Tuesday – We arrived in Portsmouth, and shortly after enjoyed a lovely dinner at the single wharf restaurant al fresco. The next morning, we were given the tour and lessons of boat life – including managing the head. Walked around to entertain ourselves with the Hinckley boat names. We were also incredibly impressed with the beauty of all the boats there.
We took a sunset dinghy cruise around the harbor learning about cove stripes and met a little puppy named Tide – to which Lindsay exclaimed “Hi Tide!” We ended the night by watching “Captain Ron” and quickly were appointed positions of “swab.” The next day we planned our duties of swabbing. “Swab in, swab out!”
Wednesday – Repairs on the Sirius continued… we borrowed the other Jay’s car (Hinckley VP) and went to check out Portsmouth. Picked up provisions for the on board cooking we planned and found a local coffee shop with the best smelling paninis… good thing Lindsay bought faken’ bacon! L&J made pesto linguini with veggie sausage & shrimp (veggie friendly, duh). We ended the night with a game of Rummikub where Jae quickly kicked everyone’s butts! Although Jessie had fun moving all the pieces around the board a few times.
Thursday – The girls started the day by taking a ride (literally biking) on the rail explorer. 6 miles of scenic water views and pit stop with red Adirondack chairs. The way back we entertained ourselves by racing up to 11.6 mph. Jae sat in the back with her feet up for part of the race and manning the brake for the crossings.
The final touches were complete (minus pickup of the genoa) and we were off sailing to Newport. Captain Jeff gave a mini lesson to L&J on getting off the dock and taking up the mainsail. Jae showed us the navigation system and we played with the arrows telling us even more boat names out on the water. We each took a turn at the helm, making our way down the waterway. “Wiggle, wiggle, wiggle” as Jeff says. He schooled us on boating vocabulary with words that have alternate urban dictionary meanings, and therefore provided a great source of entertainment for us. Such as, fetch and rage.
That night we ate @ The Deck, listened to live music and watched the sunset on the patio. A great entry into a new town! The town was bustling with tourists and the boating culture was rich. L&J joked about yacht party hopping. After dinner the crew found a bar with a band doing soundcheck for their set. They played “Love Shack” and Jae exclaimed we had to stay and dance! We first had a run-in with the local old lady drunk and got kicked out of our seats. Jeff was not having her BS, so we danced a little more and quickly bounced, the woman was a bit unstable!
J&J went home, and while we were still on West Coast time… the night was still “young”… like EARLY 30’S YOUNG! We had to be part of the ongoing party of Newport so we found more live music at The Landing. This was a scene, but we stood out like sore Cali thumbs in a floating sea of polo shirts and khakis. I guess we shouldn’t have been surprised. We made friends with a wedding party and were entertained by the “Newport Wannabe’s” or “Massholes” (not Mastholes as Jessie thought!) which were nicknames that they gave to themselves, and not familiar to us! As we walked back to our boat, we were excited to continue to explore Newport in the daylight.
Friday – We hit the town with our port-a-bikes (Bromptons) and Lindsay tried with much effort to not fall into oncoming traffic or water. She knew that if she accidentally rode off into the water, that she would have to dive down to retrieve the bike! Many compliments were received on how clever, and cool the bikes were! We found a park overlooking the big bridge and talked. We ventured back and found a great view and cocktails at The Lobster where we could see Sirius from our table. J&J went to play at the International Tennis Hall of Fame and we met them to be their personal photographers. J&J continued to make friends everywhere they went and talked the manager into re-opening the gift shop so we could all take home souvenirs. Lindsay thought she was purchasing a really cool titanium water bottle (without noticing the lack of price tag) … but it turned out to be a whopping $68! This now resides in her “Most Expensive Water Bottle Hall of Fame” in her apartment in Hollywood.
