Caribbean Walking Tours

Turquoise water, colorful towns, island food, and centuries of history — all without the tour bus. Just $9.99 per port.

15 PORTS AVAILABLE · MORE ADDED REGULARLY

🏷️ Each guide covers your whole group — couples, families, friends. One price. No per-person fees.

Available Now

AVAILABLE $9.99

Antigua

Antigua & Barbuda

🚶 10 stops 📏 ~3 miles ⏱ 4–5 hours

Heritage Quay, Redcliffe Quay, St. John's Cathedral, Fort James with cannon batteries, Fort James Beach, and Caribbean cuisine.

AVAILABLE $9.99

Aruba

Dutch Caribbean

🚶 10 stops 📏 ~2.5 miles ⏱ 4–5 hours

Fort Zoutman, Wilhelmina Park, the archaeological museum, Renaissance Marina, colorful Main Street, and Surfside Beach.

AVAILABLE $9.99

Barbados

Caribbean

🚶 10 stops 📏 ~3 miles ⏱ 4–5 hours

Bridgetown's UNESCO waterfront, Parliament buildings, a 17th-century synagogue, the historic Garrison, and George Washington House.

AVAILABLE $9.99

Bermuda

British Overseas Territory

⛴ 3 zones 📏 6–8 miles ⏱ 6–8 hours

Royal Naval Dockyard, Hamilton's pastel capital, and UNESCO St. George's — three iconic destinations by foot and ferry.

AVAILABLE $9.99

Cozumel

Mexico

🚶 9 stops 📏 ~2.6 miles ⏱ 2–3 hours

San Miguel town square, waterfront malecón, Mayan chocolate shop, beach clubs, and the best tacos on the island.

AVAILABLE $9.99

Curaçao

Dutch Caribbean

🚶 10 stops 📏 ~2.5 miles ⏱ 4–5 hours

Colorful Handelskade waterfront, Queen Emma floating bridge, Mikvé Israel-Emanuel Synagogue, Kura Hulanda Museum, and Pietermaai District.

AVAILABLE $9.99

Grand Cayman

Cayman Islands

🚶 10 stops 📏 1.8 miles ⏱ 4–5 hours

George Town waterfront, Fort George ruins, craft markets, island museum, and optional trips to Seven Mile Beach and Hell.

AVAILABLE $9.99

Grand Turk

Turks & Caicos

🚶 10 stops 📏 3.0 miles ⏱ 4–5 hours

Governor's Beach, historic Front Street, Salt Salinas with flamingos, colonial architecture, and John Glenn's splashdown site.

AVAILABLE $9.99

Key West

Florida

🚶 10 stops 📏 ~3 miles ⏱ 4–5 hours

Mallory Square, Hemingway Home, Southernmost Point, Key West Lighthouse, Duval Street, and the Historic Seaport.

AVAILABLE $9.99

Nassau

Bahamas

🚶 10 stops 📏 ~2.5 miles ⏱ 3–4 hours

Downtown to Fort Fincastle, Queen's Staircase, straw markets, Junkanoo Beach — with lunch at a local fish fry spot.

AVAILABLE $9.99

Ocho Rios

Jamaica

🚶 10 stops 📏 2.5 miles ⏱ 4–5 hours

Turtle Beach, Island Village, craft market, Ocho Rios Fort, Turtle River Park, jerk chicken, and Jamaica's vibrant north coast.

AVAILABLE $9.99

Old San Juan

Puerto Rico

🚶 11 stops 📏 2.8 miles ⏱ 4–6 hours

Colorful colonial streets, El Morro fortress, umbrella alley, local mofongo, and 500 years of history on every block.

AVAILABLE $9.99

St. Kitts

St. Kitts & Nevis

🚶 10 stops 📏 ~2 miles ⏱ 4–5 hours

The Circus clock tower, Independence Square, twin-towered cathedral, St. George's Anglican Church, a lively public market, and the national dish: goat water.

AVAILABLE $9.99

St. Maarten

Dutch Caribbean

🚶 10 stops 📏 2.0 miles ⏱ 4–5 hours

Great Bay Beach boardwalk, Front Street shopping, Guavaberry Emporium, Dutch colonial courthouse, and Caribbean flavors.

AVAILABLE $9.99

St. Thomas

U.S. Virgin Islands

🚶 10 stops 📏 ~2.5 miles ⏱ 3–4 hours

Charlotte Amalie's forts, the famous 99 Steps, Blackbeard's Castle, duty-free shopping, and panoramic harbor views.

More Ports Coming — Check Back Often

We're constantly adding new Caribbean ports and keeping existing guides fresh with updated tips, restaurant recommendations, and local intel. If your port isn't listed yet, it may be on the way.

🗺️

New Ports Added

We release new Caribbean ports regularly — bookmark this page and check back soon.

🔄

Guides Updated

Existing guides are refreshed with new restaurant picks, tips, and on-the-ground intel.

📬

Get Notified

Sign up below and we'll email you when new ports launch — never miss your next port day.

Don't Miss Your Port

Enter your email and we'll let you know as soon as new Caribbean ports go live.