Private sailing trips around Fishers island from New London, CT

Discover the Charm of Private Sailing Trips Around Fishers Island from New London, CT

Imagine gliding across Long Island Sound aboard a fully skippered yacht, with the gentle breeze in your hair and panoramic views of over 300 islands looming nearby. That’s exactly what you get with this private sailing experience from New London, hosted by Sail-Works. Whether you’re celebrating a special occasion, seeking a peaceful escape, or just want a unique way to explore Connecticut’s coast, this trip offers a flexible, personalized adventure that’s worth considering.

One of the standout features we love is how customizable this experience is — from the length of the trip to the itinerary itself. Plus, the inclusion of drinks and private, skippered sailing means the focus is on relaxation and enjoying the scenery without any worries. A potential consideration? The price is per group, so it’s best suited for those comfortable splitting the cost with friends or family, and booking 4 weeks in advance helps secure your preferred date.

This sailing trip genuinely appeals to travelers craving an authentic, intimate experience on the water. If you’re a nature lover, eager to explore hidden spots, or simply looking for a peaceful respite on the coast, this private charter really could be the highlight of your trip to New London.

Key Points

• Fully Customizable Itinerary: Tailor the trip duration and stops to suit your preferences.
• Intimate Group Experience: Perfect for families, couples, or small groups up to 6.
• Includes Refreshments: Drinks are provided, making the journey more enjoyable.
• Flexible Duration: Options from 3 hours up to 7 hours or even overnight.
• Expert Skippers: All boats are captained, ensuring safety and local knowledge.
• Authentic Views: See parts of Connecticut many visitors miss, with quiet islands and scenic spots.

An In-Depth Look at the Experience

Starting Point and Meeting Logistics

The adventure begins at 260 Pequot Ave, New London, a convenient spot near public transportation. From here, you hop aboard your private vessel, ready to set sail on a journey customized to your desires. Since this is a private tour, only your group is involved, which means no crowded decks or noisy groups — just your friends or family enjoying the water.

The Boat and Skipper

The boats are fully skippered, meaning you won’t have to worry about navigating or boat handling — just sit back and relax. The crew, including skippers like Captain Eric, receive high praise for their engaging personalities and sailing skills, as noted by past guests. One reviewer mentioned that Captain Eric is “terrific, highly engaging and an excellent sailor,” which means you’re in experienced hands.

Duration and Customization

The standard rate covers a 3-hour trip for up to 4 people, but the experience can extend up to 6-7 hours, or even overnight if you prefer. Larger groups can be accommodated with prior arrangements, so whether you want a quick afternoon cruise or a full-day adventure, your options are flexible.

What You’ll See and Do

During the trip, you’ll cruise past the Thimble Islands, a collection of charming, quiet islands perfect for exploring or swimming. Reviewers have highlighted the chance to access quiet parts of the archipelago that are otherwise difficult to reach — ideal for snorkelers or those seeking serenity away from tourist crowds.

Guests have raved about the “fantastic sailing experience” and how it’s perfect for those wanting to see Connecticut from a different perspective. Some have noted that the trip offers an excellent opportunity to see less-visited areas that many travelers miss, making it a unique addition to your coastal explorations.

Swimming and Exploration

While sailing is the main activity, the opportunity to swim in the protected waters of the islands is a big plus. Past guests appreciated the chance to dip into the water and explore shorelines inaccessible by land or larger boats. Since drinks are included, you can sip a cold beverage while soaking up the sun, making the experience both relaxing and refreshing.

The Food and Drinks

Drinks are supplied, ensuring you stay hydrated and refreshed. You might find that bringing along a small cooler with extra snacks or personal favorites could elevate your trip, but the provided drinks are a thoughtful touch included in the package.

The Overall Value

Given the price of $720 per group, the experience represents great value for a private, customizable sailing trip. For groups of up to 6, this is quite reasonable, especially considering the personalized service and the opportunity to explore little-known islands in a relaxed setting.

