I bet the title grabbed your attention!

Watch Hill Rhode Island is one of the most idyllic spots in the world. A mile of quaint little shops, historic restaurants, and home to Taylor Swifts $35 million oceanfront mansion.

Why on earth would anyone ever want to escape?

We did – five minutes after we arrived!

We had a sweet run from Old Saybrook on Monday morning. The techs from S&S were on board until 10:15 trying to get our generator working (no luck).

We left late, around 10;30, which may well have been a blessing.

It’s about 36 miles to the mouth of the harbor that divides Connecticut from Rhode Island.

I’ve been visiting Watch Hill since 2018 and the first time around Sandy Point was nerve-racking. You need to hug the beach to get the deep water and some spots are over 30’ deep.

Despite the high anxiety, as long as I followed the channel, I never saw less than 8’ of water all the way to the docks.

Until Monday.

There was a boat coming the other way that pushed me to the edge of the channel, but typically the deeper water is to the south.

I’m creeping along – just jogging the throttles. And the next thing I see on the depth sounder hit me in the pit of my stomach…

At this point, I’m in neutral hoping that the depth sounder was accurately calibrated to report exactly how much water is still under the props.

We survived and crawled to the Watch Hill Docks. Dockmaster John and Mrs. Horne did a great job tying us up and once we settled in, I asked John about the shoaling at Sandy Point.

“The dredging is overdue, it’s been three years…”

The problem is that the last couple of hundred feet is actually in Connecticut and they have no interest in bringing a rig in to dredge.

An hour later a 59’ Searay pulled in I went over to talk to the captain. He said he now considers Watch Hill to be unsafe in anything more than an hour before, or an hour after, high tide.

I checked and we came in two hours before high tide.

Simple, we’ll just leave at high tide…

Plan B Crunch

There were two problems with that idea. High tide on Tuesday was at 2:30 and there was a storm coming in. I checked a few apps and it was a serious threat.

Our next stop was Sag Harbor, 40 miles across Long Island Sound.

At this point, I was being squeezed into having to choose between running aground and battling gale-force winds.

I didn’t have time for dockwa, had to go old-school, and as we headed to Andreas for lunch, I started making phone calls.

John said we could stay longer at Watch Hill, but high tide would fall an hour later each day. If we rode out the storm and left on Wednesday, we’d be forced to wait until 3:30 to leave.

I called Stonington Yacht Club to see if I could get in on Wednesday and he said “Yes, just put in a request on dockwa,’ which I immediately did.

My final call was to Sag Harbor where I was holding a $1500 reservation for Tuesday and Wednesday night.

They said that I would get a full refund due to the Gale Warning. Within forty-five minutes, I went from pure panic to a well-constructed emergency Plan B.

Getting To Lunch

By now our Uber driver had almost reached lunch. He was a very interesting guy – the Fire Chief and a 7th-grade teacher.

Mrs. Horne engaged him in conversation and quickly uncovered that his brother was close friends with Taylor Swift’s father and had indeed attended the secret wedding at Madison Square Garden!

Side Note on Uber: Uber has finally arrived in Watch Hill, but it’s barely there. When you open the app, you see all of the typical ride options, with reasonable wait times. But when you select one, the fun begins. Both times I tried, I watched for six minutes while it searched for a driver. And both times it failed and asked me to try another ride. It took about twenty minutes to get a car to lunch and forty-five for the ride home.

Andreas Beach Club

We discovered Andreas in 2022 while biking. It’s really a cool spot on the beach with 180°+ views of Long Island Sound.

Despite the modern decor and hip music, it has an Old School vibe – it’s the kind of place my parents would take me to when I was a kid.

It’s also quite a business. They charge for parking, serve drinks on the beach, and limit diners to two -hour sittings,

I love this place. My only critique is the absence of draft beer and plastic cups. The good news is they make great beach drinks including a Skinny Margarita.

The Bang Bang Shrimp is nearly identical to the Boom Boom Shrimp at The Black Whale.

