There’s something inherently romantic about an island getaway, whether it’s to a tropical destination with turquoise water and waving palm trees or the shores of Martha’s Vineyard, where our windswept dunes, towering lighthouses, and gingerbread cottages dot the coastline. Untethered to the mainland, you and your sweetheart can unplug and reconnect.
To help you plan a perfect Martha’s Vineyard couple’s getaway, we’re bringing you our top romantic activities and ideas from sunset tours and luxury dining to simple moments and everything in between. Check them out and add a few to your itinerary.
In This Article:
- Fun on the Water
- Activities for Outdoorsy Couples
- Day-Dates and Sightseeing
- Romantic Restaurants with a View
- Best Vacation Rentals for Couples
Water Activities Perfect for Two
You can’t come to an island and expect not to spend time on or in the water. Visits in early spring may be too cold for much splashing, but summer sun warms the water, especially in areas near the Vineyard Sound, making beach days perfect for you and your love.
Pack a bag and a cooler with snacks, drinks, towels, and maybe your favorite books, and enjoy relaxing on the soft sand. Your only responsibility? Reapplying sunscreen as you bask in the joy of doing absolutely nothing.
For couples who want to do more than go to the beach, boat tours and sailing lessons are a local highlight. Here are our top picks:
The Black Dog Tall Ships Day or Sunset Sails – Assist the crew with raising the sail and then settle in for a stunning, scenic tour through some of the best sailing waters in the world.
- 3-hour tour
- Refreshments provided (BYOB picnics also allowed)
- Departs from Black Dog Wharf
- $100 per adult
Sailing Lessons from Wind’s Up – Even if you’ve never been on a sailboat before, the instructors will help you hone new skills and get your sea legs with a one- or two-hour lesson.
- Private One-Hour Lesson for Two: $200
- Options for Beginner, Intermediate, and Advanced
- Location: 199 Beach Road, Vineyard Haven, MA
Beyond lessons, Wind’s Up also rents paddleboards, kiteboards, kayaks, and other watersports equipment. If sailing isn’t your thing, you can still enjoy plenty of fun on the water during your couple’s getaway.
Ready to Secure Your Couple’s Getaway? Browse Sandcastle Realty’s Full Inventory and find your dream home-away-from-home.
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Activities for Outdoorsy Couples on Martha’s Vineyard
When you want to trade the sand and water for some dry-land activities, Martha’s Vineyard doesn’t disappoint. Spend a day or two out in nature at local preserves, hike through coastal trails, go horseback riding, or take a bike out along a wooded path. For outdoorsy couples, the options are limitless.
Wildlife Sightings:
- Cedar Tree Neck Sanctuary
- Mass Audubon’s Felix Neck Wildlife Sanctuary
- Caroline Tuthill Preserve
Martha’s Vineyard Hikes:
- Cobble Stone Beach Loop– 3.4-mile easy loop trail that passes Prospect Hill and Great Sand Bank lookouts. Benches for rest spots and great views are a plus.
- Great Rock Bight Preserve – 3.8-mile easy trail that winds through meadows and past ponds as you make your way to the beach, where, as the name implies, a great rock awaits!
Biking on Martha’s Vineyard:
Martha’s Vineyard has more than 44 miles of bike paths connecting every side of the island. Enjoy easy rides or go off-road for more of a challenge. There’s something for every skill level and intensity.
Day-Dates and Sightseeing: Martha’s Vineyard Towns You Should Visit
Edgartown is a top spot for couples who want to spend a day sightseeing and soaking in quintessential Martha’s Vineyard charm. Full of boutiques, historic homes, the Edgartown Lighthouse, and great restaurants, there’s plenty to keep you entertained for hours.
Oak Bluffs has been a staple destination for the Black community on Martha’s Vineyard since the 19th century. Rich in culture, there are fantastic local businesses like C’est La Vie, where you’ll find HBCU fraternity and sorority gear, Biscuits—excellent homemade breakfasts, and art galleries featuring everything from mixed media to photography and painting.
Oak Bluffs is also where the iconic Gingerbread Houses are, as well as the Flying Horses Carousel, originally built in 1876, and the East Chop Lighthouse—all of which make gorgeous backdrops for pictures of you and your sweetie.
