A Sunday in Boston, Massachusetts | A Sunday in Naples, Florida

The charms of Boston’s legendary (and sometimes lesser-known)
century-old establishmentsandNaples’relatively unbothered beauty
awaits their chance to pamper you.

In Boston, it takes a local’s lens to see what lies beyond games
at Fenway, droves of college students, and the Georgian brick
buildings of Harvard Yard. are so old theyre new again: the classic
men’s shops brimming with herringbone and tobacco pipes, the
wonderfully under-the-radar museums, the oyster bars and chowder
shacks, the quirky collegiate book shops. In just a few days, you
can get a sense of both Bostons old-school history and its edgy,
up-and-coming neighborhoodsfrom Beacon Hill to Fort Point.

BOSTON

Rent a bicycle from Urban Adventours and
join the cavalcade of commuters cycling along the Charles River.
Cruise east along the Esplanade, a green
masterpiece designed by Frederick Law Olmsted. On warm days,
Bostonians migrate to this popular park to sunbathe, picnic and
feed waterfowl. Take a break at the Longfellow Bridge to take in a
fantastic view of the Boston skyline.

Walk Boston Common and Beacon Hill

Red brick Federalist facades, old cobblestone streets, charming
gaslit lamp posts, quaint little shopsBeacon Hill is one of the
oldest and most picturesque neighborhoods in the country, and its
easily navigable by foot. Start off at Louisburg Square, and weave
your way through backstreets like Mt. Vernon. Willow, and West
Cedar streets. (If you have the time, stop in to see
theNichols House Museum and
theBoston Athenaeum .) Then
make your way down to Charles Street, where you can grab a quick
bite at Artu or the Beacon Hill Hotel & Bistroor trawl through the
unique boutiques that dot the thoroughfares.From Charles Street,
head to the Public GardenEnter at Beacon Street by the intersection
of Charles Street. Just past the entrance, see the famous bronze
ducklings (from Make Way For Ducklings), which you dont have to be
a kid to enjoy. Then walk past the weeping willows toward the
Lagoon and the Island, where, underneath the beautiful gray stone
and steel foot bridge, youll find the swan boats. Take a swan boat
outits one of the few touristy things in Boston thats even locals
approve of doing. (And definitely much cooler than a Duck Tour.)
Finally, pass the monuments and exit the park by walking toward
Arlington Street. From there, you can then stroll down Commonwealth
Avenueor sip an old-fashioned at the clubby, wood paneled bar at
The Taj overlooking Newbury Street.

All that time on your bike has made you hungry. Have lunch at
Stephanie’s
on Newbury
andon one of Boston’s most iconic and scenic
streets,

Walk or taxi back downtown for after-dinner drinks at the
Highball Lounge,
Bostons coolest, quirkiest retro bar. Browsethe menu of creative
cocktails, some of which are garnished with rubber duckies. Munch
on tater tot nachos and challenge your companions to a game of
Jenga. Its sure to make you feel like a kid again.

NAPLES

drive to the Mercato shopping center for lunch at The Counter, a
hip burger factory that takes a certain pride in every sandwich in
manufactures. If you think its list of nine breads and 45 toppings
is special, wait until you see a drink roster that includes
vodka-spiked blueberry lemonade, beer cocktails and mimosa shakes.
When youve stuffed yourself, walk off the carbs in the swanky
outdoor plaza where youll find local brands (Gigis Childrens
Boutique) and national chains (Nordstrom Rack) to entice you.

After shopping for an hour or so, head back to LaPlaya where
youll find a number of options for your next activity. A long nap
on the pillow-top king bed isnt a bad call. Nor is seeing whether
the spas promise of its tropical essence massage being a
mood-altering experience is mere brochure talk. Even putting the
beach concierge to work for a snack from your spot along Vanderbilt
Beach sounds great. Whatever you decide to do, just remember that
you have dinner reservations at Baleen.

At first glance, LaPlayas signature fine-dining establishment
comes off a tad formal. Glimmering chandeliers, private booths and
a snazzy waitstaff set the polished mood. But upon deeper
inspection of the diner in the polo shirt and shorts or the family
chuckling over the days parasailing exploits, you realize the place
is for anyone who appreciates good service and inventive dishes
such as Florida Keys yellowtail snapper or chili-rubbed short ribs.
An order of freshly churned guava sorbet should complete your first
day in Naples.

Since you have an early-morning tee time at LaPlaya Golf Course,
you may not be able to fit in a lavish breakfast. Luckily, the golf
club, which is just a nine-minute ride from the resort, offers
pastries, hard-boiled eggs and fruit for hotel guests and club
members. If youve signed up for a session at the prestigious David
Leadbetter Golf Academy, your one-day mini school will start at 9
a.m. If youre going at the 6,907-yard, mangrove-flanked course on
your own, head out to the first hole. A beautiful marriage of
manicured greens and natural majestyduring our particular morning
on the course, we came across turtles and anhingas, the bird thats
pictured on the LaPlaya logothe layout is one golfers will compare
favorably to anything theyve played previously in Sarasota or Ft.
Lauderdale.

Once youve completed your round, grab a cheeseburger wrap at the
clubhouse or make the breezy 20-minute drive to Cosmos Caf &
Pizzeria, an unpretentious spot that cooks up inspired pies that
could leave the Naples in Italy a little envious.

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