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Deep Dive: The Thimble Islands Cruise Is a Must-See, Here's Why · The Red Solo Traveler Podcast

• 0:07
  Speaker 1: What if I told you that in just about forty
• 0:10
  five minutes you could sail past a seventeenth century pirate hideout,
• 0:15
  an abandoned industrial granite quarry, and like the deeply secretive
• 0:21
  off grid compounds of modern billionaires. Oh wow, right, and
• 0:25
  you could see all of that without ever leaving the state.
• 0:27
  Speaker 2: Of Connecticut, which is just not what you picture at all.
• 0:29
  Speaker 1: No, not at all, because you know, when you hear
• 0:31
  the word cruise, your mind instantly jumps to a massive
• 0:34
  floating city carving its way through the Caribbean.
• 0:37
  Speaker 2: Yeah, or maybe standing on a frozen deck watching Glacier's
• 0:40
  cab in Alaska.
• 0:41
  Speaker 1: Exactly. It's this massive commitment of time and money for you.
• 0:45
  But there is actually a micro version of that exact
• 0:49
  thrilling maritime exploration tucked away just stuff Interstate ninety five.
• 0:54
  Speaker 2: It really completely dismantles our preconceived notions of what maritime
• 0:58
  exploration has to be. It does trading the sprawling midnight
• 1:02
  buffets and the three thousand passengers for a microscopic, highly
• 1:07
  intimate look at an entirely different way of life.
• 1:09
  Speaker 1: And to guide us through this hidden world. Today, we
• 1:13
  are pulling from a phenomenal travel review and guide by
• 1:16
  Louis Over at the Red Solo Traveler Substack.
• 1:19
  Speaker 2: It's a good, great piece.
• 1:20
  Speaker 1: Yeah, it's titled The Thimble Island's Cruise is a must
• 1:24
  see here's why. And it's such a great piece of
• 1:26
  writing because it doesn't just review the logistics of buying.
• 1:29
  Speaker 2: A boat ticket, right, it goes wayy ber.
• 1:31
  Speaker 1: Yeah, it rips the lid off this incredibly picturesque archipelago
• 1:34
  in the Long Island Sound, an area that basically serves
• 1:38
  as a living laboratory for extreme wealth off grid sustainability
• 1:42
  and some seriously bizarre local history.
• 1:45
  Speaker 2: Oh, the history is wild.
• 1:46
  Speaker 1: Okay, let's unpack this because before we get into the
• 1:49
  wildly wealthy subculture that currently owns these islands, we really
• 1:52
  need to understand what these symbols actually are, right, and
• 1:56
  the sheer volume of human history that has taken place
• 1:59
  on them.
• 2:00
  Speaker 2: Well, the geography is really the foundation of everything here.
• 2:02
  We're talking about an archipelago located just off the coast
• 2:05
  of Branford, Connecticut. Officially, depending on which maritime map you consult,
• 2:11
  it's a collection of over thirty small islands.
• 2:13
  Speaker 1: Although you know, reading through the background on this, I
• 2:15
  actually found reports claiming there are up to three hundred
• 2:18
  and sixty islands in the chain.
• 2:20
  Speaker 2: Yeah, I've seen those numbers too.
• 2:21
  Speaker 1: Which sounds like a massive discrepancy, right, thirty versus three
• 2:25
  hundred and sixty until you realize how tides actually work
• 2:28
  in the Long Island sound exactly, because the definition of
• 2:31
  an island gets incredibly blurry when a ten foot tide
• 2:36
  rolls in and suddenly your island is just a submerged
• 2:40
  wet rock.
• 2:41
  Speaker 2: That tidal variation is so crucial to the whole area.
• 2:44
  I mean they are named the Thimble Islands because of
• 2:47
  how they look at high tide. You just see these
• 2:49
  little thimble shaped domes of granite poking out of the water.
• 2:54
  And while they feel like a quiet, tucked away secret
• 2:57
  for the ultra rich.
• 2:57
  Speaker 1: Today, oh they definitely do.
• 2:59
  Speaker 2: They have actually been highly active spaces for centuries. I
• 3:03
  mean Dutch explorer Adrian Block mapped them back in sixteen fourteen.
• 3:06
  But you know that's just the European timeline.
• 3:09
  Speaker 1: Yeah, because long before a Dutch ship ever sailed past,
• 3:12
  the Native Americans in the region were actively inhabiting and
• 3:15
  fishing those exact waters.
