Our First Trip Together
We don’t sail to Newport, RI, but I wish we did! Instead, we just hit the road and drive the roughly 4.5 hours into New England to coordinates 41.4901° N, 71.3128° W, popularly referred to as 41 North (41o N). Long before the rings, relocating, two kids, a single-family home, and a white picket fence, we were taking our first-ever vacation (weekend getaway) together. The destination is one we go to just about every other year now. I love the ocean, NOT the beach, but there is something very humbling about being at sea, even more so being at sea on a sailboat. Newport, RI, gives me many things I enjoy on a trip, the ocean, sailing, raw bars, history, and tennis.
On our first trip, we shared a bottle of Relax riesling on the roof of our hotel, the Wyndham Onshore. We got this hotel from hotels.com (use this link for hotels, it helps us); with the deal, we could pay for the room at the regular price. Heading back for the next few years, we stayed at a less-than-impressive location that worsened yearly until we had enough.


Our most recent trip:
On our last trip up, we stayed at Hotel Viking; it’s beautiful and has that old historic charm (I think that’s an excellent way of saying expensive). However, Hotel Viking had an indoor pool! That pool saved us when it rained because the kids had a blast. Hotel Viking had another thing that brought it home for us, a rooftop bar if you’re wondering how that went (pics below); we got a bottle of wine and enjoyed the night the way we first did a decade earlier. Have you ever had one of those moments where you can see how far you have come? From a hotel we couldn’t afford, and a $6 bottle of wine on the roof watching the sunset to watch the same sunset with a bottle we bought at the hotel, a fire pit between us, and our kids getting to know all the other guests doing the same thing. The wine was only $45, but let me enjoy my moment!…


Ok, that felt good; now let’s talk about what we do in Newport…

Sailing
If you can’t tell yet, Newport is huge on boats, particularly sailboats; it was the site of America’s Cup with the 12m ships. If you want to sail on one of them, you can head over to 12 Meter Yacht Charters and sail onboard the US16 Columbia, the 1958 American’s Cup winner. If that seems like a bit much, consider taking a more relaxing leisure sail with Sightsailing or Sailing Excursions, both have Schooners, Aquidneck, and Adirondack II, respectively; you can enjoy the sights, participate if you like, and the crew will give you a fun history lesson along the way. What do we prefer? Since I have not had the chance to do the 12M sail yet, I would say Sailing Excursions sloop Eleanor was my favorite. I like the smaller boat, and yes, I do like to steer. Don’t be afraid to ask them to hoist the main up and fly the jib! If you want to sail, then sail!
Depending on the reason behind your trip, all these places (and others) do off private charters. Don’t be shy about doing something different for your next bachelor/bachelorette party or work outing. Also, not every excursion is sailing; if sailing is not your choice, I suggest you reconsider your boating outlook. Second, plenty of options do not have sails; maybe try the Rum Runner II over at Classic Cruises of Newport. Try a sunset cruise or take sailing lessons; there are a few places in Newport, but I haven’t had that opportunity yet.

Happy Hour and Drinks
Walk down Thames St or America’s Cup Ave, and you will find no shortage of establishments to grab a drink. If you prefer to take a break from the wharf, go straight on Broadway, and look to your left and right, I’m sure you will find your kind of place. If you’re like me and enjoy oysters and clams, head to Benjamin’s Raw Bar, for happy hour, head up to the second-floor bar and get ready to pay under $2 for oysters, clams, and shrimp, and keep them coming! Personally, I like to pair my Benjamin’s Happy Hour with Narragansett Ale; it’s inexpensive and local, which I think is fitting. One of the first times we were there, the waitress was the owner’s daughter, who had recently purchased the restaurant; in a town of gilded age mansions, I would say that makes her a modern-day Newport heiress. Suppose oyster shooters and 16 oz cans are not your ideal late-afternoon outing. In that case, the menu at Benjamin’s offers plenty of nautical options and steak and chicken choices for you to enjoy inside or at one of the alfresco options spread over three floors that make you feel like you are aboard a ship.
Drinks with a show
If you fancy live music with your drinks, step out of Benjamins, turn left, and walk about 150 feet to One Pelham East, we like the dueling pianos, but you can get their full schedule by clicking that link back there. There are some other spots along America’s Cup ave next to these places to grab drinks and food, but we like to venture down Thames Street for local shopping and the New England Charm; this walk also happens to bring you to one of the most kid friends places in Newport and one of our favorites O’Brien’s Pub, with indoor and outdoor options, parents will love the great outdoor area with a fountain where they put a bunch of kids toys, like fishing rods and nets, etc. all over the fountain area for the kids to play. There were plenty of other kids for them to get to know, and the parents got to hang out… maybe bring a towel, though, as the kids will undoubtedly be wet! Talk about brilliant ideas; this made it easy for us to stay and hang out as long as the kids were occupied.

