The Ultimate Guide to Day Charters in Sag Harbor
Sag Harbor is more than just a quaint Hamptons village—it’s a gateway to some of the most unforgettable sailing experiences on the East Coast. Whether you’re planning a romantic champagne sail, a lively celebration with friends, or a family escape to the waters of Shelter Island, a day charter offers the perfect blend of luxury, adventure, and local charm.
If you’re considering booking a sailing experience, this guide will walk you through everything you need to know: when to go, what to bring, where you’ll sail, and how to make the most of your day on the water.
Why Sag Harbor Is the Ideal Departure Point
What makes Sag Harbor truly special for day charters is its central location. From this historic harbor, you can reach some of the most sought-after destinations in the Hamptons within just a short sail:
Shelter Island – With multiple serene coves like Coecles Harbor and West Neck, it’s perfect for anchoring, swimming, or simply enjoying a quiet escape surrounded by nature.
Sunset Beach (Shelter Island) – A Hamptons hotspot where you can anchor just offshore, sip a cocktail on deck, and enjoy the lively scene. Two boutique hotels make this stretch especially appealing: the stylish Sunset Beach Hotel, with its iconic beachfront restaurant and bar, and the recently renovated Pridwin Hotel & Cottages, offering waterfront dining, a relaxed dock-and-dine experience, and classic Hamptons charm.
Dering Harbor (Shelter Island) – A charming, walkable village harbor lined with small cafés and restaurants. It’s the perfect spot to step ashore for coffee, fresh seafood, or a leisurely stroll through one of the island’s most picturesque enclaves.
Maidstone Beach – A relaxed and less crowded shoreline, ideal for a swim or picnic with a backdrop of unspoiled beauty.
Three Mile Harbor – Known for calm waters and vibrant sunsets, this is a favorite spot to drop anchor and unwind.
Greenport – A charming North Fork village across the bay, offering waterfront dining, historic streets, and a totally different vibe than the South Fork.
Best Times of Year to Sail
The sailing season in Sag Harbor typically runs from late May through mid-October. Each part of the season has its own magic:
Early Summer (May–June): Quieter waters, cooler breezes, and a peaceful start to the season. Perfect for couples and small groups who want a more intimate outing.
High Summer (July–August): The Hamptons are buzzing, and so are the bays. Warm water makes this the best time for swimming, paddleboarding, and jumping off the stern for a refreshing dip.
Late Summer to Fall (September–October): The “shoulder season” brings fewer crowds, crisp sunsets, and some of the most spectacular sailing conditions of the year.
What to Bring on Your Charter
Sailing is best enjoyed when you’re comfortable and prepared. Here are a few essentials we always recommend:
Sunscreen and sunglasses: The sun reflects strongly off the water. While we provide complimentary mineral sunscreen, we suggest bringing your favorite brand if you have a personal preference.
Hat: A wide-brimmed hat or cap is one of the best ways to stay cool and protected under the summer sun.
Light layers: A sweater or windbreaker can make the difference when the afternoon breeze picks up.
Swimsuit: Perfect for those refreshing mid-day dips.
Towels: We provide plush towels on board, so you can pack lighter and simply enjoy the day.
Footwear: Barefoot is best onboard, but bring sandals or flip-flops for the dock.
Drinks and snacks: Many charters (like ours at Elysian Sailing) offer champagne, wine, or catering, but you’re also welcome to bring your favorites.
Camera or phone: The Hamptons shoreline, lighthouse backdrops, and sunsets practically beg to be captured.
What’s Included Onboard with Elysian Sailing
When you sail with us, we take care of the details so you can focus on relaxing and enjoying the day. Every charter includes:
Complimentary mineral sunscreen – reef-safe and guest-ready.
Plush towels – no need to pack your own.
Spacious shaded seating – perfect for cooling off between sunbathing.
Icy champagne and curated beverages – available on select charters.
USCG-licensed captain – ensuring a safe and seamless experience.
Types of Day Charters
When planning, it helps to think about the style of experience you’re looking for:
Romantic Escape – A private sail for two, champagne on ice, and front-row seats to the sunset.
Celebrations – Birthdays, engagements, anniversaries, or just because. The boat becomes your floating venue.
Family Adventure – A relaxed day with swimming, paddleboarding, and exploring hidden beaches.
Corporate Outings – Swap the boardroom for the open sea. A fresh environment sparks new ideas and stronger bonds.
Tips for Making the Most of Your Day
Book early in peak season. Weekends in July and August fill fast. If you have a date in mind, reserve well in advance.
Go with the flow. Sailing is about the journey, not the destination. Weather and wind may adjust your course, but often that’s when the magic happens.
Unplug (at least a little). Cell service is spotty offshore—a blessing in disguise. It’s a chance to disconnect and be fully present.
Trust your captain. Licensed captains not only know the waters but also know how to keep you safe while making the experience seamless.
Bring your personality. A charter isn’t just about the boat—it’s about you. The more you bring your sense of fun, curiosity, and relaxation, the more memorable the day becomes.
Why Elysian Sailing?
At Elysian Sailing, our Lagoon 450 catamaran offers the ideal platform for day charters. With wide decks, shaded seating, and a luxurious interior, there’s space for both lively groups and quiet escapes. We host up to 12 guests, whether for a quick sail around Shelter Island or a full-day adventure to Gardiners Bay.
We believe sailing should be both luxurious and approachable—whether you’re popping champagne with friends or savoring the quiet lapping of the waves with someone special. Every charter is tailored to your group, and every detail—from safety to service—is handled with care.
With these comforts already provided, your packing list is lighter—and your day on the water is that much easier.
Final Thoughts
A Sag Harbor day charter isn’t just another activity—it’s an experience that combines the freedom of the open water with the timeless elegance of the Hamptons. Whether it’s your first time sailing or your fiftieth, each trip offers something new to discover.
So next time you’re in the Hamptons, step aboard. The wind, the water, and the wide horizon are waiting.