Discovering the Northeast USA by Sea

🖋 Featuring Blogger: Long Island Local & Yachtie Melissa McMahon

Compiled by: Randi Barry  Newport tips: Dylan Barry

Itinerant sea travel often leads to waking up in a new port and locale beyond compare. Experiencing these places by boat is an excellent opportunity to experience the lifestyle without the downside of room and board. Read on for our best crowd-sourced discoveries across the Northeast USA from fellow seafarers.

Related: Top 10 things to do in New York City.

Quick Jump: Montauk | Martha’s Vineyard | East Hampton | Sag Harbor | Newport

There is no end to the island-like Montauk Lighthouse which is very popular with tourists. About three hours from New York City, you have endless views of the Atlantic Ocean. Admission to see the lighthouse is around $11 per adult, and you can climb all the stairs to the top for that ultimate selfie or group picture. Right before you enter the stairs is a book that everyone signs their name and where they are from, you will be surprised by how different the hometowns are.

Before the admissions building for the lighthouse is a little beach path to the left. Walk down the track, and you will find yourself on a charming small beach just left of the house. There are many rocks so if preparing to climb, wear proper footwear. Visitors can climb the big stones that go all around the tower in front of the fence. Just keep in mind if there are big waves, you may get wet.

Ditch Plains in Montauk is the ultimate spot to catch some swells. Just be aware of a reefy left point and a rocky bottom.

As for restaurants in Montauk, there are so many good ones to pick from. These are Long Islander local Melissa’s top recommendations: Harvest on Fort Pond, 668 The Gig Shack, Surfside Inn, Navy Beach, Gosman’s, Arbor Mediterranean and Ruschmeyer’s Hotel & Restaurant.

Liar’s Saloon offers up $1 drafts all day and the best darn karaoke (expect to meet locals with a story), 668 The Gig Shack, The Point Bar & Grill and Sloppy Tuna. Main Street also has tons of shopping and local surf stores.

If you want a Montauk lunch with a view, check out Gosman’s Topside – the adult-only section of Gosman’s Dock. Situated overlooking the marina entrance, you can sit and watch the boats sail in and out of the harbour while enjoying their famous Lobster rolls which do live up to their reputation and $29 price tag. Their $22 Fish and Chips are also quite divine. You can even get a half dozen fresh Local Oysters for $18. Expect a two-person lunch with a beer each to set you back $90 inclusive of tip. Stop by Gosman’s Fish Market after to peruse their incredible take-home selection.

With easy access from the Sea, disembark from one of many marinas and head on over to Lynns Hula Hut. This unique Parking Lot ‘Beach’ Bar serves up Lynns specialty cocktails – gathered from her years travelling abroad – from a converted office trailer. Chill in the open air Tikki Hut with a sand in your toes and an infused drink in your hand. You will feel as though you’ve washed up in Tahiti.

Montauk Brewery has become one of the biggest breweries to visit. As New Yorks’ Eastern-most brewery, it began as a basement-run endeavour delivering hand-filled kegs to local restaurants on the back of a bike. They have grown a strong following and stream of thirsty Hamptonite visitors. As refreshing as a glass of Summer Ale, the barn-style brew house embodies their no-drama mantra ‘Come As You Are.’ Try the sample flight and get your favourite in a growler and wetsuit to go for the beach.

Eclipse massage is an on-call yoga, massage therapy and personal training for your guests and crew. Although we have not had days off here yet, Antone Diaz from Eclipse Massage in Martha’s Vineyard is very generously offering $30 off per hour for Nautic Nomads. Don’t forget to leave him a review!

🎬 Video: Martha’s Vineyard Haven Marina | Aerial Drone Footage

If you find yourself in East Hampton docked in Three Mile Harbor, you will definitely want a rental crew car or face a minimum $30 Uber ride to get anywhere. Guys, if you need a cheap and cheerful haircut before you head out exploring for the day, swing by the back of Maidstone Market & Deli – this is where the locals come for their grooming. Round the corner and start the day right with a coffee and croissant at S&S Corner Shop + Provisions. This eclectic and crafty spot has excellent espresso, freshly baked goods, and a selection of handmade wares ranging from leather aprons, handbags, ceramics, and chef shoes, to trinkets that make excellent souvenirs.

After that, head to Round Swamp Farm in Bridgehampton. This quaint Farmstead has offerings from both Land and Sea. It’s kind of a Hamptons’ must. Especially if you need some good wholesome pre-made picnic food to go. 🥂 Grab a bottle of wine to go from Wölffer Estate for a dock party or beach picnic after a tasting & cheese board in the vineyard. If you would rather head out for dinner, Sam’s Bar & Restaurant is arguably the best value for dinner in the Hamptons. The laidback vibe draws everyone from tourists to locals alike, this place gets packed though so be prepared to grab a drink at the bar while you wait for a seat.

When docked at Sag Harbor Yacht Club, there’s not much else to do in town beside Boats and Restaurants. As far as activities go, you can toss a line off the dock or back of the boat for Stripers, there is also the Sag Harbor Whaling & Historical Museum.

🎬 Video: Sag Harbor Drone Footage | Aerial Marina Views

Baron’s Cove, an all-American resort overlooking the water and a short walk to town is a great place to grab dinner on the deck and take in the stunning views. If you have a day off and feel like splashing out, you can get up 50% off last minute rooms on booking.com. Some other highly recommended dining options include; Dockside Bar & Grill, Dopo La Spiaggia, The Dock House, Page at 63 Main, Wölffer Kitchen, The Beacon, Le Bilboquet, LT Burger, and II Cappuccino.

As anyone who has been to Newport knows, Fastnet is the traditional yachtsmen and sailor bar where everyone goes to mingle, but if you are looking for a taste of history in proper New England fashion check out the White Horse Tavern. It is believed to be one of the oldest taverns in the United States. Built before 1673 its iterations have included a tavern, to assembly meeting place, to boarding house and then finally back to tavern and restaurant. It is a popular dining and drinking location serving up fresh seasonal twists on classic Eastern American fare with a Sunday Brunch including a raw bar and modern libations.

Mission Burger is a trendy spot that grinds their dogs and burgers in-house. Imbibe their liquid offerings which include local beers, wine, prosecco and sodas. And then there is Pasta Beach – make reservations, wear your New England Attire. If you want to really splash out and treat yourself, head to The Roof Deck by Grace Vanderbilt. It’s pricey but definitely worth catching a cocktail and sunset.

Bike or drive along Ocean Drive or head out for a low key mosey on Cliff Walk. If you are looking for a beach day, check out Second Beach which is more recommended over Easton’s Beach. Don’t forget your sunscreen!

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