• 3:17
  Speaker 2: Right. They knew the area incredibly well and They.
• 3:19
  Speaker 1: Had a much better, far more poetic name for the archipelago.
• 3:23
  They called it cuttam Quash, which translates to beautiful sea rocks.
• 3:27
  Speaker 2: That is a great name, it really is.
• 3:29
  Speaker 1: But the journey of these beautiful sea rocks over the
• 3:32
  next few hundred years is what completely blows my mind, Oh, golloy,
• 3:36
  because they didn't just stay quiet fishing grounds. By the
• 3:40
  seventeen hundreds and eighteen hundreds, locals were actually using them
• 3:43
  for sheep.
• 3:44
  Speaker 2: Grazing, which is just a crazy visual right.
• 3:47
  Speaker 1: It immediately begs the question, how on earth do you
• 3:50
  graze sheep on a tiny rock in the ocean.
• 3:53
  Speaker 2: Well, it sounds like a logistical nightmare, right to roll
• 3:55
  a whole flock of sheep out into the Long Island Sound,
• 3:58
  But if you look at the mechanics of early agriculture,
• 4:00
  it was actually a stroke of absolute genius. Way how so,
• 4:04
  think about the biggest threats to a flock of sheep
• 4:06
  back then. You've got predators like wolves, and you have
• 4:09
  the risk of the sheep simply wandering off. Oh sure,
• 4:12
  so if you put them on an island, you have
• 4:14
  a natural impenetrable fence. The water keeps the predators out
• 4:18
  and it keeps your livestock contained without you having to
• 4:20
  build you miles and miles of stone walls.
• 4:23
  Speaker 1: Oh wow, I never thought about that.
• 4:25
  Speaker 2: Yeah, you just row them out in the spring, let
• 4:27
  them graze all summer, and then row them back in
• 4:29
  the fall.
• 4:29
  Speaker 1: That makes total sense. The ocean is basically a free,
• 4:32
  full time security system exactly. But that agricultural phase didn't
• 4:36
  last forever either. Soon after the sheep, these tiny islands
• 4:40
  became sites for boat building and then massive granite.
• 4:44
  Speaker 2: Quarries, right heavy industry.
• 4:46
  Speaker 1: Which again conceptually is really hard to wrap your head around.
• 4:50
  How do you industrially drill and extract thousands of tons
• 4:53
  of heavy granite from a tiny rock surrounded by water.
• 4:56
  Speaker 2: You actually leverage the water itself. See the pink granite
• 5:00
  in this region was highly prized for its durability. Okay,
• 5:04
  if you quarry granite inland, you have to load it
• 5:07
  onto wagons and drag it over redded, muddy nineteenth century dirt.
• 5:12
  Speaker 1: Roads, which sounds miserable.
• 5:13
  Speaker 2: It's incredibly inefficient. But if you quarry it on an island,
• 5:16
  you can pull a massive, flat, bloomed barge right up
• 5:19
  to the litteral edge of the rock. You drill, you blast,
• 5:22
  and you load the stone directly onto the vessel.
• 5:25
  Speaker 1: Oh, that is so smart.
• 5:27
  Speaker 2: The ocean becomes this frictionless conveyor belt straight to the
• 5:30
  growing cities of New York and Boston.
• 5:33
  Speaker 1: So the water was the ultimate highway for them.
• 5:35
  Speaker 2: Exactly.
• 5:36
  Speaker 1: Add to that the actual pirate lore, because Captain William
• 5:39
  Kidds supposedly claimed one of these islands as his own,
• 5:43
  and to this day all that remains is his quote
• 5:45
  unquote harbor.
• 5:46
  Speaker 2: Yeah, the local legends are everywhere.
• 5:48
  Speaker 1: It's wild. In the span of a few centuries, the
• 5:51
  exact same rocks go from a Native American fishing ground
• 5:54
  to a pirate hideout to a heavy industrial granite quarry.
• 5:59
  Speaker 2: It's a lot of turn on.
• 6:00
  Speaker 1: It's like a rotating movie set. The backdrops does exactly
• 6:04
  the same, but the genre of the film changes every
• 6:06
  fifty years.
• 6:07
  Speaker 2: What's fascinating here is how clearly that rotating movie set
• 6:11
  actually mirrors the macroeconomic shifts of the United States. How
• 6:14
  do you well? For centuries, the thimbles were purely utilitarian.