Oysters at Benjamin’s Raw Bar.
Lunch or Dinner
Lobster Rolls are always a popular favorite New England eat, I like to think of them at the Po’boy of the northeast. If you’re on the hunt for a great lobster roll in Newport, head over to Brick Alley Pub, great eats and fun decor. If I’m there I go with the Lobster Mac & Cheese, and maybe kick that off with their french onion soup. We haven’t been there since before the pandemic, but they did have a soup, salad, and bread bar that was worth the additional cost to your meal, IMHO. As much as we do enjoy Brick Alley, it’s not our dinner spot, and there is no shortage of great places to have dinner in Newport. There is a nostalgia associated with the place we have to have dinner every time we go, and that is Sardellas. They offer great food and a prix fixe menu option along with BOYB. We had the same waiter there three times in four years, and it was great to see how we started as a couple, and now we are showing up with two kids, and he remembered us each time and commented on our growing family. I imagine we might not see him as he’s getting older too and has probably finished college by now, but to us, that is a “family” restaurant that must treat their people right.
A bit of history, with some drinks
Although not a common stop on our trips, we did have to stop at what is said to be the oldest operated tavern/restaurant in America, White Horse Tavern, bursting with 17th-century charm, that began serving patrons as a restaurant in 1673. Did I mention we love stopping at old bars? It’s like being transformed back in time. If you’re sitting there reading this thinking, these places sound great, but what if I want to eat on the water? It is Newport after all, so what better place to sit dockside at 41N 71W? A restaurant called Forty 1o North of course! It’s also a hotel, but as you can imagine it will be pricey.

The kids playing at O’Brien’s Pub.
Game, Set, Match Newport
In case you don’t know, Newport is home to the International Tennis Hall of Fame. The picturesque setting hosts the museum and an ATP250 tournament on the grass (lawn for the real fans) every July, including the annual inductions for the new hall of farmers….you can also vote every year if you want to participate. So stop by the Hall of Fame; there’s not a bad seat in the house. Take the kids to family day, shop the booths, or enjoy the stunningly aristocratic shopping along Bellevue Ave. If you find yourself out for a morning walk on Bellevue, make a quick turn on Casino Terr; tucked away back, there is Cru Cafe, grab a coffee and maybe some breakfast. I found it by mistake out for a walk with the kids in the morning; my son had to use the bathroom; not only did they tell me I didn’t have to order a coffee just to let him use the bathroom, but when we were done, they gave both kids a cookie! I did buy a coffee, in case you were wondering.