Review Insights and Real Guest Experiences

One guest shared that they took their family, including retired sailors who hadn’t been on a boat in years, and everyone “could not have had a better time.” This highlights how accessible and enjoyable the trip is, even for those who might be less experienced sailors.

Another guest praised the “highly engaging” Captain Eric, emphasizing the importance of a friendly, knowledgeable skipper for making the experience memorable. The reviews consistently mention the “fantastic” nature of the sailing, confirming that this trip hits the sweet spot of adventure and relaxation.

Practical Details and Considerations

Booking and Availability

Most travelers book about 4 weeks in advance, which suggests that securing your preferred date requires some planning. Confirmations are straightforward, and the trip can be canceled free of charge up to 24 hours before, providing flexibility if plans change or weather conditions turn unfavorable.

Weather and Cancellations

Since this is a weather-dependent activity, poor weather will result in rescheduling or a full refund. This ensures peace of mind, knowing your experience is protected against the elements.

Group Size and Additional Costs

The rate is for up to 4 people, with options to inquire about larger groups or extended trips. For groups over 6, or if you’d like a longer day sail or overnight adventure, it’s best to contact the provider directly.

Location and Accessibility

Starting at a location near public transportation makes it easy to reach the boat without hassle. After your trip, you’ll return to your starting point, making logistics straightforward.

Who Will Love This Experience?

This private sailing trip is ideal for small groups seeking an authentic, relaxed day on the water. It appeals particularly to those who enjoy customized adventures, want to explore less-visited islands, or simply wish to unwind with friends or family in a scenic setting. It’s also well-suited for celebrating special occasions or creating memorable moments in Connecticut’s coastal landscape.

If you’re a seasoned sailor or a first-time boat passenger, the experienced skippers and calm waters provide a reassuring environment. Plus, the flexibility in itinerary and duration makes it adaptable for different interests — whether you want a quick cruise, a leisurely exploration, or an overnight escape.

FAQs About Private Sailing Trips Around Fishers Island

How many people can I bring on this trip?
The standard rate is for groups up to 4 people, but you can inquire for larger groups or longer trips, up to 6 or more.

What is included in the price?
The price covers the yacht, a skipper, and drinks to keep you refreshed. Additional snacks or personal beverages can be brought along.

How long does the trip last?
Trips typically run around 3 hours but can be customized up to 6-7 hours or longer, including overnight options.

Can I customize the itinerary?
Yes, the sailing is fully customizable, allowing you to focus on specific islands, swimming spots, or scenic routes.

What should I bring?
Comfortable clothing, sun protection, and possibly a towel if you plan to swim. The boat may have some amenities, but extra personal items are encouraged.

What happens if the weather is bad?
The activity is weather-dependent. If canceled due to poor weather, you’ll be offered a different date or a full refund.

Is this activity suitable for non-sailors?
Absolutely. Since all boats are skippered, you don’t need sailing experience — just a desire to relax and enjoy the scenery.

How do I book?
Most bookings are made around 4 weeks in advance through the provider’s website or by contacting Sail-Works directly via phone or email.

Can I extend the trip or add special requests?
Yes, longer trips, overnight stays, and special arrangements can be discussed with the provider, so feel free to ask.

Final Thoughts

Choosing a private sailing excursion around Fishers Island from New London offers a fantastic way to explore Connecticut’s coastal gems in a relaxed, intimate setting. The customizable nature of the trip, the experienced crew, and the chance to access quiet, scenic islands make it stand out as an authentic experience. Whether you’re celebrating, seeking a peaceful retreat, or just eager to enjoy the water, this trip provides great value and memorable moments.

If you appreciate personalized service and love the idea of discovering hidden corners of Long Island Sound, this sailing adventure is an excellent choice. Just remember to book early, prepare for beautiful weather, and get ready to enjoy some of the best views Connecticut has to offer — all from the comfort of your private yacht.

Note: For similar experiences or additional options, explore other tours such as high-flying zipline adventures, scenic cruises, or local scavenger hunts in the area.