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The Perfect Itinerary for a Long Weekend

Cruz Bay beach

My absolute best friend in the world is visiting for the first time next week, and I could not be more excited! I’ve been busy playing travel agent for his family, and I am confident that I have created the perfect long weekend itinerary for them. With flights being so inexpensive right now, it’s the perfect time to book a last-minute, long weekend trip to see us! And if you are lucky enough to be able to pull off a quick visit, here is a great little itinerary to follow! (Click here to read a recent post about all of the cheap airfare that’s currently available.)

Day 1: Arrival Day (Thursday)

Your first travel day is never fun, Chances are you woke up sometime in the middle of the night to make it to the airport for your early morning flight. The good news is that most flights arrive in the early afternoon, so you can still have fun on arrival day.

I suggest not planning anything too grueling on arrival day because you will undoubtedly be tired from the flight. Luckily happy hour and sunset have never been categorized as grueling, so add them to the list of must-dos for day one! When you arrive on St. John, check in to your hotel, villa or condo, freshen up and then head right to the beach in Cruz Bay. Belly up to the bar or grab a seat in the sand, and enjoy the good ‘ole Caribbean life. My friends are staying at The Grande Retreat at Grande Bay next week. It’s a perfect location for those that want to be close to all of the action. The Grande Retreat is a beautiful, three-bedroom unit that was purchased by frequent tour guests of mine, who I am now lucky enough to call friends. Click here to check it out!

Spend some time on Cruz Bay beach
The Grande Retreat is a great three-bedroom condo located in Grande Bay, a complex directly across the street from Cruz Bay.
Happy hour is from 3-7pm daily at The Beach Bar.

Day 2: (Friday)

St. John is home to the best beach in the world, so that is where you should spend your first full day on island (provided there aren’t too many cruise ships over in St. Thomas that day – Click here to learn more about the cruise ships and how they can impact St. John). Trunk Bay is a quick 15-minute drive from Cruz Bay. Parking is extremely limited, so this is a beach that’s best to taxi to. It’s the only beach with an entry fee – just $5 per person, credit cards only – and it is well worth the price. Happy hour starts in the morning at Trunk Bay, so get there early if day drinking is on your agenda!

Trunk Bay has a great lunch spot, a full bar, snorkel and chair rentals, showers, and restrooms. It’s also home to the world’s only (I think!) underwater snorkeling trail. The trail is a bit of a swim, so I recommend bringing a noodle or a life vest along for the swim.

Trunk Bay
The underwater snorkeling trail is located to the left of these small cays.

Later that night, you can take a dip in your pool, enjoy a great dinner in town, or perhaps check out the sunset again. If that sounds good for you, head up to The Windmill Bar. It’s only 10 minutes from Cruz Bay, and it has some of the best sunset views on island. Taxis regularly go there around sunset time, so it’s easy to visit if you opt not to rent a car. Insider tip: They also have delicious buffalo chicken dip!

Sunset views from the Windmill Bar’s webcam

Day 3: (Saturday)

Boat days are the best days! Considering my friends have never visited the island, I figured a boat day is a must! We’re opting to stay local for this trip, so the plan is to snorkel with the turtles at Maho Bay, grab a bite at Pizza Pi, and perhaps a cocktail at Lime Out. If the water cooperates, we may even do a quick visit to Water Island, which is just off of St. Thomas.

Pizza Pi is a floating pizza boat.
Lime Out is a floating taco bar.

Have a nice dinner on night three. We have so many amazing restaurants to choose from. Click here to view Explore STJ’s searchable restaurant map. 

Day 4: (Sunday)

Since we have two teens visiting next week, we are sending them over to St. Thomas (with their parents of course!) for a water sports day at Sapphire Resort and perhaps Coral World. Sapphire has parasailing, jet skiing and other fun motorized sports that you can’t find here in St. John. Sapphire is only a five-minute taxi ride from the Red Hook ferry, so it’s a very doable day trip.

If you prefer to spend your last full day on St. John, I would suggest visiting another one of St. John’s beautiful beaches, or perhaps take an island tour with me! Together we can explore some lesser-known spots, including secluded beaches, historical sites and so much more. You can learn more about Explore STJ’s Island Tours at

Explore the island with me!

Relax over at Mongoose Junction that evening and get your shopping on. Mongoose has dozens of stores that sell a variety of items like hats, t-shirts, upscale clothing, ornaments, note cards, home goods and more.

Mongoose Junction is located in Cruz Bay.

Day 5: The Walk of Woe (Monday)

All good things must come to an end, right?

Enjoy a nice breakfast at either Cruz Bay Landing or High Tide before you do the walk of woe over to the ferry dock. But don’t worry, I’m pretty confident that you’ll start planning your next visit before you hit the dock in St. Thomas.

High Tide is located on the beach beside the ferry dock.
Cruz Bay Landing is located across the street from the ferry dock.

Looking for more information on a visit to St. John? Feel free to email me at

Have a great day everyone!

Want to learn more about St. John? Looking to take an island tour?

Learn more here –> See the island of St. John with a resident. See the nooks and crannies that many visitors miss. Explore the beaches, historical sites, perhaps a tiki bar or two, and much more. Full & half days available. Rated “Excellent” on TripAdvisor.

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