Clothing-Optional & Topless-Optional Group Trips — Unforgettable, Inclusive, Uninhibited

Escape the ordinary and dive into a vacation unlike any other: hosted group trips to lifestyle resorts where freedom, fun, and like-minded company set the tone. Whether you’re curious, experienced, or somewhere in between — we’ve got you covered.

Tom’s Trips Group- Hedonism II – Negril, Jamaica

Why Choose a Tom’s Trips Hosted Group?

• No pressure — just possibilities. Great for first-timers, seasoned lifestyle travelers, or anyone who wants a comfortable, judgment-free space. Our hosts were once beginners too, so they know how to ease you in.

• Instant community & connection. From the moment you arrive, you’ll be with a group of friendly, open-minded travelers looking to share laughs, experiences, and memories.

• Everything taken care of. From resort accommodations to curated entertainment, all you need to do is show up. We handle the logistics so you can focus on fun.

• Guided, safe, and inclusive experience. Our hosts help you get comfortable with the vibe — whether you want to “test the waters,” fully immerse yourself, or anything in between.

• Top resorts + curated group trips. Expect well-known destinations such as Hedonism II, Desire Resorts/Temptation Resort, and lifestyle cruises — all backed by Tom’s Trips decades of experience and thousands of satisfied travelers.

💥 What To Expect

Our clothing-optional and topless-optional group trips aren’t just vacations — they’re experiences. Expect:

• A welcoming, open-minded group + fun hosts who make you feel at home, from day one.

• A full resort or cruise takeover vibe: freedom, privacy, and celebrations.

• Options whether you want to chill by the pool, mingle, or dive into the full “lifestyle” experience.

• A safe, respectful environment — with guidance and community.

Who It’s For

• First-time lifestyle travelers who want a welcoming, pressure-free intro

• Experienced guests seeking parties, connection, and shared energy

• Groups or singles wanting a fun, social, like-minded crowd in top resorts

• Anyone curious about clothing-optional travel who wants support, guidance, and camaraderie

Ready to Join the Fun?

Browse our upcoming group trips to Hedonism, Desire/Temptation, Cruises & more — and discover a world where freedom meets connection.

Book now and get ready for the kind of vacation you’ll be talking about long after you’re home.