Sailing to the East Coast of the US – From Top to Bottom

Having crossed from the Mediterranean to the Caribbean, we needed to get ourselves organised to spend the hurricane season out of harm’s way in the north-eastern coast of the USA. For our American friends, getting to and from the USA is a well understood exercise, but for the rest of us that come from the rest of the world, it’s a bit of an unknown adventure.

St Augustine – the oldest City in the USA

The East Coast of the USA is a massive cruising ground, so I‘m just going to touch on our highlights, together with some important pieces of information to hopefully give a useful overview of what to expect, what you really need to know to get by, and how we went about tackling it. There is a myriad of other great articles available on specific cruising grounds that provide much more detailed information than my 20,000 foot helicopter view.

Martha’s Vineyard

The first item on the “Lets sail to the USA” agenda was to organise a USA Visa. The Visa Waiver system I had been using to travel by air to the USA was not an option when arriving by boat. I needed to find a USA Embassy and apply for a B1/B2 Visa. This involved filling in an online application and booking an interview at an Embassy. It then takes about 2 weeks for the visa to be issued, during which time they hold onto your passport so you need to plan to stay put.  In the Caribbean, US Embassies are few and far between. A lot of our friends got their Visa in Barbados and I ended up getting mine in Bermuda as we were there for a month for the Americas Cup.

George Washington’s Mt Vernon House and Museum

The next task was to consider where we would make landfall and how we would get there. The two options we considered were via the Bahamas or via Bermuda.  The Bahamas option involves following the trade winds from the Caribbean to the Bahamas and then hooking into the gulf stream to take you up the coast of the USA to your chosen port of entry. With the gulf stream running at up to 3 knots this sounds like a dream run, but any significant wind out of the north will create considerable wind against current issues that will make this route very uncomfortable and dangerous. Especially if the plan is to head around the notoriously dangerous Cape Fear and Cape Hatteras on the way to Chesapeake Bay. The other consideration when choosing this approach is the stifling heat of summer in Chesapeake Bay and everywhere south of here. We were told to visit these areas in the Autumn when the weather is a lot more pleasant.

Americas Cup – Bermuda

In our case, we chose to go via Bermuda. We were swayed by the prospect of spending a month in the absolutely stunning waters of Bermuda, watching the Americas Cup; which turned out to be one of the highlights of our cruising career. The 820nm sail from Tortola in the BVIs to Bermuda consisted of 2 days of beautiful trade winds sailing under Geneker on a broad reach, followed by 2 days of motoring in the horse latitudes, with the last day back sailing all the way to Georgetown, arriving in mid-afternoon.

Watching the America’s Cup on board La Mischief

Once in Bermuda, we sat down with our friends from Aura, Lady Rebel and Touterelle and decided to head for Newport after the Cup wrapped up in late July. In reality we could have headed anywhere from Nova Scotia in Canada down to New York as the distances from Bermuda were pretty similar. We chose Newport because it sounded straightforward and was a sailing mecca. There was a bit of synergy sailing from Bermuda, the then home of the America’s Cup, to Newport, which was the home of the cup for all those years leading up to 1983, when Australia 2’s winged keel did the job on Dennis Connor.  We were also aiming to get to Newport in time for our first 4th of July, and we had discovered that Bristol, which was a short bus ride away from Newport had the oldest parade in the USA. We were in.

4th July Celebrations in Bristol – the Oldest Parade in the USA

The 635nm sail from Bermuda to Newport was a bit frustrating. It was more motoring than we would have liked, with the only excitement being the gulf stream crossing, which was interesting rather than difficult.  With our Bachelor of Hindsight degree, a better plan would have been to head to Nova Scotia in Canada and cruise one way down the coast to Maine and beyond, thus covering more territory rather than the backtracking that we ended up doing.

Anyway back to what we really did, which was to head for Newport. The approach to Newport was fantastic, with fireworks happening all up and down the coast as we got there in early evening on the 2nd July. Check-in had its challenges, as we were anchoring out and not going to a marina. The first challenge was the US Customs and Border Protection required that we had a US mobile number for them to call us back on. Luckily, my partner Dee is a US citizen so we were able to oblige. In fact, we helped out our friends with this requirement as well using the VHF to pass messages back and forth.  We also needed to find a public jetty to pull alongside and luckily there was a couple of free options in Newport. We found ActiveCaptain to be really helpful for finding dockage and anchoring options.


