Fall in Nantucket & Martha’s Vineyard

Last month our friends at Little Gem Resorts invited us to check two dream destinations off our travel list—Nantucket and Martha’s Vineyard—and they were every bit as magical as we’d hoped! Think cobblestone streets, gray shingle cottages dripping in hydrangeas, salty ocean breezes, and that crisp hint of fall in the air. We spent a few days on each island, soaking up their unique personalities, and it was the most charming getaway—relaxing, picturesque, and completely unforgettable.

We went in September, and honestly, I can’t recommend it enough. The summer crowds had cleared, the weather was perfection (sunny days in the 70s, cool evenings for sweaters), and the flowers were still in full bloom. It felt like having the islands all to ourselves—peaceful, but still lively enough to enjoy every restaurant, shop, and bike ride without the rush.

Exclusive Sugarplum Code: Use code CASS to save 10% off accommodations for the 2025 and 2026 seasons at The Nantucket, The Winnetu, and their sister property, Lovango Resort! You can read our experience at Lovango Resort HERE.

3 Days in Nantucket //

Getting there is half the adventure! We flew from Dallas to Boston on American, then hopped a tiny Cape Air puddle jumper to ACK. The ferry’s an option too, but it involves a two-hour drive and is weather dependent, so flying saved us precious vacation time (even if the little plane made me a little sweaty!).

We stayed at The Nantucket Hotel, and I can’t imagine a more perfect home base. It’s one of those rare places that feels both historic and totally fresh at the same time—classic Nantucket charm mixed with all the modern comforts. The clapboard exterior, big front porch with rocking chairs, and friendly staff make you feel instantly welcome. Our room was spacious and cozy, with thoughtful touches that made it feel more like a charming inn than a hotel.

The location couldn’t be better—just a short stroll from downtown shops and restaurants—but it’s tucked away enough to feel peaceful. We loved starting our mornings with coffee on the porch and ending the day with dinner at their on-site restaurant, where the patio is perfect for people-watching. The Nantucket Hotel really captures that small-island magic, with service that feels personal and genuine. It’s truly a gem and made our time on the island feel extra special.

Striped Midi Skirt (Blue, Small) | Cashmere Crewneck (Small) | Flip Flops | Bucket Bag (Similar HERE) | Sunglasses | Full Details HERE

Vuori Shorts | Yeti Hat

We spent our days wandering through the cobblestone streets, popping in and out of boutiques, then rented bikes from Young’s Bicycle Shop (the hotel can arrange it) to ride out to Sconset and walk the scenic Sconset Bluff Trail—a must-do for those postcard views.

When it came to food, Cru tops the list for its stunning harbor views and fresh seafood, while Lemon Press was so good we went twice! Claudette’s made one of the best sandwiches of my life—perfect after the bluff walk. Every corner of Nantucket feels like a scene from a movie: polished, coastal, and effortlessly charming.

Cashmere Crewneck (Small) | White Jeans (size 26) | Netted Ballet Flats | Crossbody Bag (Similar HERE) | Beaded Necklace | Full Details HERE

Men’s Quince Jacket | T-Shirt

Puffer Jacket (Small) | Vuori Joggers (Small) | Hoodie (XS) | Gola Sneakers (Also HERE & HERE) | Sling Bag | Polo Hat | Dome Hoop Earrings | Full Details HERE

Puffer Jacket (Small) | Vuori Joggers (Small) | Hoodie (XS) | Gola Sneakers (Also HERE & HERE) | Sling Bag | Polo Hat | Dome Hoop Earrings | Full Details HERE

Tie Waist Shirtdress | America Sweater | Netted Ballet Flats | Sling Bag | Beaded Necklace | Full Details HERE

Sweat Shorts | Rain Jacket

Silk Halter Blouse | Cashmere Crewneck (Small) | Floral Midi Skirt (20% off!) | Netted Ballet Flats | Crossbody Bag (Similar HERE) | Beaded Necklace | Dome Hoop Earrings | Full Details HERE

Cashmere Cardigan (XS) | Shelf Tank (Small) | Stretch Wide Leg Jeans (size 26×30) | Gola Sneakers (Also HERE & HERE) | Sling Bag | Heart Charm Necklace | Sunglasses | Full Details HERE

Tie Waist Shirtdress | America Sweater | Netted Ballet Flats | Sling Bag | Beaded Necklace | Full Details HERE

3 Days in Martha’s Vineyard //

From Nantucket, we hopped the ferry to Martha’s Vineyard and checked into The Winnetu, and it’s the kind of place that makes you instantly exhale. Set just steps from South Beach, it offers the perfect mix of resort amenities and coastal charm. In summer, it’s a family favorite packed with activities (think tennis, yoga, lawn games, and even a nostalgic “family camp” vibe).

But visiting in September was a dream—the property was serene and quiet, with mostly couples enjoying the beach, bike rides, and the island’s slower pace.

Our cottage was bright, airy, and designed for comfort. The staff couldn’t have been kinder—helping us arrange bikes, restaurant reservations, and even day trips around the island. We loved dinner at The Dunes, their signature restaurant, which has the best patio for sunset cocktails. Everything about The Winnetu feels thoughtful and warm, from the friendly concierge team to the little touches like beach chairs ready to go each morning. It’s one of those rare resorts that makes you feel instantly at home… only better, because someone else makes the bed.

Sleeveless Dress (XS) | T-Strap Sandals (45% off!) | Crossbody Bag (Similar HERE) | Full Details HERE

We borrowed one of the hotel’s cars to explore the island’s little towns, stopping for sandwiches and cookies, popping into art galleries, and taking in the stunning cliffs. One of my favorite days was biking to Edgartown—so charming it doesn’t feel real—then heading back to relax by the beach with a book and a glass of wine.

Meals were another highlight: dinner on the patio at The Dunes (the hotel’s restaurant) was lovely, and Behind the Bookstore is a gem for breakfast and lunch. Don’t miss 19 Raw Oyster Bar for the best seafood and steak on the island—reservations are tough, but The Winnetu team worked their magic and made it happen!

Where Nantucket feels chic and energetic, Martha’s Vineyard has an easy, coastal calm—a little less polished, but every bit as beautiful.

Crop Tank (Small) | Vuori Joggers (Small) | Gola Sneakers (Also HERE & HERE) | Sunglasses | Full Details HERE

Drop Waist Shirtdress (XS) | America Sweater | Netted Ballet Flats | Bucket Bag (Similar HERE) | Beaded Necklace | Sunglasses | Full Details HERE

Gingham Maxi Dress (Navy Blue, Small) | Flip Flops | Sunglasses | Full Details HERE

Silk Tank Dress (Small) | Cashmere Cardigan | T-Strap Sandals (45% off!) | Crossbody Bag (Similar HERE) | Beaded Necklace | Full Details HERE

Striped Cardigan (XS) | Sleeveless Polo | Linen Shorts | Full Details HERE

on Mr. SP: Cashmere Sweater | FH Shorts // on me: Striped Cardigan (XS) | Sleeveless Polo | Linen Shorts | Full Details HERE

Visiting both islands back-to-back was the best of both worlds—two completely different personalities, each equally special. Nantucket’s refined charm and Martha’s Vineyard’s laid-back vibe make them the perfect New England pairing, especially in September when the pace slows, the weather shines, and every corner feels picture-perfect.

If you’re dreaming of your own island escape, use code CASS to save 10% off accommodations for the 2025 and 2026 seasons at The Nantucket, The Winnetu, and their sister property, Lovango Resort!—then start planning your striped-sweater, bike-riding, lobster-roll-eating adventure. You’ll fall in love just like we did.