The Best Sailing Destinations Near Narragansett Bay

While Narragansett Bay offers some of the best sailing conditions in the world, the real magic happens when you venture beyond the bay. Whether you’re looking for a weekend getaway or a longer coastal cruise, Southern New England is filled with incredible sailing destinations, each offering its own unique charm. From quaint harbors to offshore islands, here’s a guide to some of the best places to sail from Narragansett Bay.

As with any of these destinations, try to strategize around the wind if possible. Take advantage of the variations from the prevailing SW wind to time a return leg for example.

1. Block Island – The Classic Offshore Escape

Just 12 miles south of Newport, Block Island is the perfect destination for a quick offshore adventure. Whenever we get a break from the prevailing SW, consider the block! You are sure to get a nice SW to ride back home.

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Once you arrive, you’ll find:

🌊 Great Salt Pond – A well-protected anchorage with plenty of room for mooring or anchoring.
🏝️ Pristine Beaches – Some of the most beautiful, undeveloped beaches in New England.
🍽️ Lively Island Culture – From dockside dining at The Oar to exploring the charming town of New Shoreham.

2. Cuttyhunk Island – A Peaceful Retreat in the Elizabeth Islands

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Nestled at the westernmost tip of the Elizabeth Islands, Cuttyhunk is a must-visit stop for sailors looking for a quiet, unspoiled getaway. Just a short sail from Buzzards Bay, it offers a tranquil escape from the busier harbors of Martha’s Vineyard and Nantucket.

⚓ Cuttyhunk Harbor – A well-protected anchorage with moorings available and a small marina for docking.
🌅 Spectacular Views – Hike to Lookout Hill for panoramic vistas of Buzzards Bay and Vineyard Sound.
🦞 Famous Dockside Raw Bar – Enjoy fresh oysters and lobsters delivered right to your boat by the local raw bar service.
🌊 Old-World Simplicity – With no major resorts or tourist traps, Cuttyhunk feels like stepping back in time, making it a perfect spot for relaxation and stargazing.

A visit to Cuttyhunk is all about slowing down, enjoying nature, and embracing the simplicity of island life—a perfect contrast to Newport’s vibrant sailing scene.

Would you like to add navigation tips for approaching Cuttyhunk, or details on the best places to anchor? Let’s make this guide as complete as possible! ⛵✨

3. Martha’s Vineyard – Iconic New England Cruising

A bit farther east, Martha’s Vineyard is a New England sailing gem, offering both bustling harbors and secluded anchorages.

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Our Route from Cuttyhunk to Edgartown

⚓ Vineyard Haven – A protected harbor with great provisioning, restaurants, and classic wooden boats.
🌅 Edgartown – A picturesque town with elegant historic homes, world-class dining, and a vibrant sailing culture.

🌊 Menemsha – A quiet fishing village with stunning sunsets and fresh seafood right off the docks.

4. Quissett & Red Brook – Hidden Harbors on Buzzards Bay

Sailing east from Newport, Buzzards Bay offers some of the best-kept secret harbors in the region.

⛵ Quissett Harbor – A charming, well-sheltered cove near Woods Hole, known for its scenic walking trails and calm moorings.

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If you get bored with the simple serenity of Quissett harbor, just dinghy ashore, walk a couple blocks and get the trolly (or an uber) to Woods Hole. There you will find Museums, Art Galleries, Beautify scenery and great food.

⚓ Red Brook Harbor – A favorite stopping point for those heading toward the Cape Cod Canal, with excellent protection from all wind directions and a great meal at The Chart Room.

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Red Brook is one of our very favorite destinations. Anchor behind Bassetts Island or rent a mooring. Red Brook has some skinny water on the way in. Choose your route around Bassetts Island (north or south channel). They are both shallow and windy – watch the buoys! We draw 6 feet and have made it in and out at low tide with a couple feet to spare. The anchorage behind Bassetts Island is shallow. You’ll be in about 10 feet at low tide. Holding is fantastic in clean sand. The swimming here is amazing. In August, the water is almost too warm.

5. Through the Canal: Provincetown & Plymouth

For those looking to venture farther north, passing through the Cape Cod Canal opens up an entirely new cruising ground.

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🏖️ Provincetown – At the tip of Cape Cod, P-Town is an amazing sailing destination with a welcoming harbor, art-filled streets, and fantastic seafood.

⚓ Plymouth – A historic harbor with deep colonial roots, excellent marinas, and easy access to Boston’s sailing grounds.

Plan Your Next Sailing Adventure

With so many incredible destinations just a day’s sail from Narragansett Bay, it’s easy to see why Newport is one of the best home ports for cruising sailors. Whether you’re seeking quiet anchorages, lively harbors, or offshore challenges, the options are endless.

Want to learn more about sailing these waters? Visit allhandssailing.com for local sailing guides, route planning tips, and firsthand cruising experiences.