As mentioned earlier, it took forty-five minutes for our Uber ride to show. Not surprisingly, Mrs. Horne made friends with the parking lot attendant Isaiah.

He’s a great young man, studying to be an electrician, and a wonderful storyteller.

By the time we got back to the boat it was after 3:00. I spent the afternoon on the Skydeck working and Mrs. Horne went shopping.

The Olympia Tea Room

One of the iconic restaurants in Watch Hill is the Olympia Tea Room.

It was established 110 years ago by three brothers as an actual tea room. The current owners have operated the restaurant since 1980 (see Famous Not Fancy since 1916).

They do not take reservations, it’s noisy and crowded, but it offers great food at reasonable prices…

I always order the Bruno Sausage.

The sausage is homemade and always cooked perfectly. The shaved parmesan, crispy fingerlings, and garlic butter sauce are both unique and exceptional.

Back on the boat, we enjoyed the best sunset in New England.

Watch Hill Bonus Day

As a result of Plan B, we found ourselves with an extra day in Block Hill. The morning picked up where the sunset left off…

Of course, all you old-timers remember the old adage:

“Red Sky at Night, Sailor’s Delight, Red Sky in Morning, Sailors Take Warning…”

And, as you can plainly see, Tuesday morning brought red skies!

Before my Uber experience on Monday, I had reached out to our Watch Hill driver – Tonia (401 484-2921). Her van had been in the shop, but she was back in business Tuesday, so we decided to check out Westerly.

Westerly Historic District

Tonia dropped us off just before noon and about an hour before the rain was about to hit.

Westerly is a classic old New England town that probably had factories a century ago.

Westerly was first known by its Native American name Misquamicut. It was permanently settled by English colonists in 1661 and officially incorporated in 1669.

It was called Westerly because it’s the westernmost town in the colony. Westerly evolved from an agricultural and shipbuilding frontier into a renowned center for Westerly granite quarrying and a premier coastal resort destination.

Watch Hill and Misquamicut (home of Andreas) are both villages inside Westerly.

Although Westerly has a lot of cool-looking restaurants, many are closed on Tuesdays. With the rain due any minute, we ducked into the first place that looked decent.

Owl and Dove

The bar was open, but empty, so we grabbed two stools…

They have two menus – one for Morning Doves and one for Night Owls (available after 4:30 p.m.)

The morning menu was more breakfast than lunch, but there were enough options for most.

This was a home run. The chowder was thin – the way I like it, and the clam cakes were light inside.

We texted Tonia for a pick-up, but I had ten minutes to visit a guitar shop called Frets…

This may be the coolest guitar shop I’ve seen outside of Austin Vintage Guitars. If I sell a few more of my current collection, I may return by car and spend an hour or two.

Despite the time crunch, I almost bought a beautiful Peerless electric hollow body.

The Epic Storm

We were safely back on board Amazing Grace when Watch Hill got walloped by an epic thunder squall…

We were fairly well shielded by the town, but the 40-knot winds still rocked the boat. Interestingly enough, the storm only lasted about ten minutes.

The Ocean House Bistro

The other iconic restaurant in Watch Hill is the 5-star-ranked Bistro located in the $2,500/night Ocean House resort.

We’ve dined here several times and the food is always great, but the prices are a little steep.

The first time we dined at The Bistro in 2018, it was very difficult to get a reservation. Now they are on Opentable.

Although we had a reservation, we wanted to sit at the bar and there were two open seats.

At first, the bartender told us we could only get “Bar Bites,” but when we checked back with the Maitre’ D, we found that we could sit at the bar and order off the full menu if we had reservations.

I prepare Coquilles St. Jacque sometimes, but I omit the potatoes. I’ll probably add them next time!

As always, it was a great meal, as it should be for $250.

Strange Wednesday

Having grown up on Buzzards Bay, I tend to avoid leaving the dock after 11:00. Wednesday was different. High Tide was at 4:00 and we were only going to Stonington – a mere 5 miles across the state line.

Watch Hill has an excellent pump-out boat service. After a week at sea, we were due, so I called Westerly Pump-out (Channel 8) and took care of business.

