Romantic Getaway On Boston’s Waterfront

WHY GO: Formerly a cesspool, now a national model for waterfront revival, Boston Harbor is full of surprises. Two days closer than New York to Europe during Colonial times, Boston was once the favored American port and is now reclaiming its maritime history.

Romantics will adore this Boston waterfront getaway. Just steps from downtown Boston (everything in Beantown is within walking distance), and with great restaurants, top rated harbor hotels, charming cobblestone streets, and 34 islands and peninsulas to explore, there’s much to keep you and your honey as busy as you’d like to be.

Things To Do In Boston Harbor

Institute of Contemporary Art Boston MA
Boston ICA

VISIT: Institute of Contemporary Art/Boston

Part of the fun in visiting this harbor-front ICA Museum is stepping onto the walkway cantilevered right over the water. Last time I did this, thousands of gelatinous creatures floated leisurely in the water below.

An unusual jellyfish infestation in the harbor created an unexpectedly random installation-performance piece. It wasn’t much different from the avant-garde art that finds a home, either permanently or temporarily, in the coolest of Boston’s waterfront museums. $20, Tues – Sun. Thurs& Fri open until 9pm.

Boston Harbor Walk, Boston, Massachusetts

WALK: Boston Harbor Walk

Extending along the waterfront from Chelsea Creek to the Neponset River though a variety of neighborhoods, this 47-mile walkway is easily reached from hotels and features parks, boat ramps, interpretive signage, water transportation and world-class restaurants and museums. It’s the perfect esplanade to stroll hand in hand.

Couple on Bench on Boston MA Waterfront
Boston MA Waterfront

Boston is so proud of its waterfront, the city provides benches and Adirondack chairs specifically for setting a spell to gaze out at the harbor. Downtown Lewis Wharf, with its secret garden,  Sergeant’s Wharf and Long Wharf all have amenities for this “take time to smell the roses” endeavor.

WALK: The Rose F. Kennedy Greenway

What used to be the ugly Interstate is now a beautiful linear garden.  Considered the “Rooftop of the Big Dig”, the Rose F. Kennedy Greenway, a narrow slash of green, is the perfect way to get from the North End to Chinatown – a bit over a mile.

Meander through gardens, sculptures and event spaces, all the while keeping Boston Harbor over your shoulder.  Gourmet food trucks have blossomed along the way, so queue up at one that strikes your fancy, sit on any available bench, and voila – instant picnic.

Boston MA Wharf
Boston MA Wharf

DO: Boston Harbor Cruise

Yes, a bit touristy, but if you haven’t done it yet, orient yourselves on one of many narrated Boston Harbor Cruises.

Boston is tops at repurposing historic homes and buildings. And, you’ll see many on the Boston Waterfront even before your boat pulls away from Long Wharf. For example, the 1845 gray granite Customs House, that went condo, and John Hancock’s 1760 brick office building –  now a Chart House Restaurant.

Pass the “Famous Fish Pier” (from which dried and salted codfish was shipped all over the world), Logan Airport, the gleaming new towers of South Boston and fun Institute of Contemporary Art.  The US Navy once dominated the entrance to the Charles River.

Charlestown Naval Yard Boston MA Dry Dock
Dry Dock Charleston Navy Yard Boston MA

In fact, Boston was the 2nd oldest Navy Yard in the country, after Philadelphia, and had a presence here for almost 200 years before it was officially closed as a military installation in 1974. For a different perspective you’ll get great views of the Bunker Hill Monument and the Old North Church; touchstones in Revolutionary War history before heading back to the dock.

USS Constitution, Charlestown, Massachusetts

VISIT: USS Constitution at the Charlestown Navy Yard National Historical Park

Launched in 1794 the 204 ft. Tall Ship, USS Constitution, incredibly still serves as a commissioned Navy vessel with a crew of 65 officers and enlisted personnel.  Be prepared for airport-tough security to enter the USS Constitution Visitor’s Center and to go aboard “Old Ironsides.”

