It all started with a hose, a scrub brush, and a throwaway comment that turned into a plan.
Jake and Taylor had just gotten off work on Thursday, and headed down to their homeport marina to check on the boat. Ruby, their salty boat dog, hopped aboard like she owned the place. Jake started hosing down the deck while Taylor scrubbed down the cockpit cushions, mostly just as something to do to earn a round of slip side Dark n’ Stormies, but also because they’d both been daydreaming about getting the boat into a condition where they can slip the lines and take off for a long weekend cruise.
That’s when their dock neighbor, Mike, leaned over the rail of his trawler and said, “You see this weekend’s forecast? Couldn’t be better. We were up in Essex last weekend and highly recommend.” He continued, “If you go, ask for the riverside dock. It’s got the better view and catches the afternoon breeze. Just mind the current… the river’s no joke!”
Taylor looked up, eyebrow raised. “Maybe we should go.” She ducked below for her laptop, popped open Dockwa, and clicked Start New Cruise Plan. Essex went in as the first stop. In the destination notes, she typed: “Request riverside dock. Mike says better breeze + view. Watch the current.”
Jake peeked down the companionway. “We doing this?”
Taylor grinned without looking up. “We are now.”
Back at their apartment, Jake re-opened Dockwa, and got to work turning a ‘maybe’ into a mapped-out weekend. Within 45 minutes, they had a full cruise plan laid out:
✅ All dockage confirmed
✅ Fuel stops noted
✅ Local tips pinned
Each stop had its own pre-arrival notes. Jake added one for Block Island: “Tight but well travelled entrance to Great Salt Pond. Study the charts ahead.” Taylor dropped one into Watch Hill: “Perfect for Sunday. Great spot for Ruby to stretch her legs.”
With this cruise plan, everything lived in one place. No screenshots. No scribbled notes. No toggling between a dozen apps, tabs, and marina websites.
Friday Morning: No Scramble, Just Sunny Side Up Cruising
They slipped lines just after sunrise, Ruby curled up in a sunny spot on deck and the smell of fresh coffee drifting up from the galley. Jake whipped up breakfast underway. Meanwhile Taylor enjoyed the light breeze and clear skies from the helm. It was a sunny side up kind of day.
As they pulled into the marina in Essex, there was no need to converse about dockage logistics over the radio other than to tell the dock team they were on their final approach. Their slip assignment was already communicated via Dockwa chat, and thanks to Mike’s tip (and Taylor jotting it down in their Cruise Plan) they’d requested the riverside dock when booking. That little note made all the difference: they enjoyed more summer breeze, less traffic, and a straight shot to the lawn and amenities where Ruby could snooze in the grass. They wandered town, had ice cream for lunch, and spent the afternoon at the Connecticut River Museum before heading back to the boat.
Another perk? The night’s dockage came with a 25% Dockwa+ discount. “See,” Taylor said to Jake, “I told you our membership would pay for itself after just one night!”. It’s true, with 25% off their slip, they already saved more in dockage than their annual membership cost to Dockwa+
Saturday Morning: Fuel Up & Pivot On
Originally, they planned to cruise straight from Essex to Block Island, saving Watch Hill for the tail end of the trip. But as any cruiser knows, a good tip at the dock can change everything and flexibility is key.
While enjoying docktails the night before, Taylor struck up a conversation with another couple a few slips over. “We’re headed to Watch Hill tomorrow” they said, “there’s a harborfront art fair in the afternoon with local vendors, food trucks, live music... it’s kind of a big deal. Definitely worth hitting early.”
Taylor and Jake didn’t take much convincing. They opened Dockwa, messaged both marinas to swap their reservation dates, and within the hour, both confirmed. She toggled Watch Hill ahead of Block Island in their Cruise Plan and updated the notes: “Art fair in town! Harborfront event with vendors + live music. Easy launch to shore. Good walking for Ruby.”
Even better, when they tapped into the Watch Hill’s Dockwa profile to adjust their reservation dates, they spotted a surprise. A Dockwa+ mooring deal had just gone live for the weekend, offering 30% off in celebration of the event. One tap, and they were locked in. More huge savings thanks to Dockwa+.
Before departing Essex for Watch Hill, they stopped next door for fuel at a participating Dockwa+ marina. They confirmed their Dockwa+ status at the dock, and the attendant gave a nod. “You’re in luck… 20¢ off per gallon this week!”
Saturday Night: Watch Hill Win
They picked up their mooring in Watch Hill just after 1 PM. The launch arrived quickly, and soon they were ashore, wandering the art fair. The town was buzzing. Local artists lining the walkway, live music drifting across the harbor, and food trucks serving up everything from fresh seafood to fried dough. The oysters were as good as promised, and Ruby (rocking her best bandana) charmed every passerby within leash range.
They headed back to the boat under a full moon, arms full of little treasures and stomachs full of fair food. They tipped the launch driver, climbed aboard, and settled in, grateful, and a little amazed at how smoothly it had all come together.
That was the whole vibe of the weekend: spontaneous, but never chaotic.
Sunday: Block Island, Just in Time
They left Watch Hill at dawn, hoping to squeeze in a full summer day at Block. The Sound was glassy, and the rising sun turned everything gold, setting them up for success. As they cruised east, Taylor pulled up their Cruise Plan and reviewed the note they had plugged in Thursday night.
Jake kept an eye on depths as they made their final approach to the Great Salt Pond, but there were no surprises or stress. The dockhands at the marina were ready for them, and Ruby was the first one down the gangplank, headed straight for the beach.
By noon, Jake and Taylor had a round of world famous mudslides in hand, sun on their faces, and a lobster roll en route.
Monday: Back to Homeport (and Onto the Next Plan)
After a very full night of dancing at Captain Nick’s, Monday morning came a little too fast. But the weather was calm, and the ride home was smooth. They planned up and throttled back toward reality.
Jake opened their Cruise Plan one last time and scrolled through the trip: every note, every stop, every saved detail ready to be a reference for next time.
Their homeport was in view, and their well spent long weekend was behind them. Taylor leaned back against the rail, Ruby snoring softly in the sun beside her. “So... Newport for Labor Day?”
What Makes Dockwa+ Worth It?
This wasn’t a luxury charter or some megayacht itinerary. It was just a normal long weekend done right.
With Dockwa+ Jake and Taylor enjoyed:
🛥️ Slip & mooring deals that stretched their cruising budget
⛽ Fuel discounts that stacked up fast
📲 A tidy, flexible Cruise Plan tool that kept everything in one place
🧠 Pre-arrival notes that made them look like locals
🐾 Way more time for dog naps and docktails
Ready to Cruise Smarter?
Dockwa+ isn’t about prestige. It’s about making your time on the water better whether you’re gone for two days or two weeks. Your next long weekend cruise starts here.