Table of Contents

  1. Ft. Lauderdale to Martha’s Vineyard
  2. Martha’s Vineyard
  3. Martha’s Vineyard to Bermuda
  4. Bermuda to Nevis
  5. Plan B
    1. As of September 25, 2020

During these times of uncertainty, it is helpful to sketch out a preliminary 2020 sailing plan to feel like you have control over something. Also, it’s a pleasant distraction from the 24/7 coronavirus news.

Upon purchase of s/v Rachel J. Slocum, we will have the pleasure of spending time with Bill (her original owner and designer), so we can familiarize ourself with sailing a 50’ staysail schooner. The initial 2020 sailing plan is to sail 3 legs of a triangle later this year, and spending significant time in the Vineyard living aboard:

  1. Cruise Atlantic Coast from Florida to Martha’s Vineyard
    • Daysails around the Vineyard, Nantucket, Cape Cod and Newport
  2. Offshore Passage from Martha’s Vineyard to Bermuda
  3. Offshore Passage from Bermuda to Nevis, Eastern Caribbean

These we will describe in more detail below.


Ft. Lauderdale to Martha’s Vineyard

Distance: ~1,025 nautical miles (over 5 days at 8 knots)

Best time: May to June

The first leg of this journey will entirely depend on when U.S. lockdown mode is eased, specifically, when marinas open up for cruisers to sail from port to port. Even if this doesn’t happen until August or September, this plan can still hold for this year.

Our goal is probably to do a relatively fast passage offshore rather than take the ICW, which in places have a 5’ draft (our boat draws 6’).

While Andrew and I have done some late night sailing, we haven’t done any overnights. So this will be a great shakedown cruise.


Martha’s Vineyard

Best time: May to September

While the sailing season is short compared to other U.S. locales, the area makes up for it with stunning scenery and iconic culture of sailing. There is also a tremendous amount of variety, from calm, protected waters to treacherous seas for seasoned sailors. Lee Gaines describes the area as follows:

  • Cape Cod Bay provides a calm and protected sailing environment but northern winds may occasionally churn the usually placid bay into a raging sea.
  • On the southern side of the Cape, Nantucket Sound and Buzzards Bay are popular sailing spots offering easy access to Martha’s Vineyard and Nantucket. Though not as sheltered as the Cape Cod Bay, calm weather makes this area a pleasant and relatively safe boating destination.
  • The Atlantic Ocean, accessed from the eastern ports along Cape Cod’s arm, can be a treacherous boating area and should be reserved for the most competent and experienced sailors.

For me, this will be returning to a region I called home for 10 years. Sailing here in s/v Rachel J. Slocum with Andrew and becoming part of this storied tradition will make this experience surreal, as we call the Vineyard home for a few months.

To be sure, there will be coves, inlets and different marinas to check out from Newport, RI to Boston, MA. Most of all, I think it will be fun to take Andrew to places that have personal history for me: in Wellesley where I went to school, in Cambridge where I hung out with friends, and in Boston where I lived in a 300 sq ft apartment.

Thanks to Mountain Project, we’ll also be sure to check out the local crags in Massachusetts. Lower Walls near Chestnut Hill looks promising. Otherwise, the coastline offers only boulder problems. Easy to get to, but not my cup of tea.


Martha’s Vineyard to Bermuda

Distance: ~650 nautical miles (over 3 days at 8 knots)

Tropical Storms: June to November

At some point in late October/early November, we will look for a reasonable weather window to point our bow southeast and head for Bermuda. With Bill aboard taking us through the paces once again, we’ll have a short passage to Bermuda.

In the most recent outlook, the hurricane season for 2020 is expected to be more active than in years past.

  • A total of 16 named storms, eight hurricanes and four major hurricanes are expected this season.
  • This is above the 30-year average of 12 named storms, six hurricanes and three major hurricanes.

Despite its latitude and longitude – and its location so far north of the Caribbean, nearly a thousand miles north of it in fact – Bermuda is entirely frost-free, snow-free and ice-free. Why? Because the warm waters of the Gulf Stream pass near Bermuda.

Within less than a week, we will be traveling from crisp, autumnal New England weather to balmy, sub-tropical island weather. Luckily our 30-weeks to Minimalism downsizing project prepared us for these extremes.

Exploring beautiful places and capturing them on film will be our goals along with rock climbing opportunities. Deep water solo, anyone?

We won’t stay here long, because our ultimate destination is the island of Nevis, Eastern Caribbean.


Bermuda to Nevis

Distance: 900-1,000 nautical miles (over 5 days at 8 knots)

Best time: November (offshore), late November to May (via Bahamas)

Tropical Storms: June to November

Once we’ve had our fill of deep water solo in Bermuda, we’ll take a look at the weather window and head south toward the Eastern Caribbean. We haven’t decided on whether we’ll sail via Bahamas or not.

Our goal is to safely deposit Bill back at his home on Nevis.

While we were doing some of this planning, we discovered that Pinney’s Beach is one of the top attractions of the island of Nevis. Pinney also happens to be the same as Bill’s last name.


We’ll get to the bottom of that story once we make landfall.


Plan B

Many states are beginning to ease restrictions beginning this week.

We have been monitoring the news on updates with respect to California, Florida and Massachusetts since this will impact our plans in the near term. While hair salons, bowling alleys and certain retail operations are opening up, we feel it is too early to commit to any action, in light of the following:

  • potential rebound spike in number of cases, hospital admissions, and mortality
  • likely second wave in the fall of this year
  • other factors still unknown that can help shape how the “new normal” will work

The telltales we are reading come largely from the cruising community and whether marinas and services open up, and whether there is less restricted movement among ports. Until we see that happening (which will be on the trailing edge or the “leech” of trends), we’ll remain on hold.

If those trends don’t materially change until November, we will move directly forward with sailing s/v Rachel J. Slocum from Florida to the Bahamas or directly to Nevis. This scenario can hold until well into spring 2021. Either scenario would be great opportunities for us to learn the ropes on this new vessel, so we can’t complain.

As of September 25, 2020

While we wait out hurricane season in Ft Lauderdale, we are busy with moving out of our house and onto the boat. We have heard the BVIs are opening up December 1st which is promising news. For a variety of reasons, we decided with Bill to head for St. Kitts and Nevis for our maiden voyage.

Currently the country requires strict quarantine under guard for 14 days, paid for by each individual/party coming in. We are so grateful that Bill’s sister is letting us stay at her house nearby where s/v Rachel J Slocum will be moored. Thereafter, we’ll have freedom to come and go, explore the island and cruising grounds.

It’s difficult to predict how long we’ll stay there. We’re taking each day one at a time.

If you would like to delve deeper into our adventure as it unfolds, please consider joining the Serenade Wind Crew. Our sister site provides more information on what it means to be part of the crew, unlock the pirate’s booty, and receive other exclusive access and benefits.The first 50 members have a gift waiting.