Sag Harbor Yacht Charters

You’ll hear Sag Harbor called the St. Tropez of the Atlantic, and a stroll around the historic village will reveal why.

From its sophisticated wine bars and upscale beach clubs, to the beautiful Victorians and award-winning restaurants, Sag Harbor exudes a quiet cool. The village is a more in-the-know version of the Hamptons or Montauk, with all the A-list amenities to boot.

Not only is Sag Harbor worth a visit. The region is the perfect jumping off point for a luxury yacht charter. With its idyllic sand duned beaches and proximity to popular yachting stops like Block Island and Newport, Sag Harbor charters allow guests to truly enjoy the splendor and charms in quietude and grace.

Wondering what to expect on a Sag Harbor yacht charter? This guide provides a quick overview of Sag Harbor, things to do while on charter, and a sample Sag Harbor charter itinerary.

Sag Harbor: An Overview

Sag Harbor civil war monument

Sag Harbor’s history dates to the 18th century when the village was a thriving whaling port. Today, Sag Harbor still retains much of its historic charm with many of the original buildings from the whaling era still standing.

You can explore the areas history at the Sag Harbor Whaling and Historical Museum. Housed in a stunningly preserved Civil War Era home, the museum is home to a variety of artifacts from the area.

Today, the historic port is a thriving art colony and an exclusive summer hot spot. Tucked away in the alleys and Victorians, you’ll find unique art galleries and community theaters, which feature the works of local artists and performers.

The Church, a beautifully restored arts center, opened in 2021 and it’s quickly become the center of the arts scene in Sag Harbor.

Consider yourself more of a foodie?

Sag Harbor’s culinary scene is one of the best on Long Island, comparable to Montauk’s. Wine bars and award-winning restaurants fill the storefronts on Sag Harbor’s cobbled Main Street.

Enjoy waterfront dining in style at Le Bilboquet, or gather with friends at Tutto il Giorno for delectable Italian eats.

In short, Sag Harbor is a charming and historic village with a rich cultural heritage, beautiful beaches, and excellent dining options, making it a popular destination for charter guests.

Sag Harbor Yacht Charters

Sag Harbor has a storied yachting history, and the idyllic and protected harbor is one of the most desirable ports in New England. Yacht charters in the area tend to: Explore the surrounds, like Sunset Beach, the Hamptons and Block Island, or travel to nearby hotspots like Newport, Rhode Island, or Martha’s Vineyard.

Sag Harbor Yachting Overview:

  • Season – Summer (June through mid-September)
  • Conditions: Deepwater protected harbors
  • Water Temperatures: 77 degrees (in July)
  • Available Charter Yachts: All types, from luxury motor yachts, to sporty sailing yachts
  • Destinations: Block Island, Martha’s Vineyard, Newport, Shelter Island, Montauk

Ultimately, Sag Harbor is one of the best destinations for a summer yacht charter in New England. The beautiful beaches, historic cruising routes, and excellent shoreside amenities make this a perfect jumping off point to explore the region in style.

Sag Harbor Charters: Things to Do

While you cruise the protected waters of Sag Harbor, there’s a variety of activities, sights, and culture to explore. Yacht charter guests rave about:

Beautiful Beaches
Sag Harbor is home to some of the most picturesque beaches on the East Coast. Top spots include:

  • Havens Beach – Located in the heart of Sag Harbor, Havens Beach is a popular destination for swimming, sunbathing and water sports.
  • Long Beach – This secluded beach on Sag Harbor’s eastern end, is known for its scenic beauty and calm waters. Long Beach is also a popular fishing destination.
  • Sunset Beach – Often referred to as the St. Tropez of the Hamptons, nearby Sunset Beach offers a scenic sandy shore, as well as amenities like posh beach clubs, A-list restaurants, and relaxing spas.
  • Sagg Main Beach – Known for its wide stretch of sand, scenic dunes, and excellent surf, Sagg Main Beach is one of the best stops for water sports like paddle boarding and kitesurfing.
  • Food and Wine – Sag Harbor’s thriving culinary scene offers the perfect afternoon escape for charter guests. Check out the sophisticated Grappa Wine Bar, which features a collection of international and local wines and charming, Instagram-worthy decor.  The Dock House is cozy seafood restaurant well known for its seafood and lobster, that’s a short stroll from Sagg Main Beach, while Lulu Kitchen & Bar serves up delectable Mediterranean dishes and crafty cocktails.

