Gatsby on the Isles: Summer Soiree on Star Island

August 28, 2021 to August 29, 2021

A Jazz Age Jaunt to Star Island on the New Hampshire Seacoast

On August 28 & 29 ’21, the S.S. Gatsby docks in Portsmouth harbor. Come aboard for the Gatsby on the Isles, a 1920s bash on the high seas, featuring live music by the Wolverine Jazz Band, lawn games, and a picnic on the Isles of Shoals, six miles off of the New Hampshire seacoast. Join us for the day or spend the night on the island for an evening of dancing at the historic hotel. It’s a summer jaunt guaranteed to be the bee’s knees.

Visit for photographs, itineraries, and more!


All guests must have received the Covid-19 vaccine in order to attend. Guests will be required to present physical or photographic proof verifying vaccination status in Portsmouth prior to boarding. It’s so we can dance together like it’s 1921!

Masks are optional during the event (although masks of a different sort will be mandatory at our Hot Jazz Masquerade.)

Also, you must review the following waiver:


SATURDAY, AUGUST 28 – SUNDAY, AUGUST 29. Rates include roundtrip steamship fare, meals, evening entertainments including our Hot Jazz Soiree with the Wolverine Jazz Band, general shenanigans, and enjoyment of the large (and curiously heavy) wooden crates of Whitman’s Chocolate Samplers. Register here.

Saturday Night Rates:

$280 shared room (per person)

$350 single room (one person)

Rates include accommodations, meals, and steamship fare.

Boat Times

Depart Portsmouth: August 28, 2:25 pm

Depart Star: August 29, 3:15 pm

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:


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

See you on the island!