Lounge In Love on Shelter Island

Celebrate Valentine’s Day on Shelter Island with a waterfront three-course dinner at Humphreys SoCAL Dining & Music. Enjoy chef-crafted dishes, decadent desserts, and romantic marina views for an unforgettable evening.

February 14, 2026 | 5:30–9:30pm

Slip away to Shelter Island for bay views, coastal breezes, and unforgettable moments for two. Stay three or more nights in a spacious full-size suite and enjoy your 4th consecutive night free.

At Humphreys Half Moon Inn, Valentine’s Day plans come with a soundtrack. Spend the evening at Backstage LIVE with waterfront vibes and live music on Shelter Island. Catch the Memphis Soul Revue at 5:00 pm for soul and funk with a $5 cover, then keep the night going with Groove Squad at 8:00 pm for $15. It’s the perfect way for couples to mix great music, island ambiance, and a romantic night by the bay.

All February long, treat your Valentine to waterfront dining, live music, and a romantic getaway on Shelter Island with a Humphreys Half Moon Inn gift card.

Soak in the laid-back Shelter Island vibes as you wander past palms, marina views, and glowing firepits with a glass of wine in hand. Unwind in the pool or spa, then settle in beneath the tiki torches for a cozy night under the stars.

Enjoy a scenic ride for two along the Shelter Island loop with the first hour free each day. Cruise past marina views, swaying palms, and peaceful bay paths for a relaxing adventure together.

Unwind together with relaxing massage services available by appointment from 9:00am to 6:00pm. Choose from personalized Swedish, deep tissue, prenatal, or warm lava shell treatments, with optional aromatherapy and reflexology add-ons to elevate your experience. In-room and couples options available. Advance reservations recommended.