New 2026 & 2027 Voyages

A New Tropical Adventure Awaits

Get Closer in Private-Yacht Style

Get ready to experience a side of the Caribbean and Latin America few travelers ever see.

Visit breezy harbors that big ships can’t reach, like Mayreau, the smallest island in the Grenadines, and Virgin Gorda, the most picturesque of the British Virgin Islands.

Explore centuries-old colonial harbors and see some of the world’s greatest wonders, like the volcanic Pitons in St. Lucia or the impressive Panama Canal. Unwind at exclusive complimentary events like our Signature Beach Party and our onboard barbecue.

And of course, enjoy the warm, blue waters of the Caribbean and Latin America directly from your yacht with our Watersports Platform — whether you prefer to lounge on a carpet float or adventure out using any of our complimentary watersports equipment. ​

Enjoy one of the biggest highlights when you set sail on our recently transformed Wind Star sailing yacht, accommodating just 148 guests. Or come aboard our 312-guest Star Pride motor yacht, where every room is an ocean-view suite.

Reserve one of these newly released 2026 or 2027 voyages in the Caribbean and Latin America by May 31, 2025, and enjoy a complimentary All-Inclusive experience — with Wi-Fi, unlimited select wine, beer and cocktails, and gratuities — plus up to $200 onboard credit per stateroom.

See terms and conditions

 
Explore the open plazas and cobblestone streets of Old San Juan, a neighborhood with over 500 years of history.
Visit the Baths of Virgin Gorda — a series of granite boulders sculpted by the sea into natural pools and grottoes.
The Piton's two volcanic peaks, rising more than 2,400 feet, welcome you to St. Lucia.
Filter Results
Showing 35 of 115 voyages from this special
CLEAR FILTER SELECTIONS
Sort:
Destination
Ship
Dates
Duration
?
Cruise only
from
$6,099 per guest
?
All-inclusive
from
$6,099USD per guest

Star Collector: Fall Leaves & Caribbean Breezes

Port to port
Montreal to San Juan
Departure
October 9, 2026
Duration
19 Days
Ship
Star Pride
?
Cruise only
from
$2,399 per guest
?
All-inclusive
from
$2,399USD per guest

Bermuda Bliss

Port to port
Boston to San Juan
Departure
October 20, 2026
Duration
8 Days
Ship
Star Pride
?
Cruise only
from
$3,599 per guest
?
All-inclusive
from
$3,599USD per guest

Gems of the Leeward Islands

Port to port
San Juan to San Juan
Departure
October 28, 2026
Duration
11 Days
Ship
Star Pride
?
Cruise only
from
$3,999 per guest
?
All-inclusive
from
$3,999USD per guest

Star Collector: Lovely Leewards

Port to port
San Juan to San Juan
Departure
November 8, 2026
Duration
14 Days
Ship
Star Pride
?
Cruise only
from
$2,499 per guest
?
All-inclusive
from
$2,499USD per guest

Windward Islands Surf & Sunsets

Port to port
San Juan to San Juan
Departure
November 8, 2026
Duration
7 Days
Ship
Star Pride
?
Cruise only
from
$4,799 per guest
?
All-inclusive
from
$4,799USD per guest

Star Collector: Southern Caribbean Thanksgiving Jubilee

Port to port
Lisbon to Colón
Departure
November 10, 2026
Duration
25 Days
Ship
Wind Star
?
Cruise only
from
$3,999 per guest
?
All-inclusive
from
$3,999USD per guest

Star Collector: Lovely Leewards

Port to port
San Juan to San Juan
Departure
November 15, 2026
Duration
14 Days
Ship
Star Pride
?
Cruise only
from
$2,499 per guest
?
All-inclusive
from
$2,499USD per guest

San Juan & the Virgin Islands

Port to port
San Juan to San Juan
Departure
November 15, 2026
Duration
7 Days
Ship
Star Pride
?
Cruise only
from
$2,499 per guest
?
All-inclusive
from
$2,499USD per guest

Windward Islands Surf & Sunsets

Port to port
San Juan to San Juan
Departure
November 22, 2026
Duration
7 Days
Ship
Star Pride
?
Cruise only
from
$3,999 per guest
?
All-inclusive
from
$3,999USD per guest

Star Collector: Lovely Leewards

Port to port
San Juan to San Juan
Departure
November 22, 2026
Duration
14 Days
Ship
Star Pride
?
Cruise only
from
$3,499 per guest
?
All-inclusive
from
$3,499USD per guest

Colombian & Southern Caribbean Coastlines

Port to port
Bridgetown to Colón
Departure
November 24, 2026
Duration
11 Days
Ship
Wind Star
?
Cruise only
from
$5,399 per guest
?
All-inclusive
from
$5,399USD per guest

Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica via the Panama Canal

Port to port
Bridgetown to Puerto Caldera
Departure
November 24, 2026
Duration
18 Days
Ship
Wind Star
?
Cruise only
from
$2,499 per guest
?
All-inclusive
from
$2,499USD per guest

San Juan & the Virgin Islands

Port to port
San Juan to San Juan
Departure
November 29, 2026
Duration
7 Days
Ship
Star Pride
?
Cruise only
from
$3,999 per guest
?
All-inclusive
from
$3,999USD per guest

Star Collector: Lovely Leewards

Port to port
San Juan to San Juan
Departure
November 29, 2026
Duration
14 Days
Ship
Star Pride
?
Cruise only
from
$3,299 per guest
?
All-inclusive
from
$3,299USD per guest

