International, only 3 and half hours away, hot, absolutely stunning with a completely different culture. Where? Welcome to Jamaica!
Need a quick getaway to zone out for two days? Jamaica is the perfect destination!
First and foremost, don’t forget your passport! Although Jamaica is closer than half of the U.S., it’s an international destination, so a passport is required.
We left our kids behind for this brief getaway, keeping it short and making the most of every moment, as you’ll soon see!
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From vibrant neighborhoods to family-friendly activities, we’ll highlight destinations that cater to your needs while offering a rich cultural experience. Join us on this journey to discover the best places for your next family adventure!
Day 1 Arrival & Touring
We took a flight from JFK, where flights were available for about $350 round trip. For those driving, short-term parking at the airport is super convenient—pre-booking saves you money at $50/day, compared to $70 if paid on-site.
Our early morning 3.5-hour flight took off at 7:30 AM, making the drive from the greater Lakewood area a breeze— just 1 hour and 20 minutes door to door. By 11 AM, we were landing at Montego Bay Airport in Jamaica.
The bonus? Jamaica shares the same time zone, so that makes life a drop easier.
As we started our initial descent, the plane offered a stunning view of Jamaica’s famous, crystal-clear blue waters.
Customs and the airport were surprisingly quiet, with the entire process taking under 10 minutes. Honestly, most of that time was spent walking out of the terminal.
Right at the exit of the airport, a friendly guy at a booth directed us to a taxi. Jamaica’s official taxis have set rates, $35 for 1-4 people to Montego Bay and $100 for 1-4 people to Negril, about an hour and a half away. Since we only had 36 hours, we planned the trip to Montego Bay. We were picked up in a bus, and off we went!
Pro tip: Jamaica, as a former English colony, has drivers on the ‘wrong’ side of the road. Renting a car might not be the best idea, especially considering the unusual traffic patterns, minimal traffic lights, and narrow roads that often run along steep cliffsides 🙂
The drive from the airport to our hotel was quick, just about 20 minutes.
We stayed at the Hyatt Secrets St James, an adults-only all-inclusive resort that sits right next to its sister property, Breathless. We had reserved at ‘Breathless’, but something happened to the suite the night before, so they moved us to Secrets. Which turned out to be a blessing, since the grounds there were expansive and stunning.
Montego Bay has many beautiful hotels to choose from, and Secrets ranks up there in terms of rooms and grounds. (Breathless has stunning rooms but smaller grounds and no beach…) If traveling with kids, the Hyatt Ziva rates well. If you are into points, we booked a standard suite at 44K points (Chase Ultimate Rewards transferred to World Of Hyatt), then called the hotel and upgraded to the presidential suite for only $300. We had about 1600SF an outdoor jacuzzi & more – it was generally more than 2K a night!) Being that we were only there 1 night, we splurged on our night out.
As we left Breathless via golf cart to Secrets, a tour guide, named Dwayne, asked us if we wanted to check out Jamaica. Since our rooms weren’t ready until 3 PM, we decided to take him up on the offer. We dropped off our bags and headed out to explore three attractions: bamboo rafting, glass-bottom boats, and local vendor shops. He charged us $200, which included transportation and the cost of the bamboo rafting experience.
Dwayne was fantastic. He has a travel company and be reached via WhatsApp HERE. He pointed out landmarks and explained the culture and all as we drove about half an hour to the bamboo rafts where a nice guy took us on an hour ride through the river soaking up the beautiful nature and the Jamaican culture.
We just gotta point out – on the drive, we passed a Jamaican-Metziahs competitor 🙂
We grabbed some drinks and headed to Kelly’s Water Sports, about a 25-minute drive away, where we hopped on a glass-bottom boat. Since we arrived right at closing time (3 PM), we had the boat all to ourselves. The glass-bottom feature was amazing, giving us a clear view of fish, coral, and the stunning Caribbean waters beneath us. The crew was incredibly chilled, allowing us to snorkel and swim with the fish—an awesome experience that was all included in the $30 per person price!
The coolest part was when the crew took us near the airport, positioning the boat perfectly so we could watch a plane land just about 20 feet overhead. It was a pretty epic experience!
We then visited the craft market which is right across the street, where artists display and sell their handcrafted goods. The experience was certainly unique but very intense, as the vendors were very ‘assertive’ in trying to draw us in and heavily pressured us to make purchases. It felt a bit overwhelming at times – to say it nicely.
