A Sampling of New England in Five Days

The rocky coast of Kennebunkport, Maine
The rocky coast of Kennebunkport, Maine

Aaand We’re Off to A New England Adventure!

Where do I begin to tell you about all the natural beauties of New England that we saw on our trip out East?  The itinerary I will offer this time is full of variety and simply gorgeous places to visit.  We always begin an adventure to this part of the world by flying into Boston—always seems to be more reasonably priced for both flights and rental cars (just because I flirt with luxury hotel stays doesn’t mean we can’t save a buck here and there!), flight options are more abundant, and I always love ending one of these trips in a true luxury hotel in Boston.  In this part of the United States, the definition of luxury hotel/5 star resort, is a little different than say, staying at Ritz Carlton, Four Seasons, or Trump Hotels.  Once you accept this fact, you will experience and open your mind to a different type of luxury.

As with all of my suggested itineraries…the world will not crumble if you do not follow it to a tee.  This is just to get you started on your adventure and a guideline for fun.  Should you find some additional fun things to do, please email me so I can try them on my next visit.

Day 1:

Try to land in Boston by noon.  Securing your rental car will include taking a tram/bus to the rental center.  This is one big building where all the car companies are located.  We found the process to be a bit slow so get your patience ready.  Once the paperwork is completed it gets easier and you simply walk to the parking lot and pick up your car.  A Dunkin Donuts stand is on the way to the cars, so we grabbed a coffee for our drive (we may or may not have also grabbed a sprinkle donut!  I do love frosting!)

Our first stop was Kennebunkport, Maine.

Drive Time:  2 hours and 22 minutes

Cape Arundel Inn and Resort
Cape Arundel Inn and Resort

Where to Stay:  We chose Cape Arundel Inn and ResortThe property is situated in a quiet neighborhood with sweeping views of the Maine Coastline and the Bush Compound.  The front porch and the front lawn make this location ideal to sit and take in the ocean breezes.  I love the fresh white Adirondack Chairs.  The staff is attentive and they immediately make you feel right at home.

The front lawn at Cape Arundel

Rooms:  Many choices.  Try to get an oceanfront.  We booked last minute and high season, so we had to settle for the Crow’s Nest.  The Crow’s Nest is a cute second floor loft.  A word of caution:  The only way to access this room is a set of very steep stairs.  The room is in a building which is within steps of the main inn which is where your will find the restaurant, views, and front porch.

Upon arrival, our room was not ready.  This turned out to be a great thing.  The staff made us comfortable in the lounge area with two glasses of really good champagne and a gorgeous view.  The rain was coming down so we were unable to enjoy the front porch.  While we waited, numerous staff members came over and chatted with us.

So our room wasn't ready....who cares? Champagne anyone?
So our room wasn’t ready….who cares? Champagne anyone?

Once we unpacked we were ready for some exploring.  A five minute drive to the right took us to lively Dock Square.  So many darling shops and eateries.  Plan to spend a couple of hours just enjoying the sights and walking around this fun little town.  Definitely try some fried clams from the famous Clam Shack, a walk up shack where you order fried clams and lobster rolls.

We arrived back at Cape Arundel in time to shower and get ready for dinner.  We made our reservation in advance at the Inn’s restaurant Ocean.  Named one of the top 100 scenic restaurants in America, Ocean does not disappoint.  We were awarded “the” table for 2.  A lovely corner spot enveloped in picture windows and those beautiful ocean views we love.  In addition we had the view of the Bush Compound.  The wine list was outstanding.  We had to enlist our server for suggestions because we wanted to try them all.  The dinner presentation was exquisite…of course we had Maine Lobster (duh!).



Day 2:

Cape Arundel includes a wonderful breakfast with room bookings back in the two tiered Ocean Restaurant.  We lingered over coffee and made to order omelettes while conversing with some fun other guests.

Following breakfast we took a walk down to view the Bush Compound.  Be sure to walk both left and right of the Inn as there is natural beauty everywhere.  Before we checked out we took a water break sitting on the front porch and over on the lawn in the Adirondack chairs to breathe in the ocean air one more time before checking out.

Next Stop:  Meredith, New Hampshire

Drive Time:  1 hour and 55 minutes

This was the main purpose of our trip.  My friend since kindergarten and her family have a beautiful camp on Lake Winnipesaukee.  I love visiting with this family I grew up with and when she and most of her family wind up here for a week in the summer, I like to join in the fun.

One of my besties since kindergarten

Church Landing at Mill Falls is a great place to stay.  One of four inns, the rooms are rustic but nicely appointed.  Most have fireplaces, a balcony, and are steps from the lake.  In addition this property locates you within walking distance of the marketplace and EKAL Lake Activity Center for renting kayaks and canoes.

The front porch at Church Landing. A great spot to people watch.
The front porch at Church Landing. A great spot to people watch.

Obviously my plans for this part of the jaunt were filled with family time, however here is what my New Hampshire family recommends to fill the rest of Day 2:

Ride the MV Mount Washington (big boat that cruises the lake)

Climb Mt. Major (family friendly hike with blueberries at the top and stunning views of the lake)

Visit Castle in the Clouds

Time out in the Cascade Spa at your hotel.

Dinner Recommendations:  The Corner House Inn in Sandwich, Lavinia’s in Center Harbor, or the Woodshed in Moultenboro, Lago


Day 3:

Start with a complimentary coffee from the coffee bar near the lobby and take a moment to watch the world go by on the front porch in the rocking chairs.

Head to breakfast in the hotel at Lakehouse.  Enjoy sweeping views while you eat.

