Cruising from Port Jefferson, NY to Block Island recommendations

[EME]

Hi All, we are planning to take a trip this summer from Port Jefferson, NY to Block Island for our very first time. We are traveling with kids, ideally would be great to stop by 2 more destinations on the way to break up the trip. If any of you can please recommend great destinations to stop at on the way and fun things to do especially with kids ages 11, 8 and 4. Also as far as staying overnight, we are planning to sleep on the boat. Do you recommend booking a dock, mooring or anchor?? If anchoring, do most destinations allow it in certain spots? As far as time wise, we are thinking to do 5-6 days trip. Thanks so much in advance!

[fourlyons]

If you think your kids are old enough to enjoy a museum, you might consider sailing over to Mystic and going up the river to Mystic seaport. The museum has kids related activities as well as a cute walkable downtown with ice cream shops and other things kids might enjoy.
The museum itself is a whole village reenactment of Mystic seaport from the late 1800s. The kids might enjoy going on the ships and smaller boats and there's a fun game room as well as a food court or food truck area and often live music.
We always anchor on the river, just upstream from mystic seaport. As long as your boat doesn't draw more than 6 ft, you should find room to anchor, except on busy weekends during the summer. You can also rent a slip right on the museum shore as well.
In decent conditions, it's a days run from Port Jefferson to Mystic and then another day's run from Mystic to Block Island.

[Reeve21]

North Cove in Old Saybrook is a mile so north of the mouth of the Connecticut River. It is all moorings, no anchoring, but this is a federal harbor of refuge so no charge to use an empty mooring. Suggest you pick one with a yellow streamer attached which means the owner is off cruising. If you pick up one without the streamer you will have to move if the owner returns. The attraction here with kids would be protected water for kayaks, sailing dingy, swimming, etc. No commercial development, a very quiet spot with 350 degree protection.

There is a town dock with water and a very nice dingy dock at the head of the harbor. If you want to splurge the low key yacht club will provide launch service, showers, grills etc. for a daily fee which might be up to about 40 bucks. But the town facilities work pretty well for a short visit (72 hour limit).

The walk to Main Street is less than half a mile and it has most everything you might want including a very good hardware store with some marine items. West Marine, mini golf and brewery tap room are a short uber ride away. Plenty of restaurants are within walking distance.

From here you will need to time your passage through the Race to avoid adverse currents. Figure 5 to 7 hours on a sailboat to Block depending on your timing and the speed of your boat.

Block can be a tough anchorage when it gets crowded. The shallower spots fill up and the holding is ? in the deeper spots unless you have real stout gear. The town rental moorings cannot be reserved, it is first come and they are coveted. If they are full harbormaster will rent you a vacant private mooring for the night.

Dockage at Block is $$$. If you have a decent dingy stay in the salt pond, on a mooring if possible. They are appx. $50 a night.

If you like to dig clams be sure to get a license at the harbormaster's office first Kids love it and I'm pretty sure they won't have to pay, adults are about 20 bucks a week or so.

Beach your dingy at dingy beach (really, that is what you do) and walk across the main road to a 3 or 4 mile long ocean beach.

Great trip, have fun.

[EME]

Originally Posted by fourlyons

If you think your kids are old enough to enjoy a museum, you might consider sailing over to Mystic and going up the river to Mystic seaport. The museum has kids related activities as well as a cute walkable downtown with ice cream shops and other things kids might enjoy.
The museum itself is a whole village reenactment of Mystic seaport from the late 1800s. The kids might enjoy going on the ships and smaller boats and there's a fun game room as well as a food court or food truck area and often live music.
We always anchor on the river, just upstream from mystic seaport. As long as your boat doesn't draw more than 6 ft, you should find room to anchor, except on busy weekends during the summer. You can also rent a slip right on the museum shore as well.
In decent conditions, it's a days run from Port Jefferson to Mystic and then another day's run from Mystic to Block Island.

Thank you so much for the suggestion. We actually visited this museum last spring when we went to foxwoods. So kids been there, but it prob won't hurt to visit again. How about watchhill, RI? Is it midway to Block Island? Also I hear storybrook is nice place to visit. Would love to get as much info as possible. Thank you!

[EME]

Originally Posted by Reeve21

North Cove in Old Saybrook is a mile so north of the mouth of the Connecticut River. It is all moorings, no anchoring, but this is a federal harbor of refuge so no charge to use an empty mooring. Suggest you pick one with a yellow streamer attached which means the owner is off cruising. If you pick up one without the streamer you will have to move if the owner returns. The attraction here with kids would be protected water for kayaks, sailing dingy, swimming, etc. No commercial development, a very quiet spot with 350 degree protection.

