Five-Night Itinerary

Day 1: Thursday  Board Arabella in the historic harbor of downtown Newport promptly at 4pm (luggage will be accepted at 2pm).  Settle into your cabin and then spend the rest of the afternoon sightseeing and shopping.  Return to the boat, freshen up and prepare for a welcoming Smuggler's Cocktail Cruise aboard our 1929 Elco Prohibition Era Motor yacht, the Rum RunnerII, followed by dinner at your choice of Newport's more than fifty wonderful restaurants.

 Day 2: Friday  After an exciting sail, we arrive in Martha’s Vineyard and the quaint Victorian village of Oak Bluffs.  Known for its gingerbread houses and eclectic restaurants, you can spend an afternoon on the beach, or take an island tour.  Don’t forget to check out the miles of bicycle paths on Martha’s Vineyard. 

Day 3: Saturday  Arise the next morning for an exhilarating sail to Nantucket, a beautiful island 30 miles out to sea and what was once the world’s center of the whaling industry and inspiration for Melville’s novel Moby Dick.  Take a side trip on Arabella’s launch to a pristine secluded beach or explore on one of our kayaks.  Enjoy fine shopping along the cobblestoned streets of Nantucket’s 19th century downtown.  That evening, go ashore for dinner at any of Nantucket’s gourmet restaurants and enjoy the varied nightlife.

Day 4: Sunday  A late morning departure will see us on a thrilling sail to Edgartown on the island of Martha’s Vineyard, the summer playground of the rich and famous.  Explore this historic town, go to the beach or maybe go on an exploration on one of Arabella’s launches to Katama or Chappaquideck.  Evening will bring a beautiful sunset and cocktails followed by fine dining in picturesque Edgartown at the restaurant of your choice.

Day 5: Monday  After arising to a beautiful sunrise and hearty breakfast, we will weigh anchor and set sail for the enchanting island of Cuttyhunk.  This jewel of the Elizabethean Islands has one of the most picturesque harbors in all of New England.  The evening will find us on the beach for a real New England lobster bake, complete with all the trimmings.  (Lobster bake included.) 

 Day 6: Tuesday  We make a morning departure for our exhilarating sail back to Historic Newport, Rhode Island, the sailing capital of the world.  Enjoy the captain’s farewell brunch on your final day under Arabella’s billowing sails.

This is a sample itinerary.  All stops are subject to the captain’s discretion and may vary due to weather or unforeseen circumstances. 



Evening One: Rhode Island’s Sakonnet Vineyards, a fifty-acre vineyard featuring Chardonnay, Gewurztraminer, Pinot Noir, and Cabernet Franc, as well as Vidal Blanc one of the French-American hybrids, will be on board to present a selection of their finest vintages.  The vineyard’s wine production has climbed to over 50,000 cases annually with many wines receiving awards in domestic and international competitions.  For information, please visit

Evening Two: Chicama Vineyards on Martha’s Vineyard, was founded in 1971 by Catherine and George Mathiesen and their family and is the first bonded winery in the Commonwealth.  Chicama Vineyards features the first planting of European wine grapes in Massachusetts since colonial days.  The winery is now producing Hurricane Chardonney, Shiraz, Ondine (Viognier), Cranberry Satin and Sea Mist Methode Champenoise Sparkling Wine, among others.  For additional information, please visit

Evening Three: Nantucket Vineyard is a small winery located on Nantucket Island, MA, owned and operated by Dean and Melissa Long.  Nantucket Vineyards started selling wine in 1985 and since then has expanded its selection to about ten wines, including Semillon, Riesling, Pinot Gris, Chardonney, Zinfandel/Merlot blend, Zinfandel and Merlot. In addition to wines, Nantucket Vineyard also houses a whiskey distillery and brewery.  For additional information, please visit

Evening Four:  While in Edgartown, Martha’s Vineyard, Long Island wine expert Michael Cinque, owner of Amagansett Wines in the Hamptons, will be on board to talk about the evolution of Long Island wineries throughout the years and will host a tasting featuring top picks of current Long Island vintages.  For additional information on Long Island wines, please call Amagansett Wines at (631) 267-3939. 

Evening Five: Long Island Wine Expert Michael Cinque returns again to host another tasting and seminar on Long Island’s everyday whites and reds.   This evening’s tasting will take place on the beach on Cuttyhunk and will be followed by an authentic New England clambake.

*In addition, when booking the cruise, guests will have the option of reserving seats on evening two for a special prix fix Roederer Champagne tasting followed by dinner at Atria on Martha’s Vineyard.  Atria is one of the island’s premier fine-dining establishments and recently received an Award of Excellence by Wine Spectator magazine. 

*This is a sample itinerary---ports of call/vineyards are subject to change.

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