🚤 Martha's Vineyard Activity Spotlight: Cottage City Charters Private Boat Ride
Custom private charter experiences - an MVacay bucket list item!
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 outings. 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, a NorthCoast 235HT, 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.
🌊 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 no one in our group experienced motion sickness, even though we’d been a little worried beforehand.
Lou was 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!
🗒️ Visit Planning
📍 Pick-Up Locations: Oak Bluffs, Vineyard Haven, Edgartown, or Falmouth
⏰ Charter Duration: 2+ hours; fully customizable
💲 Rates: $495 for the first 2 hours / $100 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
Website: cottagecitycharters.com
📆 Charters run through October 2025 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.
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!
