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What To Think About When Planning A Sailing Vacation

If you’d like to hit the deck of a boat and go sailing for a couple of weeks, then something like a sailing vacation or private cruise might be calling your name. And if either of these trips immediately appeals to you, it’s time to get planning! 

Because a vacation on the water isn’t the kind of vacation to just stumble into! You need to prep and make a solid budget – vacations like these don’t tend to come cheap! 

As such, here are a couple crucial things to think about when putting together your itinerary for a sailing vacation.

Where You Want to Go

Boating vacations, despite the name, need to stay pretty contained. You’re not going on a commercial cruise here, where the boat is big enough and well manned enough to be on the ocean for weeks on end. 

Keep it small, cut it down, and pick just the one region to go around. 

So, do you want to stay as close to home as possible, and simply drive up to stay on or near the lakes for a few days? Or maybe you want to rent a yacht in the Caribbean and have a salty spray adventure across the North Atlantic? 


Either way, choose your spot and don’t go too far out. Not only will this keep the price of the trip down, but it’ll be far less hassle to try and plan the whole thing out!

What Will Put the Price Up

And while we’re on your budget for your sailing vacation, we need to touch on a couple of other things that’ll put the price up for you.

How long you’re sailing for

2 or 3 days? 5 days? Maybe a full 7 days? Or do you want to spend 10 to 14 days on the water? 

However long you’re sailing for, the price is going to grow exponentially. And if you were planning a 2 week long trip round the Azores or through the Mediterranean, you might end up a little disappointed by the final price tag! 

Indeed, boating vacations tend to go up by about $3000 for every extra day you’re at sea. 

Remember, they’re a luxury trip in the first place, and you’re going to need to pay for the amenities, local fees, and keeping the boat running for that length of time.

Number of guests

Once again, the more guests you have, the larger the price grows. Because you can’t fit a family of 4 onto the same boat that a couple are hiring for a romantic getaway. 

You need space, you need bathroom facilities, and you need beds for the night. And the more beds you require, and the more days you need them for, the more unattainable your sailing vacation dream can get! 

When you’re planning a sailing vacation, keep budget elements like these in mind at all times. They’ll help prevent you overspending, overplanning, and seeing your sailing dreams burn out for the year. 

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Karen LeBlanc

Karen LeBlanc is an award-winning travel journalist and storyteller, honored with two Telly Awards and four North American Travel Journalists Association (NATJA) awards for The Design Tourist travel show. As the show’s host, producer, and writer, Karen takes viewers beyond the guidebooks to explore the culture, craft, cuisine, and creativity that define the world’s most fascinating destinations.

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