Sailing Trip Planning Checklist

Check out our new Sailing Trip Planning Checklist! Preparing for the next sailing season NOW, during hurricane season, is a smart and productive use of time for sailing cruisers. While you’re hunkered down in Grenada, in the Americas, or somewhere in Mexico get to work so you’re ready to head out sailing soon! Below is a comprehensive checklist to help you get organized.

Boat Maintenance and Service

While you’re waiting for the last hurricanes to cross the Atlantic Ocean, spend time wisely. Make sure you’re boat is in great shape so that you can spend the active sailing season exploring rather than having your head in the engine compartment! Boat maintenance and servicing is a key part of the Sailing Trip Planning Checklist.

• Haul Out: If applicable, consider hauling out the boat for maintenance and bottom painting.
• Inspect Hull and Deck: Check for any signs of damage or wear and make necessary repairs.
• Engine Maintenance: Service the engine, change the oil and filters, impeller, anodes, and inspect the cooling system.
• Sail Maintenance: Inspect and repair sails, rigging, and hardware.
• Electrical Systems: Check and service all electrical systems, including batteries and wiring. Clean up any noticeable signs of corrosion.
• Plumbing Systems: Inspect and repair plumbing, including freshwater and sanitation systems. Use head servicing kits.
• Safety Equipment: Ensure all safety gear, including life jackets, flares, EPIRB, life raft, and fire extinguishers, is in good condition. This is a must-have on a Sailing Trip Planning Checklist.
• Anchoring Gear: Inspect and service your anchor, chain, and windlass. Consider swapping your anchor chain around; move the section attached to the anchor to the bitter end.
• Navigation Equipment: Check and update electronics, GPS, and charts.
• Hull Cleaning: Clean and wax the hull to prevent growth and improve performance.
• Hull Inspection: Look for any blistering or other signs of hull damage.

Provisioning and Supplies

While you’re stationary, stock up on items that are inexpensive. Also, stock items that you won’t be able to get in other areas of the world. For example, when we’re in Grenada, we grab loads of British bacon and sausages. No other island in the Caribbean has these two items. If we’re on the east coast of America, we’ll go to Costco and stock up on EVERYTHING as food gets very expensive in the Bahamas, Burmuda, and the Caribbean. Food is a big part of our Sailing Trip Planning Checklist!

• Food and Water: Stock up on non-perishable foods and drinking water for the upcoming season.
• Spares and Tools: Inventory spare parts and tools, and make any necessary purchases.
• Cleaning Supplies: Purchase cleaning supplies, including boat-specific products.
• Safety Equipment: Check and replace any expired or damaged safety equipment.
• First Aid Kit: Review and replenish your first aid kit.
• Charts and Guides: Update navigation charts and cruising guides.
• Documentation: Ensure all boat and personal documents are up to date and organized.

Personal Preparation for the Sailing Trip Planning Checklist

When we’re enjoying the hurricane season in Grenada, we get all our paperwork sorted. In our Sailing Trip Planning Checklist, we look over our active cruising season and make sure that everything is up to date, we have a rough plan on where we’re heading and where we want to end up. We’ll turn our Skylink back. We also book any vacations away from the boat.

• Travel and Health Insurance: Ensure your travel and health insurance is current and covers sailing-related activities.
• Visas and Permits: Check the visa requirements for the countries you plan to visit.
• Passports: Make sure your passport is valid for the duration of your trip.
• Crew Training: If necessary, provide or undergo crew training or refreshers.
• Communications: Set up a reliable means of communication while at sea.
• Weather Forecasting: Familiarize yourself with reliable weather forecasting sources and tools.
• Cruising Plans: Plan your itinerary and routes for the upcoming season.
• Emergency Plans: Establish and communicate emergency procedures with your crew.
• Travel Arrangements: Book flights, transportation, and accommodations as needed.

Home and Personal Affairs

Here are more suggestions for your Sailing Trip Planning Checklist. For many of us sailing cruisers, we have a home or property back on land. We also have bills or personal health matters that we have to negotiate with. Before heading out for the next sailing season, consider these areas to cover before you’re living it large on the high seas!

• Finances: Ensure bills are set up for auto-pay, and have a budget for the sailing season.
• Mail and Packages: Ensure your mail forwarding is working or you have a trusted friend collecting your mail.
• Emergency Contacts: Share your itinerary and emergency contacts with someone on land.
• Pets: Make arrangements for the care of pets or pet passport details for your upcoming cruising plans.
• Personal Health: Schedule any necessary medical appointments or vaccinations.
• Personal Security: Does anything need to be done regarding your home/property and possessions?
• Birthdays and Special Occasions: Prearrange for birthday cards and gifts to be sent during your absence.

Education and Skills – Sailing Trip Planning Checklist

• Learn and Improve: Take online courses or read books to improve your sailing and navigation skills.
• Safety Drills: Practice safety drills! We practice the Man Overboard move all the time! If you’re sailing locally during hurricane season, ensure get these practice sessions in. You want to be able to do a MOB maneuver without needing to think about it.
• Language Skills: Learn or brush up on the local language of the regions you’ll be visiting.

Community and Socializing

• Connect with Other Sailors: The cruising community is amazing! While waiting for the active season to start, make sure to meet with other cruisers, discover what their plans are, make new friends, or find new boat buddies.
• Local Knowledge: Seek advice and information from sailors who have visited the areas you plan to visit.
• Plan Social Events: Organize gatherings or events with other cruisers in the hurricane hole.

Remember that preparation can vary depending on your sailing plans and boat type, so adjust this checklist accordingly. It’s crucial to ensure your boat is in top condition, you’re well-prepared personally, and your home affairs are in order before setting sail for a new season of adventures.

Get 50+ MORE Checklists

My recently new and improved Checklists for Sailors have every checklist a sailing cruiser/boat owner would ever need. Get organized, be proactive, uncover unknowns, avoid failures, prevent accidents, and ensure you’re sailing season is filled with no surprises! Get a copy today.

Click on the guide to get more information and buy!

"After months of drafting my own inadequate checklists, a friend recommended Kimberly Browns book Checklists for Sailors. I never realized that there were so many aspects to sailing that this very comprehensive and complete book covers in ensuring that risks are minimized through thorough pre planning. In addition, the offer of the Microsoft Word soft copy has allowed me to modify, consolidate and tailor these checklists to my own personal needs. As a serious sailor in Australia and the Pacific, I would highly recommend this book." Trevor James Bavaria 45 Cruiser

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