When the summer sun graces the northeastern United States, New England’s coastline becomes one of the world’s most charming cruising grounds. Think historic harbors, shingled cottages, and lighthouses dotting rugged headlands. A New England yacht charter is equal parts coastal elegance and classic Americana: lobster pulled fresh from traps, cobblestone streets lined with boutiques, and breezy afternoons spent under sail.
This week-long, New England yacht charter itinerary blends iconic destinations like Nantucket and Martha’s Vineyard with hidden coves and postcard-worthy seaside towns. It’s the perfect mix of refinement, nostalgia, and seafaring adventure.
Day 1: Newport, Rhode Island – Gateway to New England Yachting
Begin your journey in Newport, a historic hub of sailing and luxury. After boarding your yacht at Newport Harbor, take a leisurely stroll along Bannister’s Wharf and Thames Street, where boutiques and galleries buzz with summer life.
For a taste of Newport’s grandeur, tour one of the famed Gilded Age mansions like The Breakers before returning to the yacht for your first dinner on deck. As the sun sets behind the Newport Bridge, the harbor comes alive with twinkling lights — the perfect send-off to your voyage.
Day 2: Block Island – Untouched Beauty
A short cruise brings you to Block Island, often called New England’s best-kept secret. Anchor off Crescent Beach and tender ashore to explore the island by bike or moped. Mohegan Bluffs, with its dramatic cliffs and sweeping ocean views, makes for an unforgettable stop.
Lunch can be a picnic on the beach, followed by paddleboarding in the calm shallows. In the evening, enjoy a casual lobster bake on deck or head ashore to a local seafood shack for fried clams and chowder.
Day 3: Martha’s Vineyard – Coastal Sophistication
Sail east to Martha’s Vineyard, a storied island with a mix of laid-back charm and upscale appeal. Dock at Vineyard Haven or Edgartown, where white clapboard houses and historic lighthouses set the scene.
Spend the day exploring by bicycle or jeep, from the colorful cottages of Oak Bluffs to the windswept cliffs of Aquinnah. Vineyard boutiques and art galleries make for relaxed browsing, while your crew stocks up on fresh island produce and oysters for dinner. Evening cocktails on deck pair beautifully with a Vineyard sunset.
Day 4: Nantucket – Whaling History and Island Luxury
A short sail from Martha’s Vineyard brings you to Nantucket, a picture-perfect island once known as the whaling capital of the world. Today, it’s a blend of cobblestone streets, upscale shops, and serene beaches.
Start with a visit to the Whaling Museum for a dose of history, then wander through town, where flower boxes spill over with blooms. For lunch, enjoy a beach picnic with lobster rolls and local craft beer. The afternoon is perfect for kite flying on Jetties Beach or paddleboarding in sheltered harbors.
Dinner ashore at one of Nantucket’s fine-dining restaurants caps off the day, before returning to your yacht for stargazing in the quiet anchorage.
Day 5: Cape Cod – Sandy Shores and Seaside Towns
From Nantucket, set a course toward Cape Cod. Anchor off Provincetown, a vibrant town known for its art scene, sandy dunes, and eclectic energy. Spend the morning whale watching or wandering Commercial Street’s galleries and cafés.
Alternatively, visit Chatham or Hyannis for a more relaxed slice of Cape life — think saltwater taffy, old-fashioned ice cream shops, and classic Cape Cod cottages. Dinner might feature freshly shucked Wellfleet oysters and a glass of chilled Sauvignon Blanc, enjoyed as your yacht sways gently in the harbor.
Day 6: Cuttyhunk Island – A Step Back in Time
For a quieter pace, cruise to Cuttyhunk Island, part of the Elizabeth Islands chain. This small, car-free island offers tranquility unlike anywhere else on the route. Spend the day walking scenic trails, birdwatching, or simply enjoying the stillness of a secluded anchorage.
Local fishermen often sell lobster and shellfish right from their boats, perfect for a casual deckside feast. With little nightlife and few distractions, Cuttyhunk invites you to slow down and savor the simple joys of yacht life.
Day 7: Return to Newport – A Classic Finale
On your final day, cruise back to Newport, enjoying a leisurely breakfast underway. If time allows, stop for a last swim or paddleboard session in Narragansett Bay. Back in Newport Harbor, bid farewell to your crew and take one last stroll along the waterfront before heading home.
Insider Tips: Chartering in New England
- Season: The best time for New England charters is June through September, with July and August offering the warmest weather.
- Provisioning: Newport and Martha’s Vineyard are excellent provisioning hubs, with gourmet shops and local farmers’ markets.
- Activities: Whale watching off Cape Cod, biking on Martha’s Vineyard, and exploring Nantucket’s cobblestone streets are all highlights.
- Weather: Summer brings warm days and cool evenings. A light sweater is essential for breezy nights on deck.
Wrapping Up: The Charm of New England at Sea
A New England yacht charter blends elegance and nostalgia with seaside adventure. Each stop along the route offers its own character — from the sophistication of Martha’s Vineyard to the raw beauty of Block Island and the timeless allure of Nantucket.
At sea, the experience takes on a rhythm of its own: mornings with coffee on deck, afternoons filled with swimming or exploring, evenings spent with lobster dinners under the stars. In just a week, you’ll rediscover the simple pleasures of summer by the sea — elevated by the comfort and freedom that only a private yacht charter can provide.
