Top Summer Vacation Spots

As all of us are walled up in our houses praying our summer vacations are not ruined, it seemed like it was a good time to write about my favorite long weekend trips to take in the summer.  Some of these destinations are ones I have been too many times and others just once but if you are looking to take your mind off the endless isolation by planning a trip that hopefully doesn't get cancelled this summer, here are some good options.  Also, these are in no particular order.
  • Nantucket: While there is no particular order, this may be my favorite.  30 miles off the coast of Cape Cod is the small whaling island of Nantucket.  While it's gained popularity over the past 10 - 20 years, it still has a sense of remoteness.  You can head to a beach and still feel like one of the only people out there.  My favorite spot to stay on the island is Siasconset although you can't really go wrong with any of the areas, it just depends on what you are looking for.  While you are there, be sure to check out Cisco Brewers one afternoon after the beach for a cold beer and hot lobster roll and then on the way home get a fresh pie from Bartlett farms.  You should also plan on driving out on the beach to Great Point where you may have a good slice of the beach all to yourself and then end one day sipping wine while watching the sunset in Madaket. 
Lighthouse at Great Point 
  • The North Woods of Wisconsin: Unless you hail from the upper mid-west, the thought of heading a few hundred miles south of the Canadian border probably would raise an eyebrow.  Yet summer after summer, I made the trek up to Minocqua for what is surely a summer weekend that won't disappoint.  Minocqua is an epicenter of lake life in northern Wisconsin where you have a number of lakes that are interconnected making it a perfect destination to spend an entire day just riding around on a pontoon boat.  The only thing you should look for when staying up here is that you are on the lake and will have access to a pontoon boat, that's truly all you need.  While on the lakes, keep an eye out for some islands to tie up with fellow pontooners.  After a day on lake, you should be sure to swing by the Thirsty Whale and Ottos, where you can dance the night away listening to live music. 
Lakhouse we stayed at in Minocqua 
  • Zion & Bryce: Up until a few years ago, I had never been to any National Parks that I could remember outside of the Rockies.  I was blown away to say the least.  In general, making any trip to a National Park in the summer would be a great trip but I'd highly recommend a trip out to the canyons.  Obviously the most popular park is the Grand Canyon, but there are number of other parks in the area that are great to visit, such as Zion and Bryce.  Both of these parks provide something different given the style of each.  Zion, which seemed to be a bit bigger, feels like you are out on the great frontier, something out of Lewis and Clark.  If weather permits, you have to do the Narrows (start at 6am) but also should check out Observation Point and if you dare, Angels Landing.  Bryce, which is known for the hoodoos, has more of a South Western desert feel.  The Rim trail will give you the best bang for your buck but there are a number of smaller hikes as well like Navajo Loop trail and Queens Garden. 
Zion Park from Observation Point 
  • Charleston: Heading to a southern city in the summer can be a great idea despite hot temperatures.  I've been to Charleston a few times now and would love to keep going back as it has a lot to offer.  You can choose to stay downtown or near one of the beaches.   Folley beach typically has more action but on one trip we stayed at the Isle of Palms which seemed like the better beach but is about 40 minutes from down town.  There's a lot you can do outside of the beach as well, there a number of golf courses including the famed Kiwah Island, head out onto a boat and dock up with others for a good old fashioned boat party or waste away on Shem Creek at Reds Ice House.  You of course need to check out King Street for some classic southern fare as well as for some very lively nightlife. 
Fried Chicken, Biscuits and Grits in Charleston 
  • Chicago:  When you live in New York, you tend to head out of town every weekend in the summer but it's quite the opposite in Chicago; you spend your whole year waiting for summer and are sure not to miss a weekend.  In my opinion, Chicago is the best city you can visit during the summer.  For one, all of Chicago is on Lake Michigan which feels more like the ocean than the beach.  Spending a few hours at one of the beach bars like Oak Street Beach Bar is never a bad idea for an afternoon.  There is also a number of bars/restaurants with outdoor seating/patios that are packed to the brim like Benchmark, Big Star or Parlor Pizza.  Every weekend there is also usually some sort of block party that's worth going too with the pinnacle of the summer being Lollapalooza. And of course, one of Chicago's favorite past times is heading up to Wrigley for a cubs game.  Even if you aren't going to the game, Wrigleyville will be buzzing with energy so it's a great place to walk around and stop for a few drinks.  
Chicago skyline from Lolla 
  • Montauk: The Hamptons are the place to be in the summer if you are a New Yorker with many people heading out there every weekend.  However if you are willing to trek out a little further, my preferred weekend getaway from New York is The End.  While Montauk can certainly have a scene, mostly a few places packed with 20-something year olds drinking into the oblivion, it's a little more low key than places like South Hampton or East Hampton.  My beach of choice is Ditch Plains but some of my other favorites are eating an overpriced but good lobster roll (hey it's the Hamptons) at Duryea's, the sunset at Montauket as well as picking up some fresh fish at Gosman's to grill on your own. 
Sunset from Montaucket 


  1. There are a lot of places to be visited but some of them are temporarily closed due to the spreading coronavirus infection. This is too bad, as it has stopped the entire world!


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