Costa Rica & Panama Canal

Port to port
Colón to Puerto Caldera
Departure
December 5, 2026
Duration
7 Days
Ship
Wind Star
?
Cruise only
from
$5,699 per guest
?
All-inclusive
from
$5,699USD per guest

Monteverde Cloud Forest & Arenal Volcano Cruise Tour

Port to port
Colón to Puerto Caldera
Departure
December 5, 2026
Duration
10 Days
Ship
Wind Star
?
Cruise only
from
$3,999 per guest
?
All-inclusive
from
$3,999USD per guest

Star Collector: Lovely Leewards

Port to port
San Juan to San Juan
Departure
December 6, 2026
Duration
14 Days
Ship
Star Pride
?
Cruise only
from
$2,499 per guest
?
All-inclusive
from
$2,499USD per guest

Windward Islands Surf & Sunsets

Port to port
San Juan to San Juan
Departure
December 6, 2026
Duration
7 Days
Ship
Star Pride
?
Cruise only
from
$5,699 per guest
?
All-inclusive
from
$5,699USD per guest

Monteverde Cloud Forest & Arenal Volcano Cruise Tour

Port to port
Puerto Caldera to Colón
Departure
December 8, 2026
Duration
11 Days
Ship
Wind Star
?
Cruise only
from
$3,299 per guest
?
All-inclusive
from
$3,299USD per guest

Costa Rica & Panama Canal

Port to port
Puerto Caldera to Colón
Departure
December 12, 2026
Duration
7 Days
Ship
Wind Star
?
Cruise only
from
$2,499 per guest
?
All-inclusive
from
$2,499USD per guest

San Juan & the Virgin Islands

Port to port
San Juan to San Juan
Departure
December 13, 2026
Duration
7 Days
Ship
Star Pride
?
Cruise only
from
$4,099 per guest
?
All-inclusive
from
$4,099USD per guest

Star Collector: Lovely Leewards

Port to port
San Juan to San Juan
Departure
December 13, 2026
Duration
14 Days
Ship
Star Pride
?
Cruise only
from
$5,699 per guest
?
All-inclusive
from
$5,699USD per guest

Monteverde Cloud Forest & Arenal Volcano Cruise Tour

Port to port
Colón to Puerto Caldera
Departure
December 19, 2026
Duration
10 Days
Ship
Wind Star
?
Cruise only
from
$3,299 per guest
?
All-inclusive
from
$3,299USD per guest

Costa Rica & Panama Canal

Port to port
Colón to Puerto Caldera
Departure
December 19, 2026
Duration
7 Days
Ship
Wind Star
?
Cruise only
from
$4,299 per guest
?
All-inclusive
from
$4,299USD per guest

Star Collector: Lovely Leewards

Port to port
San Juan to San Juan
Departure
December 20, 2026
Duration
14 Days
Ship
Star Pride
?
Cruise only
from
$2,699 per guest
?
All-inclusive
from
$2,699USD per guest

Windward Islands Surf & Sunsets

Port to port
San Juan to San Juan
Departure
December 20, 2026
Duration
7 Days
Ship
Star Pride
?
Cruise only
from
$5,699 per guest
?
All-inclusive
from
$5,699USD per guest

Monteverde Cloud Forest & Arenal Volcano Cruise Tour

Port to port
Puerto Caldera to Colón
Departure
December 22, 2026
Duration
11 Days
Ship
Wind Star
?
Cruise only
from
$3,299 per guest
?
All-inclusive
from
$3,299USD per guest

Costa Rica & Panama Canal

Port to port
Puerto Caldera to Colón
Departure
December 26, 2026
Duration
7 Days
Ship
Wind Star
?
Cruise only
from
$4,099 per guest
?
All-inclusive
from
$4,099USD per guest

Star Collector: Lovely Leewards

Port to port
San Juan to San Juan
Departure
December 27, 2026
Duration
14 Days
Ship
Star Pride
?
Cruise only
from
$2,699 per guest
?
All-inclusive
from
$2,699USD per guest

San Juan & the Virgin Islands

Port to port
San Juan to San Juan
Departure
December 27, 2026
Duration
7 Days
Ship
Star Pride
?
Cruise only
from
$3,299 per guest
?
All-inclusive
from
$3,299USD per guest

Costa Rica & Panama Canal

Port to port
Colón to Puerto Caldera
Departure
January 2, 2027
Duration
7 Days
Ship
Wind Star
?
Cruise only
from
$5,699 per guest
?
All-inclusive
from
$5,699USD per guest

Monteverde Cloud Forest & Arenal Volcano Cruise Tour

Port to port
Colón to Puerto Caldera
Departure
January 2, 2027
Duration
10 Days
Ship
Wind Star
?
Cruise only
from
$2,499 per guest
?
All-inclusive
from
$2,499USD per guest

Windward Islands Surf & Sunsets

Port to port
San Juan to San Juan
Departure
January 3, 2027
Duration
7 Days
Ship
Star Pride
?
Cruise only
from
$3,999 per guest
?
All-inclusive
from
$3,999USD per guest

Star Collector: Lovely Leewards

Port to port
San Juan to San Juan
Departure
January 3, 2027
Duration
14 Days
Ship
Star Pride
?
Cruise only
from
$2,499 per guest
?
All-inclusive
from
$2,499USD per guest

San Juan & the Virgin Islands

Port to port
San Juan to San Juan
Departure
January 10, 2027
Duration
7 Days
Ship
Star Pride