Travelling with Friends: 9 Destinations for When the Group Chat Becomes a Real Trip

Travelling with Friends

Every group of friends has a trip they keep almost booking. The flights get priced, the group chat lights up, someone drops a pin, and then silence. Trip planning stalls because group travel is hard to coordinate: different travel styles, competing schedules, mixed budgets. What makes a destination actually work for travel companions is the logistics: direct flights, enough variety that no one feels dragged along, walkable streets, and gathering spaces where the best moments happen without a plan.

Since 2013, Flytographer has connected travellers with trusted local photographers in 350+ destinations worldwide, capturing over six million memories. The magic of Flytographer is both the experience and the photos. These are the destinations our trusted travel advisors keep sending friend groups to when they finally meet up.

Jump in: 

1. San Juan, Puerto Rico 
2. Istanbul, Turkey 
3. Athens, Greece 
4. Montreal, Canada
5. Cape Town, South Africa 
6. Cabo San Lucas, Mexico
7. Marrakech, Morocco 
8. Santa Teresa, Costa Rica
9. Lisbon, Portugal 

Photo: Raul in San Juan for Flytographer. Friends capture memories in San Juan together with a friends photoshoot.

1. San Juan, Puerto Rico

Erin and Brett are the founders of Expedition Everywhere Travel — she’s the detail-oriented planner who makes every trip feel effortless, he’s the archaeologist and historian who makes every destination feel alive, and together they design journeys that go well beyond the guidebook. Erin and Brett say, “San Juan is one of those rare places that requires almost no coordination overhead. No currency exchange, no international data plans, direct flights from nearly every major U.S. city, and yet it genuinely feels like you’ve left the country.”

Erin and Brett are right about the minimal logistics. For a group that has been trying to make a trip happen for years, travelling with friends in San Juan removes every barrier. Old San Juan’s compact colonial grid is built for wandering: colourful facades, centuries-old fortresses, and rooftop bars with views that make everyone stop and look.

The real eating happens at La Factoria, a bar with hidden rooms that keep revealing themselves and cocktails that have earned it a spot on the World’s 50 Best Bars list. For daytime, take the group to El Yunque for swimming in natural pools beneath the rainforest canopy.

Jessica Sepulveda-Viola is a Certified Travel Advisor and the owner of Destination Known Travel. Originally from Puerto Rico, she draws on her deep cultural roots and professional expertise to design bespoke, immersive itineraries across Europe and the Caribbean. Jessica recommends, “Rent a car and head to Luquillo or Guavate for some local food, or head to Fajardo for a bioluminescent bay kayaking tour.”

Photo: Karlota in San Juan for Flytographer. Marcie and friends capture memories in San Juan together with a friends photoshoot.

2. Istanbul, Turkey

Briana Rodriguez is the founder of Via Travel, a concierge-style travel advising business helping couples, families, and groups turn dream destinations into thoughtfully planned, unforgettable journeys. Brianna says, “I lived in Turkey for a year, and Istanbul still stops me in my tracks. It’s one of those cities that earns a permanent spot on your list, not just to visit once, but to keep going back to.”

Few cities reward a group in the way that Istanbul does. The shared discoveries come fast: a Turkish breakfast spread that takes over an entire table before anyone has made a plan. Nearly 1,500 years of history under the dome of Hagia Sophia, a must-see that genuinely quiets a group down for a moment. Over 4,000 shops in the Grand Bazaar, where getting lost is the point. This is sightseeing that doesn’t feel like sightseeing. Briana recommends booking Çemberlitaş Hamamı, a hammam in continuous operation since 1584, for the group experience everyone will talk about forever.

Valerie Edman is the founder of Cultured Travel LLC and a detail-obsessed architect of seamless travel experiences. Valerie adds, “Stay at the Peninsula Istanbul. Opt for room service breakfast at least once and make sure you have plenty of time as each dish is an experience and deserves to be slowly savored.”

Travelling with friends to Istanbul will feel like a collective discovery.

Photo: Ufuk in Istanbul for Flytographer. Nadia and friends capture memories in Istanbul together with a friends photoshoot.

