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 was a very 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, where we next moved to.
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. After Breeze started nonstop service for ~$350 roundtrip from Providence to Sarasota, we shifted to that, and that flight is 2.5 hours one way. The beauty of Sarasota? One there it was just 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 to live year-round on a floating dock.
Alto II
Eventually, we moved up to a diesel 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 is Sarasota behind it:
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 park within walking distance of the PVD terminal and since I kept clothes on the boat I traveled with just a carry-on computer for to work.
In contrast to the Florida Keys which was a long rental car ride from the airport, we could visit Sarasota for a long weekend. However, Gail never enjoyed living on the boat and she 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 and we rarely took her out on the water. 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 have Alto professionally trailered by a hauler 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 haulers compete for loads. Someone delivering to FL will seek a paid load on return, to
avoid returning empty “dead heading” getting me 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
We finally had a comfortable base, condo, in downtown Sarasota with a covered spot for our Honda Fit and we still kept a boat in Marina Jack for the season. We could keep 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. But we now pay for a year-round slip which we only might use six months of the year.
It could be doable with our inexpensive-to-maintain condos plus income from our second condo at Mentone Court. At 74, I planned to keep working part-time to help sustain this “retirement” plan as long as possible! But “man plans and God laughs.”
June, 2025 update: Gail, who just turned 78, doesn’t travel anymore and it’s gotten harder for me to, so we’re staying on Cape Cod and bringing the boat up here permanently. We’ll use it summers in Cape Cod waters. We’ve put both of our SRQ condos on the market. It’s been an adventure, but all adventures must come to an end.
February, 2026 update: We bought an ocean front condo with access to a private beach in New Seabury, a village in Mashpee, MA on Cape Cod. Sounds silly to have a vacation condo 18 minutes from our main house in Cotuit on the Cape, but it is certainly easy to get to. If you, dear reader, are older with incontinence issues note the practicality of never being more than nine minutes away from a bathroom when you drive from your home to vacation place! We miss the warmth and city life, but at least we’re not done with the ocean yet.
As a result, we no longer need the condos in Sarasota, so I create this website to share all our experiences with other hoping to finding an affordable, downtown home in that beautiful city. It would be great if you bought one of our units, but my goal was to let others know its possible and what to look for and what to avoid in the process.
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 like we did. For example, you could live in downtown Washington, D.C. cheap in the Gangplank (now called the Wharf) marina and walk to the Smithsonian and other attractions.
I’d like to live on the islands off Carolinas some day for summers. BTW, in Sarasota Marina Jack has a three-year wait list, and is not a live-aboard marina, but long stays are OK especially given the super yachts that come there. There are nice live-aboard marinas north of Sarasota in Bradenton. When you find a place you love, you can stay on your boat while you find (it might take years) and fix up a land-based home making it affordable and just the way you want it.
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?
