Group Travel Ideas & Inspiration: Weddings, Friends’ Trips, Multi-Gen Vacations & More

Planning a group travel and looking for ideas for weddings, bachelorette parties, vow renewals, friends’ vacations, or multi-generational getaways? There is truly something about traveling with your people that makes every memory a little sweeter. Whether you’re celebrating something big or just want an excuse to get away together, group trips are where the best memories are made. We’ve planned hundreds of group celebrations, from destination weddings to multi-gen family vacations, and know what makes them unforgettable.

This guide is designed to help you explore fun, stress-free group travel ideas from weddings and vow renewals to milestone celebrations and family trips.

Best Types of Group Travel We Help Plan

From romantic celebrations to big family vacations, below are some of our favorite types of group travel we plan for clients year after year:

Vow renewal at Sandals South Coast — an unforgettable celebration of love in paradise.

Destination Wedding Group Travel Ideas:

Skip the stress of a buttoned up ballroom and picture saying “I do” while barefoot on the beach. Destination weddings are the ultimate two-for-one when it comes to weddings—you get your dream wedding and also a built-in vacation with all your favorite people. Plus, with beautiful beachside backdrops or an overwater chapel, a destination wedding is one everyone will remember! A few of our top booked resorts for destination weddings include Beaches Turks & Caicos, Sandals South Coast and Sandals Royal Bahamian.

See resort comparison and planning details on our Weddings & Romance page.

Multi-Generational Family Group Vacations:

Grandparents, parents, kids… everyone under one resort roof. Multi-gen trips are all about the core memories—lazy pool days, family dinners, and activities for every age. Trust me, it’s the kind of trip everyone remembers for years to come. Multi-generational groups especially love gathering at Beaches Turks & Caicos, Exuma gateway, Walt Disney World, or onboard a Disney cruise, where grandparents, parents, and kids can all enjoy the fun together.

Bachelor & Bachelorette Group Trips:

Why settle for one night out on the town when you could turn it into a whole vacay? Whether it’s an all-inclusive resort in Mexico (hello tacos & margs!), or a quick getaway to the Bahamas, bachelor/bachelorette trips are about making it a weekend (or week!) to remember….because getting married deserves so much more than just one night of celebrations! Top destinations for bachelor and bachelorette parties include Cabo, Cancun, Puerto Vallarta and the Bahamas.

Traveling Ears Vacations’ 7th Annual Group Trip — celebrating in Curaçao with nearly 30 friends for an unforgettable Caribbean getaway.

Friends’ Group Getaways & Social Trips:

Milestone birthday? Girls’ trip? Or honestly, just because you deserve it? Grab your crew and go. Think beautiful beaches, swim up bars, and endless laughs with your best friends. From lots of personal experience hosting annual friends’ trips, these types of getaways fill everyone’s buckets and are good for the soul! Check out one of our 2025 group trip at Sandals Royal Curacao here.

Vow Renewals With a View:

Already tied the knot but want to do it all over again? A vow renewal at a dreamy destination is the perfect excuse for a celebration. Big or small, it’s about celebrating your love story in a more relaxed setting and with your favorite people surrounding you. A couple of our clients’ favorite resorts for vow renewals include Beaches Negril and Sandals South Coast.

Here’s the best part: group trips usually come with extra perks and freebies for the hosts (hello, who doesn’t love that?!).

In my next post, I’ll spill all the details on group travel incentives and how you can take full advantage for booking your group with our agency and with our preferred resort partners. We’ve helped countless groups secure perks, upgrades, and stress-free planning over the years, and we’re happy to share recent examples.

Questions about group travel? Email us today at Team@TravelingEars.com or request your group quote here and we’ll help you get your group getaway off the ground!

If you’re ready to start planning a group trip everyone will remember, explore our planning guides and destination reviews for more inspiration. Tips for Planning a Successful Group Trip

Start with dates, consider guest budgets, the size of the group, ages traveling, and the type of experience you want—relaxation, adventure, nightlife, or a celebration with all the details taken care of. Then we’ll help secure resort options, group perks, room contracts, logistics, transfers, and any special events, so everyone has a smooth and memorable experience.

Group Travel FAQ

How many people make a “group” for travel perks?

Most resorts consider 5–10 rooms or 10–20 travelers a group, but this varies depending on location and season. We’ll confirm the exact threshold for your dates and destination, then structure your room block to unlock the best bonuses.

When should we book a group trip?

Ideally 9–15 months ahead normally provides the best pricing and widest availability. For peak seasons or popular resorts, 12–18 months is even better. Last-minute groups are possible, but perks and room selections may be limited.

How far ahead should we secure group airfare?

Booking 9–11 months ahead usually offers the best group air pricing and seat availability.

Can guests pay individually while still getting group perks?

Yes. Groups can reserve room blocks while allowing each traveler to pay on their own schedule.

Do resorts offer blackout dates?

Some properties have holiday blackout periods or minimum stay requirements, which we confirm before booking.

What perks can hosts earn?

Perks vary by partner and travel dates but may include free nights, room upgrades, private event credits, or complimentary rooms after a certain pickup. We’ll lay out every available incentive in writing before you commit—no surprises.

Can families and adults-only groups both be accommodated?

Absolutely. For adults-only romance getaways, explore our Sandals honeymoons & romance page. For families and multi-gen groups, start with our Beaches family getaways. (Note: Sandals is adults-only; Beaches welcomes families.)

Do we need a contract and a rooming list?

For perks and guaranteed inventory, yes. We manage the group contract, track your rooming list, monitor pickup, and handle any attrition or deadline adjustments with the resort—so you don’t have to.

Can we host private events (welcome party, rehearsal, beach dinner)?

Definitely. Many resorts offer private cocktail hours, beach bonfires, rehearsal dinners, and more. Some events are covered by group credits; others have a per-person fee. We’ll price options and lock in your venues and menus.

How does your team help throughout the process?

We’re a white-glove concierge team: we source the resort, negotiate perks, manage the contract and room block, build a booking page, coordinate transfers, handle payment reminders, coordinate all logistics of your guests’ arrival/departure, and liaise with on-site staff so your group can simply arrive and enjoy.

What’s the first step?

At the end of the day, group travel is about shared memories, shared laughter, and taking the stress out of planning so everyone can simply show up and enjoy. When you’re ready, we’ll help make it seamless.

Tell us your dates, budget, and guest estimate and we’ll present curated options with pricing and perks. Request your group quote here or email Team@TravelingEars.com to get started.