The third trick to checking in is to ensure that you ask for a US Cruising License. We missed this requirement and had to sign up for an online faxing solution, so we could fax the application in and get the license back using the eFax software running on my Mac. The other option was to drive quite a distance to pick one up. Being a foreign vessel, with the cruising license we were able to cruise the US, reporting our movements by phone whenever we moved locations. It’s very important to do this as you risk a big fine if you forget to report that you have moved spots.

Newport’s a great sailing town, rich in history with the Herreshoff museum and the cute town of Bristol where we saw the USA’s oldest 4th July parade.

From Newport, we decided to head north east up to the legendary cruising grounds of Maine. In the end, we made it as far as Camden before we had to turn around to get back to New York in time to meet my son, Alex and his girlfriend Sophie. Highlights along the way included Boston (where we were able to pick up a mooring buoy right in downtown); Salem (witches), Manchester by the Sea (cute town from the movie), P-Town (lots of colour and movement – America’s gay capital), Block Island, Martha’s Vineyard, Gloucester, Newburyport (whaling history) and Mystic (great maritime museum).

Tenants Harbor – Maine

Maine itself was a lovely cruising experience in between dodging countless thousands of lobster pots along its shallow coastline. There’s some wonderfully cute towns and nice anchorages that we managed to visit.


Back in New York in mid-August we set about tackling this great city by boat, not an easy task. We started by anchoring in Port Washington on Long Island and taking an hours train ride into New York every day. From here we motored along East river, the strait that separates Long Island from Manhattan Island, before dropping anchor right beside the Statue of Liberty. This is really only an overnight stop as they is nowhere to leave the dinghy and get into New York from here. We did however manage to drop our friends Marco and Penny off at a boat ramp and they were able to Uber home.  From here, we sailed out of the harbor and past Coney Island to Sheepshead Bay, where we got a mooring ball and caught a 40 minute subway trip into New York – much better.

From New York, we headed down the coast, via Atlantic City and the delightful town of Cape May and into Delaware Bay, before swinging into the C and D Canal, which popped us into the famous cruising grounds of Chesapeake Bay. We checked out a nice secluded river anchorage, before anchoring in downtown Baltimore, a pleasant surprise and one of our favourites. From here we headed to Annapolis, the sailing capital of the USA, where we lifted La Mischief and had some boat work done.

Surprising Baltimore

Originally our plan was to join the Sawlty Dawg Rally from Norfolk down to the BVIs but we had a change of heart and decided to go to Florida and the Bahamas on our way back to the Caribbean, despite the difficulties in heading East against the Trade Winds.

Sassafras River – Chesapeake Bay

We successfully negotiated the notorious Cape Hatteras and Cape Fear on our way to Charleston, anchoring in the river without snagging anything. Charleston was a great stop, overflowing with history, delicious food, great music and wonderful southern architecture.


Like most other international cruisers visiting the USA, we’d done the ocean miles to qualify to join the Ocean Cruising Club (OCC) and this gave us access to various Port Officers up and down the coast. Some of these Port Officers have free dock space and we took the opportunity to spend a few days with Ray and…. Like all the other Americans we met, they were friendly and generous people, inviting us for dinner, lending us their car and letting us tie up outside their house.


Onwards we pressed to St Augustine, entering through a tricky entrance that continuously shifts. Another great stop in the oldest city in the USA with its rich Spanish history. It was here we celebrated my first Thanksgiving in the rain, at a potluck lunch with 85 other cruisers.

Cape Canaveral was our next stop, leaving La Mischief in Cape Marina, so we could hop in a rental car and do some big kids stuff. We spent a full day at the Kennedy Space Centre and a couple of days in Orlando at Universal Studios. We had also timed our visit to do a one day Cruising World Seminar at Cocoa Beach, with Fatty Goodlander as the star attraction. How could we resist?

We continued down the coast of Florida, stopping at Lake Worth and Ft Lauderdale, the self-proclaimed Yachting Capital of the World. By now it was December and we anchored in Sunrise Bay for a front row seat at the Annual Christmas Boat Parade.

We left the boat in Ft Lauderdale whilst I travelled back to Australia for a month over Christmas– a 30 hour plane trip. Returning in early January, we then left for the Florida Keys, spending a wonderful couple of weeks in this interesting part of the world, getting an extra 1000W of solar panels fitted whilst in Boot Key Harbor by Seatek Marine. The highlight of the Keys is undoubtedly Key West, with its 28 happy hours, the Hemingway house museum and the Mel Fisher shipwreck museum.

After 6 magical months in the USA we left Boot Key Harbour for Bimini in the Bahamas, 120nm away. Funny thing was, we didn’t have to check out of the USA. You just leave and then just check into the Bahamas.