There is a town dock with water and a very nice dingy dock at the head of the harbor. If you want to splurge the low key yacht club will provide launch service, showers, grills etc. for a daily fee which might be up to about 40 bucks. But the town facilities work pretty well for a short visit (72 hour limit).

The walk to Main Street is less than half a mile and it has most everything you might want including a very good hardware store with some marine items. West Marine, mini golf and brewery tap room are a short uber ride away. Plenty of restaurants are within walking distance.

From here you will need to time your passage through the Race to avoid adverse currents. Figure 5 to 7 hours on a sailboat to Block depending on your timing and the speed of your boat.

Block can be a tough anchorage when it gets crowded. The shallower spots fill up and the holding is ? in the deeper spots unless you have real stout gear. The town rental moorings cannot be reserved, it is first come and they are coveted. If they are full harbormaster will rent you a vacant private mooring for the night.

Dockage at Block is $$$. If you have a decent dingy stay in the salt pond, on a mooring if possible. They are appx. $50 a night.

If you like to dig clams be sure to get a license at the harbormaster's office first Kids love it and I'm pretty sure they won't have to pay, adults are about 20 bucks a week or so.

Beach your dingy at dingy beach (really, that is what you do) and walk across the main road to a 3 or 4 mile long ocean beach.

Great trip, have fun.

Thank you so much for all the recommendations. Unfortunately we don't have a dingy yet, but hopefully most of these places will offer a taxi service. Do you know if we can reserve mooring at salt pond ahead of time or it also comes first serve? How many days do you think we'll need to stay at bloack island? Maybe we can add a stop on the way back as well? I'm thinking going from Port Jeff, making an overnight stop mid way, getting to block island, spending a day or two there, going back making another overnight stop, then heading to Port Jeff.

We are just nervous where to dock our boat as we've never done this trip.

[Plumbean]

Watch Hill is perhaps more than 60 miles from Port Jefferson, and almost all the way to Block. I haven't been there, so I can't weigh in on what it is like. Slightly shorter might be to turn the corner on the north fork and head for Greenport. Lots of options in that area (Greenport, Shelter Island, Sag Harbor, Montauk, etc.) But unless you are going to cross over to the Connecticut shore you will have a bit of a long day to get from Port Jeff anywhere (with 3 kids on board).

[Kettlewell]

My two cents is that I wouldn't go anywhere without a dinghy. Yes, Block Island does have launch service, but many places do not. Also, the kids can have a lot of fun in the dink, going to beaches, fishing, putzing around. Plus, it is a safety factor. I'm pretty sure moorings are first-come-first-served at Block with no reservations. Most harbors are like that. As others have written, anchoring there is difficult--get a mooring if in doubt.

[Reeve21]

Originally Posted by EME

Thank you so much for all the recommendations. Unfortunately we don't have a dingy yet, but hopefully most of these places will offer a taxi service. Do you know if we can reserve mooring at salt pond ahead of time or it also comes first serve? How many days do you think we'll need to stay at bloack island? Maybe we can add a stop on the way back as well? I'm thinking going from Port Jeff, making an overnight stop mid way, getting to block island, spending a day or two there, going back making another overnight stop, then heading to Port Jeff.

We are just nervous where to dock our boat as we've never done this trip.

You cannot reserve a mooring at Block. They have a launch service but the cost adds up pretty quickly and you may wait a while for a ride. Champlain's marina will take a dockage reservation, as will the Block Island Boat Basin. Payne's doesn't take reservations and they will raft you to other boats.

I have spent up to 10 days at Block at a time and not gotten bored. There is a lot to do if you like outdoor recreation. It is outside the protection of Long Island Sound and you will want fairly settled weather for the crossing. You may want to plan on more than a night or 2, good weather or bad. If you can extend your trip that would be good, as you are covering a lot of territory in 5 or 6 days. Unless you have a really fast boat and will be staying in marinas I'm afraid you may need more time to make it enjoyable, especially for the kids.

Watch Hill is very nice, but it is a long ride up the Pawcatuck River, not really on the direct route to Block from Mystic and certainly not from Saybrook or the north fork spots mentioned by another poster. Don't miss the merry go round, I think it may be the oldest in the country. There is not a lot else to do there for the kids, except the beach. You can anchor and dingy ashore to town or the beach (you really need one if you want to cruise, and given the cost of dockage it will pay for itself pretty quickly). There is also a yacht club that rents a limited number of moorings and may provide a launch service, I'm not sure about that. Great beach here at Napatree Point.