• 6:19
  They were places of hard labor, extraction and hide and
• 6:22
  stolen goods. But as the Industrial Revolution peaked in the
• 6:25
  late eighteen hundreds, the cities on the mainland became incredibly polluted, loud,
• 6:30
  and crowded. The railroads and steamboats made travel easier, and
• 6:34
  suddenly the wealthy elite needed and escaped from the very
• 6:37
  factories that made them rich.
• 6:39
  Speaker 1: That is the ultimate irony right there. They build the noisy,
• 6:42
  smoggy city and then use their massive wealth to flee
• 6:45
  to the quiet rocks.
• 6:47
  Speaker 2: Exactly. The industrial noise of the quarries fades out, and
• 6:50
  the era of the summer vacationer basically begins. Wow. They
• 6:54
  transform from places of sweat and labor into places of
• 6:57
  absolute leisure, and that transition set the stage for what
• 7:01
  the archipelago is today.
• 7:02
  Speaker 1: Yes, it really did, because while the.
• 7:04
  Speaker 2: Late eighteen hundreds brought the first wave of summer cottages,
• 7:08
  the late twentieth century brought a staggering level of extreme
• 7:11
  wealth that turned these islands into a literal playground for
• 7:14
  the mega ridge.
• 7:15
  Speaker 1: Right, let's talk about that modern era, because the consolidation
• 7:18
  of land here.
• 7:19
  Speaker 2: Is just jaw dropping. It really is.
• 7:21
  Speaker 1: For generations, these summer homes just quietly passed down through families.
• 7:25
  But then we hit the nineteen seventies, a party goods
• 7:28
  magnate named John Spenningsen buys West Crib Island in nineteen
• 7:32
  seventy six.
• 7:33
  Speaker 2: Just a nice little summer home purchase. A nice purchase, sure, Yeah.
• 7:36
  Speaker 1: But after he passes away, his widow, Christine Spenningson, goes
• 7:39
  on an absolute tear.
• 7:41
  Speaker 2: She really did.
• 7:41
  Speaker 1: Between nineteen ninety eight and two thousand and seven, she
• 7:44
  spends over thirty six million dollars buying up islands and
• 7:47
  I want to list these because the sheer volume is insane.
• 7:50
  Speaker 2: Go forth.
• 7:50
  Speaker 1: She buys Wheeler, Rogers, Phelps, Jepson, Cut into East and
• 7:54
  West Real, Belden's and East Crip.
• 7:57
  Speaker 2: That is a massive portfolio.
• 7:59
  Speaker 1: Here's where it gets really interesting. We're talking about one
• 8:02
  single person treating the Long Island sound like a personal
• 8:05
  game of Monopoly, just moving her metal boat token from
• 8:08
  rock to rock and buying literally everything in sight.
• 8:11
  Speaker 2: It is an unprecedented consolidation of prime real estate. I
• 8:14
  mean to put the math and perspective for you. There
• 8:16
  are only about twenty five and habited islands in the
• 8:18
  entire chain.
• 8:19
  Speaker 1: Wait, really only twenty five?
• 8:20
  Speaker 2: Yeah, so by purchasing ten of them, one individual essentially
• 8:24
  acquired nearly half of the habitable land in the entire community.
• 8:28
  Speaker 1: And this is where I have to push back a
• 8:29
  bit on how this is framed in the source.
• 8:31
  Speaker 2: Okay, let's hear it.
• 8:32
  Speaker 1: The travel guide praises her heavily for this, noting that
• 8:36
  she is choosing to renovate these properties rather than tearing
• 8:39
  them down to build mega mansions or commercial resorts.
• 8:43
  Speaker 2: Right, the historical preservation angle, and.
• 8:45
  Speaker 1: Sure, saving historical architecture is great, But isn't buying up
• 8:49
  half a community and turning it into a single private
• 8:52
  portfolio inherently destroying its character?
• 8:54
  Speaker 2: Anyway, that's a fair point.
• 8:56
  Speaker 1: You've essentially evicted the neighborhood to build a personal fiefdom.
• 8:59
  Speaker 2: That is the poor tension of the Thimble Islands today.
• 9:03
  It's an ongoing debate between architectural preservation and sociological preservation.
• 9:08
  Speaker 1: Yeah, that's a good way to put it.
