4 Spots Left

Jamaica · 4 Nights / 5 Days

Winter Getaway 2027 – RIU Palace Montego Bay, Jamaica

Trade winter for warm sand, infinity pools, and unlimited Caribbean all-inclusive — no planning required.

Duration

4 Nights / 5 Days

Group size

Max 30

Best For

Beach,  International

The Trip

Trade snow for sunshine.

Escape the cold and trade snow for sunshine! Join Worldwide Traveler and group leader Gary Castaldo for an unforgettable adults-only vacation at the beautiful RIU Palace Montego Bay in Jamaica. Whether you’re traveling as a couple, with friends, or on your own, this hosted group trip is the perfect opportunity to relax, unwind, and enjoy the Caribbean without the stress of planning every detail.

The Experience

Why You’ll Love RIU Palace Montego Bay

This upscale, adults-only resort offers the perfect blend of relaxation and entertainment. Guests enjoy direct beach access, multiple infinity pools, themed restaurants, premium all-inclusive dining, live entertainment, and the option to visit neighboring RIU resorts for even more dining and activities.

Perfect For:

  • Couples
  • Friends traveling together
  • Solo travelers who enjoy group travel
  • Anyone looking for a warm winter escape

Reserve Your Spot Today!

From $1,899 per person
Based on double occupancy and includes airfare from Chicago O’Hare.

Spaces are limited for this escorted group departure.

Come experience Jamaica’s warm sunshine, crystal-clear Caribbean waters, exceptional hospitality, and the ease of an escorted group vacation. Start 2027 with a tropical getaway you’ll never forget!

What’s included

  • Roundtrip airfare from Chicago O’Hare
  • Roundtrip airport/resort transfers
  • Four-night stay at the adults-only RIU Palace Montego Bay
  • 24-hour all-inclusive accommodations
  • Unlimited meals, snacks, and beverages
  • Unlimited domestic and international drinks
  • Nightly entertainment and activities
  • Beautiful beachfront location
  • Hosted by Worldwide Traveler’s Gary Castaldo

Not included

  • Gratuities beyond the all-inclusive
  • Travel insurance (we’ll help you arrange it)

  • Optional off-resort excursions & tours
  • Personal expenses & souvenirs
Winter Getaway 2027 Info
Glimpses
  • Your Host

    Gary Castaldo

    For me, travel is about the people you bring along — which is why I plan the group getaways, the celebrations, and the once-in-a-while blowouts.

January 17–21, 2027

$1,899 / person*
*based on double occupancy

$950 deposit by Aug 10, 2026 reserves your place

Additional Information

  • Free to hold for 48 hours
  • Your Host

    Gary Castaldo

    For me, travel is about the people you bring along — which is why I plan the group getaways, the celebrations, and the once-in-a-while blowouts.

More hosted departures

You might also love

  • Secrets La Romana, Dominican Republic

    Dominican Republic · 7 Nights / 8 Days

    Secrets La Romana, Dominican Republic

    January 23–30, 2027
    $2,900 / person*
    *based on double occupancy

  • Avalon Artistry II

    Germany, France & Switzerland · 11 DAYS / 10 NIGHTS

    German Grandeur with 2 Nights in Munich for Beer Enthusiasts (Westbound)

    November 08–19, 2026
    $5,900 / person*
    *based on double occupancy