East or South to St. Thomas from the Chesapeake

Feb 24, 2024
6
Island Packet 32 White Stone, VA
All, I have an Island Packet 32 that I am currently outfitting for a trip the the Virgin Islands. I have been sailing for 20 years now on the Chesapeake Bay, having circumnavigated the DelMarVa twice, with one coastal run up to Delaware. My boat is in excellent shape, is very blue water capable, and will be provisioned with all of the operational and safety equipment needed to make the run safely when ready. My question involves which route to take? Leaving from the Chesapeake, there are two routes to get to the Virgin Islands; due East across the gulf stream until you hit the doldrums, then grab the trades flowing South, dropping down on top of St. Thomas. Or you can follow the ICW South, cutting in and out of the "ditch" until you reach Stuart, FL, then follow the chain of islands eventually to St. Thomas.

Both are problematic to me for a variety of reasons. Option #1 going due East means total exposure until you reach your destination, but with proper planning and provisioning will get you there in approximately 14 days of continuous sailing. Option #2 going South using the ICW means less exposure to severe danger, but more exposure to breakdowns and damage, and is a 1 -2 month affair in getting there.

I see the advantages and disadvantages of Option #1 as follows:
Advantages: Getting there quickly, low motor hrs compared to ICW, low probability of damage/breaking something/running aground
Disadvantages: Inexperience with open ocean sailing, no exposure to 24hr sailing, full exposure to storms with no place to hide, real danger if something goes wrong

I see the advantages and disadvantagers of Option #2 as follows:
Advantages: Limited exposure to storms, easier to plan & provision for, help available if needed, ocean sailing & 24hr sailing taken in small bites
Disadvantages: Time required, wear & tear on the motor, more exposure to damage/breaking something/running aground, will cost a lot more to provision

Even with no true open ocean experience, or with 24hr sailing, I think both can still be tackled with no prior experience, so long as there is proper planning. Am I fooling myself thinking that I can tackle Option #1 for my first trip to the Carribean, or should I err on the side of caution my first time out, and take the ICW?

Paul
 

DArcy

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Feb 11, 2017
1,704
Islander Freeport 36 Ottawa
Welcome to the group!

I have not made either trip so I'm not really qualified to answer but, this is the internet so I'm going to answer anyway ;)
I have sailed in the Virgin Islands and Caribbean but not to Caribbean.

The answer may depend more on what time of year you plan on leaving. I'm not sure your assumption on breakdowns is valid, open ocean sailing provides a lot of opportunity for breakages. Less chance of a grounding though.

Heading East through the Caribbean from Florida will be up wind, pretty much the entire way at any time of year. If you head East from Virginia then turn right at some point you may have more favorable winds depending on when you leave. Looking at the Pilot Charts for the North Atlantic it looks like November and December are more likely to have favorable winds as you head South but there is more chance of a gale. The summer months have less chance of a gale but it looks like there are more South-Easterlies South of 30°N.

If you chose the offshore route you could plan a stop in Bermuda, or at least consider it as a bailout plan if things go sideways. I know one person that changed plans half way and opted to stop in Bermuda taking that route when the weather turned sour.

If you have not sailed overnight, or made passages, you may want to experiment with that closer to home to build some overnight miles before setting off for a 2 week passage. The alternative is to find someone with offshore experience and invite them along. You may need to cover return airfare and other expenses but that would probably be worth it.

The chances are you can make either one of these options work with good planning.
 

dLj

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Mar 23, 2017
3,425
Belliure 41 Sailing back to the Chesapeake
Tell us more who will be sailing, are you solo sailing? Do you have crew? If so, what experience do they have.

You should not do that trip June through November.

Do you have time constraints? Is there a reason you are putting time in your post?

Do you want to get open ocean experience? Do you want to explore the ICW? Both are good options.

dj
 
Jun 4, 2004
1,073
Hunter 410 Punta Gorda
I would not consider Option one with your experience and boat. Bad stuff can happen offshore.
 

dLj

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Mar 23, 2017
3,425
Belliure 41 Sailing back to the Chesapeake
I would not consider Option one with your experience and boat. Bad stuff can happen offshore.
@Sailgunner Not sure why you say this.

