✅ MVacay's Martha's Vineyard Trip Planning Checklist
A reallyyyyy simple checklist for first-time visitors
This checklist breaks down planning your first trip to MV step by step using only MVacay’s guides. No clutter from Pinterest, Google, or outdated saved TikToks.
When you’re ready to book, just sit down with this list, ChatGPT, and plan the best vacay ever.
Edited with new additions in April 2026!
Let’s do it:
🧳 Big Picture Planning
🚗 Decide How You’ll Get Here
Fly, drive to Woods Hole, or walk onto a ferry? Figure this out first.
→ How to Get to MV Guide📅 Check Ferry Availability (if bringing a car)
Planning to bring a vehicle? Book with Steamship Authority ASAP.
→ Ferry Tips🏨 Pick Where to Stay
Choose your town based on vibe: Edgartown = charming, Oak Bluffs = fun, Vineyard Haven = convenient.🚙 Choose On-Island Transportation
Will you need to rent a car, rely on bikes, or stick to walking and Uber?
→ How to Get Around MV Guide
🎟️ Plan Activities + Meals
🧺 Book Dining Experiences
Reserve ahead for farm dinners, cheese tastings, oyster tours, or fine dining options.
→ BIG Dining Guide, Local’s Favorite Food, Places to Make Reservations🎨 Sign Up for Classes or Workshops
Art, cooking, farming, or seasonal one-offs.
→ Adult Classes Guide🎣 Plan Outdoor Adventures
Kayaking, fishing, hiking, and beach time.
→ Beach Guide, Fishing Guide, Hikes🗺️ Use Itineraries by Town or Theme
Find recs for rainy days, day trips, and more.
→ Itineraries Page🎟️ Browse Upcoming Events
Weekend lineups, festivals, and local happenings.
→ Weekend Update Archive / 2026 Save the Dates🐚 Make a Bucket List
Save your top picks and must-do experiences.
→ MV Bucket List Post
💡 MVacay’s Pro Tips
Tick Preparedness
Bring your own tick repellant, plan to do tick checks while here, stay on paths.
→ Tick 101 and Tick Spray LinksGrocery Planning
Plan to bring as many dry goods with you as possible to save money, and then shop local at farmstands for produce, or hit Stop and Shop for meat and dairy on arrival. Or order Ahead of Arrival for provisions.
→ Groceries and Markets of MVCheck What’s New for 2026
If you’re an annual visitor get a sneak peek of what is different this year
Family Friendly Guide
If you’re coming with kids of any age, download the PDF Family Guide!
📲 While You Travel
📲 Follow @mvacay on Instagram
Real-time updates and insider tips.🔗 Bookmark MVacay.com
One-click access to events, guides, and new posts.🌟 Subscribe to the Newsletter
Get weekly recs, seasonal bucket lists and event roundups in your inbox.
💬 Pro Tip: Use ChatGPT to Help Plan Your Itinerary
I have 300+ Guides on MVacay.com and this can feel like a lot. My personal cheat code? Try using a ChatGPT prompt to create a custom itinerary using MVacay.com resources. It's a great way to organize your ideas and get suggestions tailored to your trip.
Here are a few prompt examples to get started:
“Plan a 3-day Martha’s Vineyard trip June 19-21 using MVacay.com with beach time, good seafood, a farmer’s market, and one unique class or tour each day. We have access to a car.”
“Create a rainy day itinerary for a couple visiting MV in May using MVacay.com bucket list items. Ask me clarifying questions for which types of attractions I’m interested in. We are staying in Vineyard Haven.”
“Using MVacay.com, what should I do for one full day in Oak Bluffs without a car?”
“Make a Martha’s Vineyard itinerary for a bachelorette group that includes live music, shopping, and drinks. Use MVacay.com’s bachelorette guides as a basis and tailor them for late August.”
You can copy and paste one of these into ChatGPT or tweak them to match your group’s interests.
Happy Planning!
-Lis
