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BVI Magic: Stunning Crew Snorkels The Indians + 9-Knot Sail to Cooper Island!
Sailing Doodles

BVI Magic: Stunning Crew Snorkels The Indians + 9-Knot Sail to Cooper Island!

Day 2 sailing through the British Virgin Islands and it was absolutely perfect. This morning we left Norman Island and sailed over to The Indians, one of the most breathtaking snorkel sites in the entire BVI. The water was crystal clear, the coral was vibrant, and the ladies looked amazing exploring...
New Crew, New Catamaran… and a Wild First Day in the BVI!
Sailing Doodles

New Crew, New Catamaran… and a Wild First Day in the BVI!

Join me as we kick off an incredible week-long sailing charter in the British Virgin Islands! We fly into the BVI to meet up with two new beautiful crew members and a returning favorite — Lauryn. After hopping aboard a brand-new Fountaine Pajot Elba 45, we set off on our first sail of the trip. Our...
The Last Sail of Nauti Dogs?
Sailing Doodles

The Last Sail of Nauti Dogs?

I’m sailing the boat down the East Coast for the final time before hauling her out of the water and storing her on land while the Nauti Dogs prize competition finishes up! In this episode I make the run from Atlantic City to Cape May, then across the Delaware Bay and up the Chesapeake to Annapolis,...
Living on a Boat in Manhattan for a Week!
Sailing Doodles

Living on a Boat in Manhattan for a Week!

Docked right in the heart of Manhattan at the iconic Chelsea Piers Marina, I got to experience New York City like never before — from the deck of my sailboat! I launched the dinghy and cruised down the Hudson River, exploring the skyline and even making it out to the Statue of Liberty for a once-in-...
Sailing Into New York City! Docking My Boat in the Heart of Manhattan
Sailing Doodles

Sailing Into New York City! Docking My Boat in the Heart of Manhattan

I sailed Nauti Dogs from Long Island Sound down the East River, under some of the most iconic bridges in the world, and right past the Manhattan skyline. From there, I rounded the southern tip of the island, cruised up the Hudson River, and docked right in the heart of New York City at Chelsea Piers...
Sailing South for the Winter: Solo Leaving Block Island
Sailing Doodles

Sailing South for the Winter: Solo Leaving Block Island

After leaving Newport, Rhode Island, I set sail solo—just me and the dogs—toward Block Island. It’s one of the most beautiful spots on the East Coast, but when the weather turned, it became a wild few days riding out a storm at anchor. Once the skies cleared, it was time to start the long journey so...
Your next adventure awaits! Sailingdoodles.com
Sailing Doodles
Wasn’t Supposed to Be This Rough… Solo to Newport, RI
Sailing Doodles

Wasn’t Supposed to Be This Rough… Solo to Newport, RI

Start speaking a new language in 3 weeks with Babbel 🎉. Get up to 55% OFF your subscription ➡️ Here: I set sail solo from Bridgeport, Connecticut, heading for Newport, Rhode Island — expecting a calm run up the coast. It turned out to be anything but calm. What was supposed to be an easy day quick...
Launching your career!  #youtuber #career
Sailing Doodles
Sailing Croatia with 4 Beautiful Crew | 1.5 Hour Adventure Film
Sailing Doodles

Sailing Croatia with 4 Beautiful Crew | 1.5 Hour Adventure Film

Join me and an incredible all-female crew of four as we charter a luxury catamaran to explore the jaw-dropping Croatian coast. For seven unforgettable days, we sail from Split to the islands of Hvar, Vis, and Korčula — crystal blue water, hidden coves, epic sunsets, and more laughs than we could ha...
Come sail with me! Cruise@sailingdoodles.com
Sailing Doodles
Organized Chaos: 100 Boats Depart the Annapolis Boat Show!
Sailing Doodles

Organized Chaos: 100 Boats Depart the Annapolis Boat Show!

The Annapolis Boat Show is over, but the real work begins! At sunrise, I head back to the docks to help with the massive teardown — floating docks are being dismantled, crews are casting off lines, and nearly 100 boats start departing in a well-orchestrated bit of organized chaos. I’m helping move ...
Welcome back LAURA!  With her two kids!
Sailing Doodles

Welcome back LAURA! With her two kids!

