My Suburban Escapes

When my trusty ol’ ski boat I brought up from Texas (“The Come On Y’all”) sank into the mud at the bottom of the Hudson River several years ago, I thought it best to find another way to enjoy the water. I forced myself and Husband to spend a chunk of our vacation on Cape Cod doing the required online and on-water training with Freedom Boat Club, cutting our captain teeth on BIG water. Our first time out sans captain was from Chatham’s Outermost Harbor, running the gauntlet of shallow/narrow channels with thick fog rolling in. It was terrifying. I wasn’t sure our marriage would survive Freedom, but it did. So in celebration I joined Carefree Boat Club too when they moved to my town.

Carefree came to Rye in 2019 and has grown its fleet as steadily as its membership. They now have locations in Bridgeport, Westport, Stamford and New Rochelle, as well as all over the US, BVIs, Panama and the Philippines. Freedom’s closest dock is Stamford, with franchises all up the Connecticut coast and on the North Shore.  Stamford’s harbor channel can be intimidating but is actually easier to navigate than Rye’s. It’s deep and well-marked for commercial traffic, while Milton Harbor is shallow and muddy at low tide, hiding islands and boulders and shoals (oh my!).  But I could swim home (again) if my boat sank in our harbor.

Barton and Gray Mariner’s Clubis yet another option (and my personal idea of heaven):  Hinckleys and yachts with captain and crew…and a concierge team. It was founded in 2006 and has boats in 30 harbors including Greenwich, Rowayton, NYC, Oyster Bay, Southampton, East Hampton, Sag Harbor and Watch Hill.

Boat club membership includes reciprocal usage of all boats at all locations, gassed up and ready when you arrive with crew awaiting your return. No cleaning and no maintenance. You get all the benefit of ownership without the hassle. Initiation is painless: write a check. But the training is something you should take seriously. There are no dumb questions.  All club boats are equipped with state-of-the-art Sat Nav systems, but don’t let that be your only source of information.  Travel with a chart of the area. Local knowledge is the most important thing you can learn. Fellow boaters are happy to share information.  Here’s a few things I’ve learned:

• Hire a captain as often as possible and study his actions
• Do everything for the first time at high tide…keep track of depth and make notes
• North is East and South is West. The Sound gets wider the further East you go
• Occasionally you can reserve an afternoon AND morning slot for an overnight adventure

Rye:

• STAY IN THE CHANNEL, in the “right lane” and watch your depth finder.
• Avoid Turkey Rock in Milton Harbor.
• Always go around the Scotch Caps – don’t cut through until you know damn well how to and then only at high tide.
• Mainland NY/CT shore is mostly rocky, so mistakes are unforgiving.  Long Island shores are naturally sandy. If you hit sand just wait for the tide to rise.
• Mark your heading out of Rye Playland. Use New Rochelle skyline too. Things look completely different returning than leaving.

RESTAURANTS with dock space:

Mainland NY/CT: the rivers that dump into the ports are often where the fun is. Check dock fees and reserve in advance.

• Byram River – Port Chester/Byram – Bar Taco
• Mianus River – Cos Cob/Stamford – new Cisco Brewery (a Nantucket classic) just opened and has dock space and things to do at the marina for boaters
• Five Mile River – Rowayton – Rowayton Seafood has only 1 boat slip and must book in advance
• Norwalk River – Harbor Lights (fancy), Sunset Grill (casual) at Cove Marina
• Saugatuck River – Westport – The Whelk, the Boat House, the “famous” Black Duck (some docks – harbor is a little treacherous – food’s awesome)
• Housatonic River – Stratford/Bridgeport – Boca Oyster Bar at Steelpointe Harbor in Bridgeport has live music Saturday/Sunday. Or reserve a pontoon in Stratford and go upriver to Dockside Brewery, Outriggers, Knapp’s Landing, Joey C’s Boathouse.
• Connecticut River – Old Saybrook – Fresh Salt (fancy) or Liv’s Shack (casual)

North Shore of Long Island: explore the bays:

• Port Washington – Louie’s Oyster Bar and Grill.  Easy free docking always available.  Stroll to the Ice Cream Shop after.
• Bayville – Wall’s Wharf – no dock but can beach it at high tide and swim in
• Hempstead Harbor – The Cove in Glen Cove – easy docking, tiki bar/outside dining
• Oyster Bay – can walk into village to 2 Spring
• Huntington Harbor – PRIME – plenty of dock space
• Northport – public dock from which you can walk into town to several great restaurants. The Northport Hotel is coming this fall, great for boaters. Whale’s Tale for casual meal.

Other Classics:
Charley’s Pier at Playland, Rye
PRIME – Stamford harbor
L’Escale in the Delamar Hotel – Greenwich ($$ dock fee)

Historical Excursions (do your homework first):
Execution Rocks Lighthouse, Hart Island and City Island

Public Beaches:
Glen Island Park Beach
Orchard Beach
Sherwood Island

Anchors Down and Chill
Tower and Captain’s Island, Flat Neck Point – Greenwich
Ziegler’s Cove – Darien
The Sand Hole – Oyster Bay
Lighthouse Point – New Haven

More Advanced Excursions:

• Manhattan: Head south (west?!?) through the Long Island Sound, Hell’s Gate, then through the East River along the FDR and down around the Statue of Liberty. Can dock and eat at Grand Banks Oyster Bar at Pier 25 in Hudson River Park. To circumnavigate island, continue around the southern tip of Manhattan and return up the Hudson River, cutting through at Spyten Duyvil at the draw bridge underneath the Henry Hudson at Columbia Football Stadium (call on Channel 9 or dial # posted on bridge for opening), into the Harlem River and back into the East River just above Hell’s Gate. Or continue north on the Hudson to see West Point to dine in Cold Spring at Hudson River House or get ice cream at MooMoos
• Mets Game/US Open – above my pay grade, but very doable. Research first.
• DO NOT DO CITY TRIPS IN A PONTOON! The bigger the boat, the better.
• Gateway National Recreation Area, Sandy Hook, NJ – anchor and swim
• Oak Cliff Regatta – Oyster Bay, NY
• Thimble Islands – Branford, CT