First Bareboat Charter - Upper Chesapeake

[ShinyHappy]

I have ASA through 104. I am a member of a sailing club as a skipper which means I can sail our club boats as a captain (J27's). I would like to bareboat charter a sailboat in the upper Chespeake this spring with my wife and kids. I am the only sailor at the moment but I want everyone to get the feel of being on a sailboat for longer than a few hours.

My plan is to sail for a day, anchor overnight, and return the next day. Again, this is to get everyone used to being on a sailboat overnight. I have several questions.

With my background, can I expect to be able to bareboat charter a boat?

Charters overnight seems to be scarce. I understand the charter companies need to prep the boat and chartering for an overnight trip may seem like wasted time to them.

Can anyone recommend a charter company? I'll be coming down 95 so marinas close to where 95 meets the Chesapeake are ideal but a good marina is worth driving for. I would like 30-35ish feet. There are 4 of us (kids are adults) so some space but it's not a long time so we aren't looking for hiding space.

Finally, can anyone recommend an itinerary? I'd like to sail some day one. Find a nice place to eat, overnight at anchor and return the following day. Or two nights would also work. I'd like to sail somewhere instead of just sail so there are destinations that we can count down to. Walking quaint towns, good food, fun things to do are what I hope for.

Thank you for any input.

[requiem]

Not familiar with the area, but you might try giving these guys a call: https://www.havencharters.com/index.php

Their FAQ briefly mentions some suggested anchorages, and they seem to offer what you're looking for. In terms of experience, what boat did you do your 103/104 on, and how recently? The J27s feel a bit small to me, so the weak spots might be the matter of your experience on larger boats and having a second experienced person.

[Cheyne]

Not an overnight, but Norton's in Deltaville does a 3 day.

Cheyne

[Uricanejack]

I don’t know the area, so no recommendations.
Just general comment.

A local charter company is probably familiar with a local club, odds are you are not the first customer.

The sailing school and charter company I worked for. It would be no problem to charter a boat which was incrementally a bit bigger than what you are used to sailing. Probably less keen to charter one of the bigger boats. Eg 40 plus ect until you had a couple of trips with a 30 35 ish boat. And brought it back in one piece.

They would probably be very happy to give you some advice on short local trips where to go ect. Probably also quite willing to help with getting underway and a little bit of boat handling.
Spending the night on board isn’t a big deal. You will probably find getting comfortable handling the bigger boat in tight spots and navigating somewhere new the bigger steps.
The gear is a bit bigger but pretty much works the same. If anything bigger boats probably have more easy use items like furling ect.

As for durations. Weekend charters, why not, depends on availability. A boat left sitting at the dock is not making money. Higher seasons, short term less than a week probably not keen unless it’s short notice. A week long charter is just much more lucrative and more popular. Tougher to sell the remaining days. Weekends being prime time for changeovers and short rentals.

Lower seasons with greater availability, weekends are better than leaving the boat at the dock.
If you can get away during the week, A day charter or overnight is still an option.

I quite often would take an opportunity to charter a left over boat for a weekend at short notice. Quite often for a big discount, I did have the advantage of working for them, so it was a bit of a perk.
The also used to encourage graduates of their sailing school to charter some of their smaller boats for a couple of days in low seasons. To build experience.

Turn arounds were not a big problem, The company made it clear bring boat back clean fuelled, holding tank empty and undamaged. Or pay a fee.
It still got an inspection wash down ect. But it wouldn’t take long if boat was brought back clean.
Leave it full of beer cans, garbage and unwashed dishes. Extra charge.
probably the biggest issue for the charter company was having the boat inspected by a diver. Before you get your damage deposit back. In the low season, You might have to wait a few days until the diver has enough boats to make it worth while getting wet. In busy season there is enough turn over to make it worth while every day.

Best bet just phone up a few local companies and ask.

[ShinyHappy]

Originally Posted by requiem

Not familiar with the area, but you might try giving these guys a call: https://www.havencharters.com/index.php

Their FAQ briefly mentions some suggested anchorages, and they seem to offer what you're looking for. In terms of experience, what boat did you do your 103/104 on, and how recently? The J27s feel a bit small to me, so the weak spots might be the matter of your experience on larger boats and having a second experienced person.

Thank you for replying. They are one of the companies I have a tab open for. I took 104 on a 42ish foot Beneteau about 3 years ago and 103 on a 32 foot Hunter a year before that. Otherwise it's been rented dinghies and j27's.

I figured low 30's would be a good size. I don't want too big to handle, but big enough to act like a big boat for longer trips

[ShinyHappy]

Originally Posted by Cheyne

Not an overnight, but Norton's in Deltaville does a 3 day.

Cheyne

Thanks for responding. I've seen a few 3 day charters. I'm trying to do overnight so my family gets a taste without getting antsy.

