New England Sailing Trip

Today actually started the night before. Like any good trip we didn't check the computer systems until the night before a multi-day voyage. And what do you know the boat input devices (like wind, depth, compass, etc… all the important things) were not working. After some debugging we find it's something to do with the NMEA2000 system, but can't pin down exactly which device is causing the issues. I go to bed at midnight worrying we won't be able to leave on time. Superman Jimmy of course had everything fixed in the morning. It was the AIS sensor that was attached to the NMEA system under the mast, the one place we didn't check. We were able to leave on time @ 9:00am, fill up on fuel and water, and depart on our journey. We've gotten really good at docking :). The Bay Bridge was awesome to go under. I was actually on a call with CUIMC (especially Ed) as we were going under it. A nice juxtaposition of beautiful engineering and Ed bullshitting around! The rest of the Bay was pretty quiet, especially once we got past Baltimore. It was a really lovely, calm day. The shoreline had some nice looking beaches and the occasional bluff. We finally get to the turn to the Chesapeake Delaware Canal and can see the bridge marking our final destination for the day. Chesapeake City is a cute little town right on the canal with a disproportionate number of bars and live music than what you would expect kind of in the middle of nowhere. There was a public town dock (free), but all the spaces were taken so we anchored in the little pond area with 2 other boats. The holding wasn't great, but the weather was perfect. Mom and I took the dogs for a walk around town and saw all the little restaurants and streets. We cooked some chicken sausage for dinner and listened to the live music from the boat with a beautiful sunset in the background. It was perfect.

We started today not too early, around 6:30 or so. Took the dogs for a quick walk and then back on the canal. I drove the boat off of the anchor, out of the pond, and pointed it down the canal. I actually steered the boat mostly by hand just to get some practice with the helm and how the boat responds to inputs. As we went down the canal it was very peaceful and we got to go under 4 more bridges. It was really cool and reminded me of Bridgeport in Pennsylvania when we visit Nene. The Delaware river is huge. It was cool to finally get to sail (well motor) down it as I've always wondered what it would be like every time I drive over it. Well it's wide, long, and moderately busy. Not much else to say. We saw a couple of dolphins and wondered which part George Washington boated across to defeat the Brits. Did I say it's really wide? As we approached Lewes Point I took the helm and steered us into the double breakwater protected anchorage. We dropped anchor pretty easily and dinghy over to the beach to take the dogs for a walk. There was an absurd number of dead horseshoe crabs on the beach.

I steered us out of the anchorage early in the morning. Past the breakwaters, and out into the Atlantic. We get out and I try to turn on the autopilot, but… it's not working. It takes us over an hour of manual steering + dad looking up shit on the internet to fix it. In the end I realize the autopilot does not have the correct setting selected for the compass. We had updated the software and it didn't auto select the source… lol. Once that was fixed we were fully on our way. It was a long day up the coast of New Jersey. We saw Atlantic City, some dolphins, and honestly not much else. Pretty boring day tbh. For dinner it was leftover enchiladas. I went to bed at 7 in preparation for my early morning shift.

Beep…beep…beep. Fuck it's time for my midnight to 4am shift to start. I grab a coffee and head to the helm to relieve my mom from her duties. My shift is a rough one, but I'm used to it by now. It was a beautiful night at least with a waning gibbous moon to illuminate the sky. Not much happened - I just needed to avoid one ship and otherwise I was good. The autopilot kept losing course since the rudder feedback device was incorrect (of course) so the constant need for manual adjustment probably helped keep me awake. Bobo joined me at one point too which was nice. I just listened to podcasts and chilled until I was relieved. I slept great until 8. Wake up and we're off the coast of Long Island. Another couple of hours and we pull into the inlet at Hampton Bays. We're in the Hamptons baby! Where the rich and famous all go to play. From NYC just a week ago to the nicer side of town as they say.

