Coastal Cruising 101: Planning, Preparation, and the Importance of Flexibility

When it comes to coastal cruising, there’s a lot to think about, but with the right planning, preparation, and practice, you’ll set yourself up for success (and a good time)! As someone who has spent her life cruising the Coast of Maine, all along the East Coast, and beyond, I’ve picked up a few tricks and learned some important lessons. Plus, I’ve connected with a handful of Dockwa boaters about their cruise planning experiences, so I’ll be sharing some of their wisdom and insights too.

Table of Contents: 

Planning your Trip and the Ability to Adapt
Cruise Budgeting 101
Preparing: The Importance of Gear and Boat Upkeep
Provisioning
Practice: Putting It All to the Test
Brushing Up on Traditional Navigation
Crew Briefings and the Importance of Safety
Reflections and Conclusions

Planning Your Trip

Coastal cruising is all about finding the sweet spot between adventure and logistics. As much as I’d love to fully embrace the ‘go-with-the-flow’ vagabond lifestyle on the water, the truth is that it takes quite a bit of planning to make that mindset even remotely achievable. One of the first lessons I learned is how crucial it is to stay flexible with my time. I’ll be honest, that is much easier said than done, since I don’t always have the luxury of pushing my cruises (AKA my vacations) to next week. Since time isn’t always on my side, I’ve come to realize that a flexible mindset is the key to a smooth cruise. You can plan for months, but a 10-day forecast can flip your entire itinerary upside down— which is something all boaters can relate to.

En route from Portland Maine to The Camden Classics earlier this summer

For example, earlier this season, Dockwa proudly sponsored the Camden Classics, hosted by our awesome marina partners at Lyman Morse. My crew and I were sailing up from Portland, Maine, on my boat ‘Maui’ to be there for the event. On the third day of our trip, we ended up battening down the hatches and spending an additional night in Boothbay (because a 40-mile trek to our next destination in no wind and a torrential downpour wasn’t exactly appealing). In the end, that extra day in Boothbay turned out to be one of the trip’s highlights. Fortunately, we had left Portland a few days early, allowing us the flexibility to adjust our plan when bad weather rolled through.

When it comes to documenting my cruise plans, I have yet to find a single system that works perfectly for me. Without a modern source of truth to encompass all my ever-changing needs, I make due with more casual options.

For short cruises:

• I keep things simple. For example, before our last weekend trip, my partner Jack and I jotted down our must-visit spots and rough distances on a napkin while out to dinner. (The weather quickly reshuffled those plans, but for a short trip, it worked well enough.)
• I use Dockwa to keep track of our upcoming marina reservations, and that always keeps us on course.
• Short trips don’t need much beyond a quick outline and a few flexible reservations.

For longer cruises:

• The napkin method doesn’t quite cut it when trips get more complex.
• Some boaters, like Dockwa user Rod Heckman who cruises for months at a time, rely on detailed spreadsheets to manage every stop.
• Other boaters I’ve spoken with stick to pen and paper for keeping track of their plans.
  

While I appreciate the organization, personally, I don’t want to pull out my computer every day to manually adjust a spreadsheet—it's too much for daily updates. What I really wish for is a dynamic cruise planning tool on my phone that could keep everything organized and flexible in real time, without the hassle.

Rod's cruise planning spreadsheet, built in google sheets

Important Cruise Planning Resources

• Local cruising guides: These are essential for understanding the ins and outs of your cruising area, from navigation tips to hidden gems.

• Weather apps and resources: Tools like PredictWind and WindFinder help you stay on top of weather patterns and tides ensuring safe and smooth cruising. 

• Navigation tools: I rely on both paper charts and Navionics for route planning and real-time navigation.

• Boater reviews: I ALWAYS read reviews. I use the Dockwa app to read reviews of marinas from other boaters, and Navionics to check anchorage and harbor reviews to collect tips and avoid any surprises. 

Budgeting

Budgeting for a long coastal cruise is just as crucial as plotting your course. Marina fees, provisions, fuel—it all adds up fast. And don’t forget the time (and cash) it takes just to get your boat cruise-ready in the first place! Part of your pre-cruise planning should be focused on preparing for the expenses that come with your trip.

