A Luxurious Winter Escape: Portsmouth & Kittery
Where to Stay: Luxury Boutique Bliss
Hotel Thaxter – Modern Sophistication in Portsmouth
Elegant, modern, and quietly luxurious, Hotel Thaxter wraps you in warmth from the moment you arrive. Think soft lighting, refined design, plush bedding, and curated amenities. Located downtown, it’s perfect for couples who want to walk hand-in-hand to Portsmouth restaurants, galleries, and cafés without braving long stretches of cold winter weather.
The Sailmaker’s House – Historic Elegance with Modern Comfort
For couples who love cozy character, The Sailmaker’s House in Portsmouth offers historic charm with modern touches. Original architecture and thoughtful details create a romantic hideaway for enjoying a glass of wine or warming up before venturing back into the twinkling winter streets.
Water Street Inn – Riverside Luxury in Kittery
Quiet, sophisticated, and scenic, Water Street Inn in Kittery is ideal for couples seeking tranquility with a view. Winter sunsets over the river, plush linens, and a serene, upscale feel make it the perfect Seacoast winter retreat.
48 Hours of Winter Luxury: Weekend Edition
Day 1 — Friday Evening: Arrival & Indulgence
Check-in & Unwind
Settle into your boutique room, slip into something comfortable, and enjoy a slow moment together—tea, champagne, or a winter cocktail is recommended.
Optional Luxury Add-Ons:
Pre-scheduled floral arrangement in your room
Local artisan chocolates or macarons
Dinner: Fine Dining for Two
For a luxurious winter evening, explore the Seacoast’s romantic dining options:
Black Trumpet: Globally inspired, intimate setting
Louie’s: Rustic Northern Italian elegance
Jumpin’ Jays Fish Café: Fresh, locally sourced seafood
Massimo’s: Classic Italian fine dining
Moxy: Creative small plates with Spanish tapas influence
Cure: Elevated American comfort with seasonal flair
End the night with a stroll through the quiet, frost-dusted streets before returning to your cozy winter retreat.
Day 2 — Saturday: Spa Warmth, Boutique Indulgences, and Evening Entertainment
Morning: Spa-Level Relaxation
Indulge in a warm, rejuvenating experience at one of Portsmouth’s boutique spas:
Blush Skin & Soul Spa: Facials, massage, waxing, and holistic beauty rituals
Escape & Rejuvenate Therapeutic Massage and Spa: Organic treatments and couples massage
Ash Alchemy: Esthetic and wellness services in a warm retreat setting
Brunch Options:
La Maison Navarre: French pastries and wine bar experience
The Friendly Toast: Colorful, indulgent brunch cocktails
Street: Eclectic and casual restaurant with creative offerings
Early Afternoon: Seacoast Exploration
Take a boutique shopping stroll or visit Kittery Premium Outlets for winter sales. Enjoy scenic outdoor adventures:
The Urban Forest in Portsmouth: Easy, scenic winter trails
Fort Foster Historic Site in Kittery: Snowshoeing or short hikes with panoramic coastal views
Late Afternoon: Winter Cocktails & Cozy Escapes
Sip warming drinks at:
The Wallingford Dram (Kittery): Craft cocktails
Slow Burn Lounge: Cigars welcome
Cava Tapas and Wine Bar: Excellent wine selection
Fezziwigs Food & Fountain: Ice cream bar nostalgia
Lil’s Kittery: Don’t miss the cruller
Cup of Joe: Cozy café atmosphere
Dinner and Entertainment:
Pair dinner with a live show or music performance:
The Music Hall: Historic theater with concerts, Broadway shows, films
The Music Hall Lounge: Intimate bar and lounge
Jimmy’s Jazz & Blues: Local and national jazz, blues, and soul
The Press Room: Downtown live music and DJ nights
3S Artspace: Contemporary gallery and performance space
Nightcap: Return to your inn for warm blankets and fine linens, enjoying the quiet glow of a winter night.
Day 3 — Sunday: Slow Luxury & Departure
Breakfast in Bed or Nearby:
Elephantine: Fresh pastries and coffee
Lil’s (Kittery): Cozy pastries and lattes
Ceres Bakery: Artisan breads and baked goods
Sunday Brunch with Live Music:
Jimmy’s Jazz & Blues: Jazz brunch buffet
The Press Room: Creative comfort dishes with live jazz
Blue Mermaid Island Grill (Kittery): Island-inspired brunch with relaxed live music
Optional Add-Ons for a Luxurious Send-Off:
Scenic winter drive along the New Hampshire and Maine coast
One last boutique shopping session in Portsmouth or Kittery Forepoint
With Hotel Thaxter, The Sailmaker’s House, or Water Street Inn as your home base, you’ll always have a welcoming place to slow down, thaw out, and savor quality time together. Depart refreshed, connected, and wrapped in the glow of a luxurious Seacoast winter escape.
