Quick Guide to Planning a Perfect Boat Trip

March 14th, 2024 by team

by B.J. Porter (contributing editor)

Planning boat trips is a lot of fun, but there’s only so many chances to get time off and go – you really want to get it right! While organizing a boating vacation has the same basic considerations as a land vacation, the details are different for a week or more on the boat. If you’re new to boating, some things you have to think about might surprise you.

Where will you go?

The first big question is the destination. If you’re the type of boater who likes to mix it up and do something different every season, then focus on your itinerary first. Once you know where you’re headed, you can plan how to get there, what stops to make, and how much time you’ll need.

What’s Your Cruising Range?

Knowing how far you can sail or motor in the time you have narrows your reachable destinations. The speed and tankage of your boat is only one factor. You also need to know your limits – like how long you’re willing to travel at a stretch, or if you’re comfortable moving your boat after dark or overnight.

Remember, you’re heading out on vacation for a week or two, not re-staging the Odyssey. Even if you can cover 100 miles under sail during daylight, is that how you want to do this trip? At seven knots, that’s 14 hours of sailing, so you’d need to leave at sunrise or earlier to be stopped before dark.

Your aim is for interesting and fun, not grueling. Especially on family trips!

Is it the Destination, or the Journey?

For some, getting there is half the fun. Others want to just get there. Especially families with young kids, who aren’t always up for hours on end of sailing. Breaking the trip up into shorter segments with lay days may be a better approach.

From our old mooring in upper Narragansett Bay, we could get to Nantucket in a day. It was a long day, and could be pretty tough if the wind and tides weren’t with us. Breaking it up made it more fun and relaxing. We’d leave our mooring and aim for favorite stops along the way at places like Cuttyhunk and Martha’s Vineyard before pulling into Nantucket. For the trip back, we’d usually leave early the last day and grind it home in one day.

We’d give up time in the ultimate destination and be on Nantucket for maybe four days out of the week instead of the full week. But on the way we made fun stops in beautiful places, and vacation became a traveling adventure instead of a single destination event.

But it’s not for everyone, and sailing four days out of seven or eight on a vacation may not be what your group prefers. When you’re planning, think about the journey beyond just the last stop, and you can have a more varied and interesting time.

Mooring your boat

Anchoring buys you the most flexibility because you don’t need reservations. But there’s nothing easier than time in a slip, and moorings are less expensive and secure. If you need reservations, make them early. Popular island marinas and mooring fields fill fast, and the window to book may be small.

If you’re aiming for any first-come moorings, take advantage of your vacation status to beat the weekender crowds. First-come moorings are usually gone by mid-day Saturday. So don’t move then, and plan to arrive on almost any other day. You’ll have your pick of many moorings and can stay through the weekend rush.


Without reservations, staying an extra night, leaving earlier, or changing your itinerary completely is entirely at your whim. The only times to plan carefully are busy holiday weekends when large anchorages fill quickly. The downside to anchoring (as long as you’ve anchored properly!) is you may have a long dinghy ride in to town.

Many boaters avoid anchoring, especially if they don’t trust their ground tackle or their skills. When every wind shift and sound has you checking the GPS to see if you’re dragging, it doesn’t make for a restful night. But learning to anchor and trusting your ground tackle? Absolutely worth it, for the flexibility, savings, and comfort.


Moorings are a great compromise, because they’re almost always close to the docks and they’re a fraction of the cost of a slip. In many harbors, moorings are first-come, first served. But even if you need a reservation, there may still be a few first come available.

A launch or water taxi may serve a mooring field, and you often have access to marina services on shore like restrooms, showers, and trash disposal. You won’t have to worry about dragging anchor, though your neighbors will be a little closer.


Staying in a slip means anyone can get off the boat any time, and you don’t have to coordinate dinghy trips and launches. With shore power, you’ll have creature comforts like air conditioning and hot water, and you won’t worry about running the microwave or plugging or running inverters for large drawing appliances.

But a slip is the most expensive way to stay on your boat, and you often sacrifice privacy and quiet. Some docks can be busy places, and those without gates often have non-marina traffic walking by just to check out boats. If you prefer to be in the thick of things, it’s great, but there isn’t much solitude.