We all took a walk around the water and scouted out Mill Falls Marketplace—11 distinctive shops, more dining options, brick walkways, a 40 foot waterfall, and views of the Lake.

Cheesing at the lake.
Cheesing at the lake.

 Time to head to Cape Cod. 

Drive Time:  3 hours and 15 minutes

Where to Stay:  Wequassett Resort and Golf Club in Harwich, Massachusetts.  They just earned the coveted fifth star from Forbes Travel Guide. IMG_1549

Upon arrival you will be greeted by the bell staff and taken in for check in, all while enjoying a glass of lemonade.  Once checked in, one of the bellmen will direct you where to park (parking is free), and then come to collect you on a golf cart.  After luggage is loaded, you receive a lively tour of the property and an abundance of ideas to do during your stay.  You are then delivered to your room and also get a complete explanation of how everything works.

After unpacking, we went walking the property and looking more thoroughly at the many things we could do.

Here’s why you are going to fall in love with Wequassett:

The grounds are lush and meticulous.

The steps to our waterfront room
The steps to our waterfront room

There are only 120 rooms and suites.  Even so, you have four restaurants, two pools, two beaches, beautiful views, four Har Tru Tennis Courts, a championship golf course, and too many amenities to mention.  Did I mention the service?  Unbelieveable!  We were treated like royalty.

Next up—our room came with a nice bottle of wine and snacks so we sat in the Adirondack Chairs on our balcony and enjoyed a glass of vino and the views before showering for dinner.

The view from our suite
The view from our suite

For dinner your first night you must go to Chatham.  Here’s the extra fun thing—call the front desk and they will have one of the bellmen run you into town.  On the way we got a mini tour of some things to come back to on our own.  Go in before dinner so you have plenty of time to walk around because the shops and scenery are adorable.

Dinner recommendations:  Del Mar, Impudent Oyster, Chatham Wine Bar and Restaurant, or Chatham Bars Inn Resort Dining.

We chose Impudent Oyster and it was delightful.  The service was very hands on special, the food was creative and delicious and the atmosphere is lively.  Feels like you are a part of the neighborhood and in on the secret!

Back at the hotel we had a nightcap and listened to Jazz at Libaytion.

Day 4:

Ok…you have to have to have to have a breakfast and a dinner at Twenty-Eight Atlantic…the four-star, four-diamond dining experience.

So to begin day four we did just that.  As if the 180-degree water view isn’t enough, having breakfast in an elegant setting will make your day start right.  Selections galore and all can willingly be altered to your direction.

Twenty-Eight Atlantic at breakfast time
Twenty-Eight Atlantic at breakfast time

Next on the agenda was Provincetown.  Oh what fun!  The 55 minute drive is scenic and it goes quite fast because you are visually stimulated all the way.  If you want to be cool, call it P-Town.  At the northern tip of Cape Cod, this hip little seaside town has long been known as a haven for artists, and the LGBTW Community.  We loved everything about it.  The coffee houses, the restaurants, the shops, the galleries, the views, the people.  What a fun, fun day.  Just get yourself to lively Commercial Street and walk and stop everywhere.

Just one of the many coffee stops in P-Town!
Just one of the many coffee stops in P-Town!

There is a cute women’s boutique on the way called Beth Bishop.


Once back at the hotel be sure to take some lounging time at the day’s end at the glorious pool and partake in a libation!


An 8 pm reservation at Twenty-Eight Atlantic is the perfect ending to this day.  Dinner was amazing.

Day 5

Time to head to Boston.  But not without a stop to tour Cape Cod Chips (my favorite chips in the whole wide world).  It’s fun, it’s fast, it’s free!  You even get a bag of chips at the end.


Chips were delicious…now on to Boston.  Drive time:  2 hours and 10 minutes.

One of the biggies on our list was to visit the John F. Kennedy Presidential Library.  This stop is well worth it.  First of all, it is extremely easy to find.  Parking is free and simple to maneuver.  We found it fascinating.


One really must stay at least once at The Boston Harbor Hotel.  This is exactly what I love when it comes to high end luxury hotels.  Rooms and marble baths are divine.  Definitely get a harbor view.  We had one of the larger corner rooms with panoramic views.  Highlights include the location, a lovely spa and fitness center, seasonal outdoor entertainment, and great dining choices.  Meritage Restaurant and Wine Bar is the high end. Rowe’s Wharf Sea Grille and Bar offers a wonderful menu, along with indoor or outdoor dining (they have a killer sangria!  Just saying…).   And, then a fun way to end the night…and a surprise if you don’t look for it…is The Alley Bar, which is just that, and serving an array of fun drinks.

Once settled into your room, and after you familiarize yourself with the hotel itself…go out the front door, go right and you will run into all kinds of great shopping and street vendors.  The Faneuil Hall Marketplace area is a fun way to wile away the afternoon.

A little hint if you want to score a great table outside for dinner at the hotel’s Rowe’s Wharf Sea Grille…stop by late afternoon and talk to the hostess.  They do try to accommodate hotel guests first with outdoor hot spots.  We had an awesome table, the food and service was outstanding, and the added highlight was we got to enjoy blues music all evening.

Summer in the City takes place right outside the Boston Harbor Hotel.
Summer in the City takes place right outside the Boston Harbor Hotel.

This trip gives you such a fun sampling of the East Coast.  It was quite out of our normal type of travel, but we enjoyed every minute of it and highly suggest you add it to your list!

Hope you enjoy this itinerary soon or someday!

XO, Jauntique

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