Instead of a Cruise, Fly to a Cruise Destination Using Miles & Points

I love cruising. Mostly for efficiency. When you cruise, you’re on a floating hotel where you unpack once, visit several destinations, and travel between destinations while you sleep. That’s (almost) magic. However, as with most Good Things there are trade-offs.



  1. Port Stops can be Short and Rushed. Typical stays  are as miserly as 3 hours and as generous as 10 hours. But take into account the time it takes to get on and off (and to and from) the ship and your experience of a place can feel superficial.
  2. Some Ports are Throw Away Stops. Meaning you may not care to visit one or more ports on your itinerary. This could be due to danger (real or perceived), too short a time in port (feeling rushed), you’ve Been There, Done That, or lack of interesting things to see and do at a given port.

That’s why I say Pick a Port and spend at least two nights–what’s also known in cruising parlance as taking an Overland trip. Consider it not as a replacement for cruising, but rather as an intriguing alternative you may not have otherwise considered. If your idea of cruising is all about the ship and its amenities, go no further. Otherwise, think-outside-the-ship (and its itinerary) and explore overland scenarios.



Here’s an example. While looking for an anniversary cruise to the Caribbean I thought, well, I’m not much of a Caribbean Cruise guy. My wife and I have been spoiled with the cultural and culinary riches Mediterranean cruise ports have to offer. While we prefer them the trip had to be short (wife started a new job), so no flights to Europe this time round. Living close to several Florida cruise ports, we thought a Caribbean cruise suitable. Investigating further, we couldn’t find many interesting two to three night cruises–a pity, since we do in fact love the amenities of a good ship. So we did the following as an experiment:

  1. Looked at the itineraries of several 7 night Caribbean cruises. And chose a few ports we’d like to explore singly; that is to say, just one destination for our trip.
  2. Searched flight and hotel availability. To those select Caribbean port destinations using miles and points we had and were willing to burn.



The winner was Grand Cayman. Safe and scenic, it won thusly:

  1. Southwest flew there and had award availability for our dates of interest
  2. Grand Cayman had a five star IHG property that would accept the two free night certificates we had that were about to expire–the Kimpton Seafire Resort and Spa on Seven Mile Beach

The trip is booked. We can cancel penalty-free due to the generous cancellation policies of both Southwest and IHG. It remains to be seen if we’ll take the trip or celebrate closer to home. But that’s the beauty of having a diversified points portfolio: Options. Space. And Time.

So, to reiterate, think-outside-the-ship’s itinerary, choose a group of ports you’d enjoy visiting singly, then see which ports you can visit drawing on your current points portfolio. Don’t have a portfolio of miles and points? Then your journey should Start Here.

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