The ride to Block Island was easy. We put the fishing lines in the water hoping to capitalize on the tuna season… we didn't. We passed Montauk and the lighthouse, which was really neat and then Block Island was visible in the distance. Land Ho! We arrived around 3:30pm and found a spot to anchor in the Great Salt Pond towards the northeastern side. We're pretty much in the very back as far as distance to dinghy docks goes, but I like our spot. It's quiet and behind us we can see the conservation area where people sail and kite surf. It's really cool. Once anchored dad and I dinghy over to the dock and hit the Oar Bar. We have a couple of drinks at the bar with an incredible view of the harbor. It is nice to be off the boat somewhere I know we'll be for a couple of days! This is what the grind is for. We walk around a bit and then head back to the boat to pick up Mom after her work day is over. Then we head back to the docks with the whole family (including the dogs) and walk into down town. The walk is about a mile from new harbor to New Shoreham. We walk along the waterfront and then the backstreet where we find Aldo's Italian restaurant. Aldo's prefers dogs over people so we got a nice seat outside and enjoyed some sangria and pizza. Delicious. Afterwards we returned to the boat and watched the first episode of season 3 of Squid Games.

Day 1: Block Island

Jul 15, 2025

The ride to Block Island was easy. We put the fishing lines in the water hoping to capitalize on the tuna season… we didn't. We passed Montauk and the lighthouse, which was really neat and then Block Island was visible in the distance. Land Ho! We arrived around 3:30pm and found a spot to anchor in the Great Salt Pond towards the northeastern side. We're pretty much in the very back as far as distance to dinghy docks goes, but I like our spot. It's quiet and behind us we can see the conservation area where people sail and kite surf. It's really cool. Once anchored dad and I dinghy over to the dock and hit the Oar Bar. We have a couple of drinks at the bar with an incredible view of the harbor. It is nice to be off the boat somewhere I know we'll be for a couple of days! This is what the grind is for. We walk around a bit and then head back to the boat to pick up Mom after her work day is over. Then we head back to the docks with the whole family (including the dogs) and walk into down town. The walk is about a mile from new harbor to New Shoreham. We walk along the waterfront and then the backstreet where we find Aldo's Italian restaurant. Aldo's prefers dogs over people so we got a nice seat outside and enjoyed some sangria and pizza. Delicious. Afterwards we returned to the boat and watched the first episode of season 3 of Squid Games.

Spots

1. Drinks @ The Oar

   

Day 2: Block Island

Jul 16, 2025

It's orb hunting day. Dad and I take the dinghy over to the dock and rent some bikes from Aldo's for 3 days. Only 50$ felt like a steal. First we bike into town to the Nature Conservancy to get a trail map for the entire island. We go hit the northern part of the island first in order to hit some of the high concentration orb spots like Andy's Way, Atkinson Overlook, and the North Beach. We didn't find any. At the northern lighthouse we did see some sea lions or seals (idk) in the water just off the beach. Their little noses sticking out. We walked to the lighthouse, which was open so we could check out the museum inside. It's starting to get around noon and I need to rush off to somewhere I can take my work meetings. I hate working while adventuring, but it's totally worth it! This new tech lead role has more meetings, but in terms of actual work I think it's a whole lot easier. I take the sprint checkin meeting at 12:30 behind the grocery store. It's a bit of a shit show since I can't get my microphone to work on my phone while the AirPods are plugged in. I really need to upgrade my setup for remote work. After that whole debacle I go over to the nearby park to setup for the Office Hours meeting. I find a nice bench in the shade and get my hotspot all working for my computer and it's working great. The meeting goes very well and Tri sat in the background quietly and I think he thought I did a good job. When the hour is finally over I head over to Poor People's Pub to have a beer and some buffalo chicken dip with my dad. After eating we head back to the boat and cook dinner and watch more Squid Games. I wake up in the middle of the night and go outside and there is a thick layer of fog in the harbor. It's so thick I can only see the closest 5 boat's anchor lights around us. Everything else is obscured by the gray fog. Very cool.

Day timeline

1. Farmers Market

   9:29 AM

   

2. Andy's Way

   10:00 AM

   

3. Sachem Pond

   1:00 PM

   

4. North Lighthouse

   3:00 PM

   

