Sail Watch Hill on Classic Yachts — Morning, Sunset & Private Charters

Sail Trim Again — Classic Yacht Sails and Private Charters in Westerly, Rhode Island

Sail Trim Again offers private sailing and motor-yacht experiences in Watch Hill and Fishers Island Sound, departing from Westerly, Rhode Island. With two classic vessels — the wooden yacht TRIM AGAIN and the historic motor yacht ENCORE — the company provides a variety of sails, sunset cruises, and multi-hour sightseeing tours designed for couples, families, and small groups.

Popular Trips and What to Expect

• Sail "TRIM AGAIN": Morning Glory, Afternoon Delight, Sea Breeze Sail — Relaxing wooden-yacht sails ideal for beginners and seasoned sailors, focusing on calm waters and coastal scenery.
• "ENCORE" Spectacular Sunset Cruise (2 Hours) — Private two-hour charter on Fishers Island Sound with a complimentary bottle of sparkling wine; perfect for engagements and anniversaries.
• Sail "TRIM AGAIN" Romantic Sunset — Intimate sunset sails on a classic wooden yacht, suited for romantic evenings and special family moments.
• "ENCORE" Two Hour, Three State Sightseeing, Historical & Wildlife Tour — A two-hour coastal tour highlighting Watch Hill, Stonington, and Fishers Island with wildlife viewing and local history narration.
• "ENCORE" 3HR Tri-State Historical Tour + Lunch @ Seaside Clam Lobster Shack — Extended three-hour tour with a lunch stop at a local seaside clam and lobster shack for a regional dining experience.

Why Choose Sail Trim Again

• Classic vessels: TRIM AGAIN is a wooden yacht offering traditional sailing ambiance; ENCORE is a historic motor yacht with storied past uses.
• Private charters: All sails and tours are private, tailored to the group’s schedule and occasion, from morning sails to sunset celebrations.
• Local coastal expertise: Routes focus on Watch Hill, Stonington, and Fishers Island — prime spots for lighthouses, mansions, and wildlife.

Planning Tips and Keywords for Search

When searching for the right experience, use targeted phrases that match offerings:

• "Watch Hill sailing charters"
• "Westerly Rhode Island sunset cruise"
• "private yacht charter Fishers Island Sound"
• "classic wooden yacht sail TRIM AGAIN"
• "ENCORE sightseeing tour Watch Hill Stonington"

What to Bring

• Light jacket for sea breezes
• Camera for coastal photography
• Comfortable footwear
• Any special items for celebrations (flowers, small gifts)

Booking and Occasions

Sail Trim Again accommodates a range of occasions: romantic sunsets, family outings, proposed engagements, anniversaries, and history-focused coastal tours. The two-hour and three-hour ENCORE options are ideal for sightseeing and regional meals, while TRIM AGAIN offers classic sailing ambiance for shorter or romantic sails.

For travelers seeking private, scenic, and historically minded boat experiences in Westerly, Rhode Island, Sail Trim Again represents a focused choice for traditional wooden-yacht sails and historic motor-yacht charters on Fishers Island Sound.