We decided to skip lunch and return to The Bistro for brunch.

The breakfast crowd was light and they sat up out on the porch.

After brunch we walked downtown for a little last minute shopping.

Tonia told me 10 Sandwiches had added a bar, so I went by to check it out.

Over the course of our visit, we became friends with the couple on the Searay 59 – Mark and Brenda.

Around noon we toured each other’s boat until it was 3:00 and close enough to high tide for me.

I called Stonington Yacht Club to discuss our docking and the young lady who answered: “We don’t have a reservation for you”.

I said: “I spoke to a guy on Monday and said you couldn’t take me Tuesday, but you had a spot Wednesday, He told me to make a reservation on dockwa and he’d confirm it,”

She said: “Sorry sir, you don’t have a reservation and we have no room.”

At that point my second panic attack hit. There was no wind in Warch Hill, but I looked at the wind forecast anyway to figure out what marinas were in reach.

Based on the lack of wind at the dock, I figured we could go anywhere with 50 miles. We were due on Block Island on Thursday, so I called them.

No luck.

Next up was Newport Yachting Center.

Yes! And I booked it, got Mrs. Horne on the boat and we took off around 3:15.

There was plenty of water (7’ plus) by Sandy Point and calm seas until we cleared the breakwater. Then the rollers from the south started getting bigger.

Here’s the last video I shot before the helm commanded by full attention.

By the time we passed Misquamicut, it was clear that the seas were building. About an hour from Newport, we were seeing 10-12’ swells, some breaking, and they were now down to 50’ apart.

I knew I had no gyro (because the generator was down), but for some reason, the Humphrees Interceptors were down too. These are the two systems that fight roll, and with heavy seas hitting us to beam, roll is what we were getting.

Although we always prep the boat for some turbulence, we weren’t prepared for constant 20° rolls back and forth. In the fly bridge, ottomans and guitar cases were flying around.

We could hear things crashing about in the salon, but an ottoman had lodged in the staircase making it impassable.

Mrs. Horne tried to get up and stow things, but it was too wild. I had my hands full running the boat and modulating the throttles.

I slowed slightly (from 25 MPH to 20 MPH) and ran for about 45 minutes. Slowing down didn’t really help because our only defense against the roll was our forward momentum, and momentum came from forward speed.

Once we cleared Point Judith, we turned downwind and my job changed to working the throttles to surf the waves without stuffing the bow.

We were never happier to round Fort Adams and see The Bolin at Newport Yachting Center.

We tied up around 5:00. I looked down at the dockhands and one said “You’re the only boat that came in today.”

Lessons Learned

I promised Mrs. Horne I wouldn’t put her through anything like that again. As I replayed everything in my head, I made a few mental notes:

1. Confirm Plan B’s – The booking at Stonington Yacht Club was critical and shouldn’t have taken the guy’s word – I should have double or triple confirmed.
2. Don’t trust your eyes when it comes to the weather. It was perfectly calm day in Watch Hill, so as soon as I found one forecast that looked good, I stopped looking. I never do that, I always triple check (or more).
3. Revisit the procedure for locking the boat down for heavy seas. Everything needs to be prepared for 20° rolls.

22 Bowens Haven

I quickly washed down the boat and knowing Mrs. Horne was suffering from a little PTSD, I suggested we head to 22 Bowens for a good steak.

I checked Opentable and the first open reservation was 9:30, so we went in looking for seating at the bar.

We immediately found two seats and the traumatic day quickly became ‘just another good boat story.”

The steaks were perfect (I probably wouldn’t order the gratin again). We left content and rejuvenated.

Right after we tied up on Wednesday night, the Dockmaster told us the Azimut 68 in front of us planned to leave at 8:00 a.m. and we would need to move to allow them to pass.

No problem, I had a plan, but when I went out to unplug the power, I saw that they had decided to squeeze out around us.

So of course I grabbed my phone and shot some video…

Between the captain at the helm and the NYC team with fenders, it was a very smooth departure.

The 25-mile run to Block Island was smooth and easy…

Next Up: New Harbor Block Island