Float Your Boat
Rent a sailboat from Longshore Sailing School and make some waves out on the Sound. After breezing along for an hour or two, enjoy cocktails on the patio at Splash. If the leisurely pace of kayaking is more your speed, DownUnder Kayaking hosts monthly full moon kayaking tours and sunset paddling excursions along the Saugatuck. After working up an appetite, pop into The Whelk for a dozen freshly-harvested oysters.
Dance the Night Away
Put a little swing in your step at the newly-redesigned Levitt Pavillion! Their summer concert line-up includes everything from cha-cha, to swing, to folk. After the show, shimmy up Main Street for expertly crafted cocktails at LUXE Modern Wine & Cocktails.
Turn Up the Heat
Get fired up with a cooking class for two! Karen Brownlow’s Chop Shop cooking classes allow couples to transform fresh ingredients into tantalizing tapas or spicy south of the border fare in private or group classes. All two-hour classes are held in Brownlow’s Westport kitchen and are limited to six people for an intimate feel.
Brush Up on Art
The Westport Arts Center hosts monthly Drink n’ Draw programs – they provide the supplies, including charcoal, paper, live (nude) model, wine, and snacks – you provide the creativity!
Birds and the Bees
Commune with nature at our beautiful conservation areas! The Aspetuck Land Trust offers guided hikes and bird-watching tours (Did you hear? Bird watching is super-trendy right now). Impress your date with your botanical knowledge as you identify more than 500 species of trees and wildflowers at Devil’s Den in Weston. Complete your day with a honey tasting at Red Bee Apiary in Weston where you’ll taste seven single-origin honeys perfectly paired with seasonal accompaniments; locally produced cheese, fruit, chocolate, spices, or herbs.
Massage for Two
Indulge in total relaxation during a Swedish or deep-tissue massage in the luxurious couples suite at URA the Spa in Wilton. Continue the evening with cocktails and dinner on the patio at the Cactus Rose Restaurant and Tequila Bar in Wilton Center for a sweet and spicy Apache Margarita handcrafted with Sauza 100 Anos Resposado tequila, muddled strawberry, pineapple, Serrano peppers, fresh lime juice, and blood orange puree.
Romancing the Stage
Crazy in love. That’s the premise of “Things We Do For Love,” the Alan Ayckbourn comedy presented by the Westport Country Playhouse from August 19, to September 6. After the show, slip into a cozy banquette at Post 154 for some shared small plates and reignite your old flame.
Get Your Om On
Let go of stress and tension while connecting on a spiritual level at a yoga class at Westport’s M3 Yoga Studio. Don’t worry if you’re a yoga virgin, they have classes for all levels. Now that you’ve cleansed your soul, cleanse your body with a freshly pressed juice or organic salad at Embody Fitness Gourmet.
Champagne at Sunset
Nothing could possibly be more romantic than sipping a glass of bubbly while watching the sun slip into the horizon from our own beautiful Compo beach. Pick up a bottle of your favorite spirits from Saugatuck Grain and Grape, find a quiet spot, and let the magic happen.