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How to Spend a Weekend in Montauk, NY

This year has been anything but normal. As someone that’s relied on travel and adventures for the inspiration of content and mental stability, especially through a divorce, it’s been almost laughable. (Laugh so you don’t cry kind of thing, right?)  Last summer, I was bouncing around the country from city to city. I explored so many new places by myself and with friends, not worrying about face masks, excessive sanitizing, or staying six feet from strangers. So when my friend, Rebecca, asked for me to spend a weekend in Montauk with her for her 30th birthday, I was eager to jump on a plane.

Luckily, my flight went smoothly, places are opening back up, and there’s a hint of “normalcy” in travel. We had a couple of nights at her house to catch up since we hadn’t spent time together in nearly 11 months. Then on Thursday we picked up her childhood best friend and we packed up the car for a weekend in the Hamptons, birthday balloons and White Claw included.

Traveling to Montauk During Coronavirus

I should start with the weekend that we traveled, which was the second weekend of September. Going the weekend right after Labor Day meant we were hitting the start of the shoulder season. The Hamptons busiest and most bustling season is summer, from Memorial Day weekend to Labor Day weekend. This is when all of the businesses are thriving the most, tourists are living their best lives, and the rich escape the hustle of the city, especially during quarantine. This meant the weekend we went still felt pretty busy.

However, I noticed as I was writing this, some of the local summer hot spots were already shutting down for their offseason. If there are certain restaurants you refuse to miss out on during your weekend getaway, double-check what their business hours are during your planned weekend.

Where We Stayed in Montauk – Gurney’s Star Island Resort & Marina

We arrived in Montauk on Thursday afternoon with gloomy skies and drizzling rain, but the journey was still beautiful. Charming beachside cottages and mansions lined the roads on our drive in. Our hotel, Gurney’s Star Island Resort & Marina, was located only a 7-minute drive from the little downtown area of Montauk.

The room featured two double beds, which I believe shouldn’t be a thing in hotels anymore. Just give me two queens if I’m paying Hamptons pricing, but fortunately, they were really comfortable. The resort did a good job updating the rooms to make them feel nautical chic with white wood shiplap walls, beachy accents, and a huge bathroom with an amazing shower. The water pressure is something to brag about but the lack of a full-sized mirror is something to be noted for anyone snapping #OOTD pics.

Gurney's Star Island Resort & Marina double room

Gurney’s Star Island Resort & Marina is the sister property to the beachfront resort, Gurney’s Montauk Resort & Seawater Spa. Being the only luxury beachfront hotel in Montauk, the prices reflect the prestigious location and amenities.

Luckily, the marina location is a more affordable option while still featuring the cozy luxury most people desire while staying in Montauk. A cool part about staying at either Gurney’s resorts is that you get access to the amenities at either spot. If you’re looking for a day at the beach with a private daybed, head to the beachfront Gurney’s. If you want some water sport rentals in gentle waters, head to the Gurney’s on the marina.

Day One/Travel Day:

Living in Riverdale, Rebecca is about a 3-3.5 hour drive from Montauk, New York, AKA “The End” of the Hamptons. Our travel day was pretty rough because we had non-stop rain on our drive. While Montauk and other areas of the Hamptons have airports, the majority of the visitors arrive by car, one way or another. Similar to the Florida Keys, there’s one main two lane road getting visitors and locals through the Hamptons. While there are plenty of backroads, if you’re heading straight to Montauk like us, you’d take the Montauk Highway.

Lunch Lobster Roll or The Clam Bar

On our way to Montauk, we stopped at the infamous Lunch Lobster Roll restaurant located just about 10 minutes from Montauk. Because we’re still battling this global pandemic and it was still raining, the restaurant didn’t have options for outdoor dining/seating. However, they did have a seamless and quick process for ordering outside, under an EZ Up tent, and had extra quick service. We ordered clam chowder, fish n chips, and a lobster slider which kicked off our weekend of consuming fresh seafood with nearly every single meal.

Just 30 seconds from Lunch Lobster Roll is another popular lunch spot, The Clam Bar, that came highly recommended by some locals. We planned on hitting that restaurant on our way out of town, but never made it. So, I’m adding it to my list for next time.

First Evening in Montauk

Our first afternoon and evening in Montauk included a lot of rain. The clouds were heavy in the sky and a non-stop drizzle smothered our original plans of celebrating Rebecca’s birthday dinner at a great outdoor spot (but we still made it to Duryea’s later in the trip). However, I know you’ll be greeted with great weather so for your weekend in Montauk, I suggest you kick off your weekend getaway with a private sunset cruise.

