Dates are flexible. This day-by-day plan is provisional until you choose exact travel dates.
Fly from London to Sangster International Airport in Montego Bay; allow roughly 10 hours in the air for a direct flight, plus time for check-in, immigration and baggage. Once you’ve landed, meet a pre-booked private transfer in the arrivals area. For 15 people, confirm the operator has enough seats and luggage space—this may mean booking more than one vehicle. The drive to your hotel is usually around 15–30 minutes, but can take longer with traffic or if your hotel is farther along the coast.
Check in, unpack and leave a generous pause to rest or swim before heading out. If the group has energy, Doctor’s Cave Beach on Gloucester Avenue makes an easy first outing: it’s known for calm, clear water, and the beach club typically charges an entrance fee of around US$8–10 per person, with chair and umbrella hire extra. Check the current hours and fees before setting off; a visit of one to two hours is plenty for a travel day.
For a polished waterfront welcome dinner, book Marguerites Seafood by the Sea on Gloucester Avenue. Budget roughly US$40–80 per person before drinks, and reserve ahead for a group of 15. After dinner, take a relaxed 30–45-minute stroll along the Hip Strip section of Gloucester Avenue, then call it an early night—especially if anyone is still feeling the flight.
Keep the morning deliberately slow at your resort: enjoy the pool and beach for a couple of hours, with no pressure to gather everyone at once. Check whether beach towels and loungers are included, and ask the resort team about sea conditions before swimming. Since the group is 15, agree a simple meeting point and time for lunch rather than trying to keep everyone together.
Book resort spa treatments ahead of time, especially if several people want massages; stagger appointments so others can stay by the pool. Allow around 1–2 hours per treatment, and check prices and cancellation terms directly with the spa. Later, head out for a pre-booked snorkelling or glass-bottom-boat trip in Montego Bay Marine Park. Allow 2–3 hours, including getting to the boat; confirm the operator’s departure point, transport, equipment and weather policy before paying. A shared outing can work well for mixed comfort levels, though anyone who prefers to stay dry can choose the glass-bottom boat.
Arrange group transport both ways to HouseBoat Grill in Freeport for dinner over the water. It’s a distinctive setting and a good change from resort dining; budget roughly US$35–70 per person before drinks, and reserve well in advance for a party of 15. Ask the restaurant to confirm its opening hours for your chosen day, and have your driver agree a firm pickup time and location before you sit down.
Have your pre-booked private driver collect the group in Montego Bay and take you to Falmouth; for 15 people, confirm the vehicle size, waiting arrangements and return pickup in advance. Start with a guided Falmouth Heritage Walk through the Georgian town centre, allowing around 1½–2 hours. A local guide can bring the port and sugar-era history to life, while keeping the pace comfortable for a mixed group. Book ahead and confirm the meeting point and group rate.
During the walk, stop at Falmouth Courthouse, one of the town’s best-known historic landmarks. Allow 30–45 minutes, but check access arrangements before setting out, as entry may depend on current opening hours or events. Then continue by your arranged vehicle to Good Hope Estate for a 2–3-hour visit. Confirm the available tour, group admission and timing in advance; the estate’s grounds and historic property offer a broader perspective on the region’s plantation history and landscape.
Finish at Glistening Waters Restaurant for an early dinner beside the lagoon. Budget roughly US$25–50 per person before drinks, and reserve for the group; ask about current service hours and whether your visit can be timed around the evening lagoon tours. Your driver can then return you to Montego Bay. Keep some flexibility in the schedule for traffic and the estate visit, and agree a firm pickup time before dinner.
Allow the Falmouth–Montego Bay transfer time before starting: have the first activity begin late morning, and confirm the food tour’s meeting point and timing with the operator in advance. Book a private or group experience with Jamaica Food Tours** (around 2–3 hours); for 15 people, ask whether they can keep the group together and flag any dietary needs when booking. It’s a lively way to get to know Jamaican ingredients and everyday cooking before lunch.
