Off Season Sailing Destination Checklist For Sailors

This off-season Sailing Destination Checklist is for sailors to use when deciding where to go in the off-season. Hurricanes are prominent in the Caribbean in the off-season, and in the Mediterranean, it’s the winter months when the Med is stormy. Choosing the right off-season destination is crucial.

Storms/bad weather, logistics, local conditions, and the community vary widely, making it essential to make an informed decision.

This checklist is a tool for comparing and contrasting potential havens where you can ride out the down season. From the classic hurricane holes of the Caribbean to the sheltered marinas of the Mediterranean, this checklist empowers you to find the perfect fit for your vessel, experience level, and sailing goals.

Our favorite hurricane season sailing destination – Carriacou, Grenada

Checklists for sailors are blueprints for success.

If you want over 50+ tools and resources to help sailors save time, reduce risks, avoid hidden expenses, and enable a smoother sailing experience, check out my guide, Checklists For Sailors – Passage Planning, Boat Maintenance, Cleaning, Medical & More.

And remember, no matter where you decide to go, whether you stay on your boat or not, always have a Hurricane Plan in place. Make sure to have your plan prepared way before the hurricane season starts. By doing so, you’ll reduce stress. You’ll also be ready for your insurance company’s requests and know critical actions are already sorted out.

Key Factors to Consider When Doing Off Season Sailing Destination Research

• Safety from storms and adverse weather
• Accessibility and logistical ease
• Cruising possibilities (or suitable winterizing options in the Med)
• On-shore amenities and cost of living
• The local sailing community

Charleston, South Carolina – worst place for hurricane season!

How to Use This Checklist

1. Make Copies: Create a separate copy of this checklist for each potential hurricane season destination you’re considering.
2. Gather Information: Research websites, cruising guides, sailing forums, and weather resources. These will help to answer the questions on your checklists.
3. Compare & Contrast: Once you have completed checklists for multiple destinations, compare the pros and cons across all categories to make an informed decision

Off Season Sailing Destination Checklist

Destination: [Write in destination name]

Logistics

• Passage Length: How many days of sailing to reach the destination? Are there potential stops along the way?
• Flight Accessibility: Are there direct flights to the destination or nearby islands with easy connections?
• Marina Availability: Are slips readily available? Can they be booked in advance? What are the costs?
• Mooring Field Options: Are there reliable mooring fields with good holding? What are the costs involved?
• Haul-Out Facilities: If this is an option, investigate the availability and costs of reliable haul-out yards.

Weather Patterns in the Off Season Sailing Destination

• Hurricane Risk: What is the historical frequency and intensity of hurricanes in the area?
• Typical Season: Does the hurricane season have defined start/end dates or vary year to year?
• Weather Resources: What reliable weather forecasting tools are available specifically for the region?
• Hurricane Plan: What are you options if a hurricane/storm is coming? Make sure you have your Surviving Hurricane Sailboat Checklist – prepare this BEFORE hurricane season starts.

On-Land Considerations

• Cost of Living: Research typical expenses (food, accommodation if needed, local transportation).
• Amenities: Does the destination have suitable access to provisions, fuel, marine services, etc.?
• Cruiser Community: Is there an active sailing community for support and socializing? Spending six months in a marina with no liveaboards will not be very fulfilling!

Sailing Possibilities in the Off Season Sailing Destination

• Cruising Grounds: How extensive is the “protected” sailing area? Can you explore freely, or must you stay put? (This is one of the most significant factors for heading to Grenada during Hurricane Season. Check out: Sailing in Hurricane Season – Where Do Cruisers Go?
• Island Hopping: Are there other islands within safe cruising distances? What about passages beyond the typical hurricane zone?
• Restrictions: Are there any local regulations or permits required for extended stays during hurricane season?

Additional Notes:

• Personal Priorities: Are there specific things you value in a hurricane season destination? (Ex: budget-friendliness, remote beauty, specific onshore activities)
• Experience Level: Consider your sailing experience level when evaluating each destination’s safety and suitability.

Marina di Ragusa, Sicily – the BEST winter place in the Med!

Choosing Your Off-Season Haven

Remember, there’s no single “perfect” destination for every sailor. This checklist is designed to help you prioritize what matters most to you – safety, adventure, community, or budget-friendliness.

After thoroughly researching your options, weigh the pros and cons of each location. Don’t hesitate to reach out to the local cruising communities for real-world insights and experiences. With informed planning, you can make the most of the off-season, whether exploring new waters, hunkering down in a protected harbor, or making essential boat upgrades.

Where will your off season sailing destination research take you?

Trinidad – No hurricanes during the season, but it is way too hot and way too close to Venezuela (we had pirate issues!)

Other Articles/Videos Of Interest?

• Hurricane Season On A Boat & How To Survive It!
• All About Hurricane Season & What’s the Scoop?
• 10 Reasons To Spend Hurricane Season In Grenada
• Living aboard a boat in the Mediterranean – what’s the scoop?

Any Questions or Comments?

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