Mon Tiki Sailing

Our cruise with Mon Tiki wasn’t during sunset, but that would’ve made it that much sweeter for us. Mon Tiki is a local sailing option that’s catering to the shift of Coronavirus standards by only offering private charters. I actually love this little luxury of splurging on a unique experience that you get to share with just your close friends and family. Because there were only 3 of us going, we booked the 26′ catamaran, Mon Tiki Mini, for a 2-hour sailing.

3 girls on a boat with MonTiki Sailing in Montauk, NY

I have to admit, I was a little intimidated and underwhelmed when I first saw our little sailboat, but it ended up being perfect for the 3 of us and our captain, Jeremy. We brought along a waterproof Yeti blanket, a cooler with adult beverages and waters, and a few snacks. We had an unusually chilly afternoon on the water, but it was beautiful and sunny. Jeremy knew exactly where to go to avoid the high winds and didn’t even give us shit when we asked him to take one too many photos. We also had the option of paddleboarding or jumping in the water, but my Florida blood couldn’t take the polar plunge on that day.

A private sunset sail will give you views of the marina, gorgeous Montauk homes on the water, and a solid reason to toast to a weekend getaway. If you’re looking for something bigger to fit your group, they also have a 40′ and 65′ catamaran for private sailings.

Day Two in Montauk

Breakfast with a View at Gurney’s

Whether you want an ocean view or marina view, both of the Gurney’s resorts had excellent breakfasts. We ate at both Tillie’s and Showfish during our stay and loved our meals.

breakfast views at Tillie's

If you’re just looking for a coffee and pastry to start your day, try one of the local coffee shops:
Left Hand Coffee Shop (my favorite cold brew)
Bluestone Lane Montauk Coffee Shop
Hampton Coffee Company

Montauk Highlights

For a weekend in Montauk during Coronavirus, you’ll want to hit all of the outdoor highlights. I’d suggest spending the day picking one or two of the favorites below to explore on your second day.

Montauk Lighthouse

Montauk’s Lighthouse can be found in numerous photos of the little seaside town. Nestled up to along the shore, you have the option to go up the lighthouse again. They update their website with information on visiting during Coronavirus, so be sure to check it out before making your plans. We chose not to go up the lighthouse, but to walk along the seashore and rocks surrounding the area. While it was another gloomy day for us, we loved enjoying the ocean and salty breeze. There’s an $8 parking fee.

Montauk Lighthouse

Ditch Plains Beach

This is probably the most popular spot for local surfers and a gorgeous area for soaking up the sun. To park here, you must have an East Hampton sticker on your car. Arriving by bike or foot is free, but if you want to avoid the parking fine, I suggest grabbing an Uber to drop you off for the afternoon.

We didn’t get to squeeze this into our trip, but I’m such an ocean baby. If we had more time I would’ve spent the whole day there. Want to spend the whole day at the beach? Pack up a picnic, pick up some cold beers at Montauk Brewing Co. and settle in for a day of relaxation. Montauk Brewing Co. is only offering curbside pickup during Coronavirus, so this is a great way to enjoy the local craft beers.


Again, if you’re spending a weekend in Montauk during Coronavirus, outdoor activities are best. From brief walks to longer trails, there are several options for hiking around Montauk. Most of them will feature ocean and dune views.

weekend guide to Montauk, NY

Day Two Evening

Wölffer Estate Vineyard

Wölffer Estate isn’t actually located in Montauk, but I couldn’t not rave about it in this post. It’s about a 45 minute drive to Wölffer from Montauk, but totally worth the drive. If you want to Uber, it ranged from $55-$110, one way, depending on the type of car you chose.

Wölffer Estate is a whole experience in itself. Be sure to book a reservation 2 weeks before you head out on your weekend to the Hamptons. They offer limited indoor seating, terrace seating, and lawn seating. We snagged a 6:00pm reservation one evening, but still waited about 40 minutes before we were sat on the lawn. Luckily, it was worth the wait.

Wine glass at Wolffer Estate Vineyard

The grounds of Wölffer Estate are really pretty, but if you’re familiar with Napa or other wine countries, it might be kind of basic. However, the whole place is a vibe in itself. With gorgeous indoor seating, charming terrace seating, and tables set up in between the actual grapevines, we adored the opportunity to sip on some wines on a cool September evening.

