The Ivy Handbook: THE JET PREP'S GUIDE: INSIDER SECRETS OF NEWPORT, RI

Newport, Rhode Island is one of my favorite spots in New England and is consistently underrated in my mind. I lived there for four fun years after law school and still love going back. Here are my top 10 insider tips for an amazing trip to greater Newport (the lawyer in me is screaming out that a few of these places are technically in the adjacent Middletown and Portsmouth so I had to throw in “greater”. Carry on . . . ignore the nerd typing furiously on the keyboard):

1. Take a drive around Bellevue Avenue past the mansions then to Brenton’s Point and on to Castle Hill Inn for cocktails in the Adirondack chairs on the lawn at sunset. Bonus points for a convertible with a trusty canine in the back. Double bonus points if the canine is a hunting breed.

2. Head to a Polo Match hosted by the Newport International Polo Series Saturdays in the summer at 5:00pm. This is such an exciting and festive event and open to the public. Bonus points for packing a fabulous picnic and divot stomping.

3. Take a sail on the Adirondack or a ride on the Rum Runner in Newport Harbor. Sunset is a great time for this but anytime is beautiful. Bonus points if you get the captain’s phone #.

4. Take a walk on the Cliff Walk overlooking First Beach and past the mansions. One of the prettiest walks you’ll ever take. Bonus points if you go through the creepy tunnel alone at night - you know, the one under the Chinese teahouse at Marble House.

5. Take a tour of any of the mansions. The Breakers, Rosecliff and The Elms, among others, are all fascinating and beautiful in different ways. Bonus points for going when they’re decorated for Christmas. Double bonus points for making a donation to the amazing The Preservation Society of Newport County who manages and maintains these architectural masterpieces.

6. For nature lovers, take a peaceful hike on the trails at Sachuest Point overlooking Second Beach or check out the Norman Bird Sanctuary.

7. Walk, surf, boogie board or kiteboard at Second Beach. Bonus points if you channel your inner Yankee and bike there to avoid paying for parking.

8. Finagle an invitation to a party at the New YorkYacht Club, IYRS or any of the Bellevue Avenue mansions. Bonus points for wedding crashing. Double bonus points for crashing any private Newport Race Week events.

9. Check out the Newport Jazz Festival. Bonus points for catching the festival on a boat. Double bonus points for weaving your Dad’s Pearson 36” in and out of the boat traffic while wearing a red cape and drinking Dark and Stormy’s. Not that that ever happened.

10. Take a Ghost Tour. Bonus points, of course, if you see an actual ghost. Double bonus points if the ghost is wearing authentic madras.

Chatham Ivy’s Entering Newport Tee celebrates everything we love about Newport – sailing, stately mansions, Bellevue Avenue, and tooling around in a fun ride soaking it all in. If you know anyone who loves Newport as much as we do, our Newport t-shirt makes the perfect gift! Available now at Chatham Ivy.