Cruises · 2023 · Enhanced edition

Carnival Paradise Cruise: Key West, Jamaica & Grand Cayman

A six-night Carnival Paradise cruise with a Key West pub crawl, a relaxed all-inclusive resort day in Jamaica, time in Grand Cayman, and plenty of food, comedy, games, and roulette at sea.

Trip at a glance

Dates: September 2–10, 2023
Ship: Carnival Paradise
Ports: Key West, Jamaica, and Grand Cayman
Highlights: Key West pub crawl, Jamaica resort day, elegant dinners, comedy, and sea-day downtime

September 2–3: The road to Tampa

After getting the kid settled, we left around 11 a.m. for the roughly 12-hour drive to Florida. A Chick-fil-A pimento-cheese chicken sandwich broke up the road, and we checked into La Quinta in Brandon for two nights.

Our extra day near Tampa began at Topgolf, where we spent a couple of hours playing—including a Pebble Beach simulator round—while sharing buffalo chicken dip and a pineapple drink served in a golf bag. We followed it with a dark Ice Cream Sammich beer at Bootleggers Brewing and cream-filled pastries from Ricopan Bakehouse.

Leaven Brewing supplied the strongest flight of the afternoon, including maple-bacon, red ale, and guava-passion-fruit flavors. Bullfrog Brewing was less memorable for us. We ended with a Rosati's Chicago deep-dish pizza that tasted good but proved far larger and heavier than we needed.

September 4: Boarding Carnival Paradise

We reached the port around 10:30 a.m. The parking garage sat across the main road, but we could drop everything near the ship before parking. Check-in moved quickly, and we were soon onboard with a burger and sandwich for lunch.

After the Fun Aboard, Fun Ashore presentation, we watched Tampa disappear during sail-away. Dinner included cured salmon, corn soup, chicken parmesan, and tiramisu. The salmon was chewier than I expected, but the first evening still made an easy transition into cruise mode.

September 5: A spirited walk through Key West

Breakfast was a parfait, avocado toast, and turkey bacon before we went ashore. Our pub-crawl excursion did not start until 11:30, so we had about an hour to look around first.

The crawl stopped at five bars and turned the day into a rolling tasting tour: rum punch, a White Russian and piña-colada slushie, a hurricane, tequila, a Bahama Breeze-style drink, and even a pickle shot. We also visited two distilleries, with one standing out clearly more than the other.

We returned around 4:30 for a 5:30 sail-away. Dinner brought wild boar, meatballs, salmon cakes, and roasted pineapple, followed by Deal or No Deal and free bingo. Pizza and a movie made for another early night.

September 6: Sea day and elegant night

The first sea day was intentionally simple: breakfast, roulette, lunch, bingo, and a movie. Elegant-night dinner included stuffed mushrooms, clam chowder, shrimp, and key-lime mousse. A family comedy show finished the evening.

September 7: An all-inclusive day in Jamaica

After breakfast, we browsed the small shopping area near the port and met our excursion. The main event was about five hours at an all-inclusive Secrets resort.

We moved between the pools, swim-up bars, beach, and resort activities. Drinks ranged from coffee with rum and mojitos to Red Stripe, an iceberg beer, a White Russian, and a green-tea-style cocktail. A buffet lunch kept the day easy without interrupting the pool and beach time.

Back onboard, dinner included onion soup, alligator beignets, spare ribs, and a cheese plate. With a full resort day behind us, we turned in early.

September 8: A quieter Grand Cayman visit

We went ashore around 9:30, walked the streets near George Town, and returned to the ship by noon. Because we had visited Grand Cayman before and had not planned a larger excursion, the port felt repetitive to us. Looking back, this was the stop that most needed a specific plan beyond walking and shopping.

Lunch was a burrito, followed by roulette and another elegant dinner. I ordered oysters, greens, prime rib, and cheese; my wife chose shrimp cocktail, salad, carbonara, and crème brûlée. We finished with pizza and another early night.

September 9: One final sea day

Breakfast included parfait, a salmon bagel, and corned beef for me, with an omelet and grits for my wife. The rest of the day mixed roulette, rugby, and unhurried ship time.

