How we Wound Up in Sarasota
We, Jerry and his wife, Gail, live on Cape Cod in Massachusetts where we have boated for years in the Nantucket Sound, usually to Martha’s Vineyard. So, how did we land in Sarasota?
Alto I
We started visiting Florida regularly in 01/2011 after we bought and installed a Ranger Tugs R25 (a small diesel trawler, shown below) in Sanford, FL (yes, that “Sanford” where Trayvon Martin was shot and killed not long after we arrived) on the St. John River. We named it Alto, for my wife – who sang as an alto in the Back Bay Chorale in Cambridge, Mass for years.
Alto I
We started visiting Florida regularly in 01/2011 after we bought and installed a Ranger Tugs R25 (a small diesel trawler, shown below) in Sanford, FL (yes, that “Sanford” where Trayvon Martin was shot and killed not long after we arrived) on the St. John River. We named it Alto, for my wife – who sang as an alto in the Back Bay Chorale in Cambridge, Mass for years.
The St. John River is the only US river that flows north at 1 mph, from the Orlando area up to Jacksonville. It’s home to many Manatee. You can’t go fast on it and it seemed like a safe place to get used to boating in Florida (Gail doesn’t swim). It is famous for its houseboat rentals that putt along and anchor everywhere.
The Keys
We next moved Alto to the Keys where we stored her on a rack and had it dropped into the water when we visited. It is a cheap way to have a home base in Key Largo – after paying for the boat, of course. Flying into Miami or Ft. Lauderdale we’d phone the marina to forklift it into a slip (we had use of a vacant slip for a week/month) and then re-rack it when we left, all for $448 per month including tax. Cheaper than a motel room for a couple days. Here’s a blog, AltosAdventures.com, telling the story of our Ranger Tug R25 on the St. John River, and in the Keys.
We also had part-ownership in a houseboat in Key Largo for several years but while successful, renting it out was onerous and Hurricane Irma in 2017 (a direct hit on the Keys) wore us out, even though the houseboat survived. On a floating dock it rose up and down six feet in the surge. Everything in the marina that was “fixed” to shore like the gas dock, restaurant and offices was submerged and demolished. We learned about the value of floating docks, like those at Marina Jack.
Key Largo is the first of the 90-mile chain of keys extending out from the southern tip of Florida. Closest to the airport, it still took over an hour by rented car to get there from the Miami and more from Ft. Lauderdale, after a four-hour flight from Boston. It was too expensive to taxi to, and once there we were car dependent. The marina was cool, especially with the houseboat, but we wanted something quicker and easier to commute to from Cape Cod; i.e., a destination close to an airport. A walkable town was also desirable.
Friends recommended Sarasota. Googling, I discovered Marina Jack was actually downtown. It was only a three hour flight from Boston, and then a 12-minute Uber ride from the airport (SRQ) to the marina! I visited, met the marina manager and we clicked and late in 2019 Alto moved to Marina Jack.
Alto II
Eventually, we moved up to a Ranger Tugs R31 with room for guests. We stayed on Alto II during winter visits and occasionally in the summer when it gets very, very hot. We noted the Keys, although further south, had cooler breezes than Sarasota. Luckily Alto was air conditioned. Two local captains watched over her in our absences, often for months in the summer. Alto II and Sarasota in the background:
We kept a Honda Fit in our friends’ condo garage which they used in our absence. When I visited alone I rarely needed it as I could walk anywhere in town or use an electric scooter to get around.
Sarasota became even easier to get to when Breeze Airlines offered nonstop 2 hr 40 minute flights from Providence, RI (PVD) to SRQ. PVD is about an hour and a half from our home on Cape Cod. I parked within walking distance of the PVD terminal and since I kept clothes on the boat I traveled with just a computer for to work.
In contrast to the Florida Keys, we could visit Sarasota for a long weekend. However, Gail never enjoyed living on a boat and came less often, so I looked for an affordable condo or house. It had to be downtown, because living on Alto was all about the downtown experience since we rarely took her out. Eventually we found a condo (actually two) which stimulated this website.
