Shelter Island :

If you have a bike, you can bring it with you on the Long Island Railroad from Manhattan. Otherwise, rent a bike for the day from Piccozzi’s Garage and Bike Shop for $25. You’ll find the shop easily – walk about five minutes from the ferry terminal to Bridge Street, near the Mobile gas station. While riding, keep your eyes peeled for fast-moving cars, as there are few shoulders and sidewalks on the route.

Being new to Shelter Island, I started out following a mapped trail, soon discovering that some of the most intriguing sights—tucked away beaches and charming little side streets—revealed themselves once I deviated from the path. The island is known for its stunning natural beauty, but once you’ve met your first chatty local, you’ll learn that tasty food and progressive art is also easy to find here, so expect to make a few stops along the way. There are 8,000 acres to explore on Shelter Island, but there’s no need to feel overwhelmed—the hills are gentle, yet challenging enough for the average cyclist. To see the island’s finest attributes, follow the 8-mile loop from leafy Shelter Island Heights to Crescent Beach, where you’d be wise to try a delicious cocktail at the trendy Sunset Beach Hotel -- look for the orange beach chairs. As the route progresses, you’ll find off-the-beaten-path Shell Beach and Bootleggers Alley, a remnant of the island’s wily past.

Cultural High Points
Shelter Island’s proximity to the small city of Greenport presents visitors with plenty of artistic diversions. Just a leisurely five-minute ferry ride away, Greenport touts a creative community of artists, chefs and vintners, the fruits of whose labors dot each attractive street. There are numerous galleries showing everything from artisan furniture to multimedia art, murals, sculpture and pottery. Consult the Greenport Gallery Walk website for event listings and gallery locations. Back on Shelter Island, the Boltax Gallery livens up on Friday nights, hosting a salon-style, artist-created event and reception every week. The gallery hosts a mix of local and international, young and mid-career artists. The Perlman Music Program is another point of pride for Shelter Island residents. The program, set on a rolling property just across the street from Crescent Beach, hosts a select group of talented young musicians who perform in New York City, the Hamptons and on the Shelter Island campus throughout the year – they’ve even played at the Kennedy Center in Washington D.C.

Hiking the Coastline
Shelter Island’s vast empty shores and stunning green landscapes are enough to make even the most harried city resident forget where she came from, I found. High on the fragrant, fresh air and sight of so much water, I took things further by visiting Mashomack Preserve, a 2,100-acre property overseen by the Nature Conservancy. With ten miles of coastline, and a textbook array of ecosystems – creeks, forests, salt marshes and meadows – the preserve begs for a visit. I left my bike at the rack at the visitor center before taking to the trails; choose from an easy 1.5-mile trek, or a more rigorous 11- mile hike. Giant, dinosaur-like birds called Ospreys nest here, so keep your eyes peeled.  Guided hikes are available if you call ahead. Hiking the preserve adds another level of depth to your Shelter Island experience, revealing an array of plants and animals not found elsewhere on the island. Although it’s best to attempt the longer trail with a partner, I encountered several friendly solo walkers during my 1.5-mile outing.

Serene Island Inns
There are a range of comfortable lodgings on Shelter Island, including historic inns, modern homes and cottages reminiscent of Grandma’s house. Most places require a two-night stay, and rooms fill quickly, so try to book far in advance.

For a chic and quiet place to rest, the Shelter Island Hideaway is a gorgeous, European-inspired option. The Hideaway features two properties on one-acre of perhaps the most exquisitely landscaped grounds on the island. Both the larger house and smaller (but still roomy and airy) cottage are fashionably sophisticated in both layout and decor. There is plenty of privacy on both properties, and each has its own swimming pool and luxurious outdoor patio area. The cottage touts crystal clear Koi ponds filled with goldfish, while the house features an expansive front deck, vegetable garden and large swimming pool. Kitchens in both properties are top-notch, ideal for a week or month-long stay during which you’ll want to do your own cooking. The Hideaway is in an ideal location, just across the street from Bootleggers Alley and a lovely beach where you’ll likely never see more than five or ten people.

Rooms at the House at Chase Creek Bed and Breakfast are cozy and comfortable, with a country-chic style ....