Romantic Getaways

Nantucket's Most Romantic Stays

These exceptional properties understand the art of romance, offering couples the privacy, ambiance, and special touches that transform a getaway into a cherished memory.

• 1

  The Wauwinet

  120 Wauwinet Road, Wauwinet

  Secluded on Nantucket's northeastern tip, The Wauwinet is the island's most romantic escape. This Relais & Chateaux property sits between Nantucket Bay and the Atlantic Ocean, offering couples a world away from everything. Wake to water views, spend afternoons on the private beach, and dine at Topper's, one of New England's finest restaurants. The property's complimentary jitney service whisks you to town, but many couples never leave - the sense of elegant seclusion is that intoxicating. Request a bayfront room with a private deck for sunset champagne.

• 2

  Greydon House

  17 Broad Street, Downtown

  Intimate luxury defines Greydon House, a meticulously designed boutique hotel with just 20 rooms in the heart of downtown. Every detail has been considered - from the curated art collection to the custom Italian linens. Rooms feature soaking tubs, working fireplaces, and thoughtful amenities like record players with vinyl collections. The on-site restaurant and bar create a sophisticated yet welcoming atmosphere perfect for romantic evenings. The combination of downtown convenience and cocoon-like intimacy makes Greydon House ideal for couples who want the best of both worlds.

• 3

  White Elephant

  50 Easton Street, Harbor

  The White Elephant commands one of Nantucket's most coveted locations, overlooking the harbor where yachts bob and ferries glide past. This iconic property offers a range of accommodations, from luxurious hotel rooms to private cottages with their own gardens. The sunset views from harborfront rooms are legendary - watch the sky turn gold and pink from your private balcony. The Brant Point Grill and Lola 41 provide excellent on-site dining, and you're steps from downtown. For ultimate romance, book a cottage with a water view and in-room fireplace.

• 4

  Pineapple Inn

  10 Hussey Street, Downtown

  This exquisite bed and breakfast occupies an 1838 whaling captain's home, and the romance of Nantucket's golden age permeates every corner. The 12 rooms feature four-poster beds, antique furnishings, and modern luxuries including marble bathrooms with heated floors. Wake to a gourmet breakfast served by candlelight, then retreat to the beautiful gardens with your morning coffee. The inn's quiet downtown location puts you within easy walking distance of restaurants and shops, yet feels like a private sanctuary. Personal service and attention to detail make every couple feel like honored guests.

• 5

  Union Street Inn

  7 Union Street, Downtown

  Elegant, refined, and timelessly romantic, Union Street Inn occupies a beautifully restored 1770 sea captain's home. The 12 guest rooms blend period antiques with contemporary comforts, featuring fireplaces, fine linens, and thoughtfully appointed bathrooms. Common areas include a lovely garden terrace and cozy parlor - perfect for afternoon wine and cheese. The gourmet breakfast is served at individual tables, allowing couples privacy while enjoying exceptional fare. The inn's reputation for impeccable hospitality and romantic ambiance has made it a favorite for anniversaries and honeymoons for decades.

• 6

  The Veranda House

  3 Step Lane, Downtown

  Victorian romance comes alive at The Veranda House, a boutique hotel that seamlessly blends historic charm with modern sophistication. The wrap-around veranda, for which the property is named, offers lovely harbor views and is ideal for morning coffee or evening wine. Guest rooms feature romantic touches like canopy beds, claw-foot tubs, and carefully chosen antiques. The location, tucked just above Main Street, provides easy access to shops and restaurants while maintaining a sense of peaceful retreat. Continental breakfast is served in a charming dining room or delivered to your room.

• 7

  Cliff Lodge

  9 Cliff Road, North Bluff

  Perched on the historic North Bluff overlooking Nantucket Sound, Cliff Lodge offers couples something rare: spectacular sunset views from a bed and breakfast setting. The 1771 whaling captain's home has been thoughtfully updated to offer comfortable, romantic accommodations with period charm. The rooftop widow's walk provides 360-degree views of the island and ocean - an unforgettable spot for couples to watch the sun sink into the water. Rooms are individually decorated with antiques and artwork, and breakfast is a highlight, served with harbor views.

Romantic Features to Look For

When booking a romantic stay on Nantucket, these amenities and features elevate an accommodation from nice to unforgettable.

Private Balconies and Patios

There's something undeniably romantic about having your own outdoor space. Whether it's watching the sunrise over coffee, enjoying sunset cocktails, or simply sitting together under the stars, a private balcony or patio transforms your room into a retreat. Look for rooms with harbor views, garden settings, or ocean vistas. The White Elephant's harborfront balconies and The Wauwinet's bay-view decks are particularly spectacular.

