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The Expert in Baby Boomer Travel

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The Royal Clipper in full sail. Photo courtesy of Star Clippers.

Star Clippers” Royal Clipper in full sail through the Caribbean. Photo courtesy of Star Clippers.

If romance is the universal language — and who says baby boomers have lost their sense of romance? — a Caribbean cruise is sure to spice it up with a potpourri of accents:

Perhaps a dose of “Yeah, mon” Jamaican hospitality one day, a Dutch treat on St. Maarten on another, and a dash of French joie de vivre on St. Bart’s on a third.

Or you could go British on Grand Cayman or all-American with a Spanish twist in Puerto Rico.

Stir in the Caribbean’s trademark turquoise waters, soft breezes, palm-fringed beaches, steel-drum beats, and alluring tropical ambiance, and you have the recipe for an unforgettable voyage.

Decision Time

Still, Caribbean cruises are as varied as the islands themselves, so you’ll need to make some decisions.

One is the itinerary.

Caribbean islands are strung like pearls across a million square miles of sea, with dozens of cruise ship ports beckoning among them. Most standard week-long cruises cover one of three regions — the Western, Eastern, or Southern Caribbean — though they sometimes overlap, especially on longer itineraries.

The beach at Jost Van Dyke today -- deceptively peaceful. Photo by nickelstar, on Flickr.

The beach at Jost Van Dyke, British Virgin Islands, is a popular small-chip cruise stop., Photo by nickelstar, on Flickr.

Islands often included in Western Caribbean itineraries are Jamaica, Grand Cayman, and Cozumel, Mexico.

Popular Eastern Caribbean stops include Puerto Rico, the Dominican Republic, St. Martin/Sant Maarten, St. Bart’s, St. Kitts, Antigua, the U.S. Virgin Islands, and the British Virgins.

Southern Caribbean itineraries may feature Barbados, St. Lucia, Guadeloupe, Martinique, Grenada, Aruba, Curacao, St. Vincent, and Dominica.

Itineraries may also be categorized as “Windward Island” or “Leeward Island” cruises, especially on sailing ships; the Leewards roughly coincide with the Eastern Caribbean islands, while the Windwards are more southerly.

Keep the weather in mind: while the Caribbean is generally warm year-round, the more northerly cruises may get a bit windy and chilly in winter, and the far southern islands are less prone to hurricanes in the fall.

The choice of ship is even more crucial — and more challenging, since so many cruise lines sail the Caribbean.

Small Ship or Large?

Trafalgar Falls, Dominica. Photo by Amy El-Bassioni

Trafalgar Falls, Dominica. Photo by Amy El-Bassioni

The largest ships are like floating island resorts, offering enough onboard activities to keep you going day and night. They can be great bargains, though because of their sheer size they’re usually limited to visiting the biggest, most popular ports.

Smaller ships, with their greater maneuverability, often put in at more remote, less trammeled isles.

While they generally fall into the “luxury” category, small-ship lines typically include extra perks in the rates, while offering more individual space and service.

And every cruise line, no matter what the price, has its own trademark strengths, such as creative dining plans or palatial public areas.

Some good news all-around: since Caribbean cruises often cost less than those to most other destinations, upgrading to higher-class cabins or ships tends to be more affordable. And with generally warm weather, a private veranda, say, becomes a more useful splurge.

No matter the itinerary, the ship style or size, or the cost of the Caribbean cruise, they all have much in common: the lure of the islands, the sea, the sunsets, and a flotilla of memories to take home.

With winter just a few months away (sorry about that!) it’s time to book that Caribbean cruise you’ve been thinking about, if you haven’t already.

In upcoming posts, I’ll offer some alluring possibilities.


Deal of the Day:  Aer Lingus, Ireland’s national airline, has a sale going, with fares to Ireland starting at $499 roundtrip today (September 8) through Wednesday, September 21, at 7 p.m. Eastern Time. Fares are available for travel on Aer Lingus’ scheduled, direct transatlantic services November 1, 2016, through March 31, 2017. Seats are limited, as they say, so act fast..

The $499 fares are good for Boston to Shannon, Hartford to Dublin, and New York (JFK and Newark) to Dublin. Fares from Chicago, San Francisco and Los Angeles are higher, with San Francisco the highest at $799, Los Angeles at $749 and Chicago at $629, all to Dublin.


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According to government and private surveys:

  • Leading-edge baby boomers (born between 1946 and 1955) and seniors account for four out of every five dollars spent on luxury travel today.
  • Roughly half the consumer spending money in the U.S.--more than $2 trillion--is in the hands of leading-edge baby boomers and seniors.
  • Baby boomers (born 1946-1964) travel more than any other age group.
  • When asked what they would most like to spend their money on, baby boomers answered “travel” more than any other category, including improving their health or finances.

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