Gatsby on the Isles: Summer Soiree on Star Island

August 28, 2021 to August 29, 2021

Come aboard for Gatsby on the Isles, a 1920s bash on the high seas, featuring music, lawn games, and a picnic on Star Island. Join us for the day or spend the night at the historic hotel for an evening of dancing at our Hot Jazz Soiree with the Wolverine Jazz Band. It’s a summer jaunt guaranteed to be the bee’s knees and a Star Island tradition.

Day Trip Tickets for Sunday, August 29
Available in the spring!

Gatsby Weekend Overnight Tickets: Registration opens on May 1 
Saturday, August 28 – Sunday, August 29

Room and Board starts at:
Shared Room (per person): $280
Single Room (one person): $350
Rates include room, meals, roundtrip steamship fare, and program fee

Gatsby Weekend Itinerary

Escape to Star Island for a vintage summer getaway and hot jazz soiree. The S.S. Thomas Laighton departs Portsmouth Harbor on Saturday at 2:25 pm with Gatsby Weekend guests registered at the Oceanic Hotel. Enjoy a leisurely afternoon exploring the island and historic buildings, followed by dinner, games, and then our famous hot jazz soiree in the Oceanic Dance Hall. Sunday morning, you’re invited to play pajama croquet before breakfast. Mid-morning on Sunday, Gatsby guests visiting for the day join for a lawn party and picnic, with music, refreshments, dancing on the porch, lawn games, and a swimming party in Gosport Harbor (bring your old school bathing costumes). At 3:15 pm on Sunday, the ship returns our party to Portsmouth. Visit to learn more about our timeless New England destination and see for snapshots of years past.

Hot Jazz: None Better than The Wolverines.

Music by the Wolverine Jazz Band, a copacetic seven-piece gang led by Mr. John Clark on clarinet. No bushwa, these fellows are the berries. Hire them. Follow the link to hear them perform:

What to Wear.

Sheiks and shebas, get up in your glad rags like it’s 1929. Ladies: Doll up in your favorite summer flapper dress and cloche hat. Gents: Wear your best seersucker or linen, a sharp tie and your snappiest straw hat. If you like, bring a change of formal evening clothes for the hot jazz soiree that evening. It’s a fun and casual weekend—just in another time—so dress your vintage best, but don’t let lack of picture-perfect duds prevent you from joining us!

What to Bring.

Bring your picnic lunch Saturday afternoon and your favorite vintage accoutrements. Since Gatsby guests each year bring a smorgasbord of picnic fare, we will have a potluck luncheon buffet this year for those who wish to share their picnic delicacies. Dust off your vintage picnic, croquet, and bocce sets, antique beach chairs and umbrellas, and musical instruments (for those wishing to jazz up the weekend). Each year, we also have our vintage bathing party on the Gosport Harbor beach – kudos if you bring your period wool or reproduction swim suit. Also: Please note that the Thomas Laighton has limited space, so large items may not be possible to bring aboard.

Candlestick Telephones & Kodaks Only, Please.

One of the most amazing things about choosing to step back in time is that you may find yourself more in the present. We encourage you to adopt a vintage technological mindset during Gatsby on the Isles and we ask that you not use your smartphones to text, check social media, or take photographs during the event. Film cameras, especially vintage cameras, are welcome, but please leave digital selfies and Facebook profile pics in the past on the mainland. We will have a roaming professional photographer on the island if you would like to request photographs free of charge, which will be available on social media and on the website after the event. Of course, if you need to use your cell phone, you are welcome to do so, but we ask that out of respect for other guests you use it out of sight in your room or elsewhere in the hotel. That said, we dare you to turn off your smartphone for a few hours, or, if you’re especially brave, a whole weekend! You might find the getaway more enjoyable and memorable without it. In August 1929 on Star Island, your status update is here and now, sharing this remote and beautiful place with good friends in the timeless, ephemeral moment.

Parking Information

Parking will likely not be available at the Isles of Shoals Steamship Co. lot given passenger volume, but there are a number of other locations in Portsmouth to park. The Connect Community Church parking lot (200 Chase Drive, on your left coming off of 95) is a ten minute walk from the dock. The downtown garage and other lots are also available, but parking in Portsmouth is notoriously tricky, so do plan ahead. For all parking questions and parking availability at the Steamship Co. lot, please call (800) 441-4620. Here’s a map of parking downtown:


Are the event ticket prices out of reach? We’d still love for you to join! Visit the Star Island website to learn more:

Regarding steamship passage, departure and arrival times, parking, etc., please contact the Isles of Shoals Steamship Co. at (800) 441-4620

Regarding overnight accommodations on Star Island, dining options, room registration, etc., please contact Star Island at (603) 430-6272 or by emailing the registrar, Mike Bray

For general event questions, please contact event host, Adam Irish

Follow the Gatsby on the Isles Facebook page for updates.

Sponsored by Old as Adam Antiques & Vintage Haberdashery, 33 Ceres Street, Portsmouth, NH.

See you on the island!