The Island Packet 32 is quite a seaworthy boat. The OP's sailing experience is quite good. Doesn't have off-shore experience. But we also don't know who the crew may be.

I'm pretty aware of what can happen offshore. The trip being proposed is a good beginning trip as off shore trips go.

Care to give more as to why you don't think this would be a good option?

dj
 
Aug 19, 2021
495
Hunter 280 White House Cove Marina
I have always wanted to sail from Norfolk VA to Fort Myers Fl. I thought it would be fun bounce down the east coast and sea the sites.

I was navy for 20 years and trust me the world is 70% water and once you have seen 1% of that, you have seen it all. There is one thing I do miss when out to sea, the blanket of stars once you get far enough out to see to get rid of all the light pollution.
 
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Jun 14, 2010
2,096
Robertson & Caine 2017 Leopard 40 CT
@Water Dancer fatigue will set in for the offshore route unless you have three in the watch rotation. You can do it with one capable crew (total two aboard) but it is difficult. If you don’t have at least one or two crew who are capable to stand watch alone I strongly recommend the coastal route, and (if you have at least two aboard) get some experience by making some overnight hops near-coastal.
IMHO it is unsafe to nap underway without keeping someone on watch.
Also, I think you underestimated the time needed to get south in the coastal route. Add at least one month. You will have routine weather delays, bridge delays, short daylight hours in Fall season limit ICW travel, and your windward route will all limit your weather windows.
Whether you go coastal or offshore, Nov/Dec tend to be stormy and weather patterns tend to be unstable in the North Atlantic and Eastern US, so you can’t count on a reliable long term forecast. If you hire a professional weather router don’t take their advice as gospel.
 
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dLj

.
Mar 23, 2017
3,425
Belliure 41 Sailing back to the Chesapeake
@Water Dancer fatigue will set in for the offshore route unless you have three in the watch rotation. You can do it with one capable crew (total two aboard) but it is difficult. If you don’t have at least one or two crew who are capable to stand watch alone I strongly recommend the coastal route, and (if you have at least two aboard) get some experience by making some overnight hops near-coastal.
IMHO it is unsafe to nap underway without keeping someone on watch.
Also, I think you underestimated the time needed to get south in the coastal route. Add at least one month. You will have routine weather delays, bridge delays, short daylight hours in Fall season limit ICW travel, and your windward route will all limit your weather windows.
Whether you go coastal or offshore, Nov/Dec tend to be stormy and weather patterns tend to be unstable in the North Atlantic and Eastern US, so you can’t count on a reliable long term forecast. If you hire a professional weather router don’t take their advice as gospel.
This is excellent advice!

dj
 

dLj

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Mar 23, 2017
3,425
Belliure 41 Sailing back to the Chesapeake
I was navy for 20 years and trust me the world is 70% water and once you have seen 1% of that, you have seen it all.
I'm going to have to respectfully disagree. Different parts of the worlds ocean are so different. It's quite amazing the differences in color, wildlife, wave forms, wind patterns and more..

And the stars? They must be seen in both northern latitudes, middle latitudes etc...

Just my perspective...

dj
 
Oct 26, 2010
1,904
Hunter 40.5 Beaufort, SC
How about a composite trip? Sail down the Chesapeake to Norfolk. Depending on weather and your confidence, offshore around the graveyard of the Atlantic (Hatteras) or the ICW to Wilmington/Southport. Then, again depending on weather, off shore for as much and as far as you feel comfortable planning ahead for plan "jump in" points keeping track of the weather forecast as you go. If you stay within, say 12 hours, or closer if you desire, you should be able to predict adverse conditions. The Bahama's are almost due south of Wilmington NC so if you are up to the trip with your crew you can make a beeline for that or parallel the coast (which is a mild C shape) down to Florida. You may be bucking the Gulf Stream though and closer in to shore may be able to catch some "eddys" to lessen the effect. Unless you are doing a delivery, there are some great places to "jump into", take a break and enjoy a relaxing visit. I would suggest Georgetown SC (great waterfront), Beaufort SC (great waterfront and marina or anchorage right near the town. Brunswick GA, St, Mary's GA, St. Augustine FL etc. just to name a few. Stop at as many or as few as you like. Half the fun of the sailing is the stops along the trip as much as the final destination. Don't make it a "delivery" as much as an adventure to explore place's you haven't been to yet. I know at least 2 "transiting" sailors who found the location of their next home right here in Beaufort SC doing just that.
 
