Watch Sailing & Boating Adventures Around the World

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SAYING GOODBYE TO OUR BOAT (NOT CLICKBAIT) – Ep 200
Sailing Jibsea

SAYING GOODBYE TO OUR BOAT (NOT CLICKBAIT) – Ep 200

In this episode, Sailing Jibsea says an emotional goodbye to their trusty boat Gypsy as they prepare for unexpected changes during hurricane season. Join them on their exciting journey as they navigate the intricate Intra Coastal Waterway and empty out everything from Gypsy's storied past, culm...
Sailing Grand Cayman to Chesapeake MD part 2 – Hallberg-Rassy 54 Cloudy Bay -May 2020. Season20 Ep20
Sail Cloudy Bay

Sailing Grand Cayman to Chesapeake MD part 2 – Hallberg-Rassy 54 Cloudy Bay -May 2020. Season20 Ep20

Lots of challenges on this 2nd leg of our passage: setting a 24hr mileage record; caught-out in the gulf stream; an accidental gybe; lightning storm and a thunderous leg to the infamous Hatteras shoals. Following on from part 1: after a brief stop in West Palm, Florida, we continue our passage up t...
ep50 – Sailing USA to Bermuda – Hallberg-Rassy 54 Cloudy Bay – Nov 2018
Sail Cloudy Bay

ep50 – Sailing USA to Bermuda – Hallberg-Rassy 54 Cloudy Bay – Nov 2018

After being weather bound in Norfolk VA for 8 days, s/v Cloudy Bay (Hallberg-Rassy 54) left Norfolk on the tail end of yet another large weather system. Sailing to Bermuda started on a bright but cold November day, with strong offshore winds over a flat sea. So we sailed very fast down the Virginia ...
ep49 – Sailing Chesapeake – Deal MD – Norfolk VA – Hallberg-Rassy 54 Cloudy Bay – Nov 2018
Sail Cloudy Bay

ep49 – Sailing Chesapeake – Deal MD – Norfolk VA – Hallberg-Rassy 54 Cloudy Bay – Nov 2018

s/v Cloudy Bay (Hallberg-Rassy 54) left Herring Bay MD on a crisp bright day, and after a long day of motoring we anchored in the dark, in Fisher Bay, Deltaville VA. Overnight the wind picks up, and next morning we set off for a great downwind sailing to Norfolk VA. It’s been so long since we sailed...
ep47 – Sailing Chesapeake – Betterton to Edgewater – Hallberg-Rassy 54 Cloudy Bay – Oct 2018
Sail Cloudy Bay

ep47 – Sailing Chesapeake – Betterton to Edgewater – Hallberg-Rassy 54 Cloudy Bay – Oct 2018

s/v Cloudy Bay (Hallberg-Rassy 54) left the quiet overnight anchorage of Betterton in the northern end of the Chesapeake and had a wonderful sailing trip to Edgewater on South River, just south of Annapolis. At first light wind and current against us, but it soon turned into an exhilarating upwind s...
ep46 – Sailing Delaware River – Cape May to Betterton – Hallberg-Rassy 54 Cloudy Bay – Sep 2018
Sail Cloudy Bay

ep46 – Sailing Delaware River – Cape May to Betterton – Hallberg-Rassy 54 Cloudy Bay – Sep 2018

In this sailing adventure s/v Cloudy Bay (Hallberg-Rassy 54) leaves Cape May on a bright sunny early morning and sails up the Delaware River to the Delaware canal. On the way we have an exciting sailing race with another yacht, who sneakily sailed passed us while we were enjoying breakfast! That rac...
ep45 – Sailing New York – Huntington to Cape May – Hallberg-Rassy 54 Cloudy Bay – Sep 2018
Sail Cloudy Bay

ep45 – Sailing New York – Huntington to Cape May – Hallberg-Rassy 54 Cloudy Bay – Sep 2018

After a long time weather bound in Huntington NY (Long Island), s/v Cloudy Bay (Hallberg-Rassy 54), is on the move again. This sailing trip takes us down the East River alongside Manhattan. But this time, as opposed to July when we came up the river, we have to be passing on the east side of Rooseve...
ep44 – Sailing Long Island – Greenport, Huntington & New York – HR54 Cloudy Bay – Sep 2018
Sail Cloudy Bay

ep44 – Sailing Long Island – Greenport, Huntington & New York – HR54 Cloudy Bay – Sep 2018

