Planning a group trip itinerary for eight or more friends is a special kind of chaos. Someone wants a pool. Someone else wants museums. Two people are vegan, one eats only chicken, and your college roommate will disappear every afternoon to nap. I've run three of these trips in the last two years with groups ranging from 8 to 12 people, and the only thing harder than picking the destination was picking who got to share the bathroom with whom. The trips below — Tuscany, Costa Rica, and the Cyclades — survived real groups, real arguments about dinner reservations, and one incident involving a lost passport in Paros. They work. I'd do all three again.
What this post isn't: a generic list of "top sights." What it is: three tested week-long group trip itinerary plans with real transfers, real villa and hotel names, real price bands for 2026, and a day-by-day flow that keeps everyone fed, moved, and mostly happy. You'll see exactly when to book, how to split transfers, and which dinners to lock in ahead versus leave loose. I'm not a tour operator and I'm not selling anything. Just a friend who has done this three times and wants your group to skip the mistakes we made. Grab a coffee. This one runs long because group trips deserve the detail.
Tuscany: 7 Days With a Villa Base and Day Trips
For a group of 8-10, don't split hotels between Florence and Siena. Rent one villa in the Chianti triangle — somewhere between Greve in Chianti and Castellina — and day-trip out. I used a 5-bedroom agriturismo near Panzano for our group of 9, roughly EUR 620/night in May shoulder season, which worked out to about EUR 70 per person per night with a pool and a full kitchen. Book eight months out. Seriously. The good villas on Plum Guide and Agriturismo.it are gone by February for peak summer.
Day 1 is arrival at Florence Peretola (FLR) or Pisa (PSA). Split into two rental cars from Hertz at the airport — one 7-seater, one compact. Trains don't reach the villas. Day 2, spend at the villa recovering from jet lag, grocery run at the Conad in Greve, and a long lunch by the pool. Day 3 is your Florence day: park at Piazzale Michelangelo (free) and walk down. Duomo climb tickets must be pre-booked at museiciviciflorenti.it — they sell out two weeks ahead. Day 4 is Siena and San Gimignano as a paired loop, about 45 minutes from the villa. Day 5 is a Chianti wine day: Antinori nel Chianti Classico tour at EUR 45/person, then lunch at Officina della Bistecca in Panzano (Dario Cecchini's place — book three months ahead for a group over 6). Day 6 is a slow day — pool, Lucca if anyone's restless, or a cooking class at the villa for about EUR 85/person. Day 7, drive back, fly out.
Tuscany Group Dinners and Booking Timelines
Here's where groups get burned. Italian restaurants do not love walk-ins of 8+, and the good ones will politely laugh at you. Officina della Bistecca takes group reservations by email only — write in January for a summer trip. La Bottega in Volpaia is worth the drive; book two months ahead. For the villa itself, hire a private chef for one night — our group used a woman named Lucia through the villa owner, EUR 55/person including wine, and she made hand-rolled pici with wild boar ragu that four of us still talk about. Worth it. Completely.
For the other nights, loose reservations at trattorias in Greve and Panzano are fine if you call the morning of. La Cantinetta di Rignana is the crowd pleaser — no one at the table will complain. Skip the Michelin-chasing unless half your group is into it. On my first Tuscany group trip I made the mistake of booking a tasting menu for 9 on night two — everyone was exhausted, the bill was EUR 140/person, and two people fell asleep between courses. Lesson learned.
Costa Rica: Manuel Antonio and La Fortuna in 7 Days
Costa Rica is the easiest group trip itinerary on this list because the infrastructure is built for it. Fly into SJO (San Jose). Do NOT try to drive yourselves if your group is 8+. The math on rental vehicles is worse than you think, and the roads to La Fortuna have potholes that will humble your insurance deductible. Use a private shuttle service like Interbus or SJO Shuttle — SJO to La Fortuna runs about USD 200 per van (6 pax), so two vans for a group of 10 = USD 400 total. Cheaper and saner than rentals.
Day 1: Land at SJO, shuttle straight to La Fortuna (3.5 hours). Stay at Arenal Springs Resort or Tabacon — Arenal Springs is the better group value at roughly USD 220/night for a suite that sleeps 4. Day 2: hanging bridges at Mistico in the morning (USD 29/person), Baldi hot springs in the afternoon. Day 3: Arenal 1968 hike and a waterfall rappel if your group skews active (USD 110/person through Desafio Adventure). Day 4: private shuttle La Fortuna to Manuel Antonio — this is a long transfer, about 4.5 hours, and two vans will run USD 620 total. Leave at 7 AM, stop for lunch in Esterillos. Days 5 and 6: Manuel Antonio National Park (book the guided tour through Johan Chaves on WhatsApp, USD 30/person — he finds sloths you'd walk past), plus one full beach day at Playa Biesanz. Day 7: shuttle back to SJO, fly home.
