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Montreal to San Juan

History, natural beauty, culture and cuisine are just a few of the pleasures that await you on the northern part of this voyage, before you make your way south to sparkling Caribbean islands. Start your journey in Montreal, City of a Hundred Steeples, and train your ear to the sound of French – it’s something you’ll hear throughout Quebec. Overnight in Quebec City with its UNESCO World Heritage Old Town and find 400-year-old ramparts filled with compelling history and delicious bistros. Enjoy the breathtaking seascapes of Gaspé, waves crashing against limestone cliffs and sea arches, and watch sugar maples and birch trees flout their fall colors. Retrace the battles for North America in the Fortress of Louisbourg, the UNESCO town of Lunenburg, the Citadel in Halifax, and Boston – where the Freedom Trail leads you to Paul Revere’s house and the Old North Church. Then trade in your autumn palette for a riot of spring colors – blushing pink beaches, hot pink flamingos, pastel colonial towns and turquoise waters. Multi-day stays let you take full measure of Bermuda’s natural beauty, British charms, and 500-year history. Wander the well-preserved lanes of St. George’s, a UNESCO World Heritage Site that captures what a British colonial outpost looked like in the 1600s. Take in a volley of historic forts in Bermuda, St Kitts, and San Juan – many of them UNESCO sites as well. From there, it’s on to chic French St. Bart, which has earned its celebrity endorsements with 20-odd stunning beaches and a multitude of duty-free boutiques. One beach you for-sure won’t want to miss is The Baths on Virgin Gorda, where giant granite boulders form glorious grottos and divine pools perfect for a soak or snorkel. Your voyage ends in Puerto Rico, but colorful Old San Juan and a trio of Spanish forts will keep you busy as you wait for your flight home.

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Day 1: Montreal

Montreal is full of interesting architecture and is considered by many to be the creative capital of Canada. Named a UNESCO City of Design, Montreal attractions include Basilique Notre-Dame, Stade Olympique, Canal de Lachine, Old Montreal, and Habitat 67. Enjoy a meal at one of the terraced cafes of Plateau Mont-Royal and make sure you try Kamouraska lamb, Arctic char and poutine.

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Day 2: Quebec City

A focal point of French culture and one of North America’s oldest and most beautiful cities, Quebec City sits above the St. Lawrence River on a rocky spur with 328-foot cliffs. This French-speaking city was established in 1608 with the only fortified city walls remaining in America north of Mexico, and declared a UNESCO World Heritage City. The Old Town is packed with museums, cobblestone streets and mansard-roofed houses begging to be explored. Other historic attractions include the Fairmont Chateau Frontenac, Notre Dame Basilica, Battlefields Park and Terrasse Dufferin.

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Day 3: Quebec City

A focal point of French culture and one of North America’s oldest and most beautiful cities, Quebec City sits above the St. Lawrence River on a rocky spur with 328-foot cliffs. This French-speaking city was established in 1608 with the only fortified city walls remaining in America north of Mexico, and declared a UNESCO World Heritage City. The Old Town is packed with museums, cobblestone streets and mansard-roofed houses begging to be explored. Other historic attractions include the Fairmont Chateau Frontenac, Notre Dame Basilica, Battlefields Park and Terrasse Dufferin.

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Day 5: Gaspe

Four hundred miles northeast of Quebec City lies Gaspe, one of National Geographic’s Canada’s 50 Places of a Lifetime. This wonderful wilderness area is home to four national parks; Perce Rock; North America’s largest gannet colony; lighthouses and remarkable historic sites. Visit the modern cathedral built almost entirely of wood and make sure to try some of the local specialties such as French-styled lobsters and game.

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Day 6: Cap aux Meules

With its village main street and many restaurants and bars, charming Cap aux Meules is the gateway to the Magdalen Islands Archipelago located in the middle of the Gulf of St. Lawrence. The port bustles with fishing boats, ferries, and a well-equipped marina offering a huge travel lift crane for dry dock. Sites to see include the church of St. Pierre, constructed from the wreckage of ships and the lighthouse which now warns of the offshore shoals.