• 9:09
  Speaker 2: You are absolutely right that when one entity controls half
• 9:13
  the land, the organic multi family community dynamic that existed
• 9:18
  for a century is fundamentally altered because it's just one
• 9:21
  owner now exactly. It becomes a curated collection rather than
• 9:25
  a living, breathing neighborhood. However, in the realm of ultra
• 9:30
  high net worth real estate. You have to look at
• 9:33
  what the alternative usually.
• 9:34
  Speaker 1: Is, which is total destruction.
• 9:36
  Speaker 2: Exactly in many coastal areas, developers buy historic cottages, bulldoze
• 9:42
  them to the ground and build sterile ten thousand square
• 9:45
  foot glass boxes.
• 9:46
  Speaker 1: Yeah, we see that everywhere.
• 9:48
  Speaker 2: By choosing to meticulously restore the original structures, the esthetic
• 9:52
  soul of the archipelago actually remains intact, even if the
• 9:56
  demographics have shifted dramatically.
• 9:58
  Speaker 1: Okay, I see the distinct there. You're preserving the painting
• 10:02
  even if you fired all the artists who lived in
• 10:04
  the studio.
• 10:05
  Speaker 2: That's a great analogy.
• 10:06
  Speaker 1: And the eccentricities of this wealth are everywhere out there.
• 10:09
  Beyond the spendingson purchases. You have Gary Trudeau, the creator
• 10:13
  of Doomsbury, and his wife, newscaster Jane Pauley, who own
• 10:16
  a home out there.
• 10:17
  Speaker 2: Yep.
• 10:18
  Speaker 1: Even the founders the Barnum and Bailey Circus had properties there. Historically,
• 10:22
  it naturally attracts people who want a literal moat around
• 10:26
  their private lives.
• 10:27
  Speaker 2: And that desire for absolute control extends to the physical
• 10:30
  geography itself. I mean, if the natural islands weren't enough,
• 10:34
  humans just built their own.
• 10:36
  Speaker 1: Yes, two of the islands in the chain are entirely
• 10:38
  man made. It's crazy people hauled enough rocks out into
• 10:42
  the sound to build their own foundations. And my absolute
• 10:46
  favorite quirk of the entire deep dive today, there's one
• 10:50
  tiny rock that is officially named Gazebo Island.
• 10:54
  Speaker 2: I love Gazebo Island.
• 10:55
  Speaker 1: Why because it literally only has the square footage to
• 11:00
  support one wooden gazebo. That is the absolute peak of
• 11:03
  island collecting. Buying a rock just to put a gazebo
• 11:07
  on it.
• 11:07
  Speaker 2: It's the ultimate flex of disposable income. But you know,
• 11:10
  the travel guide does a phenomenal job of grounding this
• 11:13
  whole fantasy.
• 11:13
  Speaker 1: It really does.
• 11:14
  Speaker 2: We romanticize the idea of owning a private island. For
• 11:17
  you listening, you probably picture drinking cocktails on the deck
• 11:20
  while the sun sets over the water.
• 11:22
  Speaker 1: It sounds amazing, But what.
• 11:23
  Speaker 2: We don't picture are the brutal, gritty logistics of actually
• 11:27
  keeping a house operational when it is entirely disconnected from
• 11:31
  the mainland grid.
• 11:32
  Speaker 1: I'm so glad we're getting into this, because the day
• 11:34
  to day reality of maintaining this luxury requires some intense
• 11:37
  off grid survival skills. Absolutely, it's not just a vacation home.
• 11:41
  It's a full on infrastructural puzzle. So let's look at
• 11:44
  the mechanisms of how these people actually survive out there.
• 11:47
  Speaker 2: Let's do it.
• 11:48
  Speaker 1: As we mentioned, there are roughly twenty five inhabited islands.
• 11:51
  Most of them are purely summer residences. They shutter the
• 11:54
  windows in late October and don't open back up until
• 11:57
  mid April.
• 11:58
  Speaker 2: Right because the Long Island Sound in January is a freezing,
• 12:02
  wind whipped nightmare.
• 12:03
  Speaker 1: Totally. But the craziest statistic in the entire guide. Of
• 12:07
  those twenty five inhabited islands, only nine of them have
• 12:11
  full electrical power wired from the mainland.
• 12:13
  Speaker 2: Just nine. Because laying a submarine power cable is a
• 12:17
  massive undertaking. You can't just run an extension cord underwater.
