The Best Places to Cruise to in the Fall

The Best Places to Cruise to in the Fall

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Whether you’re an avid cruiser or you’ve never taken a cruise in your life, fall is a great time to hop aboard a ship and get a taste of the cruise life. Because the summer months are usually peak season for cruises, fall tends to mean fewer crowds and lower prices. Here, our Pittsburgh Airport parking company shares some of the best places to go:

New England/Canada

When you think about the beautiful oranges, reds, and yellows of fall foliage, you probably think about New England. Come September and October, the area is known for its colorful landscapes and just north of it in Canada is no different. If you’re looking for a scenic fall cruise, consider sailing between New York City and Maine or along the St. Lawrence River between Montreal and Quebec City.

The Caribbean

Fall in the Caribbean means peak hurricane season has passed and the heat and humidity of summer have died down, so what better time to visit? With easy flights out of Florida or Puerto Rico, travelers can enjoy a variety of destinations. Whether you choose a popular place like Turks and Caicos or the Bahamas, or a lesser-known island like St. Kitts, Dominica, or Grenada, you’ll love the beautiful weather and warm, turquoise waters.


Alaskan cruises only happen during a certain time of year (late April-September), so there are only a few September dates that correspond with a fall cruise. By booking one of these dates, you’ll have the advantage of more affordable packages and smaller crowds, though the temperatures are on the chillier side (usually in the mid-50s). Nevertheless, you’ll still enjoy breathtaking glacial scenery, wildlife viewing, and local culture.


While there’s no bad time to visit Hawaii, fall is a good time to go. Not only will you avoid summer crowds and elude the busy holiday period, but you’ll have a chance to explore the area without worrying about rainy days. Most cruises dock at several different islands, giving you a chance to experience each one individually. And because Hawaii is easy to access, you can get there early or stay late to extend your vacation and explore even more.


Most travelers overlook Bermuda when considering a fall cruise, but a trip to this North Atlantic island offers a unique experience. You’ll not only get a taste of Britain (the island is a British territory), but you’ll also enjoy pink sand beaches, crystal clear waters, great duty-free shopping, and friendly locals. Plus, cruises depart from a variety of East Coast cities including Boston, New York City, and Charleston.

Across the Atlantic

While some people cruise to get to a destination, others love the actual act of cruising and spend most of their time on the ship. If you’re one of the latter, consider a transatlantic cruise during the fall. Also called a “repositioning cruise,” these cruises offer travelers the opportunity to climb aboard a ship as it moves from one part of the world to another (usually from Europe to the U.S. or vice versa). And because you spend so many days at sea, these cruises are usually deeply discounted.

Which destination sounds like the perfect one for you? No matter where you decide to go, make sure you book your Pittsburgh Airport parking reservation with PIT Stop. We offer a convenient, affordable alternative to parking at the airport.