An alternative to Watch Hill is Stonington. There is an anchorage, Dodson's rents moorings and has a launch service. Neat colonial town with lots of history, lighthouse, tiny beach. The outer anchorage and mooring field gets a little rolly at times, and there is a foghorn that bothers some folks until they get used to hearing it. If you get a mooring at Dodson's ask if they can put you closer to the head of the harbor, well past the breakwaters, nearer to their facility. They are not cheap but it is a well run marina with a nice restaurant. If you want to eat ashore make a reservation at the Dog Watch, and ask to sit outside on the back porch facing the harbor--not the outside seating near the front door--which is fine, but faces the street).


From Stonington you are under 20 miles to Block and currents are less than what you will face if you go through the Race on the west end of Fisher's Island. I would recommend Watch Hill Passage, it is well marked. The other passages closer to the east end of Fisher's Island are much narrower and can be confusing if you are not familiar with them. And they don't save much time over Watch Hill Passage.

[EME]

Originally Posted by Kettlewell

My two cents is that I wouldn't go anywhere without a dinghy. Yes, Block Island does have launch service, but many places do not. Also, the kids can have a lot of fun in the dink, going to beaches, fishing, putzing around. Plus, it is a safety factor. I'm pretty sure moorings are first-come-first-served at Block with no reservations. Most harbors are like that. As others have written, anchoring there is difficult--get a mooring if in doubt.

Thank you. That's our plan someday to get a dingy but not this summer. Sounds like so much fun for sure though! We will aim for the mooring for sure!

[EME]

Originally Posted by Reeve21

You cannot reserve a mooring at Block. They have a launch service but the cost adds up pretty quickly and you may wait a while for a ride. Champlain's marina will take a dockage reservation, as will the Block Island Boat Basin. Payne's doesn't take reservations and they will raft you to other boats.

I have spent up to 10 days at Block at a time and not gotten bored. There is a lot to do if you like outdoor recreation. It is outside the protection of Long Island Sound and you will want fairly settled weather for the crossing. You may want to plan on more than a night or 2, good weather or bad. If you can extend your trip that would be good, as you are covering a lot of territory in 5 or 6 days. Unless you have a really fast boat and will be staying in marinas I'm afraid you may need more time to make it enjoyable, especially for the kids.

Watch Hill is very nice, but it is a long ride up the Pawcatuck River, not really on the direct route to Block from Mystic and certainly not from Saybrook or the north fork spots mentioned by another poster. Don't miss the merry go round, I think it may be the oldest in the country. There is not a lot else to do there for the kids, except the beach. You can anchor and dingy ashore to town or the beach (you really need one if you want to cruise, and given the cost of dockage it will pay for itself pretty quickly). There is also a yacht club that rents a limited number of moorings and may provide a launch service, I'm not sure about that. Great beach here at Napatree Point.


An alternative to Watch Hill is Stonington. There is an anchorage, Dodson's rents moorings and has a launch service. Neat colonial town with lots of history, lighthouse, tiny beach. The outer anchorage and mooring field gets a little rolly at times, and there is a foghorn that bothers some folks until they get used to hearing it. If you get a mooring at Dodson's ask if they can put you closer to the head of the harbor, well past the breakwaters, nearer to their facility. They are not cheap but it is a well run marina with a nice restaurant. If you want to eat ashore make a reservation at the Dog Watch, and ask to sit outside on the back porch facing the harbor--not the outside seating near the front door--which is fine, but faces the street).


From Stonington you are under 20 miles to Block and currents are less than what you will face if you go through the Race on the west end of Fisher's Island. I would recommend Watch Hill Passage, it is well marked. The other passages closer to the east end of Fisher's Island are much narrower and can be confusing if you are not familiar with them. And they don't save much time over Watch Hill Passage.

Thank you so so much for such a thorough response. If we lets say leave saturday to saturday. What destination on the way to Block Island would you recommend to stop for a day or two? I'm thinking after leaving Port Jeff to stop overnight one of the destinations, then spend a day or two there, then the next morning head out towards block island, stay there for anohter 2 days or so, after block island head back home with making another overnight stop at another desitination, and then head out home. What would be the practical and on the way spots out of the ones you recommended, of course kid frienly and for kids to enjoy? We will also have our doggie with us!