Day 3: Block Island

Jul 17, 2025

Today was a slower start, which was nice. I had some work to do in the morning so we had our coffee and did some work on the boat until around 2:00pm. Then we set off for shore, the entire family and dogs. We rented a bike with a baby trailer for the dogs so we could explore the island all together. I think I had a meeting or something so I went back to the park while my parents started the ride into town. We met at Poor People's Pub to get a quick lunch before starting the uphill ride towards the Southeastern lighthouse. Well I should've known, but having the dogs in the trailer was a complete shit show. They kept trying to jump out and when we went past another dog they went insane. It was terrible. The ride itself was kind of fun though I was the one biking with them and while it was difficult I felt powerful being able to get up the hill without struggling. We never did make it all the way up the hill though since they kept jumping out so we decided it would be best to just head back to town. We got back to town and walked around a bit on the beach before biking back to the docks where we locked up the bikes and walked the beach from Oar bar to Mahogany Shoals for some drinks. Man every bar on this island allows dogs there must have been at least a dozen there. The bar was such a chill vibe too. Very reminiscent of bars in St. Thomas. It was all cash, had a ton of people, and such a great atmosphere with live music, Adirondack chairs, and you're also on a dock surrounded by all these nice boats. I had a delicious tequila drink with ghost peppers, a mud slide (with a ton of espresso :) ), and then finished it off with a beer. It was a great time. We then went back to the boat where I cooked some pasta with meat sauce and more Squid Games :). What a great day.

Day 4: Block Island

Jul 18, 2025

So this guy Aldo really has an incredible business. Not only does he have a restaurant and rent bikes, but he also has a bakery with a boat that goes around the harbor yelling “Adiamo!” and if you flag them down you can buy a pastry off of them. They even accept card! I feel like accepting card these days though is so easy and you're missing out on business if you don't. We buy a bacon egg cheese croissant, donut, pistachio muffin, and a cold brew. Delicious. We leave the boat by 9:30 in order to get our rental golf cart by 10:00. I have our dev estimation meeting at 10:00 so I bike ahead, again to the park, to take the call. It's Felipe's last day so it's a little sad. Apparently the boat anchor alarm was going off (it was really, really windy) so my dad goes back to check it out. My mom meets me at the park and we take the golf cart over to the bagel shop for some breakfast. We grab the food and then head back to pick up my Dad who had let out a little more anchor chain and backed up on it to really set it in there. We take our breakfast the long way around the island (traffic downtown was terrible) to the Southeast lighthouse where we enjoy our food, sip our coffee, and look out on the ocean over the bluffs.

Spots

1. Aldo's baked goods delivery

   

2. Southern lighthouse

   

3. Bobo Kitty Cat

   

4. Orb Found!

   

5. The Shoals

   

Day 5: Block Island

Jul 19, 2025

Today was a slow start to the day for me. It's Saturday so the farmer's market is in the park just up the road from the marina so my parents went with the dogs while I stayed on the boat. Ahhh a nice morning coffee with peace and quiet - my favorite. I took the kayak out around the salt pond and explored the area while listening to some Spanish podcasts. I went by the ship we saw when we entered the area that we thought was a military ship, but it turns out to be a fire fighter boat. Cool! Around 2pm I head over to downtown area to meet Simar at the ferry docks. He took a plane to Providence, then a bus to Point Judith, and then finally the ferry to Block Island. What a journey for him. Of course Simar is the first person off the ferry not waiting for the cars to even finish - that's my guy. We catch a cab from New Shoreham over to the new harbor and meet my dad at Mahogany Shoals for a couple drinks. Then take the dinghy back to the boat for some more drinks in the front while enjoying the evening weather and watching the wonderful sunset. This evening we watch the Squid Games finale. No spoilers here, but I loved it!

Up bright and early today to leave the anchorage for Martha's Vineyard. It's a bit windy so it's tricky to get the anchor up and the chain jams up a bit, but we get off the hook and going out the channel. Once out of the channel we get the sails up and sail around the northern point of the island and onwards east towards Martha's Vineyard. The journey is a bit boring today, but it's a good day to catch up with Simar and just chill before the work week comes around again. We put some fishing lines in, but don't get a single bite. The seas are a bit rough today so it's a bit roly, but that means we are at least sailing. Can't complain. Martha's Vineyard is finally in sight and we sail into the Vineyard Sound. Within the sound the seas calm down, but we still have enough wind to sail for a bit longer. We can start to see the mansions dotting the coast line. Martha's Vineyard has always had this prestigious, ultra-rich vibe in my mind and it's wild to see that actually playing out. Eventually we make the turn around the northern part of the island and can see our turn down into Vineyard Haven Harbor, where we will be anchoring for our time here. The houses keep getting nicer. We find a nice spot to anchor and head on over to the town of Vineyard Haven for a walk around. It's a quaint little town with a lot of cute shops and restaurants. Definitely want to try them tomorrow. It's the 50th anniversary of Jaws, which was filmed on Martha's Vineyard so we of course have to watch it. I had never seen it before and loved the movie - probably even more since we were watching it in such a cool spot. After watching the movie I couldn't help but looking at the inky black water in the nighttime and wondering what was lurking in the depths.