I became a first-time boat owner while I was still in college, and even now, after 7 years, two boats, and thousands of cruising miles under my belt, I’m still "balling on a budget." One thing I’ve learned is to plan for a few extra marina nights beyond what I expect, while also intentionally seeking out free anchorages (which of course offer perks beyond just being free!).

When I am searching for a marina, I narrow my options down using two key factors:

1. Do they have a Dockwa Deal?
   I always keep an eye out for Dockwa Deals. One of my favorite marinas of all time, Lyman Morse in Camden, Maine, historically offers great off-season discounts that I’ve definitely taken advantage of. And rumor has it Dockwa will be rolling out even more dockage (and fuel!) discounts in 2025—count me in!
   
2. What amenities do they offer?
   Amenities can really help stretch your budget. A courtesy car, for example, can save you money on Ubers or taxis when you need to provision, and free laundry and showers are simply a luxury. Plus, free Wi-Fi, and even on-site grills can make a marina feel like a 5 star experience without breaking the bank.

I’ve also chatted with plenty of boaters who are budgeting for a more established cruising lifestyle. Seasoned captain and Great Looper, Maria Langer, suggests budgeting around $100 per day for loop-specific expenses (not including boat repairs). Since Maria travels solo, that’s a per-person figure and covers everything from dockage for her 32-foot boat to food and recreation. If you are interested in saving a buck while cruising, Maria’s Nine Tips for Saving Money while Cruising the Great Loop is packed with advice that is applicable to any cruiser.

As another example, one Dockwa boater told me that he budgets between 30k and 40k for his five month cruise (including maintenance and repairs). This boater travels with a dog, and prefers to be on docks each night of his trip, which we know tends to be pricier than moorings for obvious reasons. 

On the other hand, some cruisers prefer to go off the grid—home is wherever they drop the hook. While that’s a great way to save, even the most dedicated anchorers have to face reality now and then. Repairs, maintenance, and fuel needs eventually bring everyone back to shore! Knowing how to shop for the deals in those moments makes a big difference!

Preparing: The Importance of Gear and Boat Upkeep

Preparation goes beyond just checking the weather or plotting your course. Before I head out, I make sure the boat is in tip-top shape—especially when it comes to the systems I use the most. 

One time, while approaching a mooring in Port Clyde, Maine, we discovered - with a big ‘clunk’ - that the coupler on my transmission had sheared two out of three bolts connecting the transmission to the prop shaft. I immediately put the boat in neutral, and luckily, we were still able to grab the mooring pendant to evaluate. After diving on the prop to make sure we were not tangled up in something, it was time to open up the engine compartment, where the problem became clear. Although I didn’t have the exact hardware needed, I had enough spare parts in my hardware kit to temporarily fix it (it wasn’t pretty… but it worked). We were able to limp into Camden Harbor with our interim fix, where there was a well-stocked hardware store to get the right parts.

I use a 2-tiered tackle box to organize my (smaller) spare hardware aboard Maui

Along with my pretty extensive hardware kit, I also carry extra fuel filters, impellers, oil, coolant, rigging materials, sewing materials, wiring, fuses, and a full tool kit on board. Captain Ron says it best, “If it’s gonna happen, it’s gonna happen out there!”. Be prepared for the worst! 

Note: On sailboats, avid rigging checks should be an extensive part of your pre-cruise checklist, as well as your everyday routine while actively cruising. One cotter pin could be the difference between an epic day of high wind sailing and a catastrophe.

Provisioning

When it comes to provisioning for a coastal cruise, preparation is key. Before setting sail, I always start with a detailed list of essentials. Long-lasting staples like rice, pasta, canned goods, and vacuum-sealed proteins form the backbone of easy, hearty meals like one-pot chili or stir-fry. Fresh veggies like carrots and cabbage last much longer than leafy greens. A handy tip I learned during an offshore passage some years ago: if you buy your eggs fresh from a farmers market, they don’t need refrigeration, saving you some ice box space (although securing them somewhere safe presents a different challenge, haha)! For longer trips, planning meals ahead is a game-changer, helping you avoid overpacking or running out of key ingredients mid-cruise. Oh, and remember… as the superstition states... NO BANANAS ALLOWED! They’re bad luck. So, if you want smooth sailing, leave the bananas ashore and grab some apples instead!

