I wish we were one of those couples with unlimited access to sailing. Living aboard a perfectly appointed cruising yacht in the Virgin Islands or having a coastal home with our sailboat at a nearby marina.


But for now, our jobs that have us living in landlocked Colorado are temporarily thwarting our “sail whenever we want” lifestyle. What is a sail-seeking, travel-loving couple to do with limited vacation?

One word: Sailcation.

Trust me. And please ignore that Merriam-Webster doesn’t yet consider it a real word. What do they know anyway?  In my book it is definitely a thing. Carefully crafting sailcation adventures that marry chartering sailboats in beautiful places with visits on land to the surrounding must-see spots is an ideal way to spend your hard-earned time off.

In less than two weeks our next sailcation begins. We’ll first head to Montreal for three nights, then charter a boat for a week on Lake Champlain nestled between New York and Vermont. After that, we’ll embark on a self-guided craft brewery tour around New England, finally ending our trip in Portland Maine.

A perfect sailcation.

MW.com needs to get on board. I’ll help:



/sāl kāSH(ə)n/

  1. an extended period of leisure and recreation with the trip centered around a sailing charter experience and also including time touring the surrounding areas on land.
  2. a necessary excursion to ensure maximum cultural exposure and happiness while traveling.


  1. “when we sail around the Amalfi coast should our sailcation include time in both Florence AND Rome?”

You get the idea, but in case you need more convincing, below is a list of our favorite sailcations so far:

  • For my husband’s 50th birthday, we traveled to Venice then took a ferry from Italy to Split prior to our first Croatian sailing adventure.
  • In Belize, we sailed from island to island for a week then headed into the rain forest by rented jeep for a few days exploring Mayan ruins.
  • Last September for our 5th anniversary, we sailed in British Columbia for the first time before driving the beautiful Sea to Sky highway to Whistler for a few days and then back to Vancouver.
  • Thailand for my 50th birthday volunteering to care for elephants, sailing around Phuket, then heading to Chiang Mai was our most epic sailcation yet.

Planning a sailcation is an option for everyone, even if you don’t yet have your sailing certification. Here’s how.

Step 1: Identify your desired sailing location

The heart of any good sailcation is the sailing, so start there!

If you plan to hire a captain to sail for you or if you are a seasoned sailor with abounding skills, your options are limited only by your imagination. Greece, Grenada, Guadeloupe…and those are just the G’s! If you are newer to sailing and plan to skipper your own boat, there are many options, but plan to sail in a place that has conditions that are right for your skillset; The British Virgin Islands and Croatia would be a better choice for you than, say, Belize.

It is also important to understand the sailing seasons for each location. If your vacation will be in January, choose a location in the Bahamas or the Caribbean, for example, not the Mediterranean.

Step 2: Secure the boat you will charter

Once you know where you are going, research the charter options available and put a down payment on the boat to ensure it will be available for you on the days you need. If you need a captain, make sure that is coordinated as well. Do this sooner than later. In the busier seasons inventory does go rapidly and if you start early, you will have more options.

There are many charter companies both large and small, corporate and family-owned to choose from, and they are an easy Google search away. Sunsail and Navtours are two of our favorites. You can also use peer-to-peer resources like Boataffair that allow you to rent boats directly from the boat owners, who can also arrange for a captain if you do not have your sailing certification.

The point is, secure the boat and the dates you will sail as soon as possible so that you know when you will be picking up and returning the boat.

Step 3: Complete your itinerary planning

With the sailing dates nailed down and boat pickup/drop-off times noted, you can now book flights and schedule the rest of your travel. Sure, a little extra planning is required to successfully coordinate a sailcation. But the resulting rich experience of sailing to places you can only reach by boat paired with time on land to see storied cities and hidden gems is the very best way to travel.

What are you waiting for? Start planning today to make your dreams of sailing in Sicily, Greece, Whitsundays, or Mallorca while also exploring Rome, Athens, the Outback, or Barcelona a reality.  The options for both sailing and land adventures abound.  Is your budget or time limited? That’s ok. Sailcations to San Francisco paired with a wine country jaunt or to Cape Cod with a day or two on the New England coast are perfect.

So, the question isn’t whether sailcation is a real word (it should be) or whether you will end up planning a sailcation for yourself. The important question is: Where will you go first?



Lea Maxwell

Lea Maxwell is the sailor and scribe behind Escape Under Sail, a web|blog project that connects new and future charter sailors with the resources, information, and motivation they need to competently and confidently sail beautiful destinations around the world.

Web: escapeundersail  |   Instagram: @escape_under_sail   |   Facebook: www.facebook.com/escapeundersail/

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