Grand Cayman Excursions

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Trolley Roger/ Trolley Roger Train Scenic Tour of Georgetown/ The Trolly Roger

Duty Free shops

Tour Description

Upon boarding the one and only Trolley Roger, all you need do is to sit back and enjoy the relaxing ride. Your guide for the day is an expert on the city and the country of the Cayman Islands, and expect to hear the tales and lore that make up the country's history.

You'll pass through the financial district, jam packed with over 600 banks, making George Town one of the world's largest financial capitals. Next, you'll see the central park area, home to the stature of Grand Cayman's national hero, "Mr. Jim" Bodden.

Next, you'll see the beautiful residential area of South Sound, home to a collection of old-time Caymanian houses built among beautiful Caribbean flowers and trees.

Your guide will beguile you with the tales of the island's more colorful characters, including Mrs. Keppie, the McTaggarts, the Thompsons, and pirate lore surrounding Sir Francis Drake and Blackbeard, and tales of hidden treasure.

You'll make a stop at one of the island's favorite beaches, Smith's Cove, and the final leg of your adventure will take you back towards Hog Sty Bay and the George Town Harbour area. You'll be able to take a picture of the McCoy's Villa, an immaculately restored house. Your tour ends in the center of George Town, where shopping is the order of the day.

Note: This tour features a minimum amount of walking

Activity Level:


Excursion Length: 1 Hour

10% This activity will take up about 10% of your time in port.

Tour Prices:

Royal Caribbean: Adults, from $25.75; kids, from $19.75
Celebrity: Adults, from $25.75; kids, from $19.75
Princess: from $24
NCL: Adults, from $30; kids, from $20

What You Need to Bring:

  • Comfortable shirt or top and pants or shorts
  • Comfortable walking shoes
  • Sunscreen
  • Sunglasses
  • Hat
  • Bring cash for incidentals
  • Bring your camera

Cruise Lines Offering This Tour:

Royal Caribbean icon Royal Caribbean Celebrity icon Celebrity Princess icon Princess
Holland America icon Holland America NCL icon NCL

What Else You Need to Know:

Transit to the site: You'll meet your guide at the George Town Cruise Ship dock and take a short walk to the awaiting Trolley Roger.

Who should take this tour:

  • Folks who'd like to take a unique and scenic tour of George Town
  • Folks interested in the history of the Cayman Islands
  • Folks looking for a short tour of George Town
  • Families
  • Fun seekers
  • Photographers

Traveler's Review

Trolley Roger tour in Georgetown, Grand Cayman

Rated 1 Star (1 Review)

Review Date: January 2013
Reviewer: Henrietta/Chicago
We took this tour in: December 2012
Cruise Line: Royal Caribbean

"This was the worst tour I've ever taken. The tour guide was very prejudiced against US citizens. Cayman Island residents think they are better than Americans. The tour guide was a Jamaican who was very opinionated against Americans. I did not like his conversation while he gave us an overview of how great the people are in the Cayman Islands and how terrible Americans were. If they are so great, why do they make a lot of their money from Tourists!!!!"

Who should take this tour/excursion: "Nobody!!!! Let's see how great the Cayman Islands would be without Tourists."

What you'll do


Meet guide at Cruise Ship docks

Walk to awaiting Trolley Roger trolley (5 minutes)

Tour of George Town (55 minutes)

Return to Cruise Ship docks

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