BOATING/KAYAKING
Long Island Sound
We'll start with the obvious.  Buy boat.  Buy slip in town.  Sail off into the sunset.  We envy you.

Candlewood Lake - Danbury
This sprawling manmade lake reminds me of my childhood with families out tubing and waterskiing, and grilling on the shores. Gerard’s Water's Edge Marina rents ski boats, pontoons, fishing boats, kayaks and a variety of ‘water toys,’ like skis and tubing equipment.
120 Old Town Park Road, New Milford, 860-350-BOAT

Housatonic River
Boardwalk Marina - Stratford
Right off I-95, these guys can set you up with boat, jet ski and Stand Up Paddleboard rentals.
955 Ferry Blvd., Stratford, CT 06614

Great Pond- Ridgefield
Open only during the summer, the Martin Beach Park boathouse rents single and tandem kayaks and paddle boats, accommodating the whole family.  Rental is $10/hour in addition to park admission fee.
Great Pond Road, Ridgefield, CT

Saugatuck River
Downunder CT - Westport
Guided or self-guided kayak tours for a family of even novice paddlers. $55/class and up, per person.
3575 Riverside Dr, Westport, CT 06880

Five Mile River
Downunder CT - Rowayton
Guided or self-guided kayak tours for a family of even novice paddlers.  $55/class and up, per person.
157 Rowayton Avenue, Norwalk, CT 06850

SWIMMING
Long Island Sound
Again, with the obvious.  Head to the beach in town, or purchase a seasonal beach pass for the town nearest you.  Not gonna stick your toes in the sand enough to justify the price?  Check out our list of 8 Affordable Connecticut Beaches.

Candlewood Town Park - Danbury
This park has about 200 yards of beach, along with a playground, picnic tables and concessions.  Entrance fee or seasonal pass required; $2-15 depending on residency status and age.
36 Hayestown Rd., Danbury, CT

Lake Mohegan - Fairfield
There's a beach as well as a sprinkler park and if you are a non-resident and plan to go more than twice it is worth it to get the season pass. Resident Pass $10/person.  Non-Resident $20/person.
960 Morehouse Hwy., Fairfield, CT

Wolfe Park & Great Hollow Lake- Monroe
This place is incredible.  Lake swimming or pool swimming, plus three playgrounds, tennis and basketball courts, hiking and open fields.  Entrance fee or seasonal pass required. Wolfe Park: $12/nonmembers. Children under 2, FREE.  Great Hollow Lake: $10/carload for nonresidents.
Wolfe Park, Cutlers Farm Rd., Monroe, CT 06468
Great Hollow Lake, Purdy Hill Rd., Monroe, CT 06468

SAILING
Young Mariner’s Foundation - Stamford
This organization specifically serves low-income children from the Stamford school system.  They also offer an After School Sailing program to anyone ages 8-12 at John Boccuzzi Park.  Ages 8-12, $375.
John Boccuzzi Park, 196 Southfield Avenue, Stamford, CT

Sailaway Sailing School - Bridgeport
Kids ages 9-18, can learn to sail in two-week, half-day summer courses ($425).  They also offer two, 3-day courses for families. 
Captain's Cove Seaport, 1 Bostwick Ave., Bridgeport, CT 06605

Soundwaters - Stamford
US Sailing certified instructors show 4th-6th graders the ropes every summer on Holly Pond, while emphasizing the biology of the estuary around them. $595/week-long course.
Cove Island Park, 1281 Cove Road, Stamford, CT 06902

Longshore Sailing School - Westport
It’s pretty clear after a few minutes on their website, the kids have fun here … while getting well-organized, quality instruction.  9 and up. $395-425.
Longshore Club Park, 260 Compo Road South, Westport, CT 06880

Norwalk Sailing School - Norwalk
Spend the day at Calf Pasture Beach, while your youngster spends half that time learning how to sail.  Ages 8 and up. $375/2-week course.
Calf Pasture Beach, Calf Pasture Beach Rd, Norwalk, CT 06855

Dories Summer Sailing Camp - Norwalk
The Sound Sailing Center offers kids as young as 6 the chance to set sail.  There’s a balance of boating and biology in this camp, that culminates with a trip to Sheffield Island.  $350/week.
54 Calf Pasture Beach Rd, Norwalk, CT 06855

Candlewood Yacht Club - Danbury
They don't have specific youth programs here, but every summer they offer up a handful of Saturdays to teach adults to sail ... and they are welcome to bring children 12+.  To top it all off, the 4-hour courses are FREE.  First come, first serve.
7 Shore Drive, New Fairfield, CT 06812

ROWING
Great River Rowing - Shelton
Kids 11-14 can get their oars wet during one of four weeklong summer camps on the Housatonic ($300). Great River also offers beginners the chance to move toward competition with their Summer Junior program ($625).
722 River Rd., Shelton, CT, 06484

Saugatuck Rowing Club - Westport
Learn to row year-round at this beautiful location on the Saugatuck in Westport ($750/2-week course). 
521 Riverside Ave., Westport, CT 06880

Norwalk River Rowing - Norwalk
They love new rowers here, and welcome 9th-11th graders to join their novice racing team. 
1 Moodys Lane, Norwalk, CT 06851

Greenwich Crew - Greenwich
Whether your youngster has healthy recreation in mind, or an Ivy scholarship, they’ll find a place here year-round. 
49 River Road, Cos Cob, CT 06807

STAND UP PADDLEBOARDING
Fairfield Board Company - Fairfield
These guys offer private and group lessons, so you could learn alongside your tween or she could sign up for a class with a friend (without you, duh). $50 and up/person.
1700 Post Rd, Unit B5, Fairfield, CT 06824

Downunder CT - Rowayton/Westport
Downunder instructors are trained by the Academy of Surfing & SUP Instructors.  Children must be at least 9 to paddle board on their own ($55 and up/class). Children as young as 5 can ride with a parent.  Downunder also offers SUP yoga. 
157 Rowayton Avenue, Norwalk, CT 06853
575 Riverside Dr, Westport, CT 06880

Candlewood Stand Up Paddleboard - Danbury
Paddleboards aren't exclusive to salt water! This outfitter will come to your Candlewood family compound or community beach to conduct a class ($50 and up/person).  They also offer private lessons, and the always cool (in photographs anyway) SUP yoga classes.  All offerings by appointment only.
Chatterton Marina, 5 Shore Drive, New Fairfield, CT 06812

Longshore Sailing School - Westport
If you're 12 and you can swim, you're in!  Choose from either a 5-week session or drop-in 60-min sessions (included with a board rental) around the mouth of the Saugatuck River.  If you're looking for a great way to get some one-on-one time with your kiddo, sign up early for a Saturday morning slot and figure it out together.
260 Compo Rd S., Westport, CT 06880

Great Pond- Ridgefield
Open only during the summer, the Martin Beach Park boathouse rents stand up paddlboards and offers lessons.  Rental is $10/hour in addition to park admission fee. $53-108/lesson, depending on membership.
Great Pond Road, Ridgefield, CT

Fairfield Kayak Company
If you've learned, but aren't ready to invest in a board for yourself or your children, you can rent by the half or full day here.  You can pick up or they deliver to launches from Bridgeport to Southport and beyond.
Half-day rental: $48
Full-day rental: $72
Jim or Jamie, Phone: 203-255-5315
FairfieldKayak@yahoo.com