Your journey to St. Croix kicks off on May 21, 2026, with a smooth connection through Miami on American Airlines — where you’ll link up with the rest of the brothers and take the final leg together into St. Croix. If you prefer to fly in earlier or later, just let me know — your itinerary can be adjusted to match your schedule.

You’ll be seated in Main Cabin, giving you priority boarding over standard economy, complimentary seat selection, a personal item + carry-on, and access to upgrade options if you’re looking to elevate your flight experience even further.

Whether you depart from DCA or another home airport, we’ll align your flights to ensure you arrive in St. Croix efficiently, smoothly, and ready to vibe with the crew.

St. Croix’s airport doesn’t offer a traditional VIP lounge, but it moves fast — quick customs, easy navigation, and no long waits. Once you collect your luggage, you’ll head straight to your private round-trip transportation bound for Divi Carina Bay Boutique Beach Resort.

Transfers are fully included in your package — giving you a clean, seamless, and elevated arrival experience from wheels down to check-in.

More day-by-day itinerary details will drop as we get closer to travel — stay tuned for the full rundown.

Nestled on St. Croix’s sun-drenched shoreline, Divi Carina Bay Boutique Beach Resort delivers a laid-back, elevated island escape tailored for travelers who appreciate simplicity wrapped in comfort. This adults-only, all-inclusive resort combines oceanfront views, all-day dining, premium spirits, and effortless relaxation — all set against the backdrop of the Caribbean Sea.

Wake up to panoramic sunrise views, step straight onto the sand, and enjoy a resort designed to help you unwind without distraction. From handcrafted cocktails to casual-fine dining, poolside lounging, and casino nightlife, the vibe is smooth, grown, and made for good company.

This resort was chosen with the brotherhood in mind — a space where you can smoke a cigar on the balcony, kick back with a drink, link up with the fellas, and enjoy the rhythm of island life from morning to midnight.

Not overly commercial, not overly crowded — just the right mix of comfort, convenience, and Caribbean charm for an unforgettable Cigar & Sands experience.

The Divi Carina Bay Boutique Beach Resort is located on the eastern side of St. Croix, and the closest airport is Henry E. Rohlsen Airport (STX). 

• The distance from the airport to the resort is roughly 17–20 miles. 

• In terms of drive time, that normally translates to about 30–35 minutes, depending on traffic and time of day. 

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Your pre/post-departure protection is calculated based on the total price of your package at the time of booking and is non-refundable. This cost is already included in your package unless you choose to decline the coverage.

Please note that if your package price increases prior to booking, or if you upgrade your airfare class, the protection cost may adjust accordingly. Coverage pricing is based on everyone in the room selecting protection. If only one traveler chooses coverage, please inquire for revised pricing.

Protection Pricing

Package Price (per person) Protection Cost (per person)

$1,500.01 – $3,000 = $120 

$3,000.01 – $5,000 = $150 

$5,000.01+ = $170

If you decide to decline trip protection at the time of booking, you will be required to complete and sign an Insurance Waiver before your reservation can be confirmed. This requirement applies even if you plan to purchase your own coverage independently or at a later time.

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Not included in your rate:

• Optional tours, excursions and experiences
• Any other services not noted in the above Inclusions

Rates are subject to change until booked with a minimum $489 per person deposit.