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Yachts of Fun in Long Island

Updated: Mar 23, 2020

Dreaming of a summer getaway filled with lots (and yachts) of fun, adventure, sunshine and relaxation? Long Island has been on my bucket list for a couple years now, and I originally planned a road trip to explore this slice of heaven that New Yorkers call their summer playground. However, after a bit of plotting and scheming, I was able to secure a boat (YAY) and therefore redrafted my original plans a the best way possible.

Leaving New York waterfront and heading out toward Long Island Sound.

After reading plenty of Travel Guides online and perusing my new, shiny New England Waterway Guide... I put together the most fantastic trip through Long Island that I'm pretty darn proud of. Although I traveled via boat, this trip is also easily capable of being done by car, train, plane, and a combination of them. If you're thinking about taking a boat as well, it's important to research all marinas that can accommodate you, mark your favorite ones (I like to look at location and amenities), and make slip reservations in advance!

I condensed my Long Island trip into three locations: Shelter Island, Sag Harbor, and Montauk. What's great about this area is that everything is fairly close and can be visited by a short bike, car, or boat ride. For example, I was able to make it to North Fork from Sag Harbor to check out Greenport for a little "half day trip". I also biked from Sag Harbor into The Hamptons... which was a good call because traffic can be dreadful during "the season".

My trip started by getting on the boat in New York, and then heading out the following morning. Bright-eyed and bushy-tailed, coffee in hand, I was officially starting my dream trip and en route to Shelter Island...

Shelter Island

An easy cruise down the Long Island Sound, and a few hours later I'm welcomed by this quaint island at the eastern end of Long Island. There's plenty to do here, but The Hamptons and North Fork are just a short ferry ride away.

Morning fog and drizzle over Piccozzi's Dering Harbor Marina, Shelter Island.

Where to Stay:

What to Do:

  • Rent a bike at Piccozzi's Bike Shop right across the street from the marina, it's the best way to explore the island!

  • Play a round at the Shelter Island Country Club, it's only $25 during the week.

  • Explore the cute shops, antique stores and art galleries... the local boutique, Marie Eiffel, is a MUST! The Parisian owner travels the world and sells all the splendid goodies she finds at her stores.

  • Grab some goodies from Marie Eiffel Market and go to the beach!

Where to Eat & Sip:

  • Wake up to a lovely cappuccino at Stars Cafe.

  • After your afternoon activities, enjoy a crab cake sandwich at Marie Eiffel Market...this woman basically owns this island and everything she makes is ridiculously spectacular! Pro tip: Grab a fresh loaf of French bread...MMM.

  • Make sure to secure a table at Isola...their menu features daily specials that are locally caught and to-die for. Their intimate bar turns into a magical, romantically-lit spot to have a glass of wine in the the music is spot on.

Sag Harbor

After a day and a half in Shelter Island, it was onto the "next fun place." Sag Harbor is just a short boat ride over from Shelter Island. OK sooo this was my favorite spot in Long Island...I think I enjoyed it so much because it is so quaint and just has a really nice, happy vibe. I stayed here for three nights on the boat and honestly could have stayed longer! I also loved it because you can get to all of The Hamptons via bike or short Uber ride.

Where to Stay:

What to Do:

  • Rent a bike from Sag Harbor Cycle Company (it's right across the street from the marina!) and bike to Bridgehampton for lunch...they can give you a nifty map to chart out your ride. Stop into L&W Market for an "old school" tuna sandwich or a lobster roll for a little fuel before you head back to Sag.

  • Shop the absurdly CUTE shops along Main Street! There are a slew of great art galleries, antique shops (Sag Street Antiques), and there's even a Love Shack Fancy with the all the hair bows and frilly dresses you could possibly need. The Sag Harbor Bookstore has EVERY juicy novel on your summer reading list.

  • Bike to Greenport! Check out North Fork by taking a little cruise over to this laid-back Long Island town. Have lunch on Claudio's Waterfront and explore this up-and-coming coastal strip that prides itself on their shuck-your-own oyster diffidence.

Where to Eat & Sip:

  • Morning coffee is mandatory at Grindstone (grab a donut while you're at it) or bop over to Bagel Bouy for an oh-sooo yummy bagel that are made on site daily.

  • Lunching in town? Try LT Burger, Dockside Bar, and Dock House.

  • I had dinner at two very different restaurants and loved both! For a hip & chic dining experience, try Tutto Il Giorno, an Italian restaurants with locations in Southhampton and Tribeca. The decor feels clean and cozy, and is full of high-end furnishings from Urban Zen, a contemporary lifestyle store connected to the restaurant. Order the RIGATONI and a glass of the cab and it will change your life!

  • Onto the next: Le Bilboquet. In a shingled cottage on a leafy street, directly facing the water, this little gem offers an amorous ambiance for a romantic dinner. Tip: order their famed, cajun chicken.


Montauk is known by many Long Island residents as "The End." This is because it is the easternmost point of the island and New York state. It's a definite MUST on your Long Island trip, and has lots of fun, laid-back activities to do. Plus, it's home to one of the most iconic lighthouses in America, so how could you not go?

The Montauk Point Light was the first lighthouse to be built within the state of New York.

Where to Stay:

What to Do:

  • Rent a paddle board from Paddle Diva and explore the serene coastline of Lake Montauk.

  • Gurney's resorts offer FREE bike rentals, and it's the BEST way to get around!

  • Gosman's Dock offers 14-acres of restaurants, shopping, and more. Bike or take a little boat ride over for an afternoon of strolling around this "New England style" village and grab lunch on the beautiful waterfront.

  • Hit a beach! Montauk Soundview and Ditch Plains (this place is hoppin') are great choices. You can also enjoy the pools at both Gurney's resorts...they are top-notch and also serve up some marvelous craft cocktails to cool you down on a hot, Long Island day.

  • A photo-op at the lighthouse is also a "must"...I made the rocky journey out via a small tender boat and captured some of my favorite photos from the entire trip!

Where to Eat & Sip:

  • It was easy to find my favorite coffee spot at Gurney's Star Island at their cafe, Il Forno... which doubles as an AWESOME pizza (and ice cream) spot for late night cravings. Just sayin'. Sip your morning latte on the deck which overlooks the marina, and soak in all those happy Montauk vibes.

  • One of my favorite lunches was on the upstairs patio at The Sloppy Tuna, right on Ditch Plains Beach.

  • Other great spots for lunch are Gosman's Dock, situated nicely on the entrance to the Montauk Harbor as well as Duryea's AKA the old lobster shack.

  • I enjoyed 2 dinners at both Gurney's resorts (I stayed at the marina on Star Island and also took the complimentary shuttle over to their sister resort on the ocean). Both Showfish and Scarpetta Beach offer similar atmospheres: beachy & dreamy filled with driftwood and nautical ropes and light fixtures. Both serve extremely FRESH, locally caught fish (try the Fluke) and Scarpetta is known for their insanely good spaghetti.

  • Time for some after dinner fun? Check out Surf Lodge (beware, the line to get in on the weekend can be brutal. I went back on Sunday night and it was quite enjoyable!). Also, slip into Memory Motel or cross the street and dance the night away at The Point.

And that's a wrap! From Montauk, I headed directly east to a little place called Block Island. But I'll save that trip for another post so you can fully digest Long Island & The Hamptons. If it's not on your list yet, I hope it is now. The best time to go is while it's relatively warm--it was quite busy while I was there, but I always think that adds to the fun and excitement. Make sure to look into reservations early, as lots of places allow you to make them online. Until next time, I'm off to explore some more out east!

-Golden Girl

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