Tender-Date Site looking for love

A unique and memorable dating experience in Boston awaits those who embark on a romantic Boston Sunset Sail. The city's waterfront landmarks come to life as the sun dips below the horizon, providing a picturesque backdrop for an early evening adventure with that special someone.

Sailing on the calm waters of the Boston Harbor offers a smooth and gentle experience, ideal for an intimate outing. Options for sunset cruises range from historic tall ships like the 125-foot Liberty Clipper, with a capacity of up to 90 passengers, to smaller, more exclusive vessels like the Liberty Star, perfect for a relaxing experience with up to 35 passengers on board.

For those over 21, the Boston Harbor sunset cocktail cruises provide a more grown-up atmosphere with drinks, light snacks, and music, sailing from May to September. With choices that cater to different preferences and budgets, there's a perfect Boston Sunset Sail for everyone seeking a romantic and unforgettable evening on the water.

The Experience of a Boston Sunset Sail

Scenic Views

Embarking on a Boston Sunset Sail allows passengers to witness the breathtaking beauty of the city's skyline and waterfront landmarks as the sun sets below the horizon. The experience provides a unique vantage point of the cityscape and creates lasting memories for those aboard. A sunset sail offers an unforgettable visual feast from historical sites to modern architecture.

Onboard Activities

The schooner or tall ship used for a Boston Sunset Sail is reminiscent of the classic turn-of-the-century Pilot Schooner. While on board, the friendly captain and crew are dedicated to providing a smooth and gentle sailing experience. Passengers can expect to be pampered with top-notch service throughout the journey, creating a relaxing and enjoyable atmosphere.

Additionally, passengers can participate in various onboard activities, such as raising the sails or taking a turn at the helm. This hands-on experience allows guests to feel fully immersed in the sailing adventure, and it is suitable for both beginners and experienced sailors alike.

Romantic Ambiance

A sunset sail provides the perfect setting for those seeking a unique and memorable dating experience in Boston. The romantic ambiance is created through smooth sailing, stunning views, and the golden glow of the setting sun. It is an ideal place for couples to spend quality time with one another, reconnect, and create lasting memories.

In addition, the calming waters and gentle breeze of Boston Harbor contribute to the idyllic atmosphere. Consider booking a Boston Sunset Sail for that special someone for a truly unforgettable evening.

Choosing the Right Sunset Sail

Types of Boats

There are various types of boats to choose from when planning a sunset sail in Boston. Classic tall ships and schooners offer a vintage sailing experience, while modern vessels provide a comfortable and spacious experience. Selecting a boat that suits your preferences and interests will ensure a memorable experience.

Tour Providers

Several tour providers offer sunset sails in Boston, each offering unique features and experiences. Some popular providers include:

  • Liberty Fleet of Tall Ships - Classic tall ship sunset sailing experience
  • Boston Harbor Cruises - Offers a range of sunset sail options, including cocktail cruises for adults
  • Classic Harbor Line - Sails aboard a luxury yacht with knowledgeable guides and available refreshments


Most sunset sails in Boston last between 1.5 and 2 hours, allowing ample time to take in the stunning views of the harbor and the city skyline. The duration of your sail may vary depending on boat speed, weather conditions, and provider. It's essential to consider how long you'd like to be on the water when selecting a sail experience.


Pricing varies based on the type of boat, tour provider, and included amenities. Here is a general pricing range for popular providers:

Provider Approximate Price Range
Liberty Fleet of Tall Ships $60 - $75
Boston Harbor Cruises $35 - $45
Classic Harbor Line $50 - $70

Remember that some providers may offer discounts for children and seniors or if you book in advance.

What to Expect

Departure and Check-In Process

When arriving for your Boston Sunset Sail, ensure you arrive at the designated departure location, Central Wharf, at least 30 minutes before the scheduled departure time. This allows sufficient time for the check-in process and pre-boarding safety briefings. Once aboard the vessel, guests may choose their seats and prepare to embark on an unforgettable sailing experience.