Costa Rica Group Logistics and Dinners
The thing no one tells you about Manuel Antonio: restaurants are spread out along one twisty road, and your group will need taxis between dinner and the hotel. Book a hotel within walking distance of Playitas or the main strip. For group dinners, El Avion (the converted cargo plane) takes groups of 10 with 48 hours notice — tell them you want the sunset terrace. Agua Azul is the other move, same drill, reserve by WhatsApp. Both will run about USD 35-45/person including a drink. Reasonable. By Costa Rica standards, not cheap, but reasonable.
In La Fortuna, Don Rufino is the obvious group pick and deserves the hype — book one week ahead for groups over 6. For a cheaper night, Soda La Parada is a soda (local diner) right on the main square that will happily absorb a loud group at USD 10/person. A friend who guides in La Fortuna once told me the rule: "Do one fancy dinner, one soda dinner, one hotel dinner. Your wallet and your group will both thank you." He was right. We've followed it on every trip since.
Greece: Athens, Paros, and Naxos in 7 Days
Greek island hopping with a group sounds romantic until you're dragging nine suitcases through Piraeus at 6 AM. The winning move is fewer islands, longer stays. Athens (2 nights) + Paros (2 nights) + Naxos (3 nights) is the sweet spot — minimal ferries, maximum actual beach time. This group trip itinerary survived my messiest group yet (11 people, three couples, one breakup mid-trip) and still ended with everyone hugging at the airport.
Day 1: Land at ATH. Stay at Athens Was in Plaka or NEW Hotel — both take groups and sit within a 10-minute walk of the Acropolis. Rooms run EUR 180-240/night for doubles in June. Day 2: Acropolis (first entry slot, 8 AM, pre-booked through hhticket.gr — the line by 10 AM is unhinged), lunch at Diporto near the central market, Anafiotika walk in the afternoon. Day 3: Blue Star Ferries from Piraeus to Paros, roughly 3h45 on the slow ferry, EUR 41/person one-way. BOOK IN FEBRUARY for a summer trip. The Blue Star deck seats sell out. Days 3-5 on Paros: stay in Naoussa, not Parikia (Naoussa is prettier and the dinners are better). Day 5: Blue Star hop to Naxos — it's a 50-minute crossing, and the ferry between Paros and Naxos runs several times a day. Days 5-7 on Naxos: stay in Agios Prokopios, the beach is gentler for a mixed group. Day 7: ferry back to Athens (or fly Naxos-ATH on Olympic Air, about EUR 95/person and saves 4 hours).
Greek Island Group Dinners and Ferry Booking
Ferry booking is the single most important thing to get right for a Greece group trip. Use Ferryhopper or book directly on bluestarferries.com. For any summer week in 2026, book by mid-February — late bookings mean standing-room tickets and your group of 9 scattered across a ferry deck. Reserve numbered seats (EUR 4 extra) for any crossing over an hour. Worth it.
Group dinners: in Athens, book Kuzina in Thissio for one nice night — rooftop view of the Acropolis, accepts groups of 10 with a week's notice, about EUR 45/person. In Paros, Siparos beach taverna in Santa Maria takes group reservations by phone and the grilled octopus is genuinely excellent. In Naxos, the move is Scirocco in Naxos Town for the moussaka, and a second night at Axiotissa near Kastraki which takes groups but you MUST call two days ahead. A local in Naoussa told me the one rule she gives to groups: "Never eat at the restaurants with the photo menus." I've followed it since and it has never once steered me wrong.
Budget Ballpark and Who Each Trip Suits
For a 2026 shoulder-season group trip with 8-10 people sharing costs, here's what I've actually seen land on the final spreadsheet. Tuscany villa week: USD 1,900-2,400 per person including flights from the US East Coast, villa share, rental cars, food, and activities. Costa Rica: USD 1,700-2,200 per person including flights, shuttles, hotels, and park fees. Greece: USD 2,100-2,600 per person including flights, ferries, hotels, and a reasonable dinner budget. Greece trends highest because ferries and island hotels in June-September just cost more.
Who's each one for? Tuscany works best for foodie groups in their 30s-50s — people who want slow mornings and long dinners, and don't mind driving narrow roads. Costa Rica is the active group's trip: hikers, surfers, people who want to see a sloth and also do a zipline before lunch. Greece is the beach-and-swim crowd, and it's also the best pick if your group has a mix of partiers and chill folks — the islands quietly segregate themselves by 10 PM and everyone wins. Pick based on your actual group, not the photos on Instagram.