Storage is just as important as what you bring. Boat space is tight, so pack efficiently. Use airtight containers for dry goods to keep them fresh, and store items you’ll use frequently in easy-to-reach places. Canned goods can be tucked away, but make sure you label everything clearly. Take advantage of hanging space for produce with netted hammocks. For longer trips, some cruisers I’ve met use an auditing system to track provisions. They keep a simple spreadsheet or notebook with an inventory of what’s on board, how much has been used, and what needs replenishing. It’s a great way to ensure you don’t run out of important items like cooking oil, coffee, or snacks halfway through the cruise!

Taking advantage of hanging space aboard Maui, my 1967 Alberg 35'

Provisioning for the elements is also important. This goes without saying, but always pack your foulies, even if the forecast looks clear. I pack a beanie and wool socks even during my midsummer cruises in case I am cold after a late afternoon swim in the chilly Maine ocean.

And don’t forget the fun stuff! Some of my favorite provisioning extras include prioritizing space in the lazarrett for firewood (and s’mores materials of course!). We have also started bringing a kite on trips— it’s light, takes up no space (unlike the firewood 😂), and provides unmatched joy during those lazy afternoons at anchor. From books to craft supplies, little touches of entertainment can make all the difference in creating those perfect cruising memories

Flying a kite during our 2024 September cruise

Practice: Putting It All to the Test

I cannot stress enough how important it is to put your planning and preparation to the test before your big cruise. A few years ago, I crewed on a one-of-a-kind aluminum sailboat. Weeks before the owner and guests started their regular summer sailing schedule, we went out on a shakedown sail to make sure the crew was prepared, and the systems were ready to go. Lo and behold, as we raised sails for the first time, the hardware attaching the hydraulic boom-vang to the boom completely sheared. Thankfully, this was during a test run - right near our homeport marina- and we had time and resources to fix it before the peak season began! 

Shakedown cruises are not just about systems, though—they’re also about practicing how you’ll handle different situations. I recommend doing a mini-shakedown cruise to test your anchoring techniques, docking, and even provisioning strategies. 

Brushing Up on Traditional Navigation

One of the most important skills to brush up on before a long coastal cruise is traditional navigation. Electronics are amazing—until they fail, especially in unfamiliar waters. That’s why it’s crucial to keep track of your position, so if your GPS or chart plotter goes down, you can fall back on dead reckoning and paper charts. While I haven’t had this happen firsthand (thankfully!), I make a point to practice with paper charts and a compass every now and then. I also note my location periodically while on long passages, just in case things do go dark. Especially when cruising the often foggy coast of Maine, knowing how to plot a course with only a compass and paper charts can be a lifesaver if you lose electronics and visual bearings.

Revisiting Safety Procedures: Crew Briefings are a Must

Safety onboard is everything, and revisiting your safety procedures before setting out is essential.  It’s not just for your peace of mind, but for your crew as well. Maria, who we introduced in the budgeting section of this article, wrote an exclusive story for the Dockwa blog called 6 Things Every First Mate Should Know How to Do. Give that article a read and consider implementing crew briefings next time you cruise. I always make sure my crew knows how to handle the basics, whether it's operating the VHF, deploying the anchor, or being prepared for a man-overboard.

I recommend boaters make a safety checklist tailored to their boat and cruise. Additionally, remember to share your general cruising plan with an onshore contact. It’s important that they know where you’ll be, especially if you plan to go off the grid for a bit. This way, they won’t panic if they don’t hear from you for a few days, but they’ll know when to step in and help if things go wrong.

Takeaways from the Coast 

Cruising along the tricky Maine coast has given me firsthand experience with how important it is to be prepared. Whether it's navigating 10 foot tides and strong currents, or discovering a hidden gem, the key to cruise planning is being prepared while also being adaptable. 

Coastal cruising is as much about the journey as it is about the destination. If you give yourself the time and space to plan thoughtfully, prepare thoroughly, and practice often, you’ll find that you can enjoy the ride, even when things don’t go exactly as planned.

If you’re gearing up for a cruise, or are completing one, I’d love to hear your stories, challenges, or tips you’ve picked up along the way! Let me know your own experiences or reach out for advice—I’ve got plenty of stories from my own time on the water (and from other cruisers, too) to share.

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