Coastal Cruising Experience - 100NM /5 Days
AVAILABLE: 2 Cabins
Boat: Tiger Lily
Crew: Phoebe & Xander
Price: $7,050 per cabin
Details:
Slip into summer the New England way, sailing from Newport, RI through classic cruising grounds like Martha’s Vineyard, Woods Hole, and Cuttyhunk. For five days you’ll live aboard a modern performance catamaran, hop between postcard-perfect harbors, swim off the stern, and savor long golden evenings on the hook. This trip is about ease and exploration: short sails, beautiful anchorages, and time to enjoy the simple pleasures of life on the water.
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This is relaxed coastal cruising with just the right amount of hands-on sailing. Help raise sails, take the helm when you like, and then settle into deck life with coffee at sunrise, swims in calm coves, walks ashore, and dinners under the stars.
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We choose our itinerary based on the weather, but expect daily sailing activities and excursions from one picturesque anchorage to another. Your five-day journey highlights include:
Newport Harbor: Historic sailing town and our home port
Hadley Harbor (Naushon Island): Serene, protected anchorage surrounded by nature
Martha’s Vineyard (Vineyard Haven or Oak Bluffs): Classic island charm, colorful streets, and cafés ashore
Woods Hole: Picturesque village and gateway to the Vineyard Sound
Cuttyhunk Island: Peaceful, remote harbor with sweeping views and fresh shellfish from the dock
Buzzards Bay: Open sailing with steady summer breezes and scenic coastlines
Each anchorage offers its own mix of exploration and relaxation with plenty of time to swim, paddleboard, or simply unwind.
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Warm days and reliable sea breezes are the norm. Expect highs around 75–82°F (24–28°C) with comfortable evenings. Afternoon southwesterlies often build to 10–18 knots, perfect for fun, fast coastal sails. Water temps are typically in the 70s°F (20–22°C) so refreshing swims are encouraged. Pack light layers for cooler evenings and the occasional foggy morning.
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Dinghy pickup and drop-off in Newport Harbor.
The nearest major airports are Providence (PVD) and Boston (BOS)
Please book local accommodations for the evening prior to and after our planned departure / arrival. Flexible bookings are always preferred, though we do our best to depart and arrive on schedule.
You have the option to spend the night onboard before and/or after, if you wish. This includes dinner and a light breakfast, with arrival after 4pm, and departure at 9am for $400 / night.
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Our prices are all-inclusive once aboard, covering meals, snacks, refreshments, evening sundowners, and mooring or docking fees. Not included: Transportation to/from the program and meals/drinks ashore.
Private Double Cabin - $7,050*
*Price per cabin, which may accommodate one or two persons.Cabins Currently Available - 2
Click ‘Book Now’ and fill out a submission form. We will get back to you with an invoice to reserve your cabin. After booking, we will send you more information about the passage including details on what to expect on your stay aboard, boat details, packing, etc. If you have any questions, don’t hesitate to Contact Us! Or, maybe your questions are answered elsewhere? Check out our FAQ’s!