Day 1: Martha's Vineyard

Jul 20, 2025

Up bright and early today to leave the anchorage for Martha's Vineyard. It's a bit windy so it's tricky to get the anchor up and the chain jams up a bit, but we get off the hook and going out the channel. Once out of the channel we get the sails up and sail around the northern point of the island and onwards east towards Martha's Vineyard. The journey is a bit boring today, but it's a good day to catch up with Simar and just chill before the work week comes around again. We put some fishing lines in, but don't get a single bite. The seas are a bit rough today so it's a bit roly, but that means we are at least sailing. Can't complain. Martha's Vineyard is finally in sight and we sail into the Vineyard Sound. Within the sound the seas calm down, but we still have enough wind to sail for a bit longer. We can start to see the mansions dotting the coast line. Martha's Vineyard has always had this prestigious, ultra-rich vibe in my mind and it's wild to see that actually playing out. Eventually we make the turn around the northern part of the island and can see our turn down into Vineyard Haven Harbor, where we will be anchoring for our time here. The houses keep getting nicer. We find a nice spot to anchor and head on over to the town of Vineyard Haven for a walk around. It's a quaint little town with a lot of cute shops and restaurants. Definitely want to try them tomorrow. It's the 50th anniversary of Jaws, which was filmed on Martha's Vineyard so we of course have to watch it. I had never seen it before and loved the movie - probably even more since we were watching it in such a cool spot. After watching the movie I couldn't help but looking at the inky black water in the nighttime and wondering what was lurking in the depths.

Day 2: Martha's Vineyard

Jul 21, 2025

Good old Monday's, another day of work. Can't complain though - I'm in Martha's Vineyard! My dad, Simar, and I head to Nat's Nook in town for breakfast. I take a couple of meetings and then we pop on the bus to head for the other side of the island to the town of Oak Bluffs. The bus system on the island is incredible… and free. We walk around town a bit and find a bar to grab a few beers. While the boys are indulging I start some laundry at the local laundromat. Ahhhh it feels good to get the clothes washed. Nothing like having your go to favorites clean again. We head back to the boat around 3 and I take a couple more calls. After that we just hang out on the boat, have some drinks, dinner, and call it a day. I love a nice chill day.

Day 3: Martha's Vineyard

Jul 22, 2025

Head over to Nat's Nook again, this time with just my parents while Simar sleeps in. We grab some breakfast and then my parents take the bus to explore the island while I head back to the boat, take some calls, and wait for Simar to get up. At around 1:00pm we head back to Vineyard Haven where the ferry docks are and wait for Sarah to arrive. She lives in Boston and drove to Woods Hole Mass to come stay with us for a day. When she arrives we hop on a bus over to Edgartown! It's the posh part of town. Edgartown is a quaint spot and a decent size too. I loved walking down the streets and looking at the old and sea weathered buildings. You can tell it got it's start as a fishing town. We head to a restaurant down by the water where we're joined by my parents and the pups. I got a Goombay Smash, reminding me of the ones we had in the Bahamas. To eat I grabbed the blackened Mahi sandwich and Simar of course got a whole lobster. This guy loves to eat :). After lunch we headed over to the local baseball field to catch the Vineyard Sharks. It's a baseball team made up of college players on break who are trying to keep their skills sharp. They were decent, but the game wasn't all that exciting to be honest.

Last day on Martha's Vineyard so I had to make sure to do the one thing I was the most excited for - Jumping off the Jaws bridge. It's the bridge from the movie where the lady sees the shark go into the pond and eat a guy. Now people jump off of it. Good, old-fashioned fun I say. The bridge was crowded with lots of people jumping off and taking pictures. It was such an awesome vibe. Sarah and I jumped off and tried to look cool while doing so… only one of us succeeded in that. Afterwards we headed to Morning Glory farms to check it out and had an incredibly delicious, but overly expensive burger. Then it was back to the boat where Simar and Sarah both hopped on the ferry back to the mainland while my family and I go the boat ready and departed the pattern at around 5:00pm. It's going to be a long journey back so we wanted to get ahead of it. The evening was nice and warm, with not much wind so it was just straight motoring. My shift from midnight to 4:00am was quiet with nothing much to report. I rounded the northern point of Black Island and was just passing the southern end when my shift ended and my dad took over.

