Shelter Island has a population of approximately 2,000 people, exploding to up to 5x this during the summer!
With over 12 square miles of land, there are many tourist attractions spread throughout, enticing visitors all year round.
Driving a car to the island makes perfect sense as this adds flexibility to your trip, allowing quick access to popular destinations, but is driving there possible?
Driving to Shelter Island is possible, but as there aren’t any land connections to the island, you’ll need to take a car ferry via the North and South ferry terminals for access, with a 10-minute journey time.
Attractions on the island are spaced out, so taking a car is advisable, as this allows easy access to popular places, adding flexibility to your trip.
Car ferries to Shelter Island
Access to the island is via the North and South ferries, which are two of the oldest businesses still running on the island. The North ferry departs from Greenport, New York, and the South Ferry operates from North Haven, New York.
As they’re two separate companies, ticket prices differ for each route, and times vary.
For both routes, crossing times take roughly 10 minutes, and it’s not required to make a reservation, so if you turn up at the port, you’ll be fine to buy a ticket on the deck of the boat, which is paid in cash only.
Both ferry docking points have free parking lots to park your car before boarding.
North Ferry service
The North Ferry departs from Greenport, New York, running daily between the hours of 5 am and 1 am, and times are subject to change due to seasonality.
Here’s what to expect for pricing:
- 1 driver and car same-day return, $22. Motorcycles are $10.
- 1-way driver and vehicle are $14. Motorcycles are $8.
- Travel with up to 3 additional passengers each way, costing $2 each.
- Children aged 10+ are classed as passengers.
South Ferry service
The South Ferry departs from North Haven, New York, running daily between the hours of 5:40 am and 12 am, and times are subject to change due to seasonality.
Here’s what to expect for pricing:
- 1 driver and car same-day return, $20. Motorcycles are $10.
- 1-way driver and car are $15. Motorcycles are $8.
- Additional passengers each way cost $3 each.
- Children in car seats travel free.
Car parking on Shelter Island
Car parking permits are required to park on the island between the dates of May 15th and September 15th. Parking permits can be purchased via online application or at the Town Clerk’s office, open from Mon-Fri, 9:00 am-4:00 pm.
Only ten car permits are available daily, so get there early.
You’re required to show your car registration or car rental agreement to acquire a parking permit, and the charges are as follows:
- $25 daily
- $70 weekly
- $125 monthly
- $250 seasonally
Due to the limited number of permits available, and also if you’re looking for a cheaper option for traveling to and maneuvering around the island, an optional idea is to park your car at either ferry dock. Then you can walk on the ferry with your bike, which you can use to travel around the island.
However, even though this is a less costly option, the island is quite hilly, and unless you’re very fit, then driving a car on the island is a faster and more practical way of exploring what the island has to offer.
Driving from Greenport, New York, to Sag Harbor
A popular route throughout the island, driving from Greenport to Sag Harbor, is roughly 10 miles and takes under an hour to complete.
Also, driving through the island between the two destinations is, on average, 20-30 minutes quicker than driving a car around by land, which takes about 1 hour and 20 minutes to complete.
The trip is split into four sections, as follows:
- First, take the North ferry from Greenport to Shelter Island, taking 8-10 minutes to arrive.
- Next, there is a 10-minute, 4.2-mile drive between Shelter Island and the next ferry point.
- Take the South Ferry from Shelter Island to North Haven, which is a 5-minute ride.
- The final stretch is a 7-minute, 3.5-mile drive between North Haven and Long Wharf, where you’ll drive over the connecting bridge between the two destinations.
Additionally, you’ll need about 5-10 minutes at each ferry point for boarding.
Top 5 places to drive to on Shelter Island
The island is filled with popular attractions for you to visit. Here are five great ideas for your day trip!
Also, if you feel that one day is not enough and want to stay the night on the island, then you can grab a room at the widely praised Chequit, which is a charming seaside inn located over Dering Harbor.
Kayak Shelter Island
Whether it’s lightly raining or a sunny day, Shelter Island is a joy for kayaking. Enjoy a pleasant ride around the Coecles Harbor either solo or with the family.
Single or double kayaks are available for rental, and available rental times are from one hour to a full day. Additionally, there is a 2-hour guided tour charged at $60 for adults and $30 for children under 12.
Also, if you feel like paddleboarding, then they’re also available for hire.
Whale’s Tale dessert cafe & miniature golf course
Follow the journey of the friendly Whale who once explored the island! The Whale’s Tale is a great experience for the kids, offering an 18-hole miniature golf course and an indoor arcade room with multiple games to keep everyone busy.
They also offer a variety of food and drink options, including coffee, frozen drinks, pizza, hotdogs, and many ice cream flavors and combinations to choose from!
If you enjoy walking and wildlife, then look no further than the Mashomack Preserve! Covering 2,100 acres, which is roughly 1/3 of the island’s land, then there are well-marked, wide, flat trails with freshwater marshes, creeks, varying wildlife, and picturesque views on offer!
If the reason you want to travel to Shelter Island is to escape the hustle and bustle of city life, then why not visit this family-friendly beach?
Kids can build a sandcastle while you sit back and enjoy the scenic views and calm waters, and it’s safe to swim here too, including marked swimming areas for safety.
At night, enjoy the tranquil sunsets, and even make a fire on the beach and roast some marshmallows for the ultimate evening experience!
Try some seafood
If eating seafood while viewing glistening waters and being surrounded by wildlife sounds good to you, then Shelter Island offers fresh seafood at a variety of locations.
Popular restaurants include Shelter Island Seafood, which is open 11 am-6 pm daily and offers some of the freshest local seafood on the island.
Another favorite spot includes the SALT dockside restaurant (open seasonally), offering inside and outside dining and a variety of freshly caught fish, including oysters, prawns, and tuna.
Whatever your taste, there are many food options available spread throughout the island.
It’s not only possible to drive to Shelter Island, but it’s advisable, as key locations are spread out from each other. However, as there are no land connections to the island, you’ll take a car ferry via North and South locations, and then drive to the places of your choice through the many road systems available.
If you’re only spending a day on the island, then a car is a great way to add flexibility to your trip, enabling you to view more locations than otherwise possible.