Friendly staff and bug spray for everyone!! This was a great place to visit and hike to learn…read moreabout and experience wildlife and natural beauty.

One of my favorite parts of our stay on Shelter Island! Since beaches aren't so easily accessible…read morewithout a day pass (none being offered due to COVID), we needed something to do during our stay that would take a few hours. There's a parking lot where all the trails start, so it's easy to find on google maps. There are 4 different trails you can take, depending on how long you want to spend there. We decided to do the green trail, which is the 2nd to longest trail. The map said it would take 2.5 hours (for 6 miles), but we ended up completing it in about 2 hours at a moderate pace. This trail goes along the shore line, so it was nice and breezy for a lot of it! I liked that it was more of a nature walk with a very well-marked path! Just be prepared for a lot of bug swatting. And also check for ticks at the end! If you come to Shelter Island, I'd highly recommend checking this place out. If you don't have a lot of time, the red trail only takes 45 mins.

I don't know why Greenport and the environs would choose to require a town parking permit to access…read moreits various stone beaches. Nevertheless, it does. This beach is the only one we found where you could simply drive up, park, and get in the water without spending a dime. The swimming area is marked off by safety ropes. There is at least one lifeguard on duty until 5. You're technically swimming in the Peconic River just before it empties into Gardiners Bay. The view is of Shelter Island, and it's quite charming.

The Town Beach. A cute and diverse park, beach & playground at the base of Fifth Street in…read moreGreenport. Small area for swimming (lifeguards on duty 11am-5pm in the summer), a couple fun and interesting playground structures with swings for babies and big kids, a sand floor volleyball court and wide open grassy space for running & ball-playing. Also some picnic tables & BBQ grills, public bathrooms and public parking spaces. The beach is rocky & full of shells, but fun for kids to explore.

extremely rocky. That's good though, yeah? I enjoyed it but I'll never get used to walking on rocks…read moreand shells. I was in so much pain. It's okay if you're nearby and want to be near the ocean. Other than that I was in pain. Great views

This beach is part of the Southold Town Beaches. The residents and guests in the hamlets of…read moreSouthold Town can obtain a beach sticker and have exclusive use of the beach. They have lifeguard during the summer season, so bring the crew and have fun. This is one of the best beaches to watch the sun set over the water every evening. Nice and relaxing beach with lots of walkable beach frontage. With a fishing permit you can surf cast off the beach.

Matty came and delivered two of the nicest, easiest to handle Kayaks Ive even experienced. We have…read morebeen on Shelter Island for a week and have to say with all sincerity- the hours we spent Kayaking were the #1 experience we had whilst on holiday. And- it was all around easy, great, just amazing. The delivery and pick up service is a must. We went round the harbor in Shelter Isl Heights, under the bridge to Dering Cove and just laid down to snooze on the perfect summer day. Best experience in Shelter Island and really reasonable rates! A MUST!

Definitely a must do when in Shelter Island!…read more This was a weekday getaway for myself and best friend and Venture out paddle boarding experience was the best of all! Great scenery, fun and exciting and totally safe! It's perfect for anyone, whether you're by yourself or in a group big or small! Can't wait to come back!

Peconic Water Sports - from my research - has the most boats to rent in the area. They have…read moremultiple locations, so you can toggle around on their website to see what's available. We were a group of seven, so our options were their tritoon or motorboat. But since we waited 'til the last minute, only the 'toon was available. But all good - we had a great time. You can rent for a half day (4 hours) or full day. We did a half day (1-5pm) with the option to extend it a few hours for extra $, which we turned down. Book and pay online; and show up early for waivers (every passenger must sign). They rec' showing up 15 min early for that, which we did, but after my beau did the test drive, we didn't hit the water until 15 min past our res, and then we returned 20 min early because we're unfamiliar with the time/distance to return... so we lost a half our on the water :/ Next time, we'll remember our noodles or ask about renting some water toys.

Rented a boat for a 4 hours. Nik and Eric were really chill. Had an amazing on the boat. It was…read morebrand new, amazing speakers and beautiful water. Had an amazing time!! Definitely going to be back soon. L

Foster Memorial aka Long Beach gets Max's approval. (See pic.) its a very dog-friendly beach with…read morewinding sand and parking lot shape that makes it perfect for whichever you choose to walk on. The walk is also peppered with benches to sit and enjoy the pretty setting and calm waters this Sunday in the park with Max in September.

An average, bay-side, residents-only Southampton beach located in Sag Harbor, near Bay Point, on…read morethe bay side. Beach is comprised of mainly shells and pebbles, so tread carefully. The swimming area has in-season lifeguards. Boating, jetskis, water skiing, rafting, kayaking, and kiteboarding are all okay here. Relatively quiet beach, even when crowded.

Just a lovely place to chil relax even in the winter season !!! Tranquility is so niceread more

Visit Date: October…read more22, 2021 I stopped by this beach after driving to Greenport on the way back to Babylon to pick up my son from school. I found it over the summer but they were checking for residency so I couldn't visit over the summer. This beach is very pretty but tiny. I sat on a log and admired the nature and took a lot of photos. I end up seeing a lot of beaches off season to avoid paying a fee but I'll still hang outside in the cold to admire the nature!

Water was filthy. Murky. Algae. Sea grass. Plastic bits. Gross. Beach is pebbles. Hot day and no…read moreone swimming. Life guards told me I shouldn't swim as the water was too dirty

What a great find in Greenport to spend the day at the beach. We have a beach permit/pass from the…read moreperson we're renting from for the summer so it's a no brainer. We like Kenney's beach & McCabe's on the sound but it seems that the beaches on the bay are much calmer and you can keep your umbrella up without the wind blowing it over. Very serene watching the sailboats and shelter island across the bay. The parking is really great and bathrooms are available too. P.S. Go to Billy's by the Bay (Wednesday-Sunday opened only) after to get some lobster as located on the same road :)

Had a wonderful afternoon paddling around the calm waters in Orient. So peaceful! A one hour rental…read morewas perfect for our first outing, as there wasn't a ton to see. Fair rates, helpful and friendly. Offered for us to leave valuables in the hut. Will definitely be back to paddle towards the west. Only downside (not the business's fault), is having to also pay $10 for park entry.

Best time ever... Weather and the Water were both amazing. Ali was super nice. She gave us a quick…read morelesson and even snapped a few pics. Bring bug spray the bugs are for sure happy to see you.

Booked a lesson and what a great time we had. My sister-in-law and I are retired and are always…read morelooking for new, fun things to do. This ranks as one of the best things we've done so far. We will definitely do this again. Really good exercise, too.

From the owner: Thanks to everyone that shared their early moments in surfing with us. We are available for…read moredestination private lessons until Memorial Day when we will be back in Quogue.