3. Athens, Greece

“Athens is criminally underrated as a group destination. It’s affordable, endlessly walkable, rich with food and history, and the rooftop bar scene, with the Acropolis glowing in the background, creates the kind of evening that makes everyone put their phones down.” – Erin and Brett, Expedition Everywhere Travel

It starts with the Acropolis at opening time, before the heat and the crowds arrive. Hire a guide who brings the stories to life rather than narrating dates, then give the group a free afternoon in Plaka to wander. Athens works because its rhythm suits every personality: long taverna dinners in Psiri, late-night rooftop bars, mornings at Varvakios Market where the city does its real shopping.

Chip Wilson is a Luxury Travel Advisor and the Founder of MCW Travel, designing tailor-made journeys with a focus on immersive experiences and seamless service. Chip says, “Spend a day with a private guide exploring the Acropolis and Acropolis Museum, then dive into the city’s culinary soul with tastings at Varvakios Market and meze at a local taverna. Take an unforgettable sunset drive along the Athens Riviera to Temple of Poseidon. It’s probably one of the most spectacular views in all of Greece.”

If it’s the first time the group has pulled off an international trip, Athens is the place to set the tone. 🏛️

Photo: Spyros in Athens for Flytographer. Aline and friend capture memories in Athens together with a friends photoshoot.

4. Montreal, Canada

Erica Jones is the founder of Elevated Occasions and has spent over 10 years specializing in luxury food and beverage travel around the world. Erica says, “Enjoy the charm of Old Montreal, where architecture and cobblestone streets feel frozen in time. Wander, pop into cafés, bakeries, and boutiques. There’s something worth tasting or discovering around every corner.”

Montreal is the reunion that doesn’t require a long-haul flight. European charm, world-class food, and a city that comes alive in summer with festivals, patios, and creative energy. Bars stay open until 3 AM, and the nightlife has a sophistication that surprises first-time visitors.

For a shorter getaway travelling with friends, this city delivers.

Photo: Vivian in Montreal for Flytographer. Patricia and friend capture memories in Montreal together with a friends photoshoot.

5. Cape Town, South Africa

Allyson Bauer is the founder of The Ally Escape Co. and a travel advisor with Fora Travel who specializes in crafting slow, intentional itineraries. She recommends, “Ellerman House in Bantry Bay: a 1906 Edwardian mansion above the Atlantic with 13 rooms, two pools, and a wine cellar that will derail any plans made after dinner. Cape Town does golden hour better than almost anywhere on earth, and a friend group should be outside for every single one.”

Cape Town earns the milestone reunion. Table Mountain by cable car, the penguin colony at Boulders Beach, a full day in the Cape Winelands with a driver, and Signal Hill at sunset with wine before dinner. For social energy near the waterfront, The Silo Hotel, a converted 1920s grain elevator with the Zeitz MOCAA art museum below, is the design moment of the trip.

La Parada at the V&A Waterfront does shared plates in exactly the loud, easy setting a first-night reunion calls for. Drive the Cape Peninsula to Cape Point, stop everywhere that looks beautiful (it all does), and give the trip enough days to breathe. For best friends marking a milestone, very few places compete.

6. Cabo San Lucas, Mexico

Jacqueline de Guzman is the founder of Voyavie, a bespoke luxury travel and destination event consultancy specializing in curated, high-touch journeys for discerning travelers worldwide. Jacqueline says, “Cabo offers more than just the resort experience. You can venture into San José del Cabo for a more laid-back, charming town feel, or plan group activities like boat days, beach clubs, and sunset dinners.”

Cabo San Lucas is the destination with surprising depth. Direct flights from most major North American cities get you there in under three hours from the West Coast, and the range of accommodation suits every group dynamic: lively all-inclusives for those who want the energy, boutique properties for those who don’t. The Cape, a Thompson Hotel, overlooks El Arco and strikes the balance well.

Beyond the pool, there’s a town worth exploring. Edith’s, a Baja-Guerreran institution known for mesquite-grilled seafood and tableside Caesar salad, is the kind of splurge-worthy group dinner that anchors a whole trip.

Natalie Dale is the owner of Vacationista Travel & Co, LLC, and has spent over 9 years helping our clients create experiences that last a lifetime, not just travel. Whale watching season runs December through April, and Natalie shares, “We got to experience whale watching in Cabo for the first time this passed January and it was absolutely thrilling. We even spotted a blue whale.”

