Pineapple Sailing Charters

Pineapple Sailing Charters Party Boats & Sail Yachts. We have a boat for any occasion and group size. No sailing experience necessary.
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Let us handle the job of sailing the boat while you relax…but we’re always more than happy to let our eager guests take the wheel and learn to trim sails. Our knowledgeable captain and crew are glad to teach along the way.

Perks of fall in New England.
09/24/2024

Perks of fall in New England.

Fall comes with its perks.
09/24/2024

Fall comes with its perks.

Bach Brunch Boat is underway! Grab your girl friends for Bach boat brunch vibes!
08/24/2024

Bach Brunch Boat is underway! Grab your girl friends for Bach boat brunch vibes!

Lava vibes! Sunset in
08/12/2024

Lava vibes! Sunset in

“Boats n’ Coves“ Golden Hour Edition
08/12/2024

“Boats n’ Coves“ Golden Hour Edition

Perfect swan dive from the bride-to-be!
08/05/2024

Perfect swan dive from the bride-to-be!

Island Girl. Golden Hour. Girls Trip.
07/30/2024

Island Girl. Golden Hour. Girls Trip.

Bachelorette bow babes on Calypso. Come aboard for a 2.5 hr private charter with FULL open bar & gourmet food service in...
02/28/2024

Bachelorette bow babes on Calypso. Come aboard for a 2.5 hr private charter with FULL open bar & gourmet food service in the sailing capital of the world, Newport, RI. Lounge on our cozy floats in a beautiful cove while sipping drinks and eating oysters with your girlfriends.

Bach Bubbly…on a Boat?! Yes please!
01/27/2024

Bach Bubbly…on a Boat?! Yes please!

Happy Thanksgiving!!
11/23/2023

Happy Thanksgiving!!

Celebrate your Queen on our bachelorette party boats.
11/18/2023

Celebrate your Queen on our bachelorette party boats.

Spend a few hrs floating in a beautiful cove in  .
10/24/2023

Spend a few hrs floating in a beautiful cove in .

It’s the last week for Fall Charters! Call now for a 1/2 off sail or party boat charter - 4016625598.
10/23/2023

It’s the last week for Fall Charters! Call now for a 1/2 off sail or party boat charter - 4016625598.

  on a boat? Yes please!
09/26/2023

on a boat? Yes please!

Oysters on a paddle board?! Yes please!
08/31/2023

Oysters on a paddle board?! Yes please!

Ride to/from The Water Brother movie tomorrow at Fort Adams. Leaving The Lobster Bar @ 6:00 & 7:00. Return trips after m...
08/16/2023

Ride to/from The Water Brother movie tomorrow at Fort Adams. Leaving The Lobster Bar @ 6:00 & 7:00. Return trips after movie is over. $25/passenger WITH DRINKS & snacks!! Water Brothers. Call 4016625598 to buy your ticket!

Splashing around on a hot day at
08/10/2023

Splashing around on a hot day at

Oysters anyone?
08/10/2023

Oysters anyone?

Put a ring on it!
08/08/2023

Put a ring on it!

Hanging out.
08/08/2023

Hanging out.

Making Monday feel like Saturday.
08/02/2023

Making Monday feel like Saturday.

Clouds didn’t stop us from having a good time!
07/14/2023

Clouds didn’t stop us from having a good time!

Eating oysters while floating in the ocean? While drinking Cape Cod'r….Yes please!
07/08/2023

Eating oysters while floating in the ocean? While drinking Cape Cod'r….Yes please!

Island Time kinda day.
07/05/2023

Island Time kinda day.

Bachelorettes on Island Time
06/24/2023

Bachelorettes on Island Time

Address

31 Bowen's Wharf
Newport, RI
02840

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