An Honest Montauk Travel Guide: A 2-Day Off-Season Itinerary

Living in New Jersey, the Hamptons are your rich cousin that you tend to hate on but are also low-key jealous of. Montauk was on my local bucket list but with prices reaching over $600 a night in season, it had to be scoped out earlier at half the cost. I couldn’t digest the thought of staying at an average resort a couple of hours away from home for the cost of a flight to Europe or South America. So I did my Montauk travel off-season and I’m here to tell you the honest truth about what you can expect.

I should preface that these expectations are for an average, non-clout-seeking traveler with a non-Hamptons salary. If you have a summer home or a large wallet, you probably won’t benefit from this guide. With that said, let’s get to the brutally honest Montauk travel guide for all the fellow “broke b*tches”. I’ll cover the logistics of getting there, things to do, and tell you what traveling there entails.

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Montauk Travel Guide – Most Important Things to Know

Where is Montauk

The Hamptons collectively refer to a group of towns in the Eastern part of Long Island. Montauk is at the tippy tip and it’s considered the more “low-key” of them all. What once was a quiet resort/fisherman town is now the chosen destination of many influencers that want to be seen. I wanted to see this place for myself as I’ve heard very mixed opinions about it. So I planned my 2-day route with stops along the way that would let me admire the other Hamptons even for a little and see what the hype is all about.

This itinerary is for a simple 2-day local weekend getaway. I’ll give you my best tips and first impressions that I experienced there. Before we jump into the plan though, here are some quick logistics about this destination.

Montauk Transport

Getting to Montauk is easy. The first option is to hop on the highway from NJ/NYC and in 2.5-3 hours you’ll drive through all the Hampton towns into Montauk. Note that this will not be the case in the summer when you should add an additional hour or two to your drive due to traffic. The second option is a bus from the city like the Hampton Jitney or Hampton Luxury Liner. That ranges anywhere from $30-$70 each way which is not horrible. However, it does limit you to how you’ll get around town when staying there. Lastly, you can take the good old LIRR with a ton of stops along the way for a similar rate. The main advantage of a train ride, however, is skipping that dreadful traffic.

I opted for the driving option and there was virtually no traffic getting there. However, this was done in April, off-season for that area. It took about 3 hours to reach Montauk but we also made small detours along the way.

When you arrive, getting around is easy as most of the town is more than walkable. If you want to venture out to the lighthouse, wineries, or beach though, without a car this will not be the easiest of tasks. I personally and naively estimated the town to be a bit bigger than what it ended up being so I was a tad shocked when my drive within town ended within a couple of minutes.

Hotels in Montauk

First things first, BOOK SUPER SUPER SUPER EARLY.

Montauk is a smart town, you know why? Because keeping hotel prices at $600+ a night during the season keeps the broke b*itches away. They’re doing a great job because I certainly won’t be paying that to get back there. Every travel guide you read will tell you that Gurney’s or Surf Lodge is the absolute place to be. Are they nice? Heck yes, but will I drop $1000+ for a weekend at an Instagram hotel? Probably not. Some cheaper options include Montauk Blue Hotel or Royal Atlantic.

I stayed at Sea Crest Resort in Amagansett about a 10-minute drive outside of Montauk. My room had a 1 bedroom apartment and a sea-view balcony. At $300 a weekend night, it was a great place to stay in the area (compared to the insane rates 10 minutes away). Weekdays in April/May are even sold at half that price so if you’ve been dying to see Montauk for yourself, that’s your smartest option. For a deeper dive into cool spots check out Broke Backpackers Hotel recommendations there too.

All I’m saying is that you should simply know what to expect and not be shocked when you start looking at property prices.

23908 New York — Gurney’s – Photo courtesy of hamptons.com

the surf lodge New York — Gurney’s – Photo courtesy of hamptons.com

Useful Things to Know for Montauk Travel

Most people are dressed to impress so pack your best outfits. Chances are that you’ll see many Birkins around. Old money, new money, and just money all around.
Restaurants are pricey and you’ll need a reservation almost everywhere.
Gas is insanely expensive in town. There will be at least a $2 difference compared to the average prices so fill up before getting there.
There aren’t that many things to do in Montauk aside from dining, shopping, and lounging. Unless you’re a part of that community, this destination may not be as exciting as you might think.

Your 2-Day Montauk Itinerary

Day 1: Drive through the Hamptons & explore the town

Stop 1: Hampton Bays

If you’re driving in, your first stop will be a cute restaurant called Rumba Inspired Island Cuisine & Rum Bar in the Hampton Bays. The place is cool, with fancy tiki feels on the inside, an outdoor patio, and a vintage bus outside. It had a ton of cocktail options and the food was pretty tasty. The place got packed by 11:30 am so I certainly recommend making a reservation.

The crowd was mixed. Some families celebrating birthdays with their kids, some Instagrammers, and some other fancy humans. This place was probably my favorite spot out this weekend so I genuinely recommend grabbing a meal/drink there. Aside from the restaurant, there isn’t much to do in the Hampton Bays from a touristy perspective.

