Five-Night Itinerary*:

Day One: 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 Runner II, followed by dinner at your choice of Newport's more than fifty wonderful restaurants.

Day Two: 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 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. That evening go ashore for dinner at any of Nantucket's gourmet restaurants and enjoy the varied nightlife.

Day Four: 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 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 beach 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 captain’s farewell brunch on your final day under Arabella’s billowing sails.

For the Opera House Cup Regatta and Celebrations Cruise

August 14-19th,  Call for Details!

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