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How To Plan A Joyous Roaring 20’s Themed Group Trip

Thinking about planning a group trip?  Wondering what your options are and how to bring it all together? Here are a few tips to combine your group trip with a roaring twenties theme for a joyous good time.

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How To Plan A Group Trip

There are several ways to plan a group trip.  Many small groups of less than 8 people often choose to visit a location together by booking their own transportation and going in together for a home or villa rental.  Others may choose to pick an all-inclusive resort or cruise for the group.  No matter the size of the group, you have plenty of options from self-guided to concierge plans.


  • Least expensive option for many travelers.
  • In a group, you can have an entire dormitory style room for your group.
  • Some hostels have great group activities and amenities for socializing.


Most hotels require 9 rooms minimum for a group hotel block and a deposit.  They might provide you with a reservation code to give to the group for individual reservations to receive the same rate.  Some people might not want to book the group rate if they can find a lower rate via AAA, AARP, or some other association they are affiliated with.  They may also be able to find a lower rate via the internet.  Those alternate reservations will not be counted towards the group block.

A Villa Rental

Small groups and large groups can opt for a villa rental where they share a home, townhouse, or condo for their stay.  This can be done through AirBNB, VRBO, HomeAway, or even found on popular hotel search sites as well.  Additional fees to consider include cleaning fees, taxes, adn surcharges that drastically increase the price of a rental.  The designated leader will also probably bear the responsibility of security deposits and ensuring compliance with rules in order to avoid forfeiting the security deposit.  

All-Inclusive Resorts

All-inclusive resorts offer additional benefits for the group leader such as being able to earn a room free.  They can be the more costly option depending on the resort but can also have some very affordable packages for price sensitive travelers.  They can often be booked with air or without and can include transfer options.  Depending on peak/off-peak seasonal travel, some resorts offer:

  • Complimentary rooms starting with the 5th room (and every 5th after that)
  • Free upgrades
  • Free cocktail party
  • Spa discounts
  • Group Coordinator on site

Vacation Packages

I recommend using a travel agent for customized vacation packages that include multi-city starts, multi-city stays, bus travel, transfers, rail inclusions, concierge services, and excursion planning. 

Group Cruises

  • If you book 8 cabins with double occupancy, you could sail free.
  • Discounted group rate
  • Group dining arrangements
  • Payment flexibility
  • Could include cocktail parties or meeting rooms depending on group size.
  • A great host will probably send a welcome gift to every room.

Why book your group trip with a travel agent?

  • Easy planning, pick the cruise or resort/hotel/villa and your agent handles all of your booking details for your group.
  • Travel Agents can arrange group meetings, private parties, weddings, receptions, shore excursions, group photos, and even beach activities or group t-shirts.
  • No need to collect payments, your travel agent can track, remind, and collect from each individual and keep you informed about group bookings.
  • You can have a dedicated web page with details and sign up information to direct your participants to.


Turning Your Group Trip Into A Themed Party

So, you’ve chosen the location and travel details for your group.  But, did you consider creating a themed celebration for your travels? Your location may naturally fit some themes, making it easy for you.  You might not need anything extra except a few props to get the party started.  Here’s some locations that work well with a Roaring 20s Theme

  • A prohibition era style speakeasy can be found in some of the most famous cities (New York City, San Francisco, Chicago, Los Angeles, Nashville, Washington D.C.).
  • Classic steakhouse restaurants.
  • Miami Beach and it’s Art Deco Historic District.
  • Most cruise ships have some vintage room/restaurant/bar.
  • Jazz clubs.

What Is Roaring 20s Party?

The social scenes of the 1920s were often large formal dinners with dozens of waiters appearing as if by magic. 

To throw a really good Roaring Twenties party, you’ll need a lot of flowers, a bit of money, and a long guest list.

You’ll need to let the champagne flow, have some highballs, jazz music, and definitely learn to do the Charleston.

What To Wear to a Roaring 20s Party

Gents – Great Gatsby in a tux probably comes to mind first but you could also dress like a gangster or bootlegger.  The classic golf outfit or tweed with a matching vest. Accessorize with suspenders, bow ties, or pocket squares and a fedora or newsboy cap.

