Star Collector: Fall Leaves & Caribbean Breezes
Ocean Cruise Memorii Pick
Windstar Cruises  ·  Star Pride

Star Collector: Fall Leaves & Caribbean Breezes

From Montréal to San Juan  ·  North America  ·  19 nights

Departure 9 Oct 2026
Return 28 Oct 2026
Duration 19 nights
Ports of call 12 ports
Ship Star Pride
Journey type Ocean Cruise
From
$6,931
per person
Request a Proposal
Voyage overview

What this voyage is

Windstar’s Star Plus Class of vessels – Star Pride, Star Legend and Star Breeze – each carry just over 300 guests and are hugely popular for very good reason.

These small ships accommodate 312 guests in large all-suite
accommodation, following the completion of the Star Plus
refurbishment programme in 2021 which saw the ships lengthened.
There’s a choice of restaurants, comfortable lounges, and plenty of
deck space, while the ship’s marina ensures you can enjoy the
complimentary watersports when anchored in hidden bays and tiny
coves.

Day By Day

Itinerary

1
9 Oct 2026
Montréal

Bilingual Montréal is Québec's largest city, a vibrant island metropolis with a distinctive blend of old style European charm and thrusting modernity. Architectural highlights include the beautiful Basilique Notre-Dame-de-Montréal, and the city also boasts the world's third largest botanical garden. Winters here can be harsh, but in summer the city comes alive with festivals, including the famous International Jazz Festival in June/July. Montréal is also a real Mecca for foodies, and can pose a serious threat to the waistline, with all manner of gastronomic treats on offer.

Memory Tip: Don't miss The onomatopoetic Tam Tam day if you’re around on a Sunday during the summer – go to Mont-Royal park to see, and hear, the drums.
2
10 Oct 2026
Portland

The windswept Isle of Portland is connected to the mainland by Chesil Beach, which curves west for 18 miles along the Dorset coast. The island is famous as the home of Portland stone and is rich in bird life, while just next door is the resort town of Weymouth, with its pretty Georgian harbour.

3
10 Oct 2026
Québec City

Québec City, the capital of French-speaking Canada, is one of the North American continent’s most beguiling cities. The pretty old town, a UNESCO World Heritage Site, is a joy to behold; the cobbled streets and church spires are enclosed within the old city walls, and many of the buildings date back to the 17th century

4
11 Oct 2026
Québec City
5
12 Oct 2026
At Sea
6
13 Oct 2026
Gaspé

The rugged Gaspé Peninsula is one of the most beautiful landscapes in the Canadian Maritimes, and the waters off the coast are a whale watching hotspot. Highlights include Forillon National Park, home to wildlife including moose and bears, and Bonaventure Island, where you’ll find one of the world’s biggest gannet colonies.

7
14 Oct 2026
Cap-aux-Meules (Magdalen Islands)
8
15 Oct 2026
Sydney

Sydney is the only real city on Nova Scotia’s beautiful Cape Breton island, a former steel and coal town that is reinventing itself as a cultural and culinary hub. The revitalised waterfront area is particularly appealing, and there are some interesting Loyalist-era buildings in the city’s North End district.

9
16 Oct 2026
Halifax

The natural harbour at Halifax is the second largest in the world after Sydney, and this charming city has a proud maritime heritage. Take a stroll along the historic waterfront, delve into the vibrant arts scene or explore the beautiful coastal scenery of Nova Scotia.

10
17 Oct 2026
At Sea
11
18 Oct 2026
Portland

The windswept Isle of Portland is connected to the mainland by Chesil Beach, which curves west for 18 miles along the Dorset coast. The island is famous as the home of Portland stone and is rich in bird life, while just next door is the resort town of Weymouth, with its pretty Georgian harbour.

12
19 Oct 2026
Rockland (Maine)

Rockland sits on the picturesque coastline of Midcoast Maine, a pleasant little town with a vibrant cultural scene, home to some interesting museums and galleries. Nearby attractions include the 19th century Rockland Breakwater Lighthouse and the pretty town of Camden, and this is also a great place to feast on Maine lobster.

13
20 Oct 2026
Boston

Boston is one of the oldest cities in the USA, and in amongst the skyscrapers are plenty of red-brick buildings, a Georgian architecture that lends the city a distinctly European feel. Boston is also home to a wealth of cultural riches, including the superb Museum of Fine Arts, as well as the world famous Harvard University.

14
21 Oct 2026
At Sea
15
22 Oct 2026
At Sea
16
23 Oct 2026
Hamilton

Hamilton is Bermuda’s charming capital, filled with pretty pastel-hued buildings and bursting with British colonial history. Learn more about this past at the Royal Naval Dockyard, take a stroll along colourful Front Street, or relax on one of Bermuda’s beautiful pink sand beaches.

17
24 Oct 2026
St George's

St George’s was the first permanent British settlement in Bermuda and the first capital, situated at the eastern end of the islands. The town's charming historic architecture has earned it UNESCO World Heritage Site status, and there are several interesting museums, forts and churches.

18
25 Oct 2026
St George's
19
26 Oct 2026
At Sea
20
27 Oct 2026
At Sea
21
28 Oct 2026
San Juan

Founded by the Spanish in 1521, Puerto Rico’s capital is the second oldest European settlement in the Americas. Modern San Juan is a bustling city, home to over a third of the island’s population, but the cobbled streets of the Old Town remain the biggest tourist draw.

Memory Tip: Our tip Hunt out the very best chuletas Can-Can and pastelillos – local food at its best is great. Don’t settle for sorry imitations.
What is included

Fare inclusions

Alcohol included
Daytime activities
Meals included
Soft drinks, tea and coffee included
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