After a night in Orient Bay near Greenport NY, s/v Cloudy Bay (Hallberg-Rassy 54) leaves the quiet anchorage at sunrise with a long day sail to Huntington NY. So this sailing trip takes us along the north shore of Long Island, from the north fork to Huntington. Once in Huntington we take a mooring b...
ep43 – Sailing Long Island – Shelter Island & Greenport – Hallberg-Rassy 54 Cloudy Bay – Sep 2018
Sail Cloudy Bay

ep43 – Sailing Long Island – Shelter Island & Greenport – Hallberg-Rassy 54 Cloudy Bay – Sep 2018

s/v Cloudy Bay (Hallberg-Rassy 54) left Sag Harbor on the south fork of eastern Long Island, heading for Greenport on the north fork. On the way we stop in West Neck, Shelter Island, where we run aground as we entered the lagoon. Luckily the tide was rising but not fast enough to avoid several inter...
ep42 – Sailing Long Island – Sag Harbor & The Hamptons – Hallberg-Rassy 54 Cloudy Bay – Sep 2018
Sail Cloudy Bay

ep42 – Sailing Long Island – Sag Harbor & The Hamptons – Hallberg-Rassy 54 Cloudy Bay – Sep 2018

s/v Cloudy Bay (Hallberg-Rassy 54) leaves Fisher Island CT on a foggy morning and has a slow and calm sailing trip to the south fork of Long Island NY. Not the most thrilling sailing adventure, but it was nevertheless a very pleasant sail. We anchor in Sag Harbor, where we wait for the sky to clear....
ep41 – Sailing Connecticut – Sailing Stonington – Hallberg-Rassy 54 Cloudy Bay – Sep 2018
Sail Cloudy Bay

ep41 – Sailing Connecticut – Sailing Stonington – Hallberg-Rassy 54 Cloudy Bay – Sep 2018

From Block Island RI, s/v Cloudy Bay (Hallberg-Rassy 54) is sailing across Long Island Sound towards Connecticut, on a nice beam reach in 18 kts of wind. During that sailing trip a vertical batten decided to slide out, and Glen had to rescue it, pushing it back inside the batten pocket and secure it...
ep40 – Sailing Block Island – Sailing Rhode Island – Hallberg-Rassy 54 Cloudy Bay – Sep 2018
Sail Cloudy Bay

ep40 – Sailing Block Island – Sailing Rhode Island – Hallberg-Rassy 54 Cloudy Bay – Sep 2018

From Newport, s/v Cloudy Bay (Hallberg-Rassy 54) continues the sailing east coast USA adventure to Block Island. Short sailing trip, only 20 nm away. Not much wind that day, so we had to motor most of the distance. We found Block Island very pretty, with nice beaches and a relaxed atmosphere. Simil...
ep39 – Sailing Bristol – Sailing Rhode Island – Hallberg-Rassy 54 Cloudy Bay – Sep 2018
Sail Cloudy Bay

ep39 – Sailing Bristol – Sailing Rhode Island – Hallberg-Rassy 54 Cloudy Bay – Sep 2018

After 4 days in Newport, s/v Cloudy Bay (Hallberg-Rassy 54) sailing adventure in Rhode Island continues to Bristol. Sailing from Newport to Bristol turned out to be mostly motoring, but on the return trip it was a totally different sailing experience! To begin with, it was a very calm downwind saili...
ep38 – Sailing Newport – Sailing Rhode Island – Hallberg-Rassy 54 Cloudy Bay – Sep 2018
Sail Cloudy Bay

ep38 – Sailing Newport – Sailing Rhode Island – Hallberg-Rassy 54 Cloudy Bay – Sep 2018

s/v Cloudy Bay (Hallberg-Rassy 54) sailed from Martha's Vineyard to Newport Rhode Island, with an overnight stop in Cuttyhunk Harbor in the Elizabeth Islands. In Cuttyhunk we had our first boat collision incident since we have Cloudy Bay - a yacht dragged its anchor and collided with us in the ...
ep37 – Sailing Nantucket – Sailing Massachusetts – HR54 Cloudy Bay, Aug 2018
Sail Cloudy Bay

ep37 – Sailing Nantucket – Sailing Massachusetts – HR54 Cloudy Bay, Aug 2018

s/v Cloudy Bay's (Hallberg-Rassy 54) sailing trip continues, and in this video we are sailing Cloudy Bay from Martha's Vineyard to the island of Nantucket. In Nantucket we had 4 days of bright sunshine and calm weather. We anchored sv Cloudy Bay in the busy Nantucket Harbour along side ma...
ep33 – Sailing Maine – Mount Desert Island to Camden – Hallberg-Rassy R54 Cloudy Bay – July 2018
Sail Cloudy Bay

ep33 – Sailing Maine – Mount Desert Island to Camden – Hallberg-Rassy R54 Cloudy Bay – July 2018

