Montauk might not be the first place that comes to mind for Midwesterners planning a beach escape. But after visiting, it’s now one of our favorite vacation spots. With its laid-back surf town vibe, stylish hotels, and stunning coastline, Montauk offers that rare mix of cool and cozy—like a small-town summer weekend with a coastal upgrade. In this Montauk travel guide, I’m sharing our favorite places to stay, eat, and explore, plus a few travel tips we learned along the way.
HOW TO GET THERE AND GET AROUND
We flew into LaGuardia Airport in New York City, rented a car, and made the scenic (and sometimes chaotic) drive out to Montauk, which took about three hours.
Tip: Plan your arrival carefully! Traffic can be brutal on summer weekends, especially with the surge of people heading to the Hamptons. If you’re arriving on a Friday afternoon, build in buffer time or stop for a long lunch en route.
Another option is taking the Long Island Rail Road (LIRR) to Montauk, though you’ll have less flexibility once you’re there without a car.
Having a car (and parking!) is key in Montauk. Staying downtown can make the area a lot more walkable, but if you’re planning to explore, see the light house, or enjoy a night at Surf Lodge, it’s best to have your own car on hand.
WHERE WE STAYED
My husband and I love a good hotel situation—give us great design, thoughtful amenities, and walkability to food and drinks, and we’re sold.
We stayed at Montauk Beach House, a recently renovated boutique hotel right in town—just two blocks away from the beach and walkable to coffee shops, shopping, and restaurants. Our room opened onto a private patio by the pool, and we were greeted with a bottle of rosé in celebration of our mini-moon!
The pool area felt straight out of a Bachelor in Paradise set, and we loved biking around town on the hotel’s complimentary branded bikes (and even took them to Surf Lodge one night!)
Tip: Dining in Montauk can get expensive quickly. If you’re staying more than a night or two, consider an AirBnb or house rental with a kitchen. Even just having breakfast and snacks at home can help offset the cost of going out!
WHERE WE ATE (AND DRANK)
The Clam Bar at Napeague
Our first meal in New York was at this roadside seafood shack, where we had our first (and arguably best?) lobster rolls of the trip, along with sweet potato fries, chowder, and slaw that we’re still talking about.
The Montauket
Known for its sunset views, this casual, divey spot is a must for pre-dinner drinks. We grabbed beers and rosé while watching the sun dip below the horizon—no frills, just vibes.
Sel Rrose
This spot is undeniably pretty, but service was slow when we visited. If you go, sit at the bar for a cocktail and oysters before hitting another spot for dinner.
Left Hand Coffee
This became our go-to coffee spot, just a five-minute walk from our hotel. We loved it so much we went back three times. A must-visit if you’re staying nearby.
Goldberg’s Bagels
I was so excited to try the iconic Spicy Hobo bagel sandwich—egg, bacon, hot sauce, pepper jack cheese, and a crispy hash brown patty all inside a bagel. It did not disappoint!
Duryea’s
Montauk’s most scenic lunch? This was it. No reservations, so we got lucky and were seated immediately and enjoyed oysters, crab claws, and champagne with waterfront views that felt like a Greek island vacation.
Surf Lodge
A Montauk icon! We booked a 6 PM dinner to catch live music, and the vibe was unnmatched. Highly recommend booking an early reservation if you want to stay for the music (and trust us, you do!)
Wave Crave Food Truck
We met the owner, Steve, at Surf Lodge, and he invited us to his beachfront food truck the next morning. It ended up being one of our favorite meals—breakfast wraps, whale watching, and great conversation. Bonus: Steve was on Hell’s Kitchen!
WHAT TO DO IN MONTAUK
- Beach Walks – As Midwesterners, we don’t take ocean time for granted. We loved grabbing coffee and walking the shoreline each morning!
- Poolside Lounging – If your hotel or rental has a great pool setup (like ours did), carve out the time for cocktails and sunshine.
- Explore Downtown – Lots of great little shops and boutiques to pop into, and not overly commercial!
- Catch a Show at Surf Lodge – Live music, sunset vibes, and a super fun scene. Plan ahead for this, as Ubers are scarce, parking is limited, and the reservations fill up fast. We ended up riding our hotel bikes along the Montauk Highway to get there and back. It worked out perfectly (no DD needed!)
- Visit Montauk Lighthouse – A rainy day led us to this local landmark. The museum is cute and you can climb to the top for great views. Just be prepared to wait during peak times!
- Book Surf Lessons – We didn’t have time to book a lesson, but saw lots of groups out on the water. This would be a great activity for a return trip!
WHAT TO PACK FOR SUMMER IN MONTAUK
Montauk is much more laid-back than the rest of the Hamptons, so you can skip anything too dressy. Here’s what I’d recommend:
- Comfy jeans, shorts, and casual tops
- Breezy dresses for dinners and drinks
- Linen button-downs or cardigans for layering
- Sneakers and sandals
- Swimsuits and cover-ups
- Sunhat + sunglasses
- Light sweater or jacket for cool nights
- Tote bag or crossbody for walking around town
Montauk felt like the perfect blend of elevated and approachable—from cocktails at chic waterfront restaurants to cozy mornings with coffee on the sand. It reminded us a little of our Midwest hometowns: friendly locals, relaxed energy, and a deep appreciation for summer. We’d go back in a heartbeat—and now, we’re officially lobster roll snobs.
For more East Coast summer travel ideas, be sure to check out my Newport, Rhode Island Travel Guide!