Stop 2: Southampton

The next stop isn’t so much of a stop because you can admire the beauty of Southampton from the car 🙂 Driving in the Cooper Beach direction you can spot the mansions on Meadow and Gin Lane. Although the hedges will block most of your views, it won’t be hard to see why this is the most sought-after place to be. Driving through the side streets, I appreciated the location’s beauty. Streets lined with tall trees on both sides give the place a very special vibe. If you’d like to explore more of the town, you’ll find the boutiques and restaurants clustered near Main and Jobs Street.

Stop 3: Hotel check-in

If you drove early in the morning, you might get to the hotel before check-in. I always recommend asking if your room is ready though because 7/10 times it is. I stayed at Sea Crest Resort and they let us check in early so around 2:30 pm. This particular hotel was actually nice, located in Amagansett right on the beach. The downside of an April visit is that it’s way too cold to lounge outside. While Jersey had a beautiful warm and sunny day, the cold winds of the island made the beach experience not as pleasant. However, it was nice to grab a cold beer, enjoy the peaceful views and inhale some fresh air.

To be honest I did not expect the temperature difference to be so drastic. The trees weren’t even blooming yet compared to Jersey’s super high pollen counts. I took a fall jacket with me and ended up wearing it the entire time. Make sure to check the temperature before visiting and don’t assume that it’s as warm as its 2-hour neighbor.

IMG 4547 New York — *Chilly late April beaches but hey! no crowds 🙂*

IMG 4509 New York — *Chilly late April beaches but hey! no crowds 🙂*

Stop 4: Montauk

I was so excited to check out what the hype was actually about. But this is where I have to be a major party pooper and say whomp whomp, “downtown” Montauk is not that great. There is a circle and all of its 3 streets with some shops and restaurants.

The first stop was a quick recharge at Hampton Coffee Company and Montauk Bake Shop. I wanted to stop by Left Hand Coffee for its cool vibes but it was closed. We walked around a couple of overpriced stores in that area and quickly realized that a $100+ crop top is the norm there. Being a beer fanatic, I really wanted to check out Montauk Brewing Company, but due to the long wait, I ended up getting a growler to go instead.

Here are some other places to grab a drink that most people rave about:

The Surf Lodge: hotel and restaurant known among the Instagrammers/TikTokers. Criticized for horrible service.
The Montauket: is known as the best sunset spot in town.
Navy Beach: another trendy popular place with an outdoor drinking scene.
Liar’s Saloon: located on a dock, this is your local “dive” bar.
The Point Bar and Grill: local sports bar in the area.

Stop 5: Montauk Lighthouse & Local Nature

The drive to the lighthouse is another 10-15 minutes east of the town. It was closed for renovations when I visited but the whole area was pretty nice. It was crazy windy so I didn’t get to explore much but I imagine that in the summer it’s a nice place for a stroll.

On that route 27 drive, you can find Deep Hollow Ranch, which allows you to go horseback riding in season right on the beach. Another landmark in that area is Camp Hero State Park, a nice park to get some outdoor exercise. If you love conspiracy theories, check out this article about the dark secrets of this exact park. Another nature stop is Shadmoor State Park.

If you’re craving some exercise and outdoor activities, there are many shops in Montauk offering bike rentals. From what I saw the trails there look great. Your Montauk travel wouldn’t be complete without at least getting some of its outdoor beauty in.

Stop 6: Dinner time

After exploring Montauk, we needed some rest and headed back to the hotel. Also, a cocktail before dinner never hurt anyone 🙂 Even off-season, it was hard to get a reservation a week and a half ahead of our visit so if you’re planning to visit the town, make sure to get those in ASAP. The only thing we were able to get was a “last-minute” table at Muse at the End. The food was good but the selection wasn’t the greatest and it was hugely overpriced for what it was. The crowd was a little fancier too. Overall the experience was fine but I wouldn’t say I fell in love with this place.

Here are some other highly recommended places for dinner in town:

Harvest on Fort Pond – a family-style town nook
Sammys – a low-key local staple
The Shack – a nice place right in the heart of town
Inlet Seafood – located a little further away but known for its amazing Seafood
Salivar’s Clam and Chowder House – seafood place located at the dock with a cool outdoor terrace
Gosman’s – another place on the dock with a topside terrace perfect for sunsets
Scarpetta Beach – a boujee spot at Gurney’s

Bonus stop: Nightlife in Montauk

Montauk is the place to party in the summer. At least that’s what I hear. I’m a grandma so after dinner I snuggled up in my blanket with a glass of wine and called it a day. So if all day of exploring didn’t kick your butt yet, make sure to make your way out at night. The drinking places I mentioned above usually have something going on at night.

Day 2

Stop 1: Breakfast

Since I am an espresso and a croissant kinda breakfast gal, I was happy with my chocolatey find at Hampton Coffee Company. If you’re looking for something more filling, try Joni’s a known local spot with amazing breakfast options, or Anthony’s Pancake House, a low-key spot with good prices.