Alto III
With a condo in town, we no longer needed a big boat to live on. After worrying about five named storms in 2024, I was ready to downsize. We sold Alto II and bought a new Ranger Tugs outboard R25, Alto III, with a trailer. We can pull her out in an hour if bad weather threatens. We store the trailer for $100/mo on a friend’s oversize house lot a few minutes from the condo.
Now we can trailer Alto up north for the summer on Cape Cod, avoiding hurricane season in Florida. I don’t have a diesel 3/4 ton truck, so I solicit bids on uship.com where professional haulers compete for loads. Someone delivering to Florida will seek a paid load on their way back, to avoid
traveling empty, or “dead heading” for a good deal.
Cape Cod
Alto went from Cape Cod to Sarasota (1500 miles) in two days for $3000 at the end of November. A summer dock on Cape Cod is over $10,000 so we pay for a slip in Fairhaven, MA at a working marina for $4500. It’s an hour from Cape Cod, but close to Martha’s Vineyard by sea.
We can go to Menemsha, Vineyard Haven, Oak Bluffs, but mostly to Edgartown and attach Alto to a mooring ball in the harbor ($40/night) and radio for a tender to pick us up ($4)
and deliver us to the town dock.
Photo from Facebook
Photo bt Martha’s Vineyard Auto Rental
Edgartown, like all towns on the Vineyard, is tiny and walkable. Quaint with many restaurants, but no happy hours,
Photo from Svadore.com
It exudes charm. During Christmas only white lights are permitted by town ordinance. In season, the average price for a hotel for three days is $1675, or $4000 for a week. Then
there’s airfare or ferry cost, and car rental, etc. So visiting by boat for $40/night is pretty affordable! The tender is $4pp each way, and with a tip $10 round trip – not bad.
BTW, mooring in Oak Bluffs is $50/night and Vineyard Haven is $70. Dock space anywhere is expensive and by the foot so for Alto, about 32’ long, it would cost $125–$160/night, but bathrooms and showers come with it and that’s a fraction of a hotel room in-season.
Staying on a mooring in Edgartown for $280 per week is
BTW, mooring in Oak Bluffs is $50/night and Vineyard Haven is $70. Dock space anywhere is expensive and by the foot so for Alto, about 32’ long, it would cost $125–$160/night, but bathrooms and showers come with it and that’s a fraction of a hotel room in-season.
Staying on a mooring in Edgartown for $280 per week is
cheap. You can bring and use your own dinghy to go into town for free. But in July and August a two-week mooring stay is the max. So you just anchor for free in the Vineyard Haven lagoon
Edgartown Dinghy Dock, The Hull Truth
for a few days. Then you can go back, or to Oak Bluffs, etc. I’ll have to do another blog/website on affordable Martha’s Vineyard. BTW, I’ve already done that for the St. John River area and the Florida Keys, see the AltosAdventures blog.
The Plan
Now we have a comfortable base, condo, in Sarasota with a covered spot for our Honda Fit and we still keep a boat in Marina Jack for the season. We have Alto at Marina Jack for the winter and then she spends the summer in the Nantucket Sound and Buzzard’s Bay, keeping her away from the FL hurricane season.
It’s doable with our inexpensive-to-maintain condo plus income from our second condo at Mentone Court. At 74, I’ll keep working part-time to help sustain this “retirement” plan as long as possible! When I can’t, and we go into the “home,” I’ll just rent our personal-use Sarasota condo for an extra income per month to pay for it.
June, 2025 update: Well Gail, who just turned 78, doesn’t travel anymore and it’s gotten hard for me to, so we’re staying in Cotuit on Cape Cod and bringing the boat up here permanently. We’ll use it summers only in Cape Cod waters. We’ve got one of our condos on the market and probably will sell the other one, too. It’s been an adventure, but all adventures must come to an end.
Maybe parts of our story will inspire and help you to “do stuff” and attempt living your dream; e.g. enjoying the intimacy and charm of small city-living on a budget. I don’t advise living full-time on a boat, but for seasonal use it can make good sense allowing you to live part-time, affordably, in interesting places. Then with enough research you can stay on your boat while you find and fix up a land-based site.
My remote working friends now go for months on their boats with a Star Link antenna, allowing high speed internet anywhere. What’s your excuse for not getting on-board?
