Luxury Martha’s Vineyard Travel Itinerary: Guide for Upscale Island Getaways
Dreaming of an indulgent escape to Martha’s Vineyard? Whether you’re planning a romantic weekend, a girls’ getaway, or a luxurious solo retreat, this curated luxury Martha’s Vineyard itinerary blends five-star experiences, fine dining, and scenic beauty for a trip you’ll never forget.
Day 1: Arrive in Style + Explore Elegant Edgartown
Highlights:
- Luxury hotel check-in
- Private harbor cruise
- High-end shopping and dining
Arrive via private jet or ferry and settle into one of Martha’s Vineyard’s best luxury hotels:
- Harbor View Hotel – Classic coastal elegance
- The Charlotte Inn – Boutique luxury and old-world charm
- Winnetu Oceanside Resort – Ideal for beachfront luxury
- Edgartown Inn– Historic boutique hotel
Afternoon:
- Lunch at Rosewater Market or The Newes from America Pub
- Stroll through downtown Edgartown, visiting high-end boutiques and art galleries
- Enjoy a private sailboat charter around Edgartown Harbor and Chappaquiddick
Evening:
- Dine at Alchemy, one of the island’s premier fine dining restaurants
- Grab cocktails at Behind the Bookstore (BTB) or The Port Hunter
Day 2: Full Island Tour + Spa Retreat
Highlights:
- Private island tour
- Aquinnah Cliffs and Menemsha
- Luxury spa experience
Morning:
Explore Martha’s Vineyard with a private driver and island guide. Key stops include:
- Aquinnah Cliffs – Iconic red clay cliffs with panoramic views
- Menemsha Harbor – A charming fishing village
- Chilmark – Rolling hills and stone walls
Lunch:
Enjoy a gourmet picnic curated by Black Sheep Mercantile, set up at a scenic overlook or hidden beach.
Afternoon:
- Unwind with a luxury spa treatment at Spa L’EAU MV or book a private wellness session (yoga, massage, or sound bath)
Evening:
- Dinner at L’Etoile, a refined dining experience in a romantic garden setting
Day 3: Beachside Bliss + Sunset Cruise
Highlights:
- Exclusive beach access
- Oceanfront dining
- Luxury sunset sail
Morning:
- Breakfast at Among the Flowers Café
- Lounge at South Beach or Lobsterville Beach with optional beach concierge service
- Try stand-up paddleboarding or kayaking on Katama Bay
Lunch:
- Scenic dining at Outermost Inn (Aquinnah) with seasonal gourmet fare
Afternoon:
- Visit Martha’s Vineyard Distilling Co. for a private tasting
- Boutique shopping in Oak Bluffs or Vineyard Haven – think luxury apparel and local artisan finds
Evening:
- Charter a private sunset cruise with champagne and small bites
- Finish your night with a five-star meal at Détente, known for its creative coastal cuisine
Optional Day 4: Final Indulgences + Departure
Highlights:
- Boutique breakfast
- Scenic farm visit
- Stress-free luxury transport
Morning:
- Brunch at Lucky Hank’s
- Stop by Morning Glory Farm for fresh pastries and artisan goods
- Enjoy a final scenic drive before heading to the airport or ferry
Travel Tip: Fly out from MVY Airport on a private charter or Cape Air for a seamless return.
Final Tips:
- Book early (especially June through September)
- Consider a private chef dinner at your rental villa
- Use private drivers or luxury car rentals for easy transport
- Don’t miss seasonal events like the Martha’s Vineyard Food & Wine Festival or Film Festival