We skipped the dining room while my wife napped and went with pizza, a Cuban sandwich, and a café doughnut instead. I used the complimentary drink Carnival offered on a sailing of five or more days, caught a comedy show, and spent the remaining onboard credit. It became our latest night of the cruise.

September 10: Home again

Disembarkation felt less organized than the floor-by-floor systems we had experienced elsewhere, and the terminal moved slowly. Once on the road, Arby's handled breakfast and Wayback Burgers supplied dinner during the roughly 12-hour drive home.

Final thoughts

This cruise worked best when each port had a clear purpose. Key West became a fun group tasting day, Jamaica was devoted to resort relaxation, and Grand Cayman showed us why even a familiar destination benefits from choosing one new experience in advance. The sea days filled the spaces comfortably with food, comedy, games, and just enough roulette.

Plan your own trip

Key West, Jamaica & Grand Cayman Port Guide

Our cruise gave each stop a different personality: a social pub crawl in Key West, a resort day in Jamaica, and a short walk through George Town. The biggest lesson was that a familiar port still benefits from one clear plan.

Key West: drinks, history, or the water

Our guided pub crawl made transportation and pacing easy, but Key West also rewards travelers who build the day around its history, compact streets, and waterfront.

Pub crawl

A guided crawl works well for a social day and introduces several bars without spending the port call deciding where to go next. Eat first, drink water, and pace the samples.

Old Town walk

Combine Duval Street, the Southernmost Point, and the surrounding historic streets. Distances add up in the heat, so choose priorities rather than chasing every landmark.

History and museums

Hemingway's former home, maritime history, the aquarium, and other small museums can create a more structured day close to town.

Water and sunset

Snorkeling, sailing, beaches, and waterfront time offer an alternative to bars and shopping. Match the outing to the ship's all-aboard time.

How we would plan it: Choose either a tasting-focused crawl or two historic attractions plus a relaxed meal. Trying to combine a full crawl, museums, the Southernmost Point, and a boat trip would turn a walkable port into a race.

Official Key West guide Key West attractions overview

Montego Bay: resort comfort or a look beyond the gates

An all-inclusive resort pass gave us a dependable five-hour day of pools, beach, drinks, lunch, and very little logistical work. It is a strong choice when relaxation matters more than covering ground.

Keep it relaxed

All-inclusive resort day — the closest match to our experience, with food, drinks, pools, and beach access packaged together.
Doctor's Cave Beach — a beach-focused alternative near Montego Bay's Hip Strip.
Marine Park snorkeling — a water-centered option for travelers who want more activity than a resort pool.

Add culture or adventure

Rose Hall Great House — history, architecture, sea views, and the famous White Witch legend.
Great River activities — guided tubing and other outdoor excursions provide a more active day.
Montego Bay food and shopping — build a shorter city visit around Jamaican flavors rather than only souvenir stops.

Our experience: The resort day did exactly what we wanted. Before buying a pass, compare the included food, drinks, transportation, beach access, age policy, and time actually available at the property.

Official Montego Bay activities Official Montego Bay guide

Grand Cayman: plan beyond George Town

Walking near the port left us thinking there was little new to do. The better lesson is that many of Grand Cayman's signature experiences require choosing them before stepping ashore.

Stingray City

Boat tours commonly combine the shallow sandbar with coral snorkeling or another water stop. Reserve ahead and protect enough time for the return.

Seven Mile Beach

Clear, shallow water, coral sand, snorkeling, and beach facilities make this the straightforward choice for a relaxed day away from the shops.

Reef and wreck trips

Snorkeling and diving excursions—including the Kittiwake artificial reef for qualified divers—show a side of the island that a town walk cannot.

Town plus one experience

If you still want George Town, pair a short walk and lunch with a reserved beach transfer, boat tour, or another island attraction.

What we would change: On a repeat visit, Stingray City or a dedicated Seven Mile Beach day would give the stop a clear identity. Browsing George Town alone is best when shopping truly is the goal.

Official Grand Cayman guide Popular Cayman attractions Stingray City information

Three ways to shape this cruise

Relaxed versionKey West food and a short walk, Jamaica resort pass, then Seven Mile Beach.

Social versionGuided Key West pub crawl, lively Jamaica resort day, