Ready for some summer fun and adventure? My life has been mundane for over a year like everyone else's, I'm sure. I'm ready to explore all that this island has to offer and be a tourist in my own city. I've made my own personal bucket-list of everything I want I do this summer and I'm share it with you incase you're also in desperate need for some adventure.

Most of this stuff is affordable. Of course sailing, jet-skiing, boat riding, and anything Hamptons & Montauk are are all high-ticket items, but think we all deserve some luxury after the year we've had.

  • Spend a weekend in Montauk 

Rita Cantina is a New Mexican Restaurant that just opened up that I am so excited to try. My favorite spots are Sole East, Navy Beach, Duryea's, Crow's Nest, & so much more.

  • Go sailing in Montauk with the Montiki Catamaran 
  • Go off roading at Demo Point and sleep on the beach. 

You need a surfing/fishing pass and a car with 4 wheel drive to go off roading. 

  • Wake up at sunrise and have breakfast on the beach
  • Swim in the ocean at sunset
  • Swim in the bay at sunset
  • Have dinner at Maguire's Bay Front Restaurant in Fire Island. 

You'll need to book your reservation in advance for sunset seating. They do take walk-ins, but the wait can be 45 minutes to an hour long.

  • Walk or Bike Ride to the Fire Island Lighthouse
  • Sail at Sunset in Oyster Bay. 

For more information head to the website, The public charter is $45+ tax per person. 

  • Bike ride on the Long Beach Board Walk
  • Bike ride the Jones Beach Board Walk
  • Walk/Bike Ride to Kismet and have a charcuterie picnic from Babylon Cheese Cellar.
  • Babylon Cheese Cellar is my top 5 favorite places on Long Island. 

A small tray is about $75 and feeds 10-12 people. You can place an order directly online from their website

  • Ride the Ferris Wheel at Coney Island & watch the fireworks at 9:30pm on a Friday.
  • Visit Sagamore Hill. 

There is no fee to enter the Sagamore Hill grounds, walk the nature trail or view exhibits at the Old Orchard Museum & Visitor Center

  • Kayak the Cold Spring Harbor

For more information head to

  • Kayak the Connetquot River

For more information head to

  • Visit Shelter Island & have dinner at Sunset Beach
  • Make a slip and slide
  • Create an adult field day with friends 
  • Go to a Drive in or Outdoor Movie

Drive in Movies on Thursday at the Peconic Bay Vineyards are $50 per car.

The Hamptons Film Festival also hosts a free movies night every Wednesday in East Hampton

  • Projector Movie Night in the backyard 
  • Play charades and have a bonfire
  • Play a game of Ping Pong
  • Do pilates/yoga on the beach 
  • Visit the North Fork vineyards. (Sannino vineyards is my favorite)
  • Have an Italian themed backyard dinner party
  • Take a cooking class at the Babylon Mercantile

They haven't opened classes yet because of COVID, but keep checking back. It's a great new spot in Babylon Village.  

  • Go for a boat ride to Atlantique 
  • Go jetskiing
  • Go paddleboarding. 

You can rent a paddle board from South Shore Paddleboards located in Babylon Village. It's $40 for a 2 hour rental. They also have a Sunday morning Sunrise Paddle. Stony Brook Harbor Rentals also offered Paddleboard Yoga & SUP Fitness classes

  • Have a bonfire on the beach in Amagansett

This is the only spot I know that you can legally have a bonfire. You have to make sure your bonfire is in a metal container 

  • Day trip to Sag Harbor & go for a Sunset Sail

You can rent a private boat, bring dinner and drinks with Sag Harbor Charters or you can take a public 2 hour sunset cruise with American Beauty Cruises & Charters. A few of my favorite places are American Hotel, Baron's Cove, Wainscott Inn.

  • Have a Pizza night on the beach with friends
  • Picnic at Planting Fields Arboretum & see the roses arches in late May/early June. 
  • Strawberry Picking in June at Patty’s Berries and Bunches 408 Sound Ave., Mattituck
  • Visit Lavender by the Bay in Orient Point. Blooms are in July
  • Run through the Sunflower Fields in Mattituck. (July/August)
  • Peach Picking at Hayden's Peach Orchard 561 Hulse Landing Rd, Wading River (August)
  • Tomato Picking in August.
  • Go for a picnic at Chelsea Manor in Oyster Bay. 

If there is a wedding taking place, you won't be able to get in. But Planting Fields Arboretum is just across the street. 

  • Go for a picnic at Old Westbury Gardens
  • Visit the Bronx Zoo 
  • (On Wednesday it's reduced admission. You need to book your tickets the Monday before at 5pm. Or else you can get reduced admission at your local library. 

Follow me on Instagram @ckmont for more ideas and inspiration. I'll update this list if I get anymore ideas. I'll make another one for my favorite restaurants and places to visit. Hope you have the best summer of your life. We all need it.



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