Continue to Scotchies in Coral Gardens for jerk chicken or pork, with sides such as festival or breadfruit; allow roughly US$12–25 per person. It’s a casual, open-air stop, so bring cash as a backup and expect lunch to take a little longer with a group. Then head to the Montego Bay Cultural Centre at Sam Sharpe Square for its museum and galleries, allowing about 1–1.5 hours. Check current opening arrangements and admission details before setting out, as hours and access can change.
Finish at The Pelican Grill on Gloucester Avenue for Jamaican favourites in a relaxed central setting; budget around US$20–45 per person before drinks. Book ahead and confirm they can seat all 15 together, then arrange a pre-booked vehicle back to your accommodation rather than relying on finding several taxis at dinner’s end.
Take a pre-booked private vehicle into downtown Montego Bay and start at Sam Sharpe Square. Allow 30–45 minutes to look around and hear the story of Sam Sharpe and the 1831–32 Baptist War; the square is a public space, so there’s no admission charge. Continue on foot to St James Parish Church on Church Street. Set aside another 30–45 minutes, but check with the church beforehand: access can depend on services and other parish activity, and visitors should dress respectfully.
Arrange a vehicle to Bellefield Great House and Gardens in Bellefield; it’s outside the downtown core, so don’t rely on walking between stops. Allow 1.5–2 hours for the house and gardens, and ask when booking whether a rum tasting is available and suitable for your group of 15. Confirm the tour time, group rate and current admission price in advance, as these can vary. After the visit, head back to Gloucester Avenue for dinner at The Pork Pit—a relaxed, casual finish with jerk and other Jamaican favourites. Budget roughly US$12–25 per person; it’s a popular spot, so allow a little extra time if the group arrives together.
Take a pre-booked private transfer from your resort to Montego Bay Yacht Club in Freeport; allow about 15–30 minutes from the main resort area, depending on traffic. Confirm the charter’s exact meeting point and check-in time, and aim to arrive around 30 minutes before boarding. With 15 people, check that the boat’s capacity includes everyone comfortably, and ask what’s provided—snorkelling gear, drinks, towels and a restroom can vary by charter.
Spend around 3–4 hours cruising the Montego Bay coast, with time to swim or snorkel if conditions allow. Sea state and the captain’s safety advice may affect swimming stops, so bring reef-safe sunscreen, a cover-up and any medication you need; keep valuables to a minimum. Back at Montego Bay Yacht Club, allow time to shower and change before heading to Pier One, also in Freeport, for waterfront dinner. Budget roughly US$25–55 per person before drinks; check the current menu and whether live music or nightlife is on that evening, as schedules can vary.
Book a private return transfer to Pier One in advance, with a clear pickup point and time—particularly useful for a group of 15. If anyone plans to stay for music, agree a later pickup or arrange transport back in smaller groups rather than relying on finding vehicles together at closing time.
Have breakfast at the hotel, then check out and confirm where the group’s luggage will be stored while you’re out. With 15 people, agree a clear meeting time and do a quick room check before leaving; ask the hotel to arrange any luggage handling in advance.
If your flight schedule leaves enough time, head to The Pork Pit on Gloucester Avenue for an early Jamaican lunch—think jerk chicken or pork, festival and rice and peas. Budget around US$12–25 per person. It’s a casual stop, but service can take time when a group arrives together, so call ahead and check that the timing works before committing. If you’re short on time, skip lunch rather than risk a rushed airport run.
Take a pre-booked private group transfer from the hotel—or from The Pork Pit if you stop there—to Sangster International Airport. From central Montego Bay, allow roughly 15–30 minutes’ drive, with extra buffer for traffic, loading 15 passengers and luggage, and the airport drop-off queue. Set pickup according to your confirmed flight and the airline’s recommended arrival time; check-in and security are additional, so don’t treat the drive estimate as your total airport allowance.
No packing list attached yet.