Sailing Maine back south: From our most northern Maine destination, Mount Desert Island, s/v Cloudy Bay (Hallberg-Rassy 54) starts the gentle cruise back south. In this sailing adventure we visit Winter Harbor where we buy some lobsters, then the quaint fishing village of Stonington, where we cook t...
ep32 – Sailing Maine – Sailing Boston to Mount Desert Island – HR54 Cloudy Bay – July 2018
Sail Cloudy Bay

ep32 – Sailing Maine – Sailing Boston to Mount Desert Island – HR54 Cloudy Bay – July 2018

After attending 4th ofJuly 4th celebrations in Boston, s/v Cloudy Bay (Hallberg-Rassy 54) continues the sailing adventure with an overnight passage across the cool waters of Bay of Maine to the beautiful Mount Desert Island. Sailing Maine starts from here! We anchor in Bar Harbor and visit friends ...
ep31 – Sailing New York to Boston – Hallberg-Rassy 54 Cloudy Bay – July 2018
Sail Cloudy Bay

ep31 – Sailing New York to Boston – Hallberg-Rassy 54 Cloudy Bay – July 2018

s/v Cloudy Bay (Hallberg-Rassy 54) sailing adventure continues north. After our sailing into New York Harbor and the 24hr flying visit of New York, we head into an idyllic evening, sailing Long Island Sound towards New England. The overnight passage gets us to Cape Cod Canal, then into Cape Cod Bay,...
ep29 – Sailing Savannah GA to Charleston SC – east coast USA – Hallberg-Rassy54 Cloudy Bay June 2018
Sail Cloudy Bay

ep29 – Sailing Savannah GA to Charleston SC – east coast USA – Hallberg-Rassy54 Cloudy Bay June 2018

Sailing east coast USA: After an overnight sail from Savannah GA, s/v Cloudy Bay (Hallberg-Rassy 54) arrives in Charleston SC where we spend few days visiting the town and few days in Greenville (visiting friends Caroline & David) and the Appalachian Mountains. We found Charleston very charming,...
ep28 – Sailing St.Augustin FL to Savannah GA – Sailing east coast USA – HR54 Cloudy Bay – Jun 2018
Sail Cloudy Bay

ep28 – Sailing St.Augustin FL to Savannah GA – Sailing east coast USA – HR54 Cloudy Bay – Jun 2018

s/v Cloudy Bay (Hallberg Rassy 54) starts sailing east coast of USA! We had a great birthday weekend in Savannah, the hostess city of the south, which is probably one of the most beautiful places in USA, with exceptional architecture and three centuries of history. We were very taken with its combin...
ep27 – St.Augustine Florida – Hallberg-Rassy 54 Cloudy Bay – June 2018
Sail Cloudy Bay

ep27 – St.Augustine Florida – Hallberg-Rassy 54 Cloudy Bay – June 2018

After 12 days passage, sailing from Antigua to USA, s/v Cloudy Bay (Hallberg-Rassy 54) arrives in St.Augustine, Florida, the oldest recorded town in America (1513) and the starting point of us sailing east coast USA. Here we complete the check in formalities into USA, visit St. Augustine and have tw...
1000 miles on an Outremer 5x (UMA 2.0 ?)— Sailing Uma [Step 130]
Sailing Uma

1000 miles on an Outremer 5x (UMA 2.0 ?)— Sailing Uma [Step 130]

You're just going to have to watch this video to find out. You know you want to ... 😂 oh and we also got to meet Black Riley. If you enjoyed this episode, please give it thumbs up, it helps us out a bunch :) [ WANT MORE ? ] Visit Become a patron to get instant access to The Vault, where we ...
Living the American Dream! (Sailing Ruby Rose) Ep 24
Sailing Ruby Rose

Living the American Dream! (Sailing Ruby Rose) Ep 24

This week we're finally in America living the dream! We explore Charleston, South Carolina and immerse ourselves in the local culture the only way we know how: by eating and drinking our way through the city. We try the southern classic of shrimp and grits, check out a local crawfish festival, ...
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