Working Fireplaces

Many of Nantucket's historic inns and hotels feature working fireplaces in guest rooms. There's nothing quite like curling up together in front of a crackling fire after a day exploring the island - especially during shoulder seasons when evenings turn cool. Greydon House, Pineapple Inn, and Union Street Inn all offer rooms with this romantic amenity. Ask specifically about "working" fireplaces when booking, as some are decorative only.

Soaking Tubs

After a day of beach walks, biking, or exploring cobblestone streets, a deep soaking tub is pure luxury. Many romantic properties feature oversize tubs, claw-foot antiques, or modern spa-style baths designed for two. Greydon House is particularly known for its beautiful bathrooms. Some rooms at The Wauwinet and White Elephant offer jetted tubs with views. Ask about bathroom amenities when making reservations.

In-Room Dining

Sometimes the most romantic dinner is one enjoyed in complete privacy. Many upscale properties offer room service or can arrange private in-room dining experiences. Breakfast in bed is available at most hotels - take advantage of this indulgence at least once during your stay. Some properties will set up champagne and cheese plates or dessert for special occasions. Make requests in advance.

Couples Spa Treatments

Properties with on-site spas offer couples massage rooms and romantic treatment packages. The Wauwinet features spa services that can be arranged in-room or at their wellness facility. The White Elephant offers spa treatments at their wellness center. Even properties without spas can often arrange mobile spa services to come to your room or the property grounds. These experiences make wonderful anniversary or honeymoon additions.

Romantic Activities for Couples

Nantucket offers endless opportunities for couples to create special memories together. These experiences pair perfectly with a romantic stay.

Sunset at Madaket Beach

The most romantic sunset on Nantucket happens at Madaket Beach on the island's western shore. Pack a blanket and a bottle of wine, and watch the sun sink into the ocean as the sky explodes with color. Arrive at least 30 minutes before sunset to find a good spot and settle in. Many couples make this a nightly ritual during their stay. Some hotels can arrange sunset picnic baskets.

Fine Dining for Two

Nantucket's dining scene offers some of New England's most romantic restaurants. Company of the Cauldron, with its candlelit interior and harp music, is legendary for proposals and anniversaries. The Galley Beach offers sunset dining with your feet nearly in the sand. Topper's at The Wauwinet provides a white-tablecloth experience overlooking the bay. Make reservations well in advance and mention any special occasions.

Beach Picnics

There's something wonderfully intimate about sharing a meal on a quiet stretch of beach. Several local shops prepare gourmet picnic baskets, complete with wine, cheese, charcuterie, and all the essentials. Head to a less-crowded beach like Eel Point or Dionis for privacy. Pack a blanket, arrive at golden hour, and enjoy the simple pleasure of good food with a view.

Private Sailing Charters

Few experiences are more romantic than sailing Nantucket's waters on a private charter. Sunset sails are particularly magical, with champagne and the glow of fading light on the water. Several charter companies offer intimate experiences for couples, from sleek sailboats to classic wooden vessels. Book a sunset sail for your first or last evening on the island to create a lasting memory.

Couples Massages

Start or end your day with a side-by-side massage at one of the island's spas. Several wellness centers offer couples treatment rooms where you can enjoy massages, facials, and other treatments together. This is an especially lovely way to unwind after your ferry journey or before a special dinner. Book in advance during peak season.

Proposal and Honeymoon Packages

Many Nantucket properties offer special packages designed to make proposals, honeymoons, and anniversary celebrations extraordinary.

Proposal Packages

Planning to pop the question? Several hotels will help you create the perfect moment. The Wauwinet can arrange sunset champagne on the beach or a private dinner setup. The White Elephant's concierge has coordinated countless proposals, from rose petal-strewn rooms to harborside moments. Work with property staff to plan flowers, champagne, photographers, and the perfect location. They've seen it all and know how to make the moment special - and how to keep it secret.

Honeymoon Packages

Most romantic properties offer honeymoon packages that include special touches like champagne on arrival, breakfast in bed, late checkout, and room upgrades when available. Some include dining credits, spa treatments, or sunset sail vouchers. The Wauwinet's honeymoon package is particularly comprehensive. When booking, mention that you're honeymooning - even if you don't select a formal package, most properties will add thoughtful complimentary touches.

Anniversary Celebrations

Returning couples often choose Nantucket for milestone anniversaries, and hotels are well-versed in celebrating these occasions. Special touches might include wine and cheese in your room, custom cakes, preferred restaurant reservations, and personalized notes. Some couples return to the same property year after year, building traditions and relationships with staff who remember their preferences. Be sure to mention your anniversary when booking.