The Good

  • Friendly and helpful natives.
  • One Big History lesson as you stop along the way.
  • Beautiful coastal towns with cute houses and shopping districts
  • Secluded anchorages with scenery to die for.
  • Iconic cities such as Boston, New York, Baltimore, Washington DC and Miami, several with moorings and anchorages right near down town.
  • Plenty of pump out stations – often free.
  • Shopping for boat parts on Amazon. Can get anything.
  • You get to visit famous Sailing Centres such as Newport, Mystic, Annapolis and Ft Lauderdale.

The Challenges

  • Finding nivce swimming spots. For those of us who have been spoiled with the clear and warm waters of the Med and the Carribean, the water is not that inviting for swimming – being cold and murky.
  • Dodging thousands of Lobster Traps, especially in Maine.
  • Light Winds that meant we did lots more motoring than we expected (on the flip side we largely avoided bad weather).
  • Limited Anchoring options in some places. Often anchorages are overrun by mooring balls.
  • Our air draft of over 65 feet kept us out of a lot of good spots. 99% of the ICW was off limits as was the inside of the Florida Keys because of all those 65 foot bridges.
  • Services were expensive – but quality is good.
  • Marinas were expensive and sometimes hard to find (although we liked to anchor out a lot).
  • Finding a boatyard able to lift a catamaran was more difficult than expected.

Where We Went

  • 3rd July Arrived in Newport


  • Newport
  • Bristol (bus)
  • Providence, RI (car)
  • Martha’s Vineyard
  • Gloucester
  • Boston
  • Salem
  • Portsmouth, NH
  • Portland, Maine
  • Booth Bay, Maine
  • Camden, Maine


  • Wells
  • ProvinceTown (P-Town)
  • Newburyport
  • Plymouth
  • New Bedford
  • Manchester by the Sea
  • Block Island
  • Mystic
  • New York


  • Atlantic City
  • Cape May
  • Delaware Bay
  • Chesapeake Bay
  • Baltimore
  • Washington DC (car)
  • Mt Vernon (car)
  • Philadelphia (car)


  • Chesapeake Bay
  • Annapolis (on the hard)
  • Perth (Fly)


  • Portsmouth
  • Norfolk
  • Around Cape Hatteras and Cape Fear
  • Georgetown, SC
  • Beaufort, SC
  • St Augustine


  • Cape Canaveral
  • Kennedy Space Centre (Car)
  • Orlando (Car)
  • Cocoa Beach (car)
  • Lake Worth (West Palm Beach)
  • Ft Lauderdale
  • Perth (Fly)


  • Hollywood
  • Angelfish Creek
  • Key Largo
  • Boot Key Harbor (Marathon)
  • Key West (car)


  • 1st February – Marathon to Bimini (Bahamas)

Surprising Baltimore

Leaving the Sassafras River, we headed to Baltimore, 24nm away. The anchorage in Baltimore was fantastic, right in the heart of the city with a good dinghy dock right across the road from a big Safeways supermarket and West Marine just down the road.

Around the corner was the old town with its great restaurants and bars and it was here we first caught up with Adam, Dee’s nephew. Adam lives in Baltimore and turned out to be a great tour guide as well as a great bloke showing us around not only Baltimore, but driving us to Philadelphia as well.

Sailing From New York down to Chesapeake Bay

This short video shows our sail from New York to Chesapeake Bay. We decided to do a series of day hops calling in at Atlantic City and Cape May, before heading up Delaware Bay and through the C&D Canal to Chesapeake Bay. We spent a delightful night in a quiet anchorage in Sassafras River before heading off to Baltimore to see Dee’s nephew Adam who lives there.

New York, New York

This is a video of our time in New York with Alex and Sophie. Our plan of attack for New York was to anchor in Port Washington and take the local train into Penn Station. We needed to allow 40 minutes for the dinghy ride and walk up to the train station. Then it was a 50 minute direct train into NYC. Later we transmitted the East River and anchored at the Statue of Liberty for a night before moving around to Sheepshead Bay where we took a $40 a night mooring, which included a launch service. From here we explored Coney Island and took the subway into the City.

You Can Check Out But You Can Never Leave

Tuesday was day one of the regatta and it was all aboard Hotel California Too. Steve, our skipper had experience stamped all over his forehead having done many regattas over many years in the Caribbean. At one stage he was having 500 different people racing on HC every year. Richard was in charge of assembling a crew for Steve this year and I’ve got to say he did a pretty good job. Our star was undoubtedly Annie, our Tactician who was an Olympic Silver Medallist and Americas Cup sailor. Bill was pretty handy on the foredeck having a pretty good sailing resume all the way to AC trials. Anna was Steve’s crew, hailing from Poland via Toronto and the most of us were catamaran liveaboards – Steve being the only one that owned a monohull. Having two Steves on the boat was confusing so I reverted back to Tully.

