Five-Night Itinerary*:

Day One: Board Arabella in the historic harbor of downtown Newport promptly at 4pm (luggage will be accepted at 2pm). A welcoming Smuggler's Cocktail Cruise aboard our 1929 Elco Prohibition Era Motor yacht, the Rum Runner II, will be the perfect sunset cruise, followed by dinner at your choice of Newport's more than fifty wonderful restaurants.

Day Two: A 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 Three: 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. Anchoring amongst the racing fleet in the harbor, Arabella will be the host of a VIP cocktail party to benefit the Nantucket Sailing Center. That evening go ashore for dinner at any of Nantucket's gourmet restaurants and enjoy the varied nightlife.

Day Four: Today is the exciting Opera House Cup race, one of the largest classic wooden sailboat races on the East Coast. Arabella is the privileged Spectator Boat with VIP guests and press joining us aboard to watch the racing. After the racing Arabella returns to the anchorage and brings guest in to enjoy the famed Regatta Party on Jetties Beach, or dine on your own in Nantucket if you didn't get your fill at the regatta party.

Day Five: 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 shore for a real New England Lobster Boil, complete with all the trimmings. (Lobster boil included.)

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

*All stops are subject to the captain’s discretion and may vary due to weather or unforeseen circumstances.