Having grown up in a landlocked town, boating was generally something I observed from afar while relaxing on a beach I had snuck into, white sails and hulls bobbing in the distance, hinting of fun and adventure. It was not until I became a traveling mom that the call of the sea would become part of my own family travel adventures.

My husband, a lifelong sailor and power boater, let me know early on in our relationship that maritime excursions would play a major role in family travel and activities.  And so it was that we have grown a passion in our sons, ages 4 and 5, for all things nautical.  For a traveling mom, this poses some unique challenges and some amazing family benefits too.

Along the Connecticut coastline where we live there are plenty of fun and educational destinations, meals and adventures that can be accessed and experienced by boat –  all of which, I discovered, make them so much more meaningful than if we had merely pulled up in the family station wagon. 


Thimble Islands

Whether you are cruising for an overnight, a week, or more, your trip will seem far longer due to the eerie time warp that seems to happen on the water.  Time stretches out and regular life slips away in a way that doesn’t happen on land.  Most summer nights and weekends find us on the water, and we take our 25-foot powerboat on a seven to 10-day cruise each summer too.  From Greenwich, traveling northeast, our cruise this year started with the Thimble Islands, off of Branford, Connecticut.  The Thimbles are a top pick for amazing scenic beauty. 

This archipelago of islands, some occupied, some not, became known as the “Newport of Connecticut” at the beginning of the 20th century.  Their pink granite cliffs rise straight out of the water like the fjords of Norway – motoring close by elicits a lot of “Wow, Mom, look at that!” from my young passengers.  Legend claims that the pirate Captain Kidd found the Thimbles an ideal place to bury his treasure; many of the homes on the larger islands fly the Jolly Roger in his honor, a piece of local lore my pirate loving sons soaked up like a sponge.

Just a few minutes further up the line are the towns of Clinton and Westbrook, which both offer restaurants accessible by boat.  It is important to note that bringing along an inflatable Zodiac boat outfitted with a small motor is a major asset here and elsewhere on your trip.  This smaller vessel will be your private water taxi, allowing you access to restaurants and sites regardless of whether the tide is low or high, places your boat may not fit.  In addition, if your kids are bored, a spin on the inflatable is a great way to have fun.  My 5-year-old is already a better driver than I am, and seeing his confidence in his growing maritime abilities grow was a joy to see.

Life on Board

It should be noted that, unless you have a movie-star size yacht, quarters are fairly tight on a boat.  Kids bunk together in close proximity, and there’s usually only one (very small) bathroom.  The kitchen, or galley, is a small fridge and two-burner stove, possibly a microwave as well, so meals are simple.  A grill in back of the boat is critical, for eating outside and enjoying all those amazing views at anchor. 

For me too it was liberating to be a minimal packer.  Things I traditionally took for granted, like the need for a hairdryer and many pairs of shoes, turned out to be incredibly superfluous, totally unnecessary, and a waste of precious space.  Casual, simple and machine washable are the way to go.

Being so close together seems to make us even closer as a family, sharing in tasks, swimming, sightseeing, and enjoying each others’ company 24-7.  Watching my two little guys mature so much over the course of a week, with great pride in their accomplishments and ability to lend a hand onboard, makes it all the more rewarding.

Fuel, whether gas or diesel, is usually the biggest expense of a boating trip. Bur since you’ll be sleeping onboard and eating many of your meals onboard, the cost savings of a boating vacation are huge.  You also need only unpack once, and your kids’ favorite foods and toys are right at hand. 

Elegant Essex – for Kids Too!

Turning away from the coast, we sojourned up the Connecticut River for a change of scenery, clam rolls, and the charming town of Essex.  The Connecticut River is the longest and largest river in New England, with plenty of scenic beauty rolling by.   Essex is right out of a New England postcard, gracious captains’ homes lining tree lined streets, with a sense of unhurried calm, well-edited shops and the Griswold Inn. 

The elegant Griswold Inn and Restaurant have been in continuous operation since 1776, and with the exception of some modern conveniences, the interior is largely unchanged since revolutionary days.  The dining rooms are filled with old maritime paintings and antique firearms, and the bustling bar features live music.  The night we were there, a lively band specializing in sea shanties kept the crowd on their feet laughing and dancing.

Despite its elegant and special atmosphere, the Griswold doesn’t give families a fishy glance.  Cruisers are welcome, and fancy clothes are not required.  In fact, a sign over the taproom reads, “Because we cater to yachtsmen, a coat and tie are not required.”  For a tab of around $80, we all ate well in grown-up surroundings.