We were sailing in a class with white sails only so it was pretty easy most of the time. We quickly picked out our nemesis in Spirit, a 65 foot Swan who if not for acknowledging a collision and refusing to do a 360, would have beat us into second. The boat that got first was sailed by an Italian AC skipper, a hired hand, who in the last race beat us by 3 hours (in light to non-existent winds) – Bill commented that he was never in a 20 mile race where he had come second by 3 hours. The racing was fun with the big maxis steaming past us at close quarters and the odd bit of drama after the starts.  With the last race on Saturday cancelled due to lack of wind, we found ourselves in second, due to a couple of DSQs – what a result.

Over the week, the crew gelled really well – both on and off the boat, helped along by the many regatta parties every night (both in the regatta village and one night at Shell Beach) and on the Thursday rest day at Nikki Beach. Eric and Annie kindly invited us on board their Catana 47, El Gato, which we took around to Nikki Beach for the “rest” day.

It was tough going- racing during the day and partying at night but I wouldn’t have missed it for quids. The regatta put on great live bands, French cabaret and of course pole dancers!!! Only in France could you get way with that. The awards ceremony was a hoot with Hotel California making the most noise on the podium (complete with sparklers). You would have thought we had won!!! There were bottles of Verve Clicquot everywhere and the shot of the night went to Christine who lay down in front of all the said bottles that were neatly arranged for the awards ceremony, pretending to be drunk. Later on that night she wouldn’t have needed to pretend.

Regatta over, we headed around to Columbier for a day of recuperation, followed by a final fling. We called an end to the recuperation period about 4pm and headed off to Sugar Shack, for Christine’s now famous jello shots. Matt enjoyed handing them around and took the “one for  you, one for me approach”, which came back to bite him later.  Pre-dinner drinks over, we jumped ship over to La Mischief for an Aussie BBQ dinner and yet more drinks, way past Matt’s tipping point. It’s always a good night when you have to hop into your dinghy and return various items to various boats the next day.

Then it was off back to St. Martin for a crew change.

Going Chic

For such a small island of only 25 square kilometres and a population of 10,000, Saint Barthélemy does pack a punch. Chris Columbus discovered and named it after his brother Bartolomeo – now there’s a bit of trivia for you. Now days its French, having been British and Swedish for a while back in the old days.

Up until the 1970’s, St Barths was a pretty desolate and poor island – and then they discovered tourism (or tourism discovered St Barths) and off it went. These days the rich and famous come to the island and the place is littered with big boats, high-end restaurants and top of the wuzza hotels.

But despite this, it’s still a great place to hang out. The anchorage is beautiful – crowded but still relatively easy to find a space (until of course the charterers come and anchor right next to you). The best anchorage is on the outside of the channel where the sandy bottom is great holding in 8-20m of clear water.

Having snorkeled the anchor, we took the dinghy ride into town and finished checking in (a process we’d largely done over the Internet before we got here. After a quick walk around we retired to the Bar de l’Oubli (the Bar to Forget for all you language challenged people). We ended up having dinner there before going across to Le Select, a local institution that has been running forever.

People mistake it for being the original Cheeseburger in Paradise. Jimmy Buffett evidently sold Marius rights to the Cheeseburger In Paradise tagline in exchange for his food and bar tab being free for life. Jimmy also cooked some of the first burgers at the original Le Select grill. The origins of Cheeseburger in Paradise are from the BVIs, but never mind, I still intend to eat one at Le Select.

The highlight of our night at Le Select (besides the cheap bottles of wine) was running into Dee’s friend Richard, who has been coming to St Barths forever. He was a wealth of information on the place and took us over to Josephine’s to listen to some local and travelling muso’s who were brilliant.

Next day, we dragged ourselves up and got ourselves a rental car for 30 euro a day. Not bad.  We then headed off to visit all the different beaches on the island, with their beautiful sand and clear water. We stopped at the famous Nikki Beach, and walked along the beach to the famous airport where planes take off metres above the water. We finished the day over at Marche U, the largest supermarket on the island. There’s also a Casino supermarket right next to the dinghy dock so we should be able to eat well, if not a little expensively (but not too bad).

Saturday was a clean the boat day, having got covered in salt on the way over from Saba.  Hard work done we snorkelled over to the reef and said hello to the barracuda and the squid swimming around the coral.

