suite
Deluxe Suite (Cat DS)
$9,614

Guarantee Stateroom
Guarantee Stateroom (Cat Y)
$4,014

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)
$6,814

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)
$6,394

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)
$6,604

Balcony Suite
Balcony Suite (Cat BS)
$6,254

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)
$4,574

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)
$4,854

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)
$4,644

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)
$4,364

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)
$4,224

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)
$4,014

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: Contact us for exclusive perks available on this sailing.
  • 14-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
14-night Star Collector: Lovely Leewards Cruise
14 Nights • Star Pride • Roundtrip San Juan
Nov 15, 2026
14-night Star Collector: Lovely Leewards Cruise
14 Nights • Star Pride • Roundtrip San Juan
Nov 22, 2026
14-night Star Collector: Lovely Leewards Cruise
14 Nights • Star Pride • Roundtrip San Juan
Nov 29, 2026
14-night Star Collector: Lovely Leewards Cruise
14 Nights • Star Pride • Roundtrip San Juan
Dec 06, 2026
14-night Star Collector: Lovely Leewards Cruise
14 Nights • Star Pride • Roundtrip San Juan
Signature PerksSpecial Rate
Dec 13, 2026
14-night Star Collector: Lovely Leewards Cruise
14 Nights • Star Pride • Roundtrip San Juan
Signature PerksSpecial Rate
Dec 20, 2026
14-night Star Collector: Lovely Leewards Cruise
14 Nights • Star Pride • Roundtrip San Juan
Signature PerksSpecial Rate
Dec 27, 2026
14-night Star Collector: Lovely Leewards Cruise
14 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
$4,014
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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  • 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 13, 2028
Duration 14 Nights
Offer ID 1690881
Ship Facts
Built 1988
Guests 312
Crew 150
Call Vincent Vacations: 1 (888) 883-0460

Offer Highlights

  • Duration: 14 Nights
  • Supplier: Roundtrip San Juan
  • Destination: Roundtrip San Juan
  • Starting Rate: $3902

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.