Laura — one of the original Sailing Doodles crew and a fan favorite — joins me in Annapolis for a special reunion! This time, she’s brought her two kids along for the adventure. We head to the Annapolis Boat Show, where I show her the brand-new Island Spirit 525 Catamaran — the very model I’ll be g...
My NEW Yacht Has Arrived! Delivering It to the Annapolis Boat Show
Sailing Doodles

My NEW Yacht Has Arrived! Delivering It to the Annapolis Boat Show

The long-awaited Island Spirit 525e hybrid-electric catamaran has finally made it to the U.S.! Hull #3 just arrived in Maryland, and since I’m getting Hull #5, I jumped aboard to help deliver her to the Annapolis Boat Show for her worldwide debut. Come along as we take this incredible new yacht on ...
The Ghost Crew: Sailing With Faces I Couldn’t Show
Sailing Doodles

The Ghost Crew: Sailing With Faces I Couldn’t Show

We set sail from Port Washington to Huntington Bay, Long Island — a beautiful day on the water with two amazing crew members. But after the trip, they asked not to appear in the video… so I had to blur them out. It turned into one of the most challenging edits I’ve ever done — and a strangely fittin...
You can own/win this boat! #sailing #contest
Sailing Doodles
Giving Away My Sailboat to One of You!
Sailing Doodles

Giving Away My Sailboat to One of You!

🎉 BIG ANNOUNCEMENT – I’m giving away my sailboat, and YOU could be the new owner! ⚓️ This is your chance to win "SV Nauti Dogs" a 1989 Ta Chiao CT-56 bluewater cruiser, the yacht that has taken me on so many incredible adventures. Instead of selling it the traditional way, I wanted to giv...
Sailing NYC with Emma from Flying Doodles! | East River to Long Island Sound
Sailing Doodles

Sailing NYC with Emma from Flying Doodles! | East River to Long Island Sound

We set sail right through the heart of New York City! Emma, the host of Flying Doodles, and her boyfriend join me on Nauti Dogs as we cruise past Manhattan, up the East River, and into the Long Island Sound. We make it to Port Washington, where Emma and her boyfriend wrap up their quick visit before...
Emma on her Lyra Hoop #lyra #acrobatics
Sailing Doodles
Sailing Italy’s Amalfi Coast: Naples to Capri (Full Journey Documentary)
Sailing Doodles

Sailing Italy’s Amalfi Coast: Naples to Capri (Full Journey Documentary)

Join us for an unforgettable sailing adventure along Italy’s Amalfi Coast and surrounding islands. Starting from Naples, we cruise through the colorful fishing villages of Procida, soak in the hot springs of Ischia, sail past the dramatic cliffs of Capri, anchor off Nerano, and explore the charm of ...
Goodbye Lauryn, Hello Emma | Sailing to NYC & Aerial Hoop Show at the Statue of Liberty
Sailing Doodles

Goodbye Lauryn, Hello Emma | Sailing to NYC & Aerial Hoop Show at the Statue of Liberty

We set sail from Atlantic City for our final leg with Lauryn, heading up the coast to New York City. The sail takes us right past the Statue of Liberty before we dock in Brooklyn, where it’s time to say goodbye to Lauryn… and hello to Emma from @FlyingDoodles Flying Doodles! To kick off her return...
@Lost_Lauryn is a fantastic and beautiful crewmate #crew #sailingyacht
Sailing Doodles
The HOTTEST SAILOR on the YouTube
Sailing Doodles

The HOTTEST SAILOR on the YouTube

@Lost_Lauryn is probably the most beautiful sailing on youtube today! We have engine problems as soon as we pull up anchor at Cape May and we are drifting with the wind and current. I take quick action to get the motor started and then we sail 40 miles up the New Jersey Coast to Atlantic City. We...
We Sailed From Freezing To Bikini Weather In One Day!
Sailing Doodles

We Sailed From Freezing To Bikini Weather In One Day!

We set sail at dawn from the C&D Canal bundled up in the morning chill, but by midday it turned into perfect bikini weather! With a steady breeze at our backs, we enjoyed an epic downwind run down Delaware Bay and made landfall in Cape May, New Jersey. After dropping anchor, we explored the char...
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