Gatsby on the Isles

August 25, 2018 to August 26, 2018

On August 25, 2018, the S.S. Gatsby docks in Portsmouth harbor. Come aboard for 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. Join us for just the day or spend the night on the island for an evening of dancing at the historic hotel. Proceeds benefit the nonprofit Star Island Corporation. It’s a summer jaunt guaranteed to be the bee’s knees.

Stay for the soiree at the historic island hotel, Saturday 8/25 to Sunday 8/26. Click here for overnight registration.

Visit the island for a Jazzy afternoon Saturday 8/25. Click here to buy your day trip tickets.

Ticket availability is limited and the boat will sell out. It is unlikely any tickets will be available the day of the event. Advance booking is advised.

The Itinerary

Our party will gather at 10:00 am on Saturday, August 25 at 315 Market Street in Portsmouth (the Isles of Shoals Steamship Company). The ship boards at 10:25. We’ll arrive at Star Island at noon and have the rest of the day to carouse and explore the Victorian hotel and island. The day includes a 1920s jazz band, refreshments, lawn games, and a 1920s-style beach party. Day trippers board to depart Star at 3:30 pm, arriving back in Portsmouth by 5:15 PM. Guests may book advance reservations at the hotel to spend the night for an evening of dining, dancing and delightful company. Overnight guests will depart for the mainland on Sunday August 26 at 3:00 pm and arriving at 4:45 pm. All ages are welcome.

What to Wear

Sheiks and shebas, get up in your glad rags like it’s 1924. 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 evening clothes for the hot jazz soiree that evening.

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.

Invite your friends and spread the news. Last year’s event was a roaring success with over 100 guests, so don’t miss this darb summer tradition on the seacoast.

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

Music by the Wolverine Jazz Band


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

Regarding overnight accomodations on Star Island, dining options, room registration, etc., please contact Star Island at (603) 430-6272

For general event questions, please contact adam@oldasadam

Follow the Gatsby on the Isles Facebook page for updates.

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:

See you on the island!

Room & Board Rates

These rates include lodging, meals, and ferry transportation.

Gatsby Standard Shared Standard Single
1-night $265 $335
2-night $425 $353


Ferry Schedule

Saturday, August 25
Departure: Portsmouth 10:55 a.m.
Arrival: Star Island 11:55 a.m.
Departure: Star Island 3:45 p.m.
Arrival: Portsmouth 5:15 p.m.
Sunday, August 26 (overnight guests)
Departure: Star Island 3:15 p.m.
Arrival: Portsmouth 4:45 p.m.

Monday, August 27 (2-night option) Depart Star: 11:45 a.m. Arrive Portsmouth: 1:00 p.m.


Email Adam at