We walked to the other side of the peninsula and did the Cliff Walk where we could look upon “cottages” that were actually estates with large grounds and beautiful water views. Clearly the landscapers here are well employed! We Ubered back to Sirius and then went to dinner at The Porch, a little gastropub. We had a great time and talked about Lindsay’s enthusiasm of her nutrition program at SMC and all the possible transfer options she has. It had the crew reflecting on values, the process of making big decisions and gave way to Jeff’s stories on his four colleges and finding passion in his profession. Jae insisted on us partying again, so we, with twisted arms, obliged. This time we were determined to live up to Angeleno stylings and after several outfit changes, went back out. Lindsay adorned in white chucks, and a blue satin bomber jacket with “Hotel CA” on the back, and Jessie wearing ripped jeans and a bohemian sweater. We found some local townie bars on the north end of Newport and found the local crowd to be low-key but uninterested in tourists / newcomers / us. Everything in Newport closes at 1am. Back at Sirius we sat on the bow and listened to the dissipating crowds in the streets. Simply put, no Mega Yacht parties. Just Hawaiian deck guards that questioned us when we tried to walk back to the boat! We, like J&J, made great friends with this deck guard and ended the evening with smiles on our tired faces!
Saturday – Pushed off early (not before grabbing coffees and goodies) but with poor weather conditions and light wind, we motored our way down the Sound for eight+ hours. L&J tried not to puke and had a quiet day out on the water… hoping for the sky to eventually clear in order to see the big meteor shower that night. Coming into Shelter Island, the fog took over. L&J expertly timed and executed the 2min horn blowing (see video). We went ashore briefly and then started dinner while J&J took the ferry to Greenport. We served Ahi, tofu, orzo and stuffed mushrooms.
After dinner we all laid on the bow, staring at the moving clouds, hoping to glimpse the meteors. Nope! It seemed like a day of nopes. (See exploding kitten card). The Shelter Island Yacht Club was having their annual Commodore’s Ball, so while we were star/ meteor gazing, we were also experiencing cannons shooting fireworks, and loud party-going boaters enjoying their evening! They had a really good live band, so our soundtrack for the night was pretty set!
Sunday – “What a difference a day makes!” (Jae). Sunday was the most beautiful, ideal, weather day. L&J sailed around Shelter Island, out to some open water. Getting sun and practicing our skills (mostly J though, as L was very much enjoying lying around in the sun). The expressive, aggressive, raunchy language on the Coast Guard channel quickly reminded us we were in New York! They were challenging each other and instigating fights with boaters, including chicken sounds… Bawk bawk bawk! Arriving into Sag Harbor we were impressed by the docks and mooring fields chalk full of Mega Yachts. Literally jaws on the floor. See our reflection in one of the boats! Despite our Googling efforts to identify Jimmy Buffet’s yacht, we didn’t see him or his boat there. Guess the Margaritaville will just be from Spotify this time!
We walked around town, had a happy hour and then met up with J&J at Page @ 63 Main for dinner. We reminisced on our week and J&J announced our promotions to First Mates! L&J attempted to stay caught up on Game of Thrones, but quickly passed out from the busy day.
Monday – Picked up coffees and the best donuts ever (well, maybe not better than Komodo’s on Maui) at Grindstone Donuts. We tried out the new inflatable paddle boards around the marina and tried not to fall off onto the jellyfish! We packed up and shipped out. Now on our third flight of the day (tour de Southwest) and still eating donuts from Grindstone (oops!)
We can’t express how wonderful the week and experience was and how grateful we both are to have been guests of J&J, witnessing them living out an impressive dream of sailing and exploring together. Their love of the water and each other is enchanting.
Here’s hoping we get invited back to experience the new role of first mates!
Some of our favorite boat names:
-Unsinkable II
-FOMO
-Kid’s Tuition
-Spoiled Brat (what’s in that guy’s dinghy?)
-Passing Wind
-Mary’s Ring
-Indecision
-Just a Friend
-If Only…
-Just Add Water