Weather and Sailing Conditions

Weather conditions in Boston can vary, but you can expect a smooth and gentle sail if the day is not too windy or stormy. The wind direction will determine the route taken during the Boston Sunset Sail. It may include sailing toward the outer harbor, the Boston Harbor Islands, East Boston, or the Charlestown Navy Yard. Keep in mind that the duration of the sunset sail may last between 90 minutes and two hours.

Safety Measures and Guidelines

Your safety and enjoyment are essential during the Boston Sunset Sail experience. Before departure, the crew will provide a safety briefing outlining essential guidelines for your time onboard. Personal flotation devices (lifejackets) are available on all vessels, and passengers are encouraged to follow crew instructions at all times. Additionally, guests are advised to dress appropriately for the sailing conditions and bring weather-appropriate clothing or accessories (e.g., sunglasses, hats, or sunscreen) to ensure comfort throughout the journey.

Preparation Tips

What to Wear

When preparing for a Boston Sunset Sail, dressing appropriately ensures an enjoyable experience. Due to cooler temperatures and potential ocean breezes, dressing in layers is highly recommended. This will allow you to add or remove clothing as needed quickly.

Wear comfortable, non-slip shoes that provide adequate support and grip, as boat decks can become slippery. Closed-toe shoes are preferable. Additionally, consider bringing a light jacket, as it may get cooler when the sun sets. Opt for practical and weather-appropriate clothing, such as long sleeves, pants, or leggings.

What to Bring

Packaging a few essential items when going on a Boston Sunset Sail is important. Here is a list of things to consider bringing along:

  • Camera or smartphone: Capture the stunning city skyline and harbor views during your sunset sail.
  • Sunglasses and sunscreen: Protect your eyes and skin from the sun's rays, even later in the day.
  • Binoculars: Enhance your sightseeing experience by getting a closer look at points of interest, such as Fort Independence or the USS Constitution.
  • Snacks and water: Some sunset cruises may provide refreshments, but bringing extra snacks and water for your personal needs is always a good idea.
  • Small blanket: A compact, lightweight blanket can provide added warmth on cooler evenings.
  • Seasickness remedies: If prone to motion sickness, consider bringing over-the-counter or natural remedies to ensure a comfortable sailing experience.

Preparing for your Boston Sunset Sail by dressing appropriately and packing essential items can significantly enhance your romantic experience aboard a classic tall ship, allowing you to focus on the breathtaking views and create lasting memories.

Extra Information


Boston Sunset Sails prioritize making their experience accessible to many visitors, including families, couples, and individuals. With various sail durations and times of day available, there will surely be an option to suit every schedule. For families with young children, some sunset sails even offer free admission for children under 2 years old and reduced rates for older children, making it an affordable excursion for the whole family.

Special Events and Occasions

A sunset sail in Boston Harbor is perfect for celebrating special events and occasions. Companies in the area often offer customized packages for weddings, corporate events, or anniversaries, ensuring a memorable experience for you and your guests. These special event packages can include catering, photography services, or custom event itineraries tailored to suit the needs of your occasion.

Create memorable experiences with family and friends for celebrations such as birthdays, reunions, or graduations. The unique, relaxing atmosphere aboard a sunset sail provides an excellent photo backdrop. The friendly crew is often more than happy to assist with any special requests or arrangements needed.

Pricing and Availability

The prices for a Boston sunset sail vary depending on the provider, the sail duration, and any additional services included. Generally, adult tickets can range from $50 to $72 or more, while child tickets may cost between $20 and $55. It is recommended to book your sunset sail in advance, particularly during the popular summer season, to ensure availability and the best experience possible.

Many cruise providers offer options for private bookings or group events, ensuring a personalized and unique experience. For those interested in an enhanced sailing opportunity, some providers even allow passengers to participate in handling the sails, taking this nautical experience to new heights.

Recent Posts

Copyright © 2021 Tender Dating