Shelter Island- If you live nearby it is not a big deal to take the ferry over. It cost $10.00 to drive your car onto the ferry. If you have the time I would suggest staying for 2-4 nights. It is a great getaway and it feels like you are on a secluded, beach island town.
Tip- One Taxi Place for the entire island- Go 4's- 631 749-4252- Don't Drink and Drive at NIGHT!!
Beaches
FYI- Get a beach pass!! Cost $40.00 for the week
-Cresent Beach/Sunset Beach- Most Popular beach on the island.
-Wades Beach- More of a local beach. Bring food and drinks with you.
-Shell Beach- Most Secluded Beach on the island.
Things to bring with you
Cooler, Drinks, Red Cups, Sunscreen, Lounge Chairs, Towels, Bose Speakers, Snacks, Lighters, and more.
Activities
Shelter Island Kayak Tours- (631)-749-1990- Rent a kayak!!! I like exploring on my own rather than going with a guide. Paddle to secluded coves and small beaches. Visit active osprey nests and plenty of amazing wildlife, Bring plenty of water and some snacks with you. Ask for a drybag to store all of your belongings.
Mashomack Perserve- Great hiking!!! Hikes range from 30 minutes- 4 hours
Mini-Golf- Always fun. They have delicous ice cream for sale inside.
Bring your Bike!!! Perfect place to have a lesiurley bike ride.
DRIVE!!! Go exploring. Hopefully you have an Iphone which will make this easier, if not throw caution to the wind and get lost on this magnificent island. You will propbably run into gorgeous mansions, hidden beaches, deer, and more.
Restaurants
Sweet Tomatoes- Great Calamari and pizza
Chequit- Terrayki Wings were Great
Star Cafe- My favorite Place for Breakfast!!! Everything on the menu is delicous.
I get the Breakfast Burrito- Ham, avocado, egg, cheddar- I get extra cheese!!
Bob's Seafood- Expensive but delicous!!! King Crab legs and Calamari!!!! (Small portions)
Salt- Eat Outside!! Great View. Large Beer Selection. Menu is a hit of miss- Bay Fries and Chocolate Peanut Butter dessert is AMAZING. The Lobster Roll is ok. (Bread was not grilled) DO NOT GET- Fish Tacos
Nightlife
The Island has very limited nightlife which is a good and bad thing.
The Good- if you are at the right bar it will be pretty busy because there is no where else to go!!
The Bad- Not many options
Pridwin Hotel- Great Bar- Has an outside area with tables that overlooks Creasent Beach
Chequit- Fun Bar- Small- Has a Pool Table- Certain nights they have a DJ and light show
Lodging
If you are going with more than two people try to rent a home on homeaway.com or vrbo.com
Ram's Head Inn- Great Location, Beautiful Grounds, Private Beach, and Bar is inside the hotel. Only downside is rooms are very small.
MONTAUK- A nice change of pace from the Hamptons. If you are driving out east it is worth the extra half hour drive to Montauk. Get a beach pass!!
Beaches
-Ditch Plains Beach- Beautiful Beach- If you walk towards the cliffs you may find purple sand!!!
-Ditch Witch- Eat at this Food Cart which is on the beach-East Deck Parking Lot
-Gin Beach-
-Kirk Park Beach-
-South Edison Beach- Most Popular beach- Walking distance to bars and restaurants
Activities
- Montauk Point Lighthouse- Nice drive to the light house. Great views
Restaurants
- The Surfside Inn
- Navy Beach-
-Inlet Seafood Restaurant
-Bird on the Roof- Delicious Breakfast
Nightlife
Liars Saloon
Build a fire on the Beach!!!
Lodging
Montauk Soundview Resort Hotel- Small rooms. Great Location and Private Beach