Martha’s Vineyard has been a popular Northeast beach destination for as long as I can remember, but it’s been getting quite a bit of buzz in the fashion world due in part to Ralph Lauren’s new Oak Bluffs collaboration. The collaboration is the second with James Jeter, Creative Director, Design & Brand Direction for Men’s Polo at Ralph Lauren. This time, they’re not only honoring Jeter’s esteemed Alma Mater and HBCU, Morehouse, and its equally impressive sister college, Spellman— but also the beautiful history of Oak Bluffs itself.
“Oak Bluffs’ unique history, traditions, and sense of community deeply inspire me and speak to what we are all searching for—a place where you can be free, uncontrived, joyful, and truly at home,” said Ralph Lauren, Executive Chairman and Chief Creative Officer of Ralph Lauren Corporation.
If you haven’t seen the documentary, you can view it here. Oak Bluffs was also featured in the popular Netflix show “Forever,” an adaptation of the Judy Blume novel that prompted me to update my domestic travel wishlist. Although Martha’s Vineyard has been on our radar for years I hadn’t done much research until now, which leads me to this post.
Dreamy coastal views, hydrangea-lined lanes, and breezy sophistication make Martha’s Vineyard a timeless summer escape. Whether you’re a first-time visitor or a seasoned summerer, here’s your ultimate guide to enjoying this charming New England island with grace and ease.
Getting There
- By Ferry: From Woods Hole, MA (Steamship Authority), New Bedford, or Hyannis. Book early in summer!
- By Air: Martha’s Vineyard Airport (MVY) is small but well-connected during peak season.
Pro Tip: Leave your car behind and rent a bike or scooter—parking is limited, and from what I’ve gathered, the island is best explored slowly.
Where to go-
If you’re anything like me you’ve probably heard of Edgartown and Oak Bluffs but there are actually six towns/municipalities that make up Martha’s Vineyards.
1. Edgartown
- Vibe: Elegant, historic, nautical
- Known For: White captain’s homes, boutiques, fine dining, the harbor, and lighthouse
2. Oak Bluffs
- Vibe: Colorful, lively, family-friendly
- Known For: Gingerbread cottages, beaches, carousel, nightlife, and harbor
3. Vineyard Haven (a.k.a. Tisbury)
- Vibe: Gateway town, year-round energy
- Known For: Ferry terminal, bookstores, local shops, and cafes
- Note: Vineyard Haven is a village within the town of Tisbury
4. West Tisbury
- Vibe: Rural, artsy, peaceful
- Known For: Farmer’s market, galleries, scenic drives, and nature preserves
5. Chilmark
- Vibe: Quiet, upscale, natural
- Known For: Private homes, hiking, Lucy Vincent Beach, and Chilmark Store pizza
6. Aquinnah (formerly Gay Head)
- Vibe: Remote, sacred, striking
- Known For: Clay cliffs, Wampanoag heritage, and dramatic ocean views
Each town includes smaller villages or areas (like Menemsha in Chilmark), but these six are the main municipalities.
Where to Stay
Edgartown
- Harbor View Hotel: Historic and sophisticated
- The Richard: Plush Elegant Boutique-Perfect for couples
- The Christopher-Chic Vibrant and Modern. Combines St. Barts-inspired design with Vineyard ease.
Oak Bluffs
- The Oak Bluffs Inn: Pink‑Victorian, wrap‑around porch, superb service, intimate luxury, highly rated
- Summercamp: Vibrant and playful, communal vibe, beach‑side location, great for fun-loving travelers
- Pequot Hotel: Historic waterfront charm, live music, complimentary breakfasts, and porch lounging
Aquinnah
- The Outermost Inn: Coastal boutique inn perched atop the cliffs
- The Duck Inn
Rustic-chic bed and breakfast near the cliffs with an intimate, understated elegance
What to Do
- Explore the Gingerbread Cottages in Oak Bluffs
- Sunset at Menemsha Beach – bring wine and lobster rolls
- Visit Aquinnah Cliffs for jaw-dropping coastal beauty
- Shop local in Edgartown – think linen dresses, straw hats, and artisan jewelry
- Bike the State Beach Path between Edgartown and Oak Bluffs
- Tour Island Farms like Morning Glory Farm for fresh produce
Where to Eat
- Red Cat Kitchen (Oak Bluffs): Seasonal & creative
- The Port Hunter (Edgartown): Stylish and local
- Larsen’s Fish Market (Menemsha): No frills, just lobster rolls
- Behind the Bookstore (Edgartown): Coffee + brunch hidden gem
Don’t Miss:
A slice of pie from Black Dog Bakery or Morning Glory Farm
Ice cream from Mad Martha’s
Donuts from Back Door Donuts
Packing List
- Lightweight linens and sundresses
- A wide-brim hat and oversized sunglasses
- A good book and beach tote
- Layers for breezy evenings
- Comfy walking sandals or espadrilles
Vineyard Vibe
It’s laid-back luxury. Think less makeup, more sunscreen. Effortless elegance. A glass of rosé on a porch. Conversations with artists and chefs. Slower mornings. Starry nights. Hydrangeas everywhere. That all sounds lovely to me. If you’ve been to the Vineyard, we’d love to hear your recommendations too. Let us know in the comments below.
Until Next Post,
Xo Tonya Parker
The Real Chic Life 
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