Day Itinerary
10 Activities
Day 2
150 mi
Crossing the Long Island Sound
From Rhode Island to Connecticut and over to Long Island, this day takes you to terrific stops on the East End of Long Island. Take the ferry from New London to Orient Point and enjoy the Sound views. Learn about the rich farming life on Long Island, and immerse yourself in excellent seafood culture. This day feels authentically Northeastern.
20.3 mi
40 min
09:3030 min
Caf Bar
This lovely little local café is worth veering off the main highway to enjoy. Caf Bar serves excellent coffee, and you can find a scrumptious treat to pair with it, including smoothies, toasts, and paninis. Their lox & load is amazing!
Opening Hours: Monday – Friday: 7:30 a.m. – 3:00 p.m. Saturday: 8:00 a.m. – 3:00 p.m. Sunday: 8:00 a.m. – 2:00 p.m.
Opening Hours: Monday – Friday: 7:30 a.m. – 3:00 p.m. Saturday: 8:00 a.m. – 3:00 p.m. Sunday: 8:00 a.m. – 2:00 p.m.
40.2 mi
50 min
10:5010 min
Cross Sound Ferry
This marks where you’ll board the ferry to cross the Long Island Sound to Orient Point. Bookings typically run hourly, and you can make a reservation for your vehicle and passengers here. Try to catch the 11:00 a.m. crossing.
12:305 min
Orient Point Ferry
This is the point where you’ll depart the ferry and continue on Long Island!
12.5 mi
25 min
13:0030 min
Deep Roots Farm
Now on Long Island, take a quick peak at Deep Roots Farm, a budding business with beautiful fresh vegetables and pasture-raised animals. Buy whatever happens to be in season and you won't regret it!
Deep Roots is open during daylight hours seven days a week.
Deep Roots is open during daylight hours seven days a week.
9.1 mi
15 min
13:451 hr
Love Lane Kitchen
Love Lane has a standout lunch and, if you haven't had a lobster roll or hearty sandwich yet, now is the time to do so. This local favourite has consistently good food, a cosy atmosphere, and plenty of good drinks.
Open 8:00 a.m. to 4:00 p.m. daily, and for dinner on the weekends (Friday to Monday).
Open 8:00 a.m. to 4:00 p.m. daily, and for dinner on the weekends (Friday to Monday).
2.2 mi
5 min
15:001 hr
Ev&Em Vineyards
Ev&Em creates wonderful wines on the North Fork. Visiting their vineyards is a must in the area, as the tastings, history, and space all make for a terrific stop. For an elevated experience, try reserving a tasting on the tasting deck here.
Opening Hours: Monday – Friday: 11:00 a.m. – 5:00 p.m. Saturday – Sunday: 11:00 a.m. – 6:00 p.m.
Opening Hours: Monday – Friday: 11:00 a.m. – 5:00 p.m. Saturday – Sunday: 11:00 a.m. – 6:00 p.m.
5.8 mi
15 min
16:1545 min
Garden of Eve Organic Farm & Market
Another farm! This one is unique for a few reasons: Garden of Eve is certified organic, and they have a ton of great things to do. From a brewery, a café, fresh-picked veggies, and pick your own, there’s something for everyone at this lovely local farm.
If you’re tired from travel, relax and have a beer. If you want more snacks, get out there and pick some fruits or vegetables! More information here.
Opening Hours: 1 April – Halloween Monday – Sunday: 9:00 a.m. – 6:00 p.m.
If you’re tired from travel, relax and have a beer. If you want more snacks, get out there and pick some fruits or vegetables! More information here.
Opening Hours: 1 April – Halloween Monday – Sunday: 9:00 a.m. – 6:00 p.m.
5.6 mi
15 min
17:155 min
The Big Duck
This silly gift shop is shaped like a giant duck. A classic American roadside attraction, this is worth a quick stop to check out the weird structure.
Though it closes at 5:00 p.m., you can still snap a funny photo when you arrive. Once you wrap up this stop, prepare yourself for some next-level seafood at the well-known Duryea's.
Though it closes at 5:00 p.m., you can still snap a funny photo when you arrive. Once you wrap up this stop, prepare yourself for some next-level seafood at the well-known Duryea's.
41.7 mi
1 hr 10 min
18:301 hr 30 min
Duryea's Montauk
Duryea's reinforces the idea that keeping it simple is the best way to succeed. Their incredible seafood and salads stand out for their rich flavour and pared-down ingredients. By using the very best the coast and the land has to offer, they have a great reputation for good reason. Go with your favourite fresh fish and be wowed.
Duryea's is open seasonally from May to September.
Duryea's is open seasonally from May to September.
13 mi
25 min
20:3010 hrs
The Roundtree, Amagansett
This award-winning hotel is an architectural masterpiece in a heavenly slice of Long Island. The charming interior, well-thought-out amenities, and proximity to beautiful coastline make this the clear choice for accommodation in Amagansett.
Book Now
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Book Now
If you are a TCS member and would like to book a hotel with 3% cashback, please follow the instructions via this link.