US Constitution Museum, Boston Massachusetts @GetawayMavens

VISIT: USS Constitution Museum

You’ll also want to spend at least half an hour in the terrific USS Constitution Museum where you can try your hand at hoisting a goat (blessedly plush) aboard a tall ship, pretend to be an enlisted sailor, and watch a volunteer inserting a hand-carved ship into a bottle.

You’ll learn all there is to know about the USS Constitution; that it retains ten percent of its original wood; how it got its nickname (hint; while serving honorably in the War of 1812, British cannonballs seemed to “bounce off” its live-oak, ultra durable hull); how it was saved from decay in 1830 by poet Oliver Weldell Holmes, who appealed to the patriotic sentiments of a new country, impelling the then Secretary of the Navy to declare Old Ironsides “A National Symbol.”

Naval Yard open 24 hours/day, Visitors Center, 10-5, Old Ironsides (when available) 10-4, daily, free. Museum $10-$15 admission.

Reenactor calling for revolution on a tea ship replica at the Boston Tea Party Museum in Boston, MA. #history #USA @GetawayMavens

TOUR: Boston Tea Party

Experience the thrill of Boston’s #1 Patriotic Attraction, the Boston Tea Party Experience, by taking a tour of tea ship replicas and traditional museum exhibits, spiced up with enthusiastic re-enactors and interactive virtual displays.

See if you can resist dumping bales of tea and shouting for revolution. Time your visit to begin or end at Abigail’s Tea Room for a spot of tea, scones, and historic board games. Open daily 10-5 in season, 10-4 off season, $31.95.

DO: Codzilla

Another touristy favorite, you WILL get wet on this exhilarating 2,800 horsepower speedboat. If getting drenched while taking in the Boston Skyline is your thing, Codzilla zooms up to eight times a day (check schedule) from Long Wharf. $52 for 40 minute ride.

Boston Water Taxi, Boston, Massachusetts

DO: Ferries and Water Taxis

If you are a rugged individualist and prefer getting on the water without narration or reservations, a bunch of ferries can take you to various landings in the Boston area and out to the Boston Harbor Islands.

Restaurants In Boston Harbor

EAT: Locals Love

Boston is known for it’s seafood, so you’ll find dozens (if not hundreds) of options on the waterfront. Among them the famous Legal Seafoods (which has extended far beyond Boston). But relative newcomers like Lolita, Pier 6, and Reelhouse are upping the food game on Boston’s burgeoning harbor.

Photo of thick New England Chowder from Sail Loft Boston MA

EAT/SNACK: The Sail Loft

In a former sail-making factory a few blocks from the teaming-with-tourists Long Wharf, the tiny, unpretentious Sail Loft is a local hotspot. Overlooking a marina, this restaurant has what many consider “the best chowda” in Boston.  That’s a high bar for any restaurant.

But it’s tough to argue when the mug of thick, stewlike New England Clam Chowder is set down on the table.  “The secret is not so secret,” says the owner.  “Lot’s of cream, butter…..and dill.”

Where To Stay In Boston Harbor

Lobby, Envoy Hotel, Boston MA

STAY: The Envoy Hotel

As one of the top Boston Seaport hotels, The Envoy has earned a “Maven Favorite” review with link above.

View of Boston Harbor from Boston Yacht Haven room

STAY: Boston Yacht Haven Inn and Marina

Off the radar for most out of towners, and even Bostonians, the ten-room boutique Boston Yacht Haven Inn and Marina is one of the most romantic places to stay in the city.

Overnight within a swan dive of Boston Harbor, ferries gliding by your sundrenched, nautically appointed room and private deck. To top it off, this secluded spot is just steps from the historic Italian North End.

Try for a corner room, with picture windows on two sides and decks with lounge chairs. Yacht Haven is an official “find,” for sure. $275-$800 per night includes continental breakfast, free wi-fi.

House Boats on Boston MA Waterfront
House Boats on Boston MA Waterfront

STAY: Green Turtle Floating B&B

And if you really need to be on the water, actually, really, truly, try to score a room onboard Green Turtle. It’s actually a floating bed and breakfast and has earned accolades from Yankee Magazine and fans. From $299 per night.

Weekend Getaways In Boston


  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine,, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.