[Stu Jackson]

First thing that came to my mind is: How comfortable are you in docking a bigger boat? I know you said you'd anchor out, but then you have to bring it back. When we did our first BB in the BVIs, we owned a 22 footer for a few years, but hadn't docked the 32 footer we BB'd. Turned out we didn't ever have to dock it. Just thought it might be something for you to consider, plan for and deal with beforehand if you need to. Good luck, have a great trip.

[Cuvee]

Check out Waypoint Annapolis https://waypoints.com/destinations/annapolis-md/

They offer day sail through multi-day bareboat charter options.

Annapolis is great town to visit. For a 1 day charter I would sail to St Michaels (25 nm). Easy anchoring or rent a slip. Another great, small town to visit with plenty of dining options, interesting shops, and the Chesapeake Bay Maritime Museum.

[obrient5150]

I sail out of Annapolis. If you can find a charter from there, a nice 3 day trip (if the winds are favorable) would be:
Day 1 - Sail to Wye River and anchor
Day 2 - St. Michaels - anchor and take water taxi to town
Day 3 - Return to Annapolis

Another destination is Galesville on the western shore. Less to do than St. Michaels but a shorter sail. Nice anchorage on the Rhode River for night 1.

You say your wife and kids are non-sailors. Make sure they enjoy the cruise and want to do it again. Have you done day sails with them?

If the weather is bad reconsider your plans to avoid a bad experience that sours them on sailing.

Tom

[letsgetsailing3]

I've chartered from Annapolis Sailing School before.


I took some classes there, but I bet they'll charter a boat to you.


It's been a while, but crossing the bay to St Michaels is really nice.

[Kd9truck]

Sounds like you have the skills, you week spot sounds like it could be in the anchoring skill set but docking could give you some anxiety, just take it slow have the fam around to toss lines and fend of things if a hot approach is necessary due to wind and current.
I jumped from a Beneteau 28 to a Jeanneau 44 with no issue and I enjoy the longer hull leanth as it spans the wave troths, significantly less tossing about, go bigger if your fam has tender stomachs. Imho

[zstine]

I've chartered from Havre De Grace at the north tip of the bay, but with the channel, you can't do an overnight. but they had small boats and were fine with inexperienced captains.

Haven yacht charters in Rock Hall is a nice location for an overnight since you could do a day sail and anchor back in the creek there. You can do the same from Annapolis. there's plenty of places to anchor right near Annapolis. with an overnight, don't plan to go anywhere!

An overnight is not practical in general. Keep in mind the first day includes a safety brief, a boat walk through, and likely a skills test motor around. It will be mid afternoon before you actually get to leave the dock. If you want to be anchored for dinner, you will have a few hours at most to sail. I highly recommend at least 3 days. Otherwise sailing is going to feel like a big PITA... who wants half a day of safety BS for 2 hours of sailing?

[Checkswrecks]

A second for Annapolis Sailing School. They just brought on a new boat so if not already sold they may be willing to rent Stargazer, their old (clean) Catalina 30. It's a Model II so it has the walk thru transom.

St. Michael's is beautiful but if it is too far or too many hours underway for kids, you could cross the Bay to Rock Hall. There are a number of water accessible restaurants on the west side too, such as Point house off the Magothy, Rumor Reel in Pasadena, and Brewers Landing on Back Creek. Watch the charts, depths, and markers if staying on the west side (really on both sides), because there are old trash dumps, shoals, and other surprises.

[zstine]

Just to explain what happens on day 1 of a charter..

Day 1:
- Board the boat at 9am.
- 10am they come do a walk through to show you the safety gear and systems on the boat.
- 11am you go to the office for a cruising brief and they show you a chart of where to go/not-go.
- Noon, lunch break.
- at 1pm they do your check ride.
- somewhere between 2pm and 3pm you get the boat to yourself.

If he wants to go out to dinner, he's got to have the hook down like 5-6pm latest. That gives him 2 or 3 hours. in a small boat sailing he's lucky to average 5knts. So like 10 miles range... From Annapolis, Rock hall & St. Mike's are out. Maybe he can make the Magothy, but he's better off planning to anchor in the Severn and just day sail. An overnight charter is just not practical to go anywhere.

Some charter companies offer to add a half day (so 2.5 day)... In other words, you get to board the night before your charter starts. Then it is be possible to get off the dock by noon. You may be able to make Rock Hall or maybe St. Michael's, but 'sailing' that distance will be very weather dependent (read unlikely) as they will need to make near hull speed and not beat/tack as that would add too much distance.

[letsgetsailing3]

If he has ASA 104 certification in hand, why do they need to do a check ride?


Seems to me he can do the boat check in and chart review in about an hour. I concur with the "check in the night before" suggestion.