Water Sports
The inviting and calm waters of Sag Harbor make this a favorite spot for water-based adventures. Some must-dos include:

  • Swimming / Sunbathing – Enjoy the calm waters of the Atlantic Ocean at Sag Harbor’s popular swimming beaches, including Havens and Long Beach.
  • Kayaking: Explore the peaceful waterways of Sag Harbor via sea kayak, such as the Sag Harbor Cove and the Peconic Bay.
  • Stand-Up Paddleboarding: The calm, protected waters in Sag Harbor make this an ideal destination for stand-up paddleboarding.
  • Sailing – Sag Harbor has a rich sailing history; experience the thrill of sailing in the beautiful deep waters of the area.
  • Jet Skiing / Water Skiing – Peconic Bay is a playground for thrilling jet ski and water-skiing adventures.
  • Festivals and Events – During the summer yachting season, Sag Harbor’s events calendar is full of arts, food, music, and live entertainment events. A few can’t-miss festivals include HarborFest Arts & Crafts Fair, which features one-of-a-kind artisan fares, and the Sag Harbor Music Festival, a summer music fest featuring local and regional artists.

Sag Harbor Yacht Charter Itinerary

The itinerary for your Sag Harbor charter can be personalized, but you’ll likely want to explore hotspots throughout the region, including Block Island and Martha’s Vineyard. Here’s a sample Sag Harbor itinerary for a 4-day sailing charter from Sag Harbor to Newport, Rhode Island:

Day 1 – Sag Harbor to Block Island

Block Island

This 30-nautical mile cruise leaves Sag Harbor, on south shore of the Long Island Sound, with a lunchtime cruise past Montauk to Block Island. Block Island, at the mouth of Long Island Sound, is renowned for its charming downtown, which is home to boutiques, cafes, and watering holes, and its charming seaside vibes.

After exploring downtown, you might choose to crisscross the island via bicycle, as there’s a network of biking trails with picturesque views. You can also ride to the top of Mohegan Bluffs, to catch the sunset, or hike down to the rugged Mohegan Bluffs Beach.

Finally, enjoy a chef-prepared tasting menu on board from the island’s historic harbor, or grab a nightcap cocktail in one of the waterfront’s famed saloons.

Day 2 – Block Island to Martha’s Vineyard

Martha's Vineyard yacht charters

Set sail in the morning for your Day 2 adventure to Martha’s Vineyard. The exhilarating sail will take you through Block Island Sound to the affluent summer colony on the Vineyard.

Spend the afternoon exploring the enhancing, elm tree-lined streets on Martha’s Vineyard, or relax on one of the island’s picturesque beaches. You’ll find a variety of shops and galleries to explore downtown, as well as bike trails and hiking trails to explore. Edgartown, the enchanting harbor on Martha’s Vineyard’s east end, offers a smattering of award-winning restaurants and wine bars, or you might choose to adventure to Menemsha Beach on the island’s north shore, an expansive sandy stretch with nearby chowder houses and a promenade for sunset strolls.

Day 3 – Martha’s Vineyard to Newport, Rhode Island

Newport bridge

Embark on the 30-nautical mile trek from Martha’s Vineyard to historic Newport. The colonial village, which its grandiose mansions, has a rich, storied sailing history, and it’s one of the region’s favorite yachting destinations.

During the summer months, the events calendar is packed full of regattas and festivals, and the historic waterfront is always bustling. Newport’s culinary scene includes a variety of trendy cocktail bars, as well as cozy eateries.

Day 4 – Newport, Rhode Island to Sag Harbor

Sag Harbor house

Your return voyage begins with an alfresco breakfast onboard. Enjoy the sights of Newport’s waterfront, as it wakes up and comes to life. The fine sail is a 60-nautical mile cruise back to Sag Harbor, where you’ll pass by the picturesque villages along the coast of Long Island Sound, like Mystic and Shelter Island.

Explore Sag Harbor This Summer

Contact a broker with Worldwide Boat today to reserve your summer charter in Sag Harbor. This is the perfect location for a family yachting vacation, or for corporate events, birthday celebrations, or romantic anniversary getaways.