Wölffer has small bites and chacturie boards with several options to fill you up. We ended up making it our dinner, too. Between two flat breads, cheese for days, meats for every taste bud, and warm baguettes, we were in heaven. We got to indulge in the wonderful wine, complement our cheeses, and feel like life was basically normal for a night. Overall, I’d say Wölffer Estate is a “must” if you’re visiting the Hamptons.

Girl sipping bubbly at Wolffer Estate

Day Three in Montauk

As you wrap up your weekend in Montauk, you’ll want to slip in some last-minute must-do’s. If you haven’t noticed, food is pretty much a total experience in itself in Montauk. Don’t go big on breakfast today because you’ll want to head to Duryea’s for an early lunch.

Duryea’s for Lunch

Duryea’s is right on the water and has an incredible view. If you want to guarantee a spot on the water, we heard from more locals that the best tip is to have lunch at Duryeas and arrive about 20 minutes before they open. It’s also important to know that because of the outdoor dining, Duryeas will close for the day if it’s raining.

It’s a popular spot and because of Coronavirus, there’s only outdoor dining along with first-come, first-serve seating. We arrived about 30 minutes before sunset and while it seemed like it would be impossible to get a parking spot, much less a table, on a Saturday night, we lucked out. While the restaurant is first come, first serve, they also have picnic tables in the front of the restaurant available for anyone not putting their name on the list for the waterfront dining. If it’s a busy day, snag a picnic table instead of waiting 2+ hours.

Lobster rolls

I had my first ever cold lobster roll at Duryeas and it lived up to the hype. We also shared the calamari, which we all agreed was some of the best we’ve ever had. The calamari is served with eel sauce and I don’t think I’ll ever want to go back to anything else.

Downtown Montauk

What’s a weekend in Montauk without exploring the heart of the town? Downtown Montauk is lined with shops and restaurants. It’s perfect for an afternoon stroll, coffee break, or little outdoor happy hour. While a lot of locals would tell you to avoid the souvenir shops, I’m a fan of supporting local stores. One of my favorite shops in the area was called Wyld Blue which had a lot of high-end consignment items and brand new clothes and accessories. I mean, look at the vibe of this shop in this photo!

Wyld Blue boutique in Montauk, NY

You don’t need a lot of time to check walk the streets of downtown Montauk, so pop in and out of the shops on your way out of town. It’s easy to find some hidden gems and sweet souvenirs of “The End of the World”.

As you drive the Montauk Highway leaving the Hamptons, you can also stop in East Hampton for some high-end shopping.

Weekend in Montauk Recap:

• We felt really safe in Montauk during Coronavirus. Gurney’s took precaution with Coronavirus by sanitizing and deep-cleaning the rooms with extra care. All of the employees wore masks and guests were encouraged to wear masks even when walking around outdoors, but they were only required inside the lobby and walking to your table at the restaurant. Restaurants had strict mask requirements and other than that, we spent the majority of our time outside.

Where We Stayed:

Gurney’s Star Island Resort & Marina OR
Gurney’s Montauk Resort & Seawater Spa

Of course, there are other great options like gorgeous AirBnB’s and boutique hotels.

Favorite Restaurants:

Duryea’s [fresh seafood with a gorgeous view]
Shagwong Tavern [lobster mac n cheese and oysters]
Tillie’s [oceanfront dining]
Showfish [marinafront dining]
Montauk Circle Burger [offered dine-in and I had the best brussel sprout salad of my life]

Other popular spots we didn’t make it to but were highly recommended:
The Crow’s Nest [Inn with outdoor dining & drinks, but dining closes during offseason]
The Montauket [drinks with a sunset view near Duryea’s]
Ditch Witch [food truck]
• Liar’s Saloon [outdoor dive bar]
The Clam Bar [highly recommended by locals]
Joni’s Kitchen [located next to Left Hand Coffee, it’s another local’s favorite]

**The only meal we didn’t really enjoy was Anthony’s Pancake House. It was a very plain and mediocre restaurant compared to the rest.**

Things to Do During a Weekend in Montauk:

• Sunset sail with MonTiki Sailing
• Visit Ditch Plains beach
• Explore Montauk Lighthouse
• Hiking at Shadmoor State Park and beyond
• Horseback riding at Rita’s Stable
• Wine tasting at Wölffer’s Estate Vineyard [about a 45 minute drive from Montauk]
• Eat and shop in downtown Montauk
• Relax and soak in the laid-back lifestyle of a luxurious seaside town!

Trip map courtesy of Wanderlog, a trip planner

If you’ve spent a weekend in Montauk, let me know your favorite things to do or anything I should add to the list! If you’re planning a trip, drop a comment, send an email, or save this post on Pinterest!

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