Classic New England beauty

New England’s charming coastlines and quaint towns make it ideal for summer vacation charters. Whether you want to get away for a long weekend or a full month, let Whisper and its crew help you plan and carry out a fully customized adventure.

Day One: Begin your New England charter adventure in historic Newport, Rhode Island. Take in the sights and sounds of Bowen’s and Bannister’s Wharves before meeting Captain Clive Youlten and crew on the waterfront nearby. Enjoy lunch, prepared by Whisper’s Chef Chris Deighan, while sailing south to Block Island for an overnight anchorage. Popular with summer tourists, the tiny island boasts a plethora of activities, including cycling, hiking, sailing and fishing. For dinner, don’t miss The Oar Restaurant, famous for its mudslides and clam cakes. 

Day Two: Take a trip into town for some shopping and exploring before cruising to Martha’s Vineyard, Massachusetts for an overnight anchorage. This famous island retreat attracts visitors from far and wide during the summer months with its charming features and friendly locals. Before a tasty dinner onboard Whisper, visit Oak Bluffs to check out its Gingerbread cottages and Edgartown to enjoy the many shops that line its streets. 

Day Three: See all that Martha’s Vineyard has to offer with one of the island’s famed bus tours before sailing over to Chappaquiddick Island, off the eastern end of Martha’s Vineyard, for an afternoon of fishing and swimming. For dinner, anchor in the harbor off Edgartown and head in for an island brewed pint and some live music at the Wharf Pub and Restaurant. 

Day Four: Catch the sunrise from Whisper as it sets sail to Nantucket, Massachusetts for the next overnight anchorage. Hop off the boat at Straight Wharf and head to lunch at Toppers at the Wauwinet Inn, which offers unforgettable local cuisine and scenic views of Nantucket Bay. Walk down the cobbled streets to the Whaling Museum for a full history of the island. After a sunset dining experience onboard Whisper, head back to land and take a taxi to the center of the island for live music and entertainment at the Chicken Box. 

Day Five: Spend the morning catching the rays at Brant Point beach before renting bikes and tracing the island’s many nooks and crannies, including the charming village of Siasconset on the eastern end of Nantucket. Finish the day with a plate of fresh seafood at the Brant Point Grille. 

Day Six: Wake up to the sound of halyards clinking against the mast as the crew prepares for its cruise back to Newport. After Whisper docks at the Newport Shipyard, spend the late afternoon perusing art galleries and boutiques in Brick Alley and on lower Thames Street before enjoying local oysters and other delicious fare at the Moorings Restaurant and Grill, which overlooks Newport Harbor. 

Day Seven: Spend your final day touring Ocean Drive and visiting the historic mansions on Bellevue before heading to Gooseberry Beach in the late afternoon for a beach barbecue. Interested in additional destinations and itineraries?