💍 Guide to Getting Engaged on Martha's Vineyard
tips for planning a proposal, top location picks for MV in 2025
I want to help YOU plan a magical Martha's Vineyard proposal! I called in help from a few local experts 😉 so you can plan an engagement that's as unique as you and your fiancé-to-be. This guide shares the best spots and insider tips from four amazing island photographers/planners who capture hundreds of special moments each year.
Of course I have my own MV engagement story! In 2020, my now-husband planned an intimate proposal at my family's home in Oak Bluffs, followed by celebratory photos at West Chop. It was a private moment somewhere beautiful and meaningful to us, so don’t let this guide convince you that you have to do anything flashy if that isn’t authentic to you. That's what makes Vineyard proposals so special - they can include both private moments and stunning photo opportunities.
📍 Best Locations for a Vineyard Proposal
Island photographers have captured hundreds of "yes!" moments and know exactly where to find that perfect mix of scenery, privacy, and personal connection for your proposal.
Aquinnah Cliffs & Moshup Beach – Dramatic backdrop, golden hour magic
"I absolutely love capturing surprise engagement proposals on the beach in Aquinnah, especially during the golden hour. The soft, warm light creates a magical atmosphere, perfectly complementing the stunning backdrop of the iconic clay cliffs." – Angelina from AnicaBanica Photography
Edgartown Lighthouse – Classic, accessible, near dining and celebrations
"During the summer, the Edgartown Lighthouse remains a classic choice, offering a variety of stunning backdrops. After the session, many Edgartown restaurants are just a short walk away, making it easy to continue the celebration with dinner and drinks." – David Welch from David Welch Photography
Menemsha Beach – Iconic sunset spot, lots of nautical scenery
Lambert’s Cove Beach & Sheriff’s Meadow Sanctuary – Quiet, scenic, and intimate
"I try to stay away from the popular go-to spots on the island and have a conversation with my couples to see what spots are meaningful for them, or if they have memories that we can recreate." – Larisa Stinga from Larisa Stinga Photography
On the Water or Near a Lighthouse – Private sailboat or catboat charter
"Some of my most remarkable sessions near the lighthouse included capturing proposals atop the lighthouse itself or photographing and droning a proposal aboard the iconic catboat charter as it returned to the harbor." – David Welch
🎉 How to Make the Proposal Special
Creating a magical proposal moment goes beyond just picking a beautiful location — here's how to add those personal elements that make the moment feel completely authentic to your relationship.
📸 Hire a Photographer to Capture the Moment
Plan a surprise proposal with a professional photographer, and for their expertise.
Be sure to book early because top photographers fill up early.
Spring and fall proposals offer increased likelihood that you have an empty beach.
Consider the best times for lighting (sunrise and sunset)
🌿 Plan a Picnic
Juliana from MV Picnics specializes in custom setups at the location of your choosing, and she has a ton of experience with surprises too. Imagine an elaborate spread with champagne, flowers, and personalized touches—all arranged before you arrive.
🎶 Add a Personal Touch
Include shared pastimes like biking or visiting a favorite spot
“I try to stay away of the popular go to spots on the island and have a conversation with my couples and see what spots are meaningful for them, or if they have memories that we can recreate.” - Larisa Stinga
Think beyond the basics by incorporating meaningful elements that tell your unique story—whether that's a playlist of your favorite songs, involving family members, or bringing special mementos to the proposal.
"Last summer I helped a client plan an engagement shoot in August at the summit lookout area by the shops. The day turned out perfect…The soon-to-be groom had his mom, dad, and sister give the soon-to-be bride a stone with a message as she walked to the top of the hill. John Legend's 'All Of Me' played as they neared the top steps. I stood in the corner facing the lighthouse, pretending to sightsee as a tourist, hiding the small banner saying 'Marry Me' in the corner. After the groom proposed, we continued our session on Moshup Beach and captured the sunset while they both danced in celebration." – Kye Howell from So Focused Photography
🍽️ Extend the Engagement Celebration
Romantic Dinners: Many Vineyard restaurants will go above and beyond for an engagement dinner, be sure to coordinate prior to your evening. Be sure to book early as reservations are tricky in July and August.
Romantic Hotels: Our top picks for places would be: Nobnocket, Edgartown Collection, Hob Knob and Harbor View Hotel
A Full Itinerary: Make it a full weekend experience - plan a romantic weekend around the proposal - here’s a sample itinerary if you need inspo.
💍 Engagement Planning Checklist
✅ 3+ Months Before
Coordinate with a photographer (book early, especially for summer weekends)
Pick a location with the photographer and discuss logistics
Book travel and accommodations if you’re visiting from off-island
✅ 2 Months Before
Finalize a rain plan (indoor alternative, reschedule backup date)
Plan any special touches (music, family involvement, surprise elements)
✅ 1 Month Before
Make dinner reservations at a restaurant
Arrange for any proposal accessories (champagne, flowers, personalized gifts)
✅ Day Of / Week Of Proposal
Relax, take a deep breath, and enjoy the moment!
Congratulations on your engagement-to-be!
And a special thank you to David, Larisa, Kye and Angelina for their contributions to this article!
