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Cuttyhunk Fishing Club offers a charming seaside breakfast experience with classic American dishes served on a veranda overlooking the harbor, blending historic island ambiance with fresh, hearty meals. Its scenic views and cozy atmosphere make it a must-visit on Cuttyhunk Island.
Cuttyhunk Raw Bar offers fresh, locally harvested oysters, clams, and classic New England seafood like chowder, served right at the fishing dock or delivered to your boat for a laid-back island dining experience. Enjoy the unique flavors of Cuttyhunk in a casual, waterside setting.
Cuttyhunk Lobster Shack offers fresh, classic seafood like steamed lobster and clams in a casual, seaside setting right by the fishing dock—perfect for enjoying a relaxed meal on the island or taking it back to your boat.
Soprano's Pizza serves delicious, high-quality pizzas with fresh ingredients and fast delivery, offering a variety of options including gluten-free and vegan choices in a friendly, casual setting. It's a local favorite known for great taste and excellent service.
Penikese Island offers a rare blend of serene hiking, exceptional birdwatching with over 150 species, and vibrant snorkeling in pristine waters, perfect for nature lovers and adventurous explorers seeking a unique New England island experience.
Cuttyhunk Pond Docks offer a peaceful spot for boating enthusiasts and nature lovers to launch kayaks, fish, or simply enjoy the scenic harbor views. It’s perfect for those seeking a relaxing water adventure amid the island’s charming, historic setting.
Lookout Park offers breathtaking panoramic views from high atop Lookout Mountain, where you can see up to seven states on a clear day—perfect for families, photographers, and anyone who loves natural beauty and a bit of adventure. Its scenic overlooks and unique rock formations make it a memorable stop for all ages.
Step into the heart of Cuttyhunk’s past at the Historical Society, where fascinating exhibits and island stories bring local heritage to life—perfect for curious travelers and history lovers eager to connect with the unique culture and maritime legacy of this charming island community.
Peak Chum Mountain offers a rewarding hike with stunning panoramic views, perfect for outdoor enthusiasts who enjoy a mix of challenging trails and natural beauty. It’s ideal for hikers seeking a peaceful mountain escape with impressive scenery.
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Nov 17, 2025 | $400 | Available |
| Nov 18, 2025 | $400 | Available |
| Nov 19, 2025 | $400 | Available |
| Nov 20, 2025 | $400 | Available |
| Nov 21, 2025 | $527 | Available |
| Nov 22, 2025 | $527 | Available |
| Nov 23, 2025 | $527 | Available |
| Nov 24, 2025 | $527 | Available |
| Nov 25, 2025 | $527 | Available |
| Nov 26, 2025 | $527 | Available |
| Nov 27, 2025 | $527 | Available |
| Nov 28, 2025 | $533 | Available |
| Nov 29, 2025 | $533 | Available |
| Nov 30, 2025 | $533 | Available |
| Dec 1, 2025 | $400 | Available |
| Dec 2, 2025 | $400 | Available |
| Dec 3, 2025 | $400 | Available |
| Dec 4, 2025 | $400 | Available |
| Dec 5, 2025 | $507 | Available |
| Dec 6, 2025 | $514 | Available |
| Dec 7, 2025 | $400 | Available |
| Dec 8, 2025 | $400 | Available |
| Dec 9, 2025 | $400 | Available |
| Dec 10, 2025 | $400 | Available |
| Dec 11, 2025 | $400 | Available |
| Dec 12, 2025 | $533 | Available |
| Dec 13, 2025 | $540 | Available |
| Dec 14, 2025 | $400 | Available |
| Dec 15, 2025 | $400 | Available |
| Dec 16, 2025 | $400 | Available |
| Dec 17, 2025 | $400 | Available |
| Dec 18, 2025 | $400 | Available |
| Dec 19, 2025 | $579 | Available |
| Dec 20, 2025 | $878 | Available |
| Dec 21, 2025 | $878 | Available |
| Dec 22, 2025 | $884 | Available |
| Dec 23, 2025 | $891 | Available |
| Dec 24, 2025 | $897 | Available |
| Dec 25, 2025 | $904 | Available |
| Dec 26, 2025 | $910 | Available |
| Dec 27, 2025 | $910 | Available |
| Dec 28, 2025 | $917 | Available |
| Dec 29, 2025 | $917 | Available |
| Dec 30, 2025 | $923 | Available |
| Dec 31, 2025 | $923 | Available |
| Jan 1, 2026 | $858 | Available |
| Jan 2, 2026 | $858 | Available |
| Jan 3, 2026 | $858 | Available |
| Jan 4, 2026 | $446 | Available |
| Jan 5, 2026 | $446 | Available |
| Jan 6, 2026 | $446 | Available |
| Jan 7, 2026 | $446 | Available |
| Jan 8, 2026 | $446 | Available |
| Jan 9, 2026 | $600 | Available |
| Jan 10, 2026 | $600 | Available |
| Jan 11, 2026 | $450 | Available |
| Jan 12, 2026 | $450 | Available |
| Jan 13, 2026 | $450 | Available |
| Jan 14, 2026 | $450 | Available |
| Jan 15, 2026 | $450 | Available |
| Jan 16, 2026 | $690 | Available |
| Jan 17, 2026 | $690 | Available |
| Jan 18, 2026 | $690 | Available |
| Jan 19, 2026 | $690 | Available |
| Jan 20, 2026 | $450 | Available |
| Jan 21, 2026 | $450 | Available |
| Jan 22, 2026 | $450 | Available |
| Jan 23, 2026 | $600 | Available |
| Jan 24, 2026 | $600 | Available |
| Jan 25, 2026 | $450 | Available |
| Jan 26, 2026 | $450 | Available |
| Jan 27, 2026 | $450 | Available |
| Jan 28, 2026 | $450 | Available |
| Jan 29, 2026 | $450 | Available |
| Jan 30, 2026 | $600 | Available |
| Jan 31, 2026 | $600 | Available |
| Feb 1, 2026 | $450 | Available |
| Feb 2, 2026 | $450 | Available |
| Feb 3, 2026 | $450 | Available |
| Feb 4, 2026 | $450 | Available |
| Feb 5, 2026 | $450 | Available |
| Feb 6, 2026 | $600 | Available |
| Feb 7, 2026 | $600 | Available |
| Feb 8, 2026 | $450 | Available |
| Feb 9, 2026 | $450 | Available |
| Feb 10, 2026 | $450 | Available |
| Feb 11, 2026 | $450 | Available |
| Feb 12, 2026 | $450 | Available |
| Feb 13, 2026 | $690 | Available |
| Feb 14, 2026 | $690 | Available |
| Feb 15, 2026 | $690 | Not Available |