Do's and Don'ts for Group Trip Itineraries
| Do's | Don'ts |
|---|---|
| Book villas and ferries 6-8 months ahead for summer | Don't wait until April for July bookings — the good stuff is gone |
| Use private shuttles in Costa Rica, not rentals | Don't try to drive 10 people in 3 rental cars through Arenal roads |
| Pre-book Duomo, Acropolis, and Manuel Antonio park tickets | Don't show up at 10 AM and expect walk-in entry — you'll wait 2 hours |
| Assign one person per day as "logistics lead" | Don't let decisions be made by group consensus at dinner — nothing gets decided |
| Reserve group dinners 2-8 weeks out depending on country | Don't try walk-ins for 8+ in Italy — they'll say no politely |
| Build in one lazy villa/pool day per week | Don't schedule every day — someone will hate it |
| Split costs via Splitwise from day one | Don't "settle up later" — it never works cleanly |
| Book Blue Star ferries with numbered seats | Don't buy deck-only tickets for a 4-hour crossing with a group |
| Hire a private chef for one villa night in Tuscany | Don't underestimate the Italian restaurant vs group of 9 problem |
| Tell your group the rough daily budget upfront | Don't surprise anyone with a EUR 140 tasting menu on night two |
| Pack a paper copy of everyone's passport info | Don't assume cell service on remote roads in Costa Rica |
FAQs
How far in advance should we book a group trip itinerary for 8+ people?
For summer 2026 trips in Europe, lock flights and main accommodation 7-9 months out. Villas and the best island hotels in Greece sell out by February for peak July-August weeks. Costa Rica is more forgiving — 4-5 months is usually enough, except for Manuel Antonio hotels in late December through January, which book up by September. Ferry bookings for Greece specifically should happen as soon as the schedules drop in mid-February.
Is it cheaper for a group to rent a villa or book multiple hotel rooms?
For groups of 8 or more, villas almost always win in Tuscany and Greece if you're staying 4+ nights in one place. In Chianti, a 5-bedroom villa at EUR 620/night sleeps 10 at EUR 62/person versus EUR 150-200/person for equivalent hotel rooms. Costa Rica is the exception — hotels there are often cheaper per person than a villa rental once you factor in food and the fact that restaurants are spread out, and resort day passes are often included.
How do you handle group dinners in Italy with 10 people?
Book by email two to eight weeks out, depending on the restaurant's profile. Good Italian restaurants typically set a fixed menu or shortened menu for groups over 8 — accept this and stop fighting it. Also confirm the day of the reservation by phone. I've had two no-show-the-restaurant-forgot situations that a morning call would have caught. For the villa itself, hiring a private chef for one night is the single best money you'll spend on a Tuscany group trip.
Can you do Costa Rica's Manuel Antonio and La Fortuna without a rental car?
Absolutely, and I'd argue you should. Private shuttles from companies like Interbus, SJO Shuttle, or Manuel Antonio Travels handle the full circuit for about USD 400-620 per van leg for a group. Within La Fortuna and Manuel Antonio, taxis and Uber (which works in both now as of 2026) cover everything. No one in my groups has ever regretted skipping the rental car. Several have regretted the opposite.
Which Greek islands are best for a first group trip?
Paros and Naxos. Santorini looks stunning in photos but is a nightmare for groups — the main roads are packed, restaurants don't love reservations for 10, and the hotel prices are double Paros or Naxos for similar quality. Paros has the nightlife and food in Naoussa, Naxos has the long swimmable beaches and a more relaxed vibe. Combining the two with a short Blue Star crossing in the middle is the easiest group trip itinerary in the Cyclades.
How do we keep a group of 8+ friends from getting on each other's nerves?
Honest answer: build in space. Don't schedule every meal, every activity, every evening. Our rule is two mandatory group activities per day max — usually breakfast at the villa and one dinner — and the rest is optional. Also, pick one person per day to be "decision lead" and let them actually decide things instead of polling the group. Group decision-making at a dinner table is the fastest way to ruin a vacation.
What should we budget for a 7-day group trip to Europe or Costa Rica in 2026?
For a reasonably comfortable trip sharing costs across 8-10 people, plan USD 1,700-2,600 per person all-in including international flights from the US. Greece runs highest due to peak-season ferry and hotel pricing. Costa Rica is the most forgiving on budget. Tuscany sits in the middle and swings based on how fancy your villa is. These numbers assume shoulder season (May-June or September-October) — high summer adds roughly 20-30 percent.
Do we need travel insurance for a group trip?
Yes, and for groups especially so. Someone will get sick, miss a flight, or sprain an ankle on a Costa Rica hike. I use World Nomads for international group trips — about USD 65-90 per person for a week of coverage with adventure activities included. Make it a hard requirement for the group before anyone books flights. If one person bails day-of, insurance is the only thing that stops it from becoming a group-wide financial headache.