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Weddings

About

Yes! We do, we do, we do! Schooner America 2.0 has set the stage for many a small wedding ceremony, reception, rehearsal dinner, proposal or brunch gathering. It has also entertained the salty-inclined bachelor and bachelorette parties. It’s a great way to host your special day in a private, classy way that embraces one of the more magical, iconic activities here in Key West.

Dedicated to providing the most perfect hospitality and sailing experience one could find in Key West, Classic Harbor Line hopes for the privilege of escorting you on a breathtaking excursion aboard the most elegant vessels in the local Key West fleet: Schooner America 2.0.

For more information about your event please contact Adam Miller at 305-890-6485

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Frequently asked questions

Do you have a site fee for wedding receptions at your venue?

Yes

What is the starting site fee for wedding receptions during peak season?

$3,806

Do you have a site fee for wedding ceremonies at your venue?

Yes

What is the starting site fee for wedding ceremonies during peak season?

$500

How many event spaces or rooms does your venue offer?

1

Describe your venue:

Boat/Yacht

What kind of settings are available?

Uncovered Outdoor

Which of the following wedding events does your venue service?

Ceremony
Reception
Bridal Shower
Engagement Party

What catering services do you offer?

Outside Cake

Reviews of Classic Harbor Line Key West

Gisselle
Gisselle Sent on 01/11/2026
5 out of 5 rating

Bst day of our lives!

I spent my wedding day aboard one of Classic Harbor Line’s schooner sailboat, and it was truly the best day of my life. From start to finish, the experience was nothing short of spectacular. The crew went above and beyond to make us feel welcomed and cared for, not just like guests, but like family.

The service was exceptional in every way. Every detail was handled with such professionalism and warmth that we were able to fully relax and enjoy the moment. The sail itself was breathtaking, creating the perfect backdrop for our ceremony and celebration. Our family and friends are still talking about how amazing everything was! the atmosphere, the views, the crew, the food and the overall experience.

If you’re considering a unique, intimate, and unforgettable venue for a special event, I cannot recommend Classic Harbor Line highly enough. They helped make our wedding day absolutely perfect.
M
Michael Sent on 08/06/2014
5 out of 5 rating
We were married on a Sunday on the 130pm afternoon sail. Reverend Sunny Andrachio, the General Manager of the vessel married Rasa and I. The ceremony and weather were perfect. Sunny did a magnificent job reciting his lovely vows and Captain Andrew and crew were charming hosts.
Our best man, Randy, was kind enough to record the ceremony on my iPhone and a kind guest, John, held Rasa's phone so my mom could watch the ceremony on Skype. Dear friend TonyScullin.com shot some amazing photographs as Schooner America sailed the very light chop with ease. It was Rasa's childhood dream to marry on a sail boat and America filled that wish with gusto. Although our wedding was not a private charter and strangers shared our experience, they added to the quiet revelry. Anyone planning a wedding between November and May (Schooner America 2.0 spends the summers in Manhattan sailing around the Statue of Liberty) should consider this majestic vessel and your dreams will come true. Ours certainly did...many thanks to Sunny and everyone at Classic Harbor Line.
We're all about trust. Our community relies on honest reviews to help you make those big decisions with ease.

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Classic Harbor Line Key West frequently asked questions

The space offered by Classic Harbor Line Key West for wedding events is known for:
  • Boat/Yacht
Classic Harbor Line Key West offers the following indoor/outdoor options for weddings:
  • Uncovered Outdoor
Classic Harbor Line Key West offers the following types of wedding events:
  • Ceremony
  • Reception
  • Bridal Shower
  • Engagement Party
Classic Harbor Line Key West is recommended by 100% of couples who have used their services. Their overall rating is 5.0, with the same score awarded for quality of service, flexibility, value, professionalism and average response time.
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