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Jan 11, 2014
11,436
Sabre 362 113 Fair Haven, NY
The big question is crew. Solo or with a crew?

The next issue is sailing over night(s). It is an entirely different experience than sailing during daylight hours and for some being well out of sight of land can be unnerving. It would be better to gain experience sailing overnight before heading out on a 2-3 week offshore journey. It will be safer to get some experience and have safe time to regroup in a safe place.

The nonstop trip is not just about sailing and navigating, it is about living in a boat for weeks and sailing and navigating. Living aboard can be the most challenging, nothing is easier in a moving boat, especially if the weather turns sour. Cooking, sleeping, moving, and even using the head become more challenging.

You might want to get a copy of Jimmy Cornell's World Cruising Routes and study the options. The direct route you are considering is sometimes called I 65, sail east until you get to Longitude 65 W and then turn south. That route can be taken from anywhere along the east coast.

Given your limited experience with sailing overnight for multiple days, you might consider working your way down to GeorgeTown, Bahamas with a combination of ICW and off shore jumps. This will provide opportunities to learn what works best for you and your crew with longer sailing times. While many people cross to the Bahamas to enter at Bimini or West End, essentially long day sails, there are other routes that will give you more offshore experience and land you deeper into the Bahamas, entering at the Berry Islands or Nassau.

The one place I would absolutely avoid is going around Cape Hatteras. The IP 32 is small enough to easily transit the Dismal Swamp Canal, a really pretty route in the fall. Once you reach Morehead City NC, there will be opportunities to make off shore jumps all the way down the coast as weather and will provide.

Good Luck!
 
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Feb 24, 2024
6
Island Packet 32 White Stone, VA
All, many questions, I will try to answer. I would not make this trip solo, and plan to bring two crew members with me for this run (3 total). I am lucky that where I am on the Chesapeake, I am part of a large sailboat community, and I know a number of sailors who have already expressed interest in going whenever I am ready. All of the possible crew members have similar experience to me, own a sailboat themselves, some are members of a yacht club and have racing experience, one is even a rigger. However, all of us only have limited ocean experience (predominantly coastal, as most of us sailors). I do not have any strict time constraints on me in taking this trip, as I am in business for myself, so I can reserve large blocks of time off to take an extended trip. But on the otherhand, I am not retired, so I do not have the flexibility of taking off an entire season. That shared, I can reasonably reserve 4 - 6 weeks for the trip described. My main concern other than finding a good weather window that would give me the best chance of success in safely making this passage taking the East Route (Option #1) are the variables that can crop up at night that are vastly more difficult to handle than in daylight, and the ensuing fatigue that will undoubtedly set in with a slim but capable crew. The Southern Route (Option #2) I see as very doable with boat/crew/experience, but my worries there are that I will not have enough time to either reach or enjoy St. Thomas, and the exessive motor hours such a trip would require, even if I were to fall short of my destination. It seems to me that when most sailors get to the point that I am at now, and yurn to undertake a more ambitious trip like the one described, they usually talk themselves out of it due to the sheer size that such an endeavor requires. I have never been one to not accept a challenge, but at the same time I have to be realistic in my capabilities. My sense is that Option #1 is doable for me, but that I will never be able to know or learn enough beforehand to control all of the variables that could arise. So my question to the group then comes down to faith in my own ability as described. Am I crazy to take this leap of faith in me by taking the Eastern Route the first time?
 
