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Want Fewer Crowds and Better Prices? Read This

  • Writer: Kenneth Reece
    Kenneth Reece
  • 5 hours ago
  • 3 min read

Lately, I've realized I keep having the same question from clients over and over again:


"When is the best time to travel?"


My answer is probably not what most people expect...


Not during peak season.


Don't get me wrong, there are times when peak season makes sense. (Like a river cruise to see the tulips in bloom ) But if you're looking for a great balance of weather, value, and fewer crowds, I often find myself recommending what the travel industry calls "shoulder season."


These are the weeks just before or after the busiest travel periods. In many cases, you can enjoy the same destination with lower prices, smaller crowds, and a more relaxed experience.


Here are three of my favorites:


Caribbean Cruises


Many travelers immediately think about escaping to the Caribbean in January, February, or March.


And for good reason. The weather is wonderful.


But personally, I love cruising the Caribbean in September, October, and November.


The temperatures are a little more comfortable than summer, the humidity starts to ease up, and cruise fares are often lower than you'll find during the winter months.


I know what some of you are thinking.


"What about hurricanes?"


The nice thing about cruising is that ships aren't tied to one location. If a storm develops, cruise lines can and do adjust itineraries to sail around it. It's very different from staying at a resort where you may have limited options if a storm approaches.


I've enjoyed many Caribbean cruises during the fall, and it's still one of my favorite times of year to sail.


Alaska


If you've followed me for any length of time, you probably know how much I love Alaska.

While summer gets most of the attention, September is my favorite month to visit.


The mountains begin showing hints of autumn color, wildlife is active, and cruise fares are often lower than you'll find during the height of summer.


One September cruise stands out in particular. We were among the last ships of the season to visit the ports, and many of the shops were preparing to close for the winter the very next day. The sales were incredible.


For me, Alaska in September feels a little quieter, a little more relaxed, and every bit as beautiful.


Italy


I've visited Italy twice in November, and I would happily go back again tomorrow!  Well this fall; it's too hot for sightseeing in Rome, for me now.


The summer crowds are gone. Restaurant reservations are easier to get. Popular sights are less crowded, and you can actually slow down and enjoy the experience.


There's something special about wandering through Rome, Florence, Venice, or Pompeii when they aren't packed shoulder-to-shoulder with visitors.


The weather is generally pleasant, the atmosphere feels more local, and the overall experience is far more relaxed than what you'll find in the middle of summer.


The Bottom Line


Every destination has its own sweet spot.


For me, that often means September, October, and November.


As someone who has cruised Alaska in September, explored Italy in November, and spent many autumn days sailing the Caribbean, I can honestly say some of my favorite travel memories have happened during shoulder season.


Another favorite? The Disney Parks during the holiday season. While there's really no such thing as a slow time at Disney anymore, the period between just after Thanksgiving and the first two weeks of December is one of my favorite times to visit. The parks are beautifully decorated, the holiday entertainment is in full swing, and there is something truly magical about seeing Disney dressed up for Christmas.


The good news is that it's not too late to plan a fall getaway of your own. Whether you're dreaming of an Alaska cruise, a Caribbean escape, a European adventure with fewer crowds, or even a holiday visit to Disney, there are still some wonderful opportunities available this year.


Want to work with Kenneth? Visit his page to fill out a quote request form, or contact him below!



 1-678-478-9158


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