For a group trip south of the border, Cabo earns its reputation.

Photo: Diana in Cabo San Lucas for Flytographer. Phoebe and friend capture memories in Cabo together with a friends photoshoot.

7. Marrakesh, Morocco

“Marrakesh has a way of becoming the trip the group talks about longest, because nothing about it is predictable, and every hour seems to produce a story.” – Erin and Brett, Expedition Everywhere Travel

Staying together in a riad transforms Marrakesh into something deeply communal. Riad El Fenn, spanning eight interconnected riads with three pools, a rooftop terrace, and a contemporary African art collection, sets exactly the right tone.

The eating is extraordinary. Le Tobsil is the group dinner that becomes the anchor memory: course after course in a candlelit courtyard, live Gnaoua musicians, and no menu. For the souks, hire a private guide for the first morning; the medina is labyrinthine by design. Leave room for spontaneity: some of the best moments come from spending time in the riad courtyard between outings, not from a packed itinerary.

Carrie-Ann Milnes is a family travel specialist and Founder of A Blonde’s Adventures, with over 5 years of experience, helping busy mums plan memorable, affordable holidays that are easy, flexible, and truly family first. Carrie-Ann says, “Definitely book Jardin Majorelle in advance (early time slot is best). It’s beautiful and one of those places that actually lives up to the hype. I’d also really recommend a day trip to the Atlas Mountains with a camel ride, it’s such a nice contrast to the busy city and one of those experiences that makes the trip feel a bit more special.”

Photo: Ilyass in Marrakesh for Flytographer. Bethany and friends capture memories in Marrakesh together with a friends photoshoot.

 8. Santa Teresa, Costa Rica

“Santa Teresa is the kind of place where the best agenda is not having anything to do. But if you fancy, there’s daily yoga, surfing, and healthy meals on site.” – Valerie Edman, founder of Cultured Travel LLC

Santa Teresa is where groups go when they agree on exactly one thing: they want to slow down. The Nicoya Peninsula, one of only five Blue Zones in the world, has a pace of life that makes everyone exhale within minutes of arriving. Days revolve around the beach, surf lessons, and long meals; evenings end with the sun dropping into the ocean.

Hotel Nantipa, a beachfront boutique property and member of Small Luxury Hotels of the World, offers the right mix of comfort and ease: bungalows and villas tucked among the trees, a wellness centre, and a restaurant that matches the setting. For group dining, Koji’s Restaurant is a local favourite for Japanese cuisine using fresh local seafood (open Tuesday through Saturday, cash only). This is travelling with friends at its most unhurried. 🌊

9. Lisbon, Portugal

“Lisbon offers a broad range of accommodations, from boutique hotels in Chiado and Bairro Alto to larger properties, making it easy to find something that fits different budgets within the same group.” – Jacqueline de Guzman, Voyavie

Lisbon is ideal for groups with mixed budgets and varied energy levels. The city is effortlessly social: walkable neighbourhoods, miradouros made for sunset gatherings, and a culture built around long meals and late nights. Every hilltop seems to reveal new places worth stopping for.

Irene Ribé has travelled all over the world and specializes in helping plan trips for couples and families in Europe. Irene recommends staying at “Memmo Alfama to experience the oldest part of the city with great service or the Hyatt Regency Lisbon for amazing rooftop views and being close to the water.” Irene also maps out the eating: Cervejaria Ramiro for seafood (the tiger prawns are legendary, and you finish with a steak sandwich, as tradition demands), Tapisco for tapas, and Mercado da Ribeira for when the group can’t agree.

Day trips to Sintra or the coastal town of Cascais are both under an hour away. Travelling with friends in Lisbon feels like something you could do every year. 

Photo: Claudia in Lisbon for Flytographer. Nicole and friends capture memories in Lisbon together with a friends photoshoot.

Capturing Memories with Your Favourite People

The best group trips aren’t the most elaborately planned. They’re the ones where the destination does the heavy lifting, and every place on this list turns travelling with friends into a travel experience worth repeating.

Wherever your crew lands, a Flytographer shoot captures the trip long after the group chat goes quiet. Book a local photographer in any of our 350+ destinations and come home with wall-worthy photos of the people who matter most. Next time the group chat lights up, don’t let it go quiet. 💙