Montreal to San Juan, 9 Oct 2026 (19 nights)


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Your itinerary
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Montréal is the largest city in Canada's Québec province. It’s set on an island in the Saint Lawrence River and named after Mt. Royal, the triple-peaked hill at its heart. Its boroughs, many of which were once independent cities, include neighbourhoods ranging from cobblestoned, French colonial Vieux-Montréal – with the Gothic Revival Notre-Dame Basilica at its centre – to bohemian Plateau.
Québec City sits on the Saint Lawrence River in Canada's mostly French-speaking Québec province. Dating to 1608, it has a fortified colonial core, Vieux-Québec and Place Royale, with stone buildings and narrow streets. This area is the site of the towering Château Frontenac Hotel and imposing Citadelle of Québec. The Petit Champlain district’s cobblestone streets are lined with bistros and boutiques.
Québec City sits on the Saint Lawrence River in Canada's mostly French-speaking Québec province. Dating to 1608, it has a fortified colonial core, Vieux-Québec and Place Royale, with stone buildings and narrow streets. This area is the site of the towering Château Frontenac Hotel and imposing Citadelle of Québec. The Petit Champlain district’s cobblestone streets are lined with bistros and boutiques.
Gaspé is a city at the tip of the Gaspé Peninsula in the Gaspésie–Îles-de-la-Madeleine region of eastern Quebec in Canada. Gaspé is located about 650 km northeast of Quebec City, and 350 km east of Rimouski. As of the 2011 Canadian Census, the city had a total population of 15,163
Halifax, an Atlantic Ocean port in eastern Canada, is the provincial capital of Nova Scotia. A major business centre, it’s also known for its maritime history. The city’s dominated by the hilltop Citadel, a star-shaped fort completed in the 1850s. Waterfront warehouses known as the Historic Properties recall Halifax’s days as a trading hub for privateers, notably during the War of 1812
Rockland is a town in Plymouth County, Massachusetts, United States. The population was 17,489 at the 2010 census. As of December 31, 2009, there were 11,809 registered voters in the community.
Boston is the capital and most populous city of the Commonwealth of Massachusetts in the United States and 21st most populous city in the United States. The city proper covers 48.4 square miles with an estimated population of 692,600 in 2019, also making it the most populous city in New England.
Hamilton is the capital city of Bermuda, a British island territory in the North Atlantic. Along the harbour, Front Street features pastel-coloured colonial buildings and high-end shops. The stone Cathedral of the Most Holy Trinity has a tower with city views. The Bermuda Underwater Exploration Institute offers ocean discovery exhibits. Northeast is the Bermuda Aquarium, Museum and Zoo, home to sharks and turtles.
Hamilton is the capital city of Bermuda, a British island territory in the North Atlantic. Along the harbour, Front Street features pastel-coloured colonial buildings and high-end shops. The stone Cathedral of the Most Holy Trinity has a tower with city views. The Bermuda Underwater Exploration Institute offers ocean discovery exhibits. Northeast is the Bermuda Aquarium, Museum and Zoo, home to sharks and turtles.
St. George's is a town on St. George's Island, in Bermuda. It's known for being the territory's first English settlement. Colonial buildings on and around central King's Square include the 18th-century town hall. Nearby, the Tucker House Museum is a typical home from the 1700s, with displays of crystal, silver and period furniture. Other notable landmarks include St. Peter's Church, founded in 1612.
St. George's is a town on St. George's Island, in Bermuda. It's known for being the territory's first English settlement. Colonial buildings on and around central King's Square include the 18th-century town hall. Nearby, the Tucker House Museum is a typical home from the 1700s, with displays of crystal, silver and period furniture. Other notable landmarks include St. Peter's Church, founded in 1612.
San Juan, Puerto Rico's capital and largest city, sits on the island's Atlantic coast. Its widest beach fronts the Isla Verde resort strip, known for its bars, nightclubs and casinos. Cobblestoned Old San Juan features colorful Spanish colonial buildings and 16th-century landmarks including El Morro and La Fortaleza, massive fortresses with sweeping ocean views, as well as the Paseo de la Princesa bayside promenade.
What's included
Fare overview
This sailing is shown as a cruise-only guide fare with Windstar Cruises. The fare is linked to the ship, itinerary and cabin category you choose. Drinks packages, gratuities, Wi-Fi, flights, transfers and shore experiences are only treated as included where they are confirmed before booking.

Sailing aboard
Star Pride
Your ship
With only 212 guests, a Star Pride cruise will make you feel like you're on board your own private small ship almost as soon as you step aboard. The sitting area of your spacious, newly refurbished suite gives you an expansive ocean view — making it a welcome retreat. When you're ready to make an appearance, the lounges, club, screening room, and library are waiting to be explored. Take some "you" time in the tranquil WindSpa . . . enjoy a dip in the pool . . . work off that decadent dessert in the Fitness Center . . . and, of course, you are always welcome to visit the Bridge to examine navigation charts with the Captain. 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.
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