#BMWRoadTrip: Three Day Adventure


Where can you go for a quick three-day weekend to escape the everyday and feel like you’ve really gotten away from it all? Where can you have a summer adventure without leaving Long Island and dine, shop, chill and enjoy the outdoors? Take a drive to Shelter Island on this three-day BMW Road Trip.

Removed from the hustle of the Hamptons, SHELTER ISLAND feels like a remote retreat yet is just a ferry ride away. Sandwiched between the North and South Forks of Long Island and surrounded by water, Shelter Island truly comes to life in the summer season. Sugar merchant Nathaniel Sylvester settled on the island in 1652, and since then it has remained a spectacular place where you can delight in its natural beauty and local pleasures.

Venture out onto the water on a stand-up paddle board.

Venture out onto the water on a stand-up paddle board


Catch the ferry from North Haven for a 5-minute trip to Shelter Island’s south shore.  Operating for more than 100 years, the SOUTH FERRY COMPANY is the longest continuously family run ferry company in the US. There’s a boat every 15 minutes, and you can board on foot, by bike or in your BMW.  The Lt. Joe Theinert, the Southside or the Sunset will take you across scenic Shelter Island Sound from 5:40am to 1:45am daily.
(135 S. Ferry Road, Shelter Island (631) 749-1200, www.SouthFerry.com)

Check into the popular beachside resort SUNSET BEACH and feel like you’ve escaped to the south of France. The stylish hotel tends to attract a well-heeled crowd with offerings such as a Parisian-style restaurant, chic boutique and trendy ping pong tables. Each of the 20 rooms provides guests a private terrace, bay views and Kiehl’s products. There is no excuse to not get physical – the staff will help to accommodate all types of sunny activities – biking, golf, tennis, volleyball, sailing, yoga, kayaking – but it’s just too easy to chill here.
(35 Shore Road, Shelter Island Heights, (631) 749-2001, www.SunsetBeachLI.com)

Score a sweet spot on CRESCENT BEACH and relax.  For guests, the Sunset Beach staff will set up an umbrella, secure chairs and bring over a drink to sip on.  There is typically a surge of people on the weekends, so enjoy the tranquility of a weekday.

Venture out onto the water on a stand-up paddleboard.  Owned and operated by Shelter Island locals, VENTURE OUT SHELTER ISLAND is where you can rent equipment and rookies can pick up moves. Owner Matty Stromberg says, “Sometimes people who visit never leave one spot, so we offer free transportation to anywhere on the Island as well as free drop off and pick up of your Paddle Board rental”. You’ll get an on-beach mini lesson with a normal rental.  Sunset paddles are encouraged because, as Matty explains, “the sunsets are out of control in the summer. Every night the sky is on fire.”
(21 N Ferry Rd # H, Shelter Island, NY 11964, (631) 749-5644, www.VentureOutSI.com)

Dine by sunset at SUNSET BEACH. Per the name, the whole point of staying at Sunset Beach is for the sunsets. The views are so magnificent that it takes dining outdoors to another level.  The tables that are lined along the upper level’s outer edge are where you want to be seated.  Watch the sun sink into the water as you savor a glass of SUNSET BEACH RESERVE ROSE with your meal. Then dine on classic French dishes while you attempt to identify the celebrity clientele seated beside you.

La Maison Blanche

La Maison Blanche


Drop in for some local flavor at the SHELTER ISLAND HEIGHTS PHARMACY. The simple pleasures found inside include an old-school soda fountain counter, local newspapers and souvenir treats. For certain, you’ll overhear some townie gossip.
(19 Grand Ave, Shelter Island Heights, NY 11965, (631) 749-0445)

Get a history lesson at SYLVESTER MANOR, an estate-turned-organic farm, historic plantation and a lively arts and education center. “The site has centered on the culture of food for most of its 360-year history and is considered the most intact historic plantation north of Virginia,” explains Executive Director Cara Loriz. Her tip, “Enjoy Saturday mornings at our farmstand all summer – a beehive of farming and social gathering featuring worksongs, chef demos, tastings and more.” Don’t miss their Open House dates, when you can tour the Manor House and the 243-acre grounds. (12-3pm, June 13, July 4 & 18, August 1 & 15).
(80 N. Ferry Road, Shelter Island, (631) 749-0626, www.SylvesterManor.org)

Play pétanque followed by dinner at Shelter Island House, formerly named LA MAISON BLANCHE. This charming, open-year-round, boutique hotel has a designated area where players can partake in the French game. Then find a seat inside or outdoors in the garden for dinner and cocktails. Much of the menu from this award-winning restaurant comes from local sources. No other place on the island offers a lamb burger – a very popular item on the late-night take out menu. Just as popular are the fresh pastries sold at their bistro bakery.
(11 Stearns Point Road, Shelter Island Heights NY 11965, (631) 749-1633, www.MaisonBlancheHotel.com)


Top Deck Dining at Sunset Beach

Top Deck Dining at Sunset Beach

Wake up to “The Sunset” breakfast at SUNSET BEACH. Make your way to the intimate Cafe on street-level and splurge on coffee, croissants and fruit preserves as you contemplate today’s adventure.

Grab a bike and go into the heart of the island for a visit to BLACK CAT BOOKS. Dawn Hedberg, the woman behind the business, is forever seeking out new and collectible books. Browse and discover new books, used ones, rare collectibles and first editions from over 20,000 titles in this cherished non-digital environment.
(54 N. Ferry Road, Shelter Island 11964,  (631) 725-8654, www.BlackCatBooks.com)

Hike the pristine protected land of the MASHOMACK PRESERVE. Comprising nearly one-third of Shelter Island, the 2,039 stunning acres are protected and preserved by The Nature Conservancy. Select one of four nature trails that vary in distance from 1.5 miles to 10 miles roundtrip. Paths overlook gorgeous views of distinct natural habitats – forests, ponds, open fields, freshwater marshes and shorelines – making it the perfect place to encounter an osprey or two. Keeping up with your new friends is not a worry.
(47 S. Ferry Road, Shelter Island, (631) 749-1001, www.Nature.org/Mashomack)

Nourish yourself with a good eat before heading home at Marie Eiffel Market, formerly REDDINGS MARKET. You’ll find something for everyone, with shelves stocked with standard grocery finds, bins of local produce and cases filled with local fish and grass fed meats. This gourmet market offers snacks that range from simple pizzas to inventive sandwiches. Sugar addicts will not want to miss the made-to-order Cotton Candy offered in variety of yummy flavors.
(184 N. Ferry Road, Shelter Island (631) 749-0003, www.MarieEiffelMarket.com)

TIME TO HEAD HOME – Your three-day adventure is almost over, but the best part is to come….the drive home in your BMW.

Taking a road trip? Share it with us on social. Tweet a photo of you and your Bimmer using #BMWRoadTrip or tell us about your trip on Facebook using #‎BMWRoadTrip.


About Author

Competition BMW of Smithtown

Checkmate Magazine appeals to the competitive side of the BMW driver who views life as a journey, not a destination. Someone who defines success not by winning or losing, but by how one responds to both. Checkmate is the first of its kind, a publication written exclusively for consumers by an automotive dealership.

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