• 12:20
  Speaker 1: No, definitely not.
• 12:21
  Speaker 2: The cables are incredibly expensive, they have to be deep
• 12:24
  trenched into the seafloor, and they are constantly at risk
• 12:27
  of being snagged by boat anchors or degraded by the saltwater.
• 12:31
  Speaker 1: Oh I didn't even think about boat ank.
• 12:33
  Speaker 2: Well, it's a huge issue. In fact, Wheeler Island, which
• 12:35
  is one of the closest to the shore only recently
• 12:38
  managed to get mainland power and water installed.
• 12:40
  Speaker 1: So what does the majority of the archipelago do. Let's
• 12:44
  look at Money Island, good example. It has a cluster
• 12:47
  of about twenty houses on it and the entire island
• 12:49
  runs one on solar.
• 12:51
  Speaker 2: Power YEP, completely off grid.
• 12:53
  Speaker 1: And this isn't just because they are like deeply passionate environmentalists.
• 12:58
  It's because nobody wants to spend ten million dollars on
• 13:01
  an island oasis only to have their pristine ocean view
• 13:05
  ruined by thick, ugly power lines strung between.
• 13:09
  Speaker 2: The rocks exactly, so they turned to solar panels and
• 13:12
  wind turbines.
• 13:13
  Speaker 1: Which completely changes how you interact with your own home.
• 13:16
  You aren't just paying a utility bill anymore. You literally
• 13:18
  are the utility.
• 13:20
  Speaker 2: Company you are. And if you are running a modern
• 13:22
  house on solar power, you have to maintain massive, heavy
• 13:26
  battery banks hidden away in the basement to store that energy.
• 13:30
  You have to constantly monitor your load. You can't just
• 13:33
  run the air conditioning, the dishwasher, and the laundry machine
• 13:36
  all at the same time on a cloudy Tuesday, or
• 13:39
  you will drain your batteries and literally be sitting in
• 13:42
  the dark.
• 13:43
  Speaker 1: It's like being a billionaire off grid homespeader.
• 13:45
  Speaker 2: That's exactly what it.
• 13:46
  Speaker 1: Is, and the power is just the beginning of the headache.
• 13:48
  The water situation is even more precarious. You can't drill
• 13:52
  a traditional well on a solid granite rock surrounded by
• 13:55
  the ocean.
• 13:56
  Speaker 2: No, because you'll just hit salt water immediately right.
• 13:59
  Speaker 1: So, while about forty percent of the islands have managed
• 14:02
  to get water piped in from the mainland, the rest
• 14:05
  rely heavily on rainwater harvesting.
• 14:08
  Speaker 2: Think about the math of that for a second. Your
• 14:10
  ability to take a shower, boil pasta, or even flush
• 14:14
  your toilet is entirely dependent on the square footage of
• 14:18
  your roof and the frequency of coastal rainstorms. That is
• 14:21
  so wild. They use these elaborate gutter systems that feed
• 14:25
  into massive underground cisterns coupled with heavy duty filtration and
• 14:29
  UV purification systems. Wow, but if there is a dry
• 14:33
  spell in August, you are nervously watching a gauge drop,
• 14:37
  knowing that if you run out you have to literally
• 14:40
  import water by boat.
• 14:41
  Speaker 1: That sounds incredibly stressful. You bite this amazing private oasis
• 14:45
  to escape the world but you are utterly at the
• 14:47
  mercy of the local weather report completely, plus just the
• 14:50
  sheer logistics of home maintenance. The guide makes a really
• 14:53
  great point about this. Imagine your sink starts leaking, or
• 14:56
  your solar inverter blows out.
• 14:58
  Speaker 2: Oh good luck.
• 14:59
  Speaker 1: Right, You can't just call a plumber and have them
• 15:01
  pull their van into your driveway. You have to find
• 15:03
  a contractor willing to load all their heavy tools onto
• 15:06
  a skiff, navigate the tides, and dock at your private rock.
• 15:11
  Speaker 2: If we connect this to the bigger picture, it really
• 15:14
  reveals a deeply ironic paradox about this entire subculture. How
• 15:19
  so well, the entire premise of buying a private island
• 15:23
  is the pursuit of ultimate, uncompromising independence. You want to
• 15:27
  be a sovereign citizen of your own kingdoms.
