🚤 Martha's Vineyard Activity Spotlight: Cottage City Charters Private Boat Ride
Custom private charter excursions - an MVacay bucket list item! Updated for 2026
Every summer I’m eager to get out on the water, and we recently experienced a private boat ride with Cottage City Charters. I chose them because they could customize every detail to make it toddler-friendly for our two little ones. It was the perfect way to dip our toes into boating with kids. The calm, safe ride is now one of my top recommendations for families or groups looking to get out on the water.
Here’s everything to know if you’re thinking about planning your own ride:
🎖️ About Cottage City Charters
Captain Lou, a year-round islander with over 30 years of experience sailing Vineyard and Nantucket Sound, runs Cottage City Charters with a focus on safe, scenic, and fully personalized boat excursions. You can book a romantic sunset cruise, a special celebration, or a laid-back day trip—Lou makes it easy to tailor the experience to your group.
The boat is designed for comfort and stability with open-air seating and a dry cabin. Charters can depart from Oak Bluffs, Edgartown, Vineyard Haven, or Falmouth. If your group is larger than six, Lou can coordinate with other licensed local captains to arrange a multi-boat experience. He recentlyhad trips to Nantucket, Cuttyhunk, Naushon/Elizabeth Islands, and Newport RI.
🌊 The Boat Experience
We rode with Captain Lou on a dreamy, hazy June evening. Our 90-minute charter from Vineyard Haven to Oak Bluffs was the perfect introduction to boating with toddlers. The pace was slow and peaceful—gentle enough that my kids (and mom!) felt safe, and he was able to adapt to a slower pace.
Lou is warm, knowledgeable, and instantly put us at ease. He had cold waters ready, a cooler for anything we brought, and was happy to answer our questions about the island while adjusting the route to match our preferences. The views of East Chop in the early summer haze were absolutely stunning, and the whole ride felt relaxed and personal. We’ll definitely be back for a longer trip next time!
The boat itself is a 31 feet long 2024 Northcoast pilot house boat with tons of storage in the V berth in the bow. The sizeable pilot house in the middle of the boat provides protection from weather. It has a large open stern with plenty of seating, two 250 horsepower Yamaha outboard motors and a private bathroom. While Lou is not a hard core fishing charter, he has plenty of gear and is happy to include fishing into a broader family charter experience.
🗒️ Visit Planning
📍 Pick-Up Locations: Oak Bluffs, Vineyard Haven, Edgartown, or Falmouth
⏰ Charter Duration: 2+ hours; fully customizable
💲 Rates: $595 for the first 2 hours / $125 for each additional 30 minutes
(Max 6 passengers; larger group coordination available upon request)🧺 What’s Included: Bottled water, Coast Guard-approved life jackets, onboard restroom, cooler, Bluetooth speaker. Food and drink arrangements available upon request.
📞 Booking & Inquiries:
Text or call 781-718-1483
Email: info@cottagecitycharters.com
Social Media: @cottagecitycharters
Website: cottagecitycharters.com
📆 Charters run through October 2026 and require a 25% deposit to book. Final payment is due three days before your sail. Weather cancellations are fully refunded at the captain’s discretion. Mention MVacay when you book!
Lou’s Upgraded Boat for 2026
Pro Tip: Be sure to ask Captain Lou about his Ginger Bread house on Oak Bluffs Harbor (where he visited his grandmother as a kid) as he’s been known to offer charter clients a tour! You might also ask about his home made limoncello hobby!