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Day 7: Sydney, Nova Scotia, Canada

Sydney is the largest city on Cape Breton Island where the hub of activity can be found at the waterfront where you’ll find the world’s largest fiddle. A popular tourist destination, grab a Cape Breton Artisan Trail Map and immerse yourself in the lives of local artisans. Hit Casino Nova Scotia or take a mining tour with the help of a local miner. Check out the year-round indoor Cape Breton Farmers’ Market or discover the history of the Membertou people at their Heritage Park.

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Day 8: Halifax

The capital of Nova Scotia was ranked the 4th best place to live in Canada back in 2012. It is a city with more pubs and clubs per capita than any other Canadian city and even one of the mayors was a brewmaster. The boardwalk on the waterfront follows the water’s edge and is lined with unique shops. Halifax is home to the longest running saltwater ferry and a 200-year-old restored fishing village. Be sure to find time to try fabled donair (pita, meat and sauce), the official food of Halifax.

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Day 10: Portland

The New England charm of Portland is a delightful mix of stylish and sophisticated, modest and folksy, with a reputation for great dining. There is a plethora of local art and music, lovely parks and a pleasing array of 19^th century architecture including beautiful Victorian-era homes. The cobblestone lanes of the Old Port district waterfront are alive with working fishing piers and warehouses converted into shops and restaurants.

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Day 11: Rockland

Rockland is a classic Maine coastal town and the lobster capital of the world. It has been recognized by National Geographic Travel as the “Top Adventure Town in Maine,” and “Coolest Small Town in US” by Budget Travel. Downtown Rockland is full of historic homes, shops and restaurants serving fresh local seafood. An impressive collection of Maine art can be found at the Farnsworth Art Museum and Wyeth Center. Bordering Penobscot Bay, Rockland is also known internationally as one of the best recreational sailing areas of the world.

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Day 12: Boston

Founded in 1630 by Puritan settlers, Boston is one of the oldest cities in the U.S. It was a pivotal place during the American Revolution for the Boston Massacre, the Boston Tea Party, the Battle of Bunker Hill and the Siege of Boston. Tourists to Boston see the Faneuil Hall Marketplace, the JFK Library and Museum, the Museum of Fine Arts, the New England Aquarium, and the USS Constitution.

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Day 15: Hamilton

The capital of Bermuda is the energetic heart of Bermuda. A walk along Front Street on the harbor features interesting pastel-colored colonial buildings and boutiques. Sites to see here include the Cathedral of the Most Holy Trinity, built in 1869 with a tower that displays panoramic views of the city. Find the Bermuda National Gallery and the Bermuda Aquarium, Museum and Zoo.

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Day 16: Hamilton

The capital of Bermuda is the energetic heart of Bermuda. A walk along Front Street on the harbor features interesting pastel-colored colonial buildings and boutiques. Sites to see here include the Cathedral of the Most Holy Trinity, built in 1869 with a tower that displays panoramic views of the city. Find the Bermuda National Gallery and the Bermuda Aquarium, Museum and Zoo.

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Day 16: St. George's

In 2000 St. George’s was named a UNESCO World Heritage Site, founded in 1609 by an English ship that got blown off course, Strolling the streets of St George’s will feel like a step back in time. The well-preserved buildings and fortress have made it a haven of British colonial architecture including St. Peter’s Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore’s Jungle, Cooper’s Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.

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Day 17: St. George's

In 2000 St. George’s was named a UNESCO World Heritage Site, founded in 1609 by an English ship that got blown off course, Strolling the streets of St George’s will feel like a step back in time. The well-preserved buildings and fortress have made it a haven of British colonial architecture including St. Peter’s Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore’s Jungle, Cooper’s Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.

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Day 20: San Juan

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.