• 15:29
  Speaker 1: Sleep everyone else out exactly.
• 15:31
  Speaker 2: But the extreme isolation of that environment actually forces the
• 15:34
  exact opposite. It demands a hyper awareness of your natural
• 15:38
  surroundings sunlight, rainfall, wind direction, and more importantly, it forces
• 15:44
  a deeply tight knit reliance on your neighbors.
• 15:46
  Speaker 1: Oh that's the twist. You flee society to be alone,
• 15:49
  and you end up needing your neighbors more than ever.
• 15:51
  Speaker 2: Exactly when a storm rolls in and a dock gets
• 15:54
  damaged or a solar array fails, you can't just wait
• 15:57
  for the mainland cavalry. You rely on I'm the guy
• 16:00
  on the next island over who happens to have a
• 16:02
  spare part or a heavy winch. They have to share resources, knowledge,
• 16:07
  and physical labor just to survive harmoniously in a highly
• 16:12
  delicate ecosystem. Wow, so the pursuit of total isolation actually
• 16:16
  breeds a forced intensive micro community.
• 16:20
  Speaker 1: It's a fascinating sociological experiment basically playing out on granite rocks.
• 16:24
  But honestly, as much as I love dissecting the psychology
• 16:28
  of the off grid billionaire homestudter, living there sounds exhausting.
• 16:31
  Speaker 2: Oh, it's a ton of work.
• 16:32
  Speaker 1: It is a massive, unending logistical chore, which brings us
• 16:36
  to the real genius of the travel guide we're looking
• 16:39
  at today.
• 16:39
  Speaker 2: Yeah, the crews itself.
• 16:41
  Speaker 1: Right, You and I and you listening right now can
• 16:44
  experience all the magic, see the pirate coves, marvel at
• 16:47
  the solar setups, and take in the stunning architecture without
• 16:50
  ever having to worry about a broken water system.
• 16:52
  Speaker 2: And that is where the forty five minute micro cruse
• 16:54
  comes in. It is the perfect distillation of the Thimble
• 16:57
  Islands experience, engineered for the traveler who want's the insight
• 17:01
  without any of the hassle.
• 17:02
  Speaker 1: So let's break down the mechanics of how you actually
• 17:04
  do this, because it's brilliantly simple.
• 17:06
  Speaker 2: It is.
• 17:07
  Speaker 1: If you want to see this hidden world, you navigate
• 17:10
  to the town dock at four Indian Point Road in Branford, Connecticut.
• 17:15
  There is a small fleet of local tour boats, specifically
• 17:18
  the Sea Mist, the Volsunga, the Fourth, and the Islander.
• 17:21
  Speaker 2: They've been doing this for years.
• 17:23
  Speaker 1: They operate heavily from June through August, essentially running tours
• 17:27
  that alternate every hour on the weekends, with some shoulder
• 17:30
  season availability in the spring and.
• 17:32
  Speaker 2: Fall, and it is highly advised to book your tickets
• 17:35
  in advance online. Definitely, these aren't massive anonymous ferries. The
• 17:39
  Sea Mist, for example, only accommodates about twenty five passengers.
• 17:43
  Speaker 1: Oh that is tiny, right.
• 17:45
  Speaker 2: So if you show up on a pristine Saturday in
• 17:48
  mid July without a reservation, you're likely going to be
• 17:51
  left standing on the dock.
• 17:52
  Speaker 1: Good to know, and a quick logistical heads up from
• 17:55
  the guide on that front. Parking near the dock can
• 17:57
  be a bit of a scavender hunt, but there is
• 18:00
  free street parking if you are patient, or you can
• 18:02
  park it a nearby church for a small donation. That's
• 18:05
  a great tip, also a very practical piece of advice
• 18:07
  from the author. These boats are small and they do
• 18:10
  not have sprawling facilities. Use the public restrooms in the
• 18:15
  grassy park next to the beach before you board.
• 18:18
  Speaker 2: Yes, very important.
• 18:19
  Speaker 1: You do not want to be halfway through the tour
• 18:21
  staring at Gazebo Island wishing you had planned ahead.
• 18:24
  Speaker 2: It's the unglamorous but essential reality of small craft maritime travel.
• 18:30
  And speaking of small craft realities, the guide rightly suggests
• 18:34
  bringing dramamine if you are prone to motion sickness.