A stroll around Essex village showcases lots of shops appealing to parents and children alike, and right next to the town dock you’ll find the Connecticut River Museum.  Its lawn is a great place to stop and enjoy an ice cream, since it boasts the best view of the harbor.  Inside are outstanding exhibits on regional history, shipbuilding, native Americans, and a full-size replica of the American Turtle, the very first submarine, invented in 1776, another big hit with kids.

Leaving Essex and the Connecticut River, reluctantly, we journeyed on to Noank and the entrance to Mystic Harbor.  Motoring past Noank, you will want to pull up to Abbotts, long renowned as the best place in the state for lobster roll.  For around $12 per roll, it’s a delicious taste of the sea.  You will not be disappointed as you and the kids bite into this hot buttery delight, followed by their fabulous chowder.  Abbots will also pack fresh lobster for you so you can steam dinner on board.  Next door, Costello’s Clam Bar serves up the bivalve in every possible way. 

Mystic:  Maritime Heritage Comes Alive

Entering Mystic Harbor was my boys’ favorite part of the trip, as this old maritime town is a kids’ paradise.  The busy town, with its drawbridge, downtown, and Mystic Pizza are all great fun, and the inflatable makes every outing a great adventure.  Mystic Seaport, of course is a big draw for families, but when you visit by boat our New England heritage really resonates.  Traveling like our founding fathers, but with a motor, we explored the superstars of the Seaport – the old whaling ships, moored a stone’s throw from us.

The showstopper is the Charles W. Morgan, the only original surviving whaling ship of that bygone era.  Visitors are welcome aboard to tour the old ship’s whale catching and blubber boiling operations.  For under $100, including snacks, a family of four can take in a fabulous taste of the whaling industry of old.  The ships are spectacularly lit at night at the end of the Mystic Harbor, where the town also offers free anchorage to transient boaters.  It is the best place in town to overnight – and cocktails on deck after the kids have gone to sleep, a panorama of ancient ships in front of us, is a sublime way to end a busy day.

Practical Matters

Rainy days are the bane of a boater’s existence, but you must plan for one or two.  Being prepared with books, games, and DVDs onboard is crucial to entertaining kids who will grow bored very quickly, and to your sanity too.  

Be sure and pack a “meds bag” and first aid kit packed with the basics, along with a thermometer, and any remedies kids and adults may need (Tums, Tylenol, etc.)  It is so much easier to have everything at your fingertips when someone doesn’t feel well in the middle of the night, rather than worry and wonder where the closest pharmacy is, especially when anchored offshore.

Wherever you choose to stop on your voyage, you may have a choice of either spending the night in a marina’s transient dock slip, where charges are generally $2.50 per foot of boatlength (still far cheaper than a hotel room), on a marina’s mooring in a bay or cove (less expensive), or at anchor  in an approved anchorage (no cost).  My personal favorite is the mooring – an island of privacy without neighbors in the next slip, and launch service to take you ashore when you want.

Previous cruises have taken us up to Watch Hill Point and Block Island, and then down to Long Island, but this year a sailing commitment meant my husband and older son had to get back home.  Nonetheless, there was time for one more stop before returning home. 


Northport, Long Island, is right across from Greenwich on the Long Island Sound, but after an afternoon there we always feel like we have been away for much longer.  Northport has a bit of a 1940’s vibe to it and for the little ones there are two great playgrounds too.  The Shipwreck Diner is a must and has amazing breakfasts for adults and kids.  Northport’s Cow Harbor Parade in September is great fun and highly recommended, especially as fall’s first hint of color touches the treetops.  Community clubs, school bands, fire engines and even greyhound rescue groups come together in small town celebration.

In the end, in boating we’ve discovered a family closeness and a pastime we can enjoy for three seasons.  And for me, the best part came on the last day, returning to our own mooring back in Greenwich, watching my sons take turns driving the boat with my husband.  There were other boaters passing us in the channel, but one really grabbed my eye – a white-haired elderly man probably in his mid-80’s who waved hello from the helm of his own boat, and my little guys, just starting out, smiled and waved back.  As these captains acknowledged one another, I realized I had helped give my kids something they could enjoy and learn from all their lives, too.

Lisa Tella is a writer based in Greenwich, Connecticut and a mother of two (three including greyhound).