Ladies – Typically flappers dresses come to mind, I mean when else can we wear one? Casually though, a long skirt with pleats and cardigan sweater works well. A long kimono overcoat with palazzo pants.  Lavish accessories could include a tiara, silk shawl, feather boa, long pearl necklace, or a feather headband. 

Why Is A Cruise The Perfect Setting For Your Roaring 20s Party?

A cruise will give you access to a formal dining space with great waiters.  Some cruises will even provide dining entertainment (on Carnival, the waiters do an entire dancing routine).  


You can keep the easy-going party vibe all week long with something for everyone to enjoy.

On formal nights, you can get all dolled up in your roaring 20s outfits. The ultimate free dinner party happens on the 1st or only formal night during your cruise.  You can enjoy that magical feeling of servers swirling all around you without the cost.  

You have access that night to several photographers with beautiful backgrounds that somehow fit your theme perfectly!

You may be able to avoid the need for 20s party decorations depending on the ship you choose, there may already be perfectly themed dinners and bars.  For instance, the Carnival Alchemy Bar is a vintage-themed cocktail pharmacy with custom elixirs. The Alchemy martini tasting is a must see experience.  (Not yet available on some ships but coming soon to Celebration, Radiance, & Mardi Gras)  

Carnival’s Piano Bars are great for sing-a-longs with gorgeous themed decor. 

A Roaring 20s Birthday Party – Gatsby Style Cruising

This was as close as I would get to taking everyone out on my own private yacht.  There were plenty of opportunities for everyone to do their own thing and still connect with each other.  A good group trip plan should include some structure, some flexibility, and lots of fun.

  1. Choose a cruise with decor and pricing that fit the theme and possible participants.  I went with Carnival Elation because there really is something for everyone, entire families were invited.
  2. Created a web page invite with all the details at least 6 – 9 months in advance to allow people time to make payments affordably.  
  3. Sail away party on deck (arrive early, fills quickly).
  4. Included a formal night of Roaring 20’s outfits and group photo expectations.
  5. Took special photos with almost every photographer that night also.
  6. 2nd formal night was dedicated to A Hot White Night Party – everyone was instructed to bring a white outfit.
  7. Held group social hour during a private meeting scheduled in the Mark Twain library – played Taboo as a group.
  8. Pre-planned activities included optional excursions:
    1. Rented golf carts in Grand Turk and explored the island caravan style in our golf carts at our own pace.
    2. Puerto Plata countryside-safari tour with Outback Adventures on an open air truck visiting a coffee plantation, with a Dominican family-style lunch, tobacco rolling, chocolate making, and beach time.
  9. Final breakfast together before disembarking.

We also enjoyed karaoke, pool deck time, waterslides, game shows, late night dancing, casino games, dinners, lunches, martini tasting, and comedy shows together sometimes in small groups and sometimes with everyone.  It’s a great way to spend good quality time together and still have private moments individually by not expecting everyone to do everything together at all times.

20s Decor Ideas & Games

While definitely not needed, it was very simple to add some simple 20s decorations to my cabin.  I also created magnetic cabin decorations for each participant (which did not stick BTW!) These were simply made with pre-packaged Gatsby photo booth props and large magnets applied to the back of each one.  While they did not stick to the cabin doors, they did stick to metal in the room.  

TIP: Magnetic hooks from the dollar store make stateroom decorating easy and quick.  They stick to the ceiling or the tracks and you can easily hang a banner or stars.

Welcome Bags – Reusable Mesh Tote Beach Bags for everyone with a few cruising and party essentials.  

How To Plan A Joyous Roaring 20's Themed Group TripHow To Plan A Joyous Roaring 20's Themed Group Trip
How To Plan A Joyous Roaring 20's Themed Group TripHow To Plan A Joyous Roaring 20's Themed Group Trip
How To Plan A Joyous Roaring 20's Themed Group TripHow To Plan A Joyous Roaring 20's Themed Group Trip

A few special touches can be added but just getting everyone together and enjoying your time can be enough.  Enjoy some giggle water and have a roaring good time!


Happy Wandering!

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