• 18:37
  Speaker 1: Oh does he get rough out there?
• 18:39
  Speaker 2: Well, the Long Island Sound can get choppy and you
• 18:42
  will definitely feel the ocean moving beneath you.
• 18:44
  Speaker 1: Right, this isn't a theme park ride on a rail.
• 18:46
  It's a real working boat out on the open water,
• 18:49
  and you'll be guided by local captains like Captain Mike
• 18:52
  on the seamst who actually narrate the entire forty five
• 18:55
  minute journey.
• 18:56
  Speaker 2: The storytelling is the best part.
• 18:58
  Speaker 1: They weave together the history of the Native Americ Smercans,
• 19:00
  the pirates, the granite quarries, and the modern real estate
• 19:03
  monopolies while you are physically floating right past them. So
• 19:07
  what does this all mean? Why are we highlighting a
• 19:09
  forty five minute boat ride in Connecticut.
• 19:11
  Speaker 2: Because it represents a brilliant democratization of a highly exclusive space.
• 19:16
  Speaker 1: I love that.
• 19:17
  Speaker 2: The barriers to entry for the Thimble Islands are astronomical. Hey,
• 19:22
  unless you have thirty six million dollars to play real
• 19:25
  estate monopoly or the intense dedication to maintain an off
• 19:28
  grid solar compound through a freezing New England winter, you
• 19:32
  are locked out of this world.
• 19:34
  Speaker 1: Yeah, almost everyone is.
• 19:36
  Speaker 2: But for the price of a modest boat ticket, the
• 19:38
  barrier is completely lifted. You get a curated bird's eye
• 19:42
  view into a fiercely guarded subculture you really do. You
• 19:44
  get to observe their architecture, analyze their reliance on sustainable tech,
• 19:49
  and understand the deep history of the region, all in
• 19:52
  under an hour.
• 19:53
  Speaker 1: It is the ultimate travel hack for the curious mind.
• 19:56
  For you listening, if you are driving up Interstate ninety five,
• 19:59
  doing that gru trek between New York and Boston or
• 20:02
  heading up to Rhode Island. I mean, why sit and
• 20:04
  mumper to bumber traffic the entire time? Seriously, you can
• 20:07
  literally pull off the highway, stretch your legs, and immerse
• 20:10
  yourself in a completely different reality. It's highly accessible, it's
• 20:13
  incredibly budget friendly, and it's perfect for solo travelers who
• 20:18
  just want a quick hit of adventure without committing to
• 20:21
  a week long itinerary.
• 20:23
  Speaker 2: It's incredible when you step back and look at the
• 20:24
  sheer density of what we've uncovered today. It really is.
• 20:27
  In one forty five minute loop off the coast of Branford,
• 20:31
  you are slicing through centuries of human ambition. You've got
• 20:35
  Native American history, the logistics of colonial sheep farming, industrial
• 20:40
  scale granite extraction, seventeenth century pirate lore, and the modern
• 20:44
  paradox of billionaires relying on rain water just to flush
• 20:47
  their toilets.
• 20:48
  Speaker 1: That's a lot for forty five minutes, all.
• 20:49
  Speaker 2: Of it packed onto an archipelago of beautiful sea rocks
• 20:53
  that most people just speed right past on the highway.
• 20:55
  Speaker 1: It is a remarkable concentration of history packed into a
• 20:58
  microscopic geographic foo print, but you know it leaves you
• 21:02
  with a fascinating psychological question to ponder.
• 21:04
  Speaker 2: Oh what's that?
• 21:06
  Speaker 1: Well, if you suddenly acquired unlimited resources tomorrow, would you
• 21:10
  actually choose the ultimate, uncompromising isolation of your own private island,
• 21:15
  knowing that you'd be entirely at the mercy of nature
• 21:17
  for your most basic survival needs.
• 21:20
  Speaker 2: Or is the romantic illusion of total independence far better
• 21:24
  left as a forty five minute vacation.
• 21:26
  Speaker 1: Oh that is a brilliant question to chew on. Is
• 21:28
  the fantasy of the private island actually better than the
• 21:31
  reality of owning one? Something for you to ponder the
• 21:34
  next time you're stuck in mainland traffic greaming of a getaway.
• 21:38
  Thank you so much for joining us on this deep
• 21:40
  dive into the Thimble Islands. As always, keep questioning, keep exploring,
• 21:43
  and stay curious.