Weather and Contingencies

A schedule can be a cruising sailor’s worst enemy, and reservations for your vacation may press you into making moves and passages you might prefer to skip. That’s why you make a fallback plan, in case a big low pressure system rolls in while you’re between stops.

When planning any trip, plot a few bailout stops along the way. Plot your primary route assuming good weather, then look along it for safe places to duck in if the weather turns bad. Use the “Fork Route” feature to create a dump off route. Most chartplotter software has this.

What happens if the weather disrupts your trip for one or more days when you have a reservation, and it’s unsafe to leave the harbor? Can you stay where you are, or will you need to move to an anchorage or other location? Remember, it never hurts to ask, because if the weather is too nasty for you to move on, there’s a good chance it’s also too nasty for people coming in with reservations to make it.

Activities, Equipment, and Recreation

When you’re choosing stops, look at what there is to do, and what you might need to bring, reserve, or dress for. Some harbors are busy destinations with restaurants, theaters, tours, bike and car rentals, and on-shore games and attractions. Others are so peaceful and isolated. You’d be doing well to find a coffee cart or a sandwich shop and you’ll need to bring your own fun.

This is extra important planning for family trips, since children will want to get off the boat to explore or go to the beach. Consider what you could do, so you’ve got the fishing poles, swim suits, float toys and clothes that you need.

Provisioning and Preparation

Dining out on shore is always fun, but it can get expensive and bad weather can keep your crew boat-bound. Get your stores set before you leave.

Most populated islands have a grocery, but selection is limited and prices can be high. It’s always a good idea to have enough meals planned and stowed so you can keep everyone fed for a few days without going ashore.

If your boat has a freezer, you may carry enough for a week or more. But many coastal boats have limited freezer space, small galleys, and no microwave. Unless cooking is a passion for you, stick to simpler meals, especially those you can partially prepare in advance. One-pan meals are ideal, as are grilled meals (if you have a grill) which keep cleanup and prep times low.

Planning Resources

Published cruising guys can be excellent resources. Find them at online vendors, in chandleries, and some bookstores. They’ll have contact information and details about marinas, stores, services, and popular activities and restaurants. Be sure to check the publication date before you buy. Planning your trip around information that’s a decade or two out of date might get you some surprises when you arrive!

There are also good online resources that are up to date. The most comprehensive is Waterway Guides](https://www.waterwayguide.com) which can be purchased to integrate with iNavX or accessed separately. Some other helpful sites are U.S. Harbors, and CoastalBoating,net, and Marinas.com.

For regional information, many local cruising clubs and organizations offer their own insight, as do government entities which manage parks, moorings and marinas.

Examples include:

Boston Sailing Center Cruising Guide

Cruising Club of America’s Cruising Guide to Maine

Online Cruising Guide – information on Southern California, Mexico, and the Caribbean.

There are many others out there, and you’ll need to do some clever searches to find them for your region. Including terms like “cruising guide” and “sailing guide” are good places to start. Even if you’re planning to stay in a marina, searches for “anchorage” and “anchoring” in your sailing area often turn up excellent results.

Leave it Open for Fun

Finally, the biggest takeaway we had for planning was to avoid over-planning. A tight schedule can put you in some tricky sailing situations if bad weather arises. So leave plenty of time, have some wiggle room to stay or extend if you love a new location, and make sure you leave plenty of time for fun on shore and in the harbor!

3 Responses to “Quick Guide to Planning a Perfect Boat Trip”

March 25, 2024 at 9:45 pm, Peter Barclay said:

Please do forget about Cambridge as a destination. The town is a 5 min walk from the city marina and yacht club. It is the home of the only major resort on the bay and the only place where you can step off and play golf – Hyatt Regency Chesapeake Bay. More importantly, though, it is also the home of Harriet Tubman and the historic downtown. Come for a visit!


April 05, 2024 at 6:37 pm, Jack K said:

I think you meant to say “don’t forget” to visit Cambridge.


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