At around noon we pull into Hampton Bays again to refuel, take the dogs for a needed walk, and get a bit of rest before continuing. It's really hard doing overnighters and also working. And sleeping while underway is usually pretty un-optimal as well so it wasn't great. But it feels good making progress. We leave Hampton Bays around 4pm and I take a long shift at the helm from 7:00pm until around 3:00am. My mom wasn't feeling well so I thought I'd help out and take her shift. I listened to Anthony Bourdain's self narration of his book. During my shift I had the fun task of avoiding what seemed like hundreds of sailboats going in the opposite direction of us north around Long Island. Apparently there was a race that left from New York City that morning where they race around Long Island. It gave me something to do at least, trying to predict where the boats were going and picking the optimal line through them while staying as much on course as possible. The going was painstakingly slow tonight, we averaged about 3 knots.

New York, New York! I woke up in the morning as we were heading past the final stretches of Long Island. Passing Coney Island I could see the amusement rides, boardwalk, and could even imagine the small of Nathan's Hotdogs! We were getting close! We passed under the Staten Island Bridge, through the Narrows, and there she was - New York City. It's incredible to be pulling into New York Harbor on your own boat. I had just been in the city for work a couple weeks before and now I was back on my own terms. It's so cool to see the sights from a different vantage point. We pull up right behind the Statue of Liberty and drop our anchor. It's wild you can just stay literally 100meters away from the statue. Right there while all the tourists take the ferries to the island we are just anchored there and enjoying the view from our own boat. Just wow. My friend Josh lives in Jersey City, which is perfect since we were anchored pretty close to the Jersey shore. I ordered a Jersey style (better than NY don't hate me) and he picked it up on his way to the nearest parking lot from us. I picked him up on the dinghy and we had a lovely couple hours chatting, eating pizza, and enjoying the experience. The plan was to drop him off on land and then he would come back with his girlfriend and other friends in a couple hours. However, pretty much 5 minutes after I dropped him off and returned to the boat and incredibly strong storm rolled through. We're talking 30mph winds, raging seas, and lightning within half a mile of the boat. Well this isn't anything new to us, but it sure made it impossible to get Josh back on the boat. Oh well it was fun while it lasted. My family and I weathered out the storm and choppy seas while enjoying the view of the statue and the city as it lit up in the nighttime. In the city that never sleeps I was feeling pretty tired so called it an early night.

Well we're on the move again back through the narrows, under the Staten Island bridge and down the Jersey Shore. It's going to be our last long push and overnighter, but we're all excited to be getting closer to home. Nothing eventful really happens today. I read a bit of Lord of the Rings and work on AdventureMapper, but that's really it. At least it's a great sailing day with wind perfectly abeam of us and we get cruising at nearly 8 knots. Wooohoo! I take my usual shift from 12:00 - 4:00am and head to bed just as we're nearing the mouth of the Delaware.

Well there was another crazy storm last night, but nothing that Captain Jimmy couldn't handle. I take over his shift around 9:00am and we steadily head up the Delaware. We hit the tide change just right so the current was in our favor and we were continuing to make good time, even with our sails down. We get to the start of the Chesapeake - Delaware Canal and it feels like we're so close. Everyone is super, super excited to get into Chesapeake City today to have a drink and enjoy a relaxing night at a great anchorage before our final day. We get in around 2:00pm, anchor in the same place as last time, and head to shore. After walking the dogs we hit the tiki bar and have a few very strong drinks. After that we returned to the boat, cooked some pork chops, and called it a night.

Up bright and early it feels good knowing that this is our last day. It's been a really fun journey, but super rushed so I'm just ready for it to be over. It's a beautiful day to end it on with the sun shining after all the rain and calm waters in the Bay. We can't get the sails up, but at this point no one cares. We pass all the familiar sights we saw on the way up. Eventually I can spot the Bay Bridge in the distance. It's the indicator that we're getting really close. It gets closer and closer until we're under it and then can see Annapolis and our slip at the marina. We pull in and after some struggle getting the lines on the poles we are finally done! Well not done, there's cleaning to do, but at this point I feel great. We power through the cleaning with the thought of dinner @ Adam's on Fourth on our minds. What a trip.

Adam's on 4th to celebrate the adventure.