Then we had Richard, Donna and Bill over for an Aussie BBQ on the back of La Mischief. Richard set up the Latitude 38 magazine and splits his time between 2 boats here in St Barths, a canal boat in Europe and a cat in California. Donna and Richard are almost St Barths locals, having been coming here for the last 100 years, so they filled us in on a lot of island stuff.

Moving onto Sunday, we pushed the lazy button and didn’t do much. Barbara spent the morning with Cliff, whilst Dee and I didn’t do much. Cliff and Barbara returned after lunch and we dinghied over to the 68 foot Swan that Cliff was skipper on. Cliff was getting too close to Rambler 88, who had installed a mooring for race week, so he decided to motor on down to Columbier for the night. He towed our dinghy and we had a look see at a very nice bay, before heading back in our dinghy to pick up Jennifer from the St Martin Ferry in time for yet another regatta party.

And then it was time for the Regatta!












Dead Men Tell No Tales!

The island of Saba is forbidding and steep, a natural fortress, and so the island became a private sanctuary for smugglers and pirates. The most notable native Saban pirate was Hiram Beakes, who famously quipped, “Dead men tell no tales”.

Saba has had a chequered history, having been French for 12 years, English for 18 years and Dutch for 345 years.

We got to Saba in the early afternoon and discovered the wind pretty well swirls around the island – when its blowing there is no lee shore – the wind tends to bend around the west coast. Saba is pretty impressive on approach with steep cliffs dropping off into the ocean.It is a challenging spot to go to. It’s just a big volcano that comes straight out of the ocean, with no natural harbours anywhere.

We came around the northern end and past Ladder Bay. Out came the binoculars to spy on Elsa, a once impressive 150T super yacht who was up on the rocks having broken free of a Marine Parks mooring 5 or so nights ago when Gloria was there. Our Barbados 50 friends Kirakou had come to grief in this same bay, having wrapped the mooring line around their twin keels and chafing through, ending up also on the rocks. By the time we got there, Kirakou had been refloated and put on a barge to be hopefully fixed up.

We passed by around the corner to the main “port” of Wells Bay.  There’s some mooring buoys, both in the Marine Park and at of Wells Bay, but we chose to anchor n 20m of water and quite a swell. Safely anchored, we went and checked in, paying the customs fees and the Marine Parks fee that is mandatory.  We then retired to the one and only bar in Wells Bay and had a great chat with the local Spanish bar owner and the local fishermen, who filled us in on their version of the Elsa saga.

Next day it was off in a taxi for a bit of an island tour. We went up “The Road That Couldn’t Be Built”, as its name implies it is a road from Wells Bay to a town called The Bottom that the Dutch authorities said could never be built, but that didn’t deter a local who did a road building correspondence course and got the job done. True Story!!!  

We continued on up the road to another picturesque town called Windwardside before ducking over to see the spectacular and somewhat scary airport that looks like the deck of an aircraft carrier. We did a short hike through some impressive rain forest before heading back to Windwardside to book our diving for the next day, our main reason for coming to Saba There’s a good walk to the tallest part of the island which we passed on but next time it looks like something we should do.

The diving next day was both spectacular and frustrating. Frustrating because I had a leaky hose and had to cut my first dive short. To make matters worse the toothpaste trick on my new mask didn’t work and I couldn’t see what I was trying to photograph. The second dive was a bit better with a loaner reg and some mask cleaner. Meanwhile Dee and Barbara really enjoyed their diving on Saba.

We had planned to do a couple of days diving here but in the end we had to leave early because of the horrible anchoring/mooring field that had quite a swell running through it.

So apologies as the photos I took didn’t show off how good Saba diving is.Will definitely come back for some more next year but will pick our weather and swell window better.

The highlight of the island was hanging out with the local fishermen and the salvage crew we met who were working on rescuing the 150 ft Elsa from her resting place wedged on the rocks. We bought three lobster off Nikky, the local fisherman on our last night and headed off with Justin Time (no kidding!) up to Lollipops Hotel to BBQ them up.

It turned out to be a great night as we chatted to some very interesting salvagers, some of which had worked on the Costa Concordia. Lollipops is a bit of an institution on Saba and it was interesting to hang out there with its rather eccentric owner and a few of its regulars.

Evening over, it was time to get down the mountain and back to the boat. No probs – they just called the local cop who gave us a lift down in his very impressive 4×4. Another interesting night in our journey through life.

Next morning it was into the dinghy for a roughish ride into Customs and Immigration to check out before bashing our way to St Barths for a bit of Les Voiles action and partying.