Enjoying some tennis at the International Tennis Hall of Fame July, 2016.
Mansions
Ok, so have you been reading this whole time thinking, is he ever going to mention the mansions?! NO! They are not mansions; they are simply GRAND, OPULENT summer “cottages” that happen to be the size of mansions and took an entire staff to operate. These holiday domiciles of the super-rich from the Gilded Age are a must-see if you go to Newport. Happy? Well, I guess if you want to peek into the past and see how the elite socialites of the time spent their summers, you can go visit them by following this link to the Preservation Society of Newport County. Don’t just visit to see what being wealthy was like; appreciate the architecture, the art, and history!
There is so much to these buildings that they tell a story of advancing technology, wonder, and money. By the way, did you know silverware was actually made of silver? And that they used to keep it locked in a safe? And travel with it from their main homestead to their summer cottage? I’m sure parts of that you did know, me too, but the tours can be guided or audio guided so you can set your own pace. If you happen to be there with kids, The Breakers, (when you’re rich, you get to name your house), the summer cottage of the Vanderbilt’s, has a fun scavenger hunt for kids that will give you a chance to experience the whole property and keep the kids engaged throughout.
Surprisingly, our children really enjoy touring these types of locations. Check out how they held up touring various locations in Paris here!
In conclusion
From our first trip to our most recent one, Newport has remained one of my favorite places to spend time. Have you been? Did you do the Cliff Walk? Let us know if you have been to these places and what you loved (or didn’t) about Newport. Oh, and btw, the sheets are not the sails…

Wyndham Onshore Rooftop with our bottle of wine, 2010.

Sunset from the rooftop, 2010.

Sunset from our most recent trip in June, 2021.
Check out some of the great tours Newport has to offer below:
One more place to add to my bucket list. Newport, RI, looks fabulous. I’ve been researching a trip to that region and this looks great. Thanks for sharing.
Absolutely worth the trip! Depending on where you traveling from, its close enough to also hit Boston. We stopped in Newport for lunch on a trip home from Boston. It’s not the most direct way back for us, but it was an easy detour.
Enjoyed reading this article. Loved the sunset pictures a lot. 😍
Your kids are adorable 😍♥️
Thank you, I swear that sunset looks better every time. We haven’t taken a sunset sail yet, that might have to be next!
I saw the breakers last year but now I want to go back to see all you’re describing here!
Definitely go for it! Follow The Preservations Society of Newport County, their instagram is newport_mansions….they are always updating events.
Wow this is so cool, will def go there one day!
This looks like so much fun!
Your travel blogs are always interesting to read. You have your readers emmersed and captivated into your travel experiences. New England sounds like a great weekend getwlaway. The Food Explora in me will definitely enjoy the food culture there.
Thank you so much! Speaking of food, I realize now that I did not mention clam chowder at all. I think I get too distracted by the raw bars.
Newport sounds amazing!! That makes me want to book a trip to New England!!
Definitely book that trip! We love it there!
I love the east coast, harbors, and sunsets! Looks like a great destination for a trip!
We love the NE coast. We stopped at Bar Harbor, ME on a cruise years ago, that was a beautiful coast town to visit.
I really enjoyed this! I’m on the east coast and really want to visit this beautiful place! Thanks for sharing.
We clearly recommend it haha! It truly is beautiful!
What an amazing trip! The photos are just stunning and we can tell you had so much fun in family. It’s absolutely amazing. And seafood for under 2$ – what a delicious dream!
Great deal on the seafood! It is a beautiful place, we love it!
Wow the Viking hotel looks incredible! I think I would spend all day on the rooftop!xxx
Ugh the views were amazing! I wish I was there right now (in the summer warmth, not New England fall, haha).
I’ve always wanted to visit New England and hoping to do so in 2023. Thanks for some great suggestions on where to stay, and to where to visit!
This sounds amazing! That sunset is beautiful and looks like you all had an amazing time!
This reminds me of a trip I did to the New England coast 20 years ago. My hubby and I moved back to the East Coast right before COVID and are planning to do a trip next fall, I loved the sailing and the food!
The sailing is beautiful! The East Coast definitely has its perks!
Looks like you all had a wonderful time! Your travel blogs are awesome.
Thank You!
It was lovely seeing photos from your first trip to Newport in 2010 to your latest in 2021. Things have definitely changed over the years!
I have never been to Rhode Island, but I think it would be fun to visit! I personally would like the mansion or summer cottages as you call them haha
This sounds like such a wonderful and memorable trip! I love sharing a glass of wine on rooftops and sometimes it’s just nice to splurge! Thanks for sharing!
I have never been to the New England area, but it is definitely on my list. Thanks for the great information!
Bar Harbor, Maine is another beautiful part of New England. Hope you get there one day!