[psk125]

Watch Hill is sort of cute, but can be tricky to get into because the sandy channel can shift around a bit. (The boat we went there in drew 6'6".) Stonington is easier, but Dodson's is so overpriced we don't go there anymore. The yacht club has slips for almost the same price as Dodson's moorings.
Mystic is a great place, but it is a good long ways from Port Jefferson - 64 miles. At five knots (you don't say what kind of boat you have-we used 5 knots to plan trips on our J/36) that makes for a LONG day. Especially if it's hot and you have three children aboard. The 4 year-old is not going to last 11 hours. Stopping at Noank Shipyard might shorten the trip a bit, since it's at the river mouth, and you could Uber to Mystic pretty easily, but it's still a long way. Starting out with such a long haul might instigate a mutiny. Making shorter hops might be a better idea. Depending upon the wind, it might be good to have several options in your quiver.
There is a nice anchorage on the northeast side of Charles Island in Milford. Charles Island is a bird sanctuary where egrets nest in the trees. Watching them fly in and out is like an Olympic gymnastics performance. Further along would be the Thimble Islands, but anchoring there is difficult (read dangerous) because the granite that creates the islands does not provide much holding. We got stuck in a slip in Branford once and had to wait for the tide to rise before being able to leave, but that is also a possible stopover point. Guilford Yacht Club has slips (no moorings) for visiting boats, but they're obviously not free. When we were there (pre-Uber) they had bicycles available to ride into town, which has some nice restaurants and other shops. Duck Island Roads, off Westbrook, is an anchorage about 40 miles from Port Jeff. Just ashore from that is Pilot's Point Marina in Westbrook, which has a pool and other facilities that might be useful. From there, Mystic and then Block Island should be easy. Getting a mooring at Block Island can be a problem, especially on weekends or holidays. For the return trip, another place with stores, restaurants and a neat carousel is Greenport. Shelter Island is a bit calmer. We also enjoyed stopping at Fisher's Island, though the ice cream store and the gift shop are about all we found there, and it's a bit of a walk. Sag Harbor's Harbormaster has found us moorings several times when we put in there, and the town is quite pretty and lively. Three Mile Harbor is a huge anchoring basin, essentially surrounded by parks and open space, so not a lot for children to do unless you have kayaks & paddle boards.
This thread should give you some good ideas to plan around. Don't forget to take the tides into consideration with your routing, especially in Plum Gut, The Race, and Fisher's Island Sound. They can help or hurt with a 3 knot push.

[donradcliffe]

Originally Posted by EME

Thank you so so much for such a thorough response. If we lets say leave saturday to saturday. What destination on the way to Block Island would you recommend to stop for a day or two? I'm thinking after leaving Port Jeff to stop overnight one of the destinations, then spend a day or two there, then the next morning head out towards block island, stay there for anohter 2 days or so, after block island head back home with making another overnight stop at another desitination, and then head out home. What would be the practical and on the way spots out of the ones you recommended, of course kid frienly and for kids to enjoy? We will also have our doggie with us!

The worst trips are the ones where you follow a detailed schedule. Put slack days in and you can sit out bad weather or stay another day if the gang wants to.

[mbianka]

You might make a stop at Mattituck a 25 mile hop east of Port Jefferson. Reserve some dock space at the marina at the end of the inlet. The marina there has a restaurant and pool. It's also a quick nice walk into town for other restaurants and ice cream.

[malbert73]

We’ve been cruising from Chesapeake to NE for a bunch of years with our 2 kids.
Block island is one of our favorites. If no dinghy you’ll have to get a dock to really enjoy it. One of the must do activities for ours is going to the entrance channel
Beach which is fun for swimming, exploring, fishing, and watching the boats come and go. But you’d need a dinghy.
Lots of great stops along the way- if you have no dinghy I’d recommend Saybrook Point marina in CT. Nice place with a couple of pools, a restaurant, and other resort stuff. You can rent or use bikes from the onsite resort. Not cheap but a nice spot along the way. We went to Block I from there in 1/2 day by timing the currents

[Reeve21]

Originally Posted by EME

Thank you so much for all the recommendations. Unfortunately we don't have a dingy yet, but hopefully most of these places will offer a taxi service. Do you know if we can reserve mooring at salt pond ahead of time or it also comes first serve? How many days do you think we'll need to stay at bloack island? Maybe we can add a stop on the way back as well? I'm thinking going from Port Jeff, making an overnight stop mid way, getting to block island, spending a day or two there, going back making another overnight stop, then heading to Port Jeff.

We are just nervous where to dock our boat as we've never done this trip.

You are looking at about 70 nautical miles to Block, and Old Saybrook is about half way. You could also stop at Orient By the Sea which would shave a few miles, but the navigation is a little more challenging as you may need to time your passage through Plum Gut to avoid strong adverse currents (I don't know your boat or its speed).


So you have 2 pretty long back to back days if you are in a sailboat, and 2 more to get back, and your whole trip is 5 to 6 days. The math doesn't work for me :-).


As someone else said, Mattituck is nice and would make for a shorter first day. Then on to Saybrook/Stonington/Mystic and finally to Block. That will be a more enjoyable trip for your crew, but you will need more than 5 or 6 days.