Pro tip: Start by cutting the initial price in half, then begin negotiating from there. Jamaicans are very into negotiating prices!
We finally arrived at the hotel around 5 PM. Since it was an all-inclusive resort, we had the chance to meet the chef and arrange for fresh fruits and vegetables to be delivered to our room.
We also had access to unlimited snacks and drinks, though the snack bar offerings were fairly basic, with options being granola bars, Pringles, and M&M’s (Cholov Stam). But remember to bring your own food! Read on to hear about Chabad Kosher food nearby – which was closed when we went…
Protip: Do not drink the tap water. Before showering, let the water run for about 5 seconds to allow the ‘brown water to pass through.’
Montego Bay doesn’t really have a central nightlife hub for tourists, but the resorts more than make up for it. Our hotel had a Jamaican concert, you can grab a quiet peaceful night swim, bike around the property, night tennis, and many other activities.
Day 2:
The next morning, we requested a late checkout, reminding them that Hyatt members are entitled to stay until 2 PM, which they begrudgingly accommodated. With our flight scheduled for after 6 PM, we had plenty of time to enjoy the stunning hotel grounds.
Heads Up: Service in Jamaica might not meet the level you’d typically expect. The happy, laid-back culture of the island is reflected in the pace and style of service. If you’re used to destinations like Cancun or Puerto Rico, you’ll likely find those places offer a higher standard of service by comparison.
We took advantage of the complimentary kayaking and had an incredible 10-15-minute tubing adventure. The ride was intense, thrillingly fast, and worth it at $40 per person.
Pro Tip: The sun in Jamaica is much stronger than in the US (since it is closer to the equator), and you can get a serious sunburn in under 2 hours.
We then checked out, got a cab from the entrance to the resort which was dropping off a passenger, and went to the Hip-Strip. The first driver quoted us $40, while the second offered $15—giving us a clear sense of how the ‘pricing game’ works.
The Hip Strip is a long block lined with shops where locals sell various items, though it’s quite touristy, and many products are imported. Chabad has a kosher food spot there, and we had the privilege of meeting the Rabbi and Rebbetzin. They run a store called “Kosher Hot Spot,” which offers falafel and more, with plans to expand to shawarma during peak seasons. The store was being remodeled when we went and is set to re-open in early December. It will have Jamaican vibes, and if you come with a group – best to give them a heads up 1-2 days in advance.
They shared the challenges of importing kosher chicken and meat into Jamaica, noting how expensive and complex the process can be. The Chabad center occasionally holds minyanim on Shabbos, and there are several nearby hotels. Chabad also offers Shabbos meals. For more details, it’s best to visit their website and reach out directly to inquire about minyanim, meals, and other arrangements.
In the past 10 years, the Rabbi has helped over 500 people put on tefillin for the first time. With many cruise ships stopping in Jamaica for the day, Chabad sees these visits as a unique opportunity to help visitors reconnect with their roots!
Overall, the hipstrip felt a bit overrated. While it was interesting, it had a slightly unsettling vibe. A fellow put some weed in our pocket and said ‘Only $50 for you, love.’ That was definitely an interesting and rather memorable episode 🙂
We recommend spending no more than 30 minutes there, preferably as a quick stop on your way to the airport (it’s only about 5 minutes from the airport.)
Safety:
We felt very safe within the resort, as it is gated and appears well-secured. When going outside, it’s important to stick with guides or official taxi drivers, easily identified by their white shirts. We highly recommend using a tour guide—they provide a safer experience, and it doesn’t cost extra!
Conclusion
Our trip to Jamaica was a short but unforgettable tropical escape. The country is stunning and surprisingly affordable. The Jamaican people are incredibly happy, and their laid-back culture is truly fascinating. While the service was slower than we’re used to, it matched the relaxed, easygoing vibe of the island.
We just wrapped up an exciting trip to Jamaica, and we’d love to hear your thoughts on our recap! Comment below! What city should we explore next? Whether it’s a favorite destination or a hidden gem, your suggestions are invaluable to us! Please comment below! To reach our travel team, click HERE
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I went to Switzerland in the summer in a Europe trip and it was so good I returned the following year! Would highly recommend Swiss alps in the summertime. Some favorites were Mount Pilatus and Mount Titlus
Tip. The train tickets are very expensive. Get daily passes in advance. If you want I have a chareidi man in Israel who gets them discounted.