Stop 2: Winery

Since this is a two-day itinerary, I recommend stopping by a winery on your drive home. Long Island is known for its wineries and a lot of people love taking their private buses there for special occasions. There are a ton of places in the Hamptons to get some quality wine so if one more person recommends Wolffer Estate and their rosè, I might quite vomit on myself. Don’t get me wrong, their rose is good but the spot became more famous for getting the Instagram picture with a location tag than the actual wine.

Here are some additional picks for you to choose from. Don’t forget to make a reservation if you’d like a tasting.

Channing Daughters– Bridgehampton. A charming winery with a unique sculpture garden. Tastings are $25 a person and they also have small snacks available for purchase. Wine prices are typically ranging from $18 to its most expensive bottle at $60.
Jamesport – Jamesport. Beautiful outdoor space with a kitchen on-site that serves delicious pizzas. They do have tastings by reservation and most of their bottles run between $20-$35.
Clovis Point – Jamesport. This is a by-reservation-only spot with very specific reservation and on-site rules. Their prices are a little steeper but they have a nice outdoor space and high reviews!

North Fork wineries may be a little further out however if you have some extra time during your Montauk travel and want to see that part of Long Island, this is a good excuse to venture out in this direction.

Duck Walk – Southold. The North Fork wineries are stealing Hampton’s spotlight. Duck Walk offers $12 tastings with reservations and allows you to purchase some snacks in addition to allowing you to bring your own picnic. A ton of their wines are under $20 too. Some of their reviews however are concerning many commenting on the disrespectful staff. Remember, sometimes you get what you pay for 🙂
Kontokosta – Greenport. Located even further into the North Fork, this modern winery currently offers bottle sales only and no tastings due to COVID. They’re by reservation only and do not allow outside food. It’s located on the water allowing for some unique views however familiarise yourself with all their current policies before visiting.

C57A9576 New York — Jamesport Winery – Photo courtesy of their website

channing horizontal 0025 Layer 17 New York — Jamesport Winery – Photo courtesy of their website

Other miscellaneous stops along the way:

Before ending your Montauk getaway, make sure to grab a fresh lobster roll at The Clam Bar in Amagansett. I will vouch for 100% for its quality and it was totally worth the $30.

Carissa’s Bakery is highly rated in East Hampton and located centrally if you’d want to peek into this Hampton’s lifestyle.

If you’re planning to stop somewhere else on your drive home, Tutto Il Giorno in Southampton and Sag Harbor won’t disappoint. The food is delicious and the space is very bohemian chic but expects steep prices.

Summer Time Beach Time

Since I visited Montauk off-season, going to the beach was not an option. However, in its peak season, this is one of the major reasons to visit this area. Since I am not one to give you beach advice as I only spent some time on one in Amagansett, I would check out this simple beach guide by On Montauk, to give you a better idea of what to expect from each. Here is a beach list and descriptions from their website:

Amsterdam Beach: hike to access, remote but worth the hike.
Ditch Pains Beach: surfer, popular, and with permit parking.
Edison Beach: central popular beach with limited public parking.
Gin Beach: quiet family beach with permit parking.
Hither Hills: family beach with public parking.
Kirk Park Beach: recommend the beach if you’re only in town for a day. Public parking.
Montauk Point State Park Beach: not really a lounging beach, rocky for hiking. Public parking.
Navy Road Beach: pebbly quiet beach, lots of boats.

Final Thoughts on Montauk Travel

Would I visit Montauk again? Probably not. Ugh, I hate to dislike places but let me explain why Montauk is not as dreamy as you might imagine it is.

First, this is not a place for a 5 or even 6-figure income person. Even the off-season rates are nuts and paying $1000+ for a weekend in peak season for a hotel is just silly. To put things in perspective, I spent two weeks backpacking in Peru for a little over that. Yes I know I’m comparing a South American country with a famous resort town in NY but if you’re an explorer like me, you get the point. I call myself a champagne backpacker because as much as I love nice things and spending money on experiences, a trip to Montauk is contributing nothing to my travel life.

Second, there really isn’t that much to do in this town. When I tell you that you can see everything there is to see in less than a day, I mean it. Aside from restaurants, a couple of nature preserves, and boutique shops, there is nothing special to do there.

Third, this is a spot to be seen and take pictures to say you spent a day in the Hamptons. As much as I like my pictures and posting about my travels, I do things for the sake of the experiences first. If I don’t like a place, I will be honest about it and not feed you bs that it’s a wonderful place to be.

But change my mind.

I’m certain my perspective on Montauk travel would be 1000 times different if I stayed in a large house with a nice pool or got that $1000 a night resort room without even thinking about the price. This post is aimed at an average Kasia who is looking to explore what her backyard has to offer.

So with huge disappointment, I vote Montauk a pass.

But Kasia, you traveled there off-season. What do you know? Well to compare, I had a phenomenal off-season experience in Newport, Rhode Island so if you’re curious about what made it different, find it in my post about it.

So should you visit Montauk?

Depends on what you’re looking for. I gave you all the tools and opinions to make that decision for yourself. Here is the research I gathered to make it easier to decide whether Montauk travel is for you.

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An Honest Montauk Travel Guide: A 2-Day Off-Season Itinerary