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Old 04-03-2022, 06:50   #16
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Re: First Bareboat Charter - Upper Chesapeake

I don't have much experience with bareboat chartering. I did it once on Tampa Bay. While the charter company didn't have me do a check ride with one of their crew, they did do a very thorough orientation to the boat going over all the systems. As a result, we didn't get out until noon on the first day of our three-day charter. This limited us as to where we could go. Consider chartering for more than one day.

I have spent the last 6 years sailing the upper Chesapeake. I agree with those who've recommended chartering out of Annapolis. It's a great place to explore in it's own right. If you charter for more than one day, then sail across to St. Michael's. It's a great little town with great places to eat and explore.

I don't know where you've sailed before. You need to pay attention to the depths of the Bay. It's not unusual to be sailing in water with depths of 10-15 feet and it can get very shallow very quickly. Ask the charter company if the charter includes TowBoat US. You may need it.

Lastly, you share the Bay with the watermen who earn their living harvesting crabs. Give them a wide berth. You also need to keep a sharp lookout for crab trap buoys. Some of them are plainly marked, but many are not. I've even seen plastic milk jigs being used as a marker. You do not want to accidentally run over a crab trap buoy. It can get entangled on your prop or rudder and you'll find yourself making slower headway or even dead in the water if your engine was running and it gets snarled on the prop shaft. I speak from experience.
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Old 04-03-2022, 06:59   #17
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Re: First Bareboat Charter - Upper Chesapeake

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Originally Posted by letsgetsailing3 View Post
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.
It's completely up to the charter company if they feel he needs a check ride. I have 25years of sailing, 10 years owner operator of a Tartan 41, I sailed from NJ to Grenada and back over 10k miles in that trip alone, 4 completed week-long charters as captain and several more as crew, And they still make me do a check ride! In the USVI, CYOA had my wife, not me, do the check ride as they require 2 competent captains (check ride was over 2 hours long)... And yes, he could do the check-in and chart review in an hour, maybe, but will the charter company have personnel dedicated to his charter and nobody else? I have found that they spread their time to other duties/charters and what could be done in an hour usually takes several hours.

Yes, it is possible he may not have to do a check ride and it is possible he could be off the dock in an hour, but I think he should call the charter company and ask these specific questions. In my experience, it is a half day ordeal to leave the dock.
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Old 04-03-2022, 07:12   #18
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Re: First Bareboat Charter - Upper Chesapeake

This is now 'ancient history' but... our first charters were in the upper Chesapeake in the early 80's. We chartered out of the Sailing Emporium in Rock Hall. First trip was as you: me the wife and two kids. We took a 27' Mariner for a week - that was plenty big enough for the four of us.

On the first trip, we sailed over to the Magothy River and anchored for the first night. Was an easy day-sail under good conditions. Other places to check out are St, Michael's and Annapolis. We anchored at St, Michael's and used the city docks in Annapolis. If conditions are really good consider sailing down to Thomas Point to see the lighthouse and hole up in the South River for the night.

I would suggest a weekend charter Fri-Sun. (I'm not sure you could even find an overnight.) Fri-Sun has you on the boat two nights and that should be manageable. As I recall, we came down to the boat on Friday and checked in, spent the night in the slip, and sailed off on Sat morning.


As to 'check-rides'? I haven't chartered now for 25+ years but was always able to get out of them. I always sent my sailing resume, with references; the check-rides were never mentioned up-front or in the literature/contract. I would point that out, and agree to take someone out to verify I could handle the boat, but... I wasn't going to pay for their time and they would have to have someone pick them up from where every we were planning to spend the first night. Worked every time.
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Old 04-03-2022, 13:09   #19
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Re: First Bareboat Charter - Upper Chesapeake

Haven charters out of Rock Hall, md. Great owners, great company.

https://www.havencharters.com/

I chartered there for years before I bought my boat. Rock Hall is adorable! (I bought my boat and stayed in Rock Hall as home port). There is a small beach, it's walkable with shops and restaurants and fun stuff for kids. Multiple protected anchorages within 4 hours sailing in many different directions so you can always sai regardless of wind direction. For example, Dobbins island, eagle cove, Bodkin creek, hart miller island, Sue creek swan creek, fairlee creek.

Annapolis is 18 NM southwest, and St. Michaels is 21 NM southeast.

The miles river has awesome anchorages, shaw bay, the wye river, cox creek, you name it!

Check out haven charters. We won't be disappointed. You can tell Jacki and Dave that I recommended them.

Have fun!!

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Old 11-03-2022, 08:47   #20
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Re: First Bareboat Charter - Upper Chesapeake

I sailed the Chesapeake for a few decades before I moved to New England. Wonderful sailing. My favorite months were June (not so many jellyfish that can make the water unswimmable) and September (not as hot as mid-summer and the delicious local crabs are really fat by then).

Question: has all the family been out in rolling seas? I'm asking for seasickness can ruin a weekend for everyone on board. In hotter weather, the notorious Cheasapeake line squalls can blow up to 80 knots or more on very short notice. Keep and eye on the northwest to see them coming and get your sails down.

Also, are you familiar wih chart plotters? These devices are very useful in the shallower water of the rivers.

My favorite towns/rivers are Chestertown on the Chester River and Oxford on the Tred Avon. These towns are probably too distant for a 2-nighter, unless you find a charterer nearby. Easton, further up the Tred Avon is another nice, somewhat larger town.

If you have a choice of a shallower draft yacht, take it, for some of the prettiest, quietest anchorages don't have much water depth.

There are several books and cruising guides for the Chesapeake.

Enjoy your first family overnighter. With decent weather, it will be memorable.
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Old 11-03-2022, 10:11   #21
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Re: First Bareboat Charter - Upper Chesapeake

ShinyHappy, I will add my endorsement for Haven Charters. They were my first bareboat charter. During our pre-departure inspection, we found that one of the stove knobs did not work. Not a big deal, we could have made do, but they fixed it immediately. They reviewed my itinerary and made some suggestions for improving it. They were satisfied enough with my sailing resume that no demonstration run was required. And if we had any doubts about redocking, they were willing to help us with that.
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Old 13-03-2022, 15:36   #22
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Re: First Bareboat Charter - Upper Chesapeake

Good recommendations posted, used to sail in the Annapolis area quite a bit. In the White Hall Bay area (radio towers, North of Annapolis), may want to check out Cantler's for crabs on Mill Creek. South of Annapolis, Harness Creek had some good "hurricane holes". The Annapolis sailing school used to do overnight group trips but I don't think that's what your looking for. On St. Michaels the locals can get a bit salty, we were docked at the museum and were standing in line to get into a restaurant when this drunk kid started accosting people in the line and the police seemed somewhat hesitant to do much about it, believe they said he was a relative of the Mayor or some council member. Doubt that has changed much so I would put some thought into establishments you visit in the smaller towns. Remember staying in a place by Annapolis and about 05:00 was awakened by must have been twenty lawn tractors, found out later they were water men who lost their drivers licenses and that's how they got to work. Rock Hall is another port, NE of Annapolis. Baltimore Harbor might also be of interest to you. I've docked in Annapolis Harbor and other than the "way too much money crowd" that you may encounter there the rate wasn't bad. The jellies used to be bad in that area and the summer forecast is a usually a "chance of thunderstorms" loop. Be prepared to get bombarded by bugs under the bay bridge and the fog in that area can be impressive.
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Old 14-03-2022, 08:20   #23
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Re: First Bareboat Charter - Upper Chesapeake

I agree, Haven Charters in Rock Hall. Call them and I'm sure your experience should work. Rock Hall, best little town short of St Michaels. Not very good to plan one night, 2 or 3 works best.
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Old 14-03-2022, 12:57   #24
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Re: First Bareboat Charter - Upper Chesapeake

Cool! Exactly how we started out some decades ago.

First, a J27, fabulous boat that it is, is too small for a weekend if you're trying to get your bride and offspring to fall in love with sailing.

Second, Haven Charters in Rock Hall, Md. has 2 Beneteau 38.1 yachts for charter. Those two boats are newer so will feel modern, clean and roomy. Twin wheels so lots of space for everyone in the cockpit. Don't be intimidated! A sloop is a sloop is a sloop and a newer bigger boat is actually going to be easier to handle than an older smaller boat. The only tricky part will be under power around the dock. But that's gonna be tricky regardless. Learn which way the boat prop walks in reverse while you're at your first anchorage, (likely to starboard) and do everything in slow motion when around immovable objects. Your crew can fend off if you're not raging into or out of the slip.

First boat we ever chartered was a Sabre 30 out of there. A really odd thing about that boat is the the prop shaft does not come out the center line but is off too starboard and angled in that direction. Of course I didn't know that and it probably took 10 tries backing it down before I figured out it's movement well enough to get it into the slip! I'm sure the people inside were laughing at us. Afterward they told me what the problem was and said they forgot to mention it in the checkout. Uh huh, "forgot". I could only laugh with them cuz it was pretty amusing. Point is, no matter what happens, don't get frustrated, stay calm, laugh at your mistakes. You will be making them so you might as well enjoy it.

Have Fun!! (Oh yeah, don't let anyone take any long showers!)
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Old 20-03-2022, 05:33   #25
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Re: First Bareboat Charter - Upper Chesapeake

Thank you all for your great comments! Each of my family members has been on the water with me one way or another.

Haven Charters seems to be the choice. It is in a good spot for me so I will be looking hard there.

Thanks again for all the great comments, I need to read and re-read it to take it all in.
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Old 21-03-2022, 07:49   #26
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Re: First Bareboat Charter - Upper Chesapeake

Shiny,

When you get closer to chartering, let me know. I can give you some local knowledge.

Ben
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Old 22-03-2022, 10:11   #27
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Re: First Bareboat Charter - Upper Chesapeake

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Shiny,

When you get closer to chartering, let me know. I can give you some local knowledge.

Ben
Thank you, Ben!
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Old 02-04-2022, 07:23   #28
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Re: First Bareboat Charter - Upper Chesapeake

Definite 2nd to Haven Charters. Great, helpful, people
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