Romantic Martha’s Vineyard Restaurants with a View
After a day on the water or exploring the island, nothing beats getting dressed up for a romantic dinner date. On Martha’s Vineyard, you’ll find some of the best seafood on the East Coast. Here are our favorite spots for dinner with a view:
Bettini Restaurant – Located in the Harbor View Hotel, Bettini makes fine dining approachable with unpretentious charm. Large windows flood the space with views of the coast, and their menu is a celebration of contemporary American fare.
- Dinner: Thursday-Saturday, 5 PM – 9 PM
- Reservations recommended
- Recommended Dish: Curry Spice Seared Alaskan Halibut
- Price: $$$
- Menu
Beach Road – Views of the water reinforce the restaurant’s commitment to fresh, local ingredients and set the tone for a romantic evening, especially at golden hour as the sun sets over the lagoon.
- Dinner: Wednesday-Saturday, 5 PM – Close (varies)
- Reservations Recommended
- Recommended Dish: Littleneck clams from the raw bar, blistered shishitos, and the braised short rib
- Price: $$-$$$
- Menu
Atlantic Fish & Chophouse – Fresh-catch specialties are front and center at this beautiful waterfront restaurant. Choose indoor or outdoor seating and indulge in Mediterranean flavors that pair perfectly with their curated wine collection.
- Dinner: Open seasonally beginning July 1, every day but Tuesday, 12 PM – 9 PM
- No Reservations
- Recommended Dish: Chilean sea bass with grilled vegetables and fried leeks
- Price: $$$
- Menu
Vacation Rentals for Your Martha’s Vineyard Romantic Getaway
Featured Rental: 1964 Vineyard Haven
Once you decide where you’re going, the next most important decision is where you’ll stay. On Martha’s Vineyard, Sandcastle Realty has been helping guests find and secure dream-come-true rentals for years, and is ready to assist you in this process, too!
Our inventory is extensive and spans the entire island. Choose from pet-friendly properties, homes with private pools, rentals on the water, or use the advanced search options to find just the right amenities for you. Once you’ve found the home you want, reserve it directly through our easy-to-use form to secure your stay.
Booking directly with Sandcastle not only guarantees you a direct line to local experts from booking through to checkout, but it also grants you the best rate on your stay because you’re bypassing all the extra fees that online travel sites add to your cost. Keep that money in your pocket for nights out with your love, and get ready for an incredible romantic getaway to Martha’s Vineyard!
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Frequently Asked Questions about Martha's Vineyard Couple's Getaways
What’s the best time of year for a Martha’s Vineyard couples getaway?
Memorial Day through Labor Day are ideal for couples. The weather is warm, and all the island businesses are open. While this is the busiest time of year, it's also the time when you can literally do anything you want: dine at the best restaurants, take all the tours you want, see all the sights—summertime truly has it all.
Do we need to book ferry tickets in advance?
Yes — especially in summer. Passenger tickets can sell out on weekends, and vehicle reservations fill up even earlier. If you’re planning to bring a car, book several months ahead for peak season. If you’re traveling as a couple without a vehicle, you’ll have more flexibility, but it’s still smart to secure tickets at least a few weeks in advance.
Should we bring a car, or can we get around without one?
For most couples, you can easily skip the car. Martha’s Vineyard has over 44 miles of bike paths, reliable bus service connecting the towns, and rideshares available in-season. Staying centrally — like in Edgartown, Oak Bluffs, or Vineyard Haven — allows you to walk to restaurants, shops, and the harbor. If you’re planning to stay up-island for privacy and seclusion, having a car can be helpful.
Do we need dinner reservations?
Absolutely during summer. Make reservations at least 1–2 weeks ahead for popular restaurants—earlier for holiday weekends. Shoulder season is more flexible, but booking ahead still guarantees you the time and view you want.
What are memorable proposal or anniversary ideas on Martha’s Vineyard?
- Sunset sail with champagne
- Private beach picnic at golden hour
- Lighthouse backdrop photos
- A surprise dinner reservation followed by a harbor walk
- A quiet moment at Aquinnah Cliffs at sunset