Oct 22, 2014
21,105
CAL 35 Cruiser #21 moored EVERETT WA
There is always a first time.... Only you can untie the lines.

Just to add to the thinking.. Your route would likely take you through the Bermuda triangle.
1709224580945.png
 

dLj

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Mar 23, 2017
3,425
Belliure 41 Sailing back to the Chesapeake
All, many questions, I will try to answer. I would not make this trip solo, and plan to bring two crew members with me for this run (3 total). I am lucky that where I am on the Chesapeake, I am part of a large sailboat community, and I know a number of sailors who have already expressed interest in going whenever I am ready. All of the possible crew members have similar experience to me, own a sailboat themselves, some are members of a yacht club and have racing experience, one is even a rigger. However, all of us only have limited ocean experience (predominantly coastal, as most of us sailors). I do not have any strict time constraints on me in taking this trip, as I am in business for myself, so I can reserve large blocks of time off to take an extended trip. But on the otherhand, I am not retired, so I do not have the flexibility of taking off an entire season. That shared, I can reasonably reserve 4 - 6 weeks for the trip described. My main concern other than finding a good weather window that would give me the best chance of success in safely making this passage taking the East Route (Option #1) are the variables that can crop up at night that are vastly more difficult to handle than in daylight, and the ensuing fatigue that will undoubtedly set in with a slim but capable crew. The Southern Route (Option #2) I see as very doable with boat/crew/experience, but my worries there are that I will not have enough time to either reach or enjoy St. Thomas, and the exessive motor hours such a trip would require, even if I were to fall short of my destination. It seems to me that when most sailors get to the point that I am at now, and yurn to undertake a more ambitious trip like the one described, they usually talk themselves out of it due to the sheer size that such an endeavor requires. I have never been one to not accept a challenge, but at the same time I have to be realistic in my capabilities. My sense is that Option #1 is doable for me, but that I will never be able to know or learn enough beforehand to control all of the variables that could arise. So my question to the group then comes down to faith in my own ability as described. Am I crazy to take this leap of faith in me by taking the Eastern Route the first time?
Three on a trip like this is perfect. You won't have fatigue issues. I did a somewhat larger trip with two and we worked very well together. There was a couple times we did experience some fatigue but between the two of us we just worked together the get both of us back up.

Then I did a substantially longer trip with 3 total and there was never fatigue coming in. On a boat your size, I'd say three is a really good number.

We all learn by doing. The more you do the more you learn. It never ends.

I think if you want to do the off shore trip - with three people - you are in a good place. But you have to decide....

dj
 
Oct 26, 2010
1,904
Hunter 40.5 Beaufort, SC
Only you can decide but without anyone on your crew that has done extended offshore sailing I-65 may be a bit of a stretch (read ill advised). What is so special about a St. Thomas as the final destination? Are you planning on turning around and coming straight back after a few days or weeks in St. Thomas? IMHO its not the destination as much as the voyage.

You may want to check with your insurance carrier and make sure you are covered for that distance off shore? Some have restrictions in the fine print.
 
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Jan 19, 2010
12,377
Hobie 16 & Rhodes 22 Skeeter Charleston
I don't have any experience to offer but I do have some obervations that might be informative. I live in Charleston SC. I'm lucky enought to drive a boat to work most days and so I see what is on the water here... I see a lot of cruising sailors who come into the harbor and anchor over for a few days/weeks. Along the Ashley river there are two official and many unofficial anchorages. The boats turn over fairly regularly so ... I think it is fair to say that Charleston is a favorite spot to stop over. The ICW runs right through it and it is also a hopping off point for skips outside.
 
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Oct 26, 2010
1,904
Hunter 40.5 Beaufort, SC
Didn't mean to leave Charleston out of the mix of great places to stop. It has a marina that is an easy uber ride from the historic town and, as harbor's go isn't too far from a near-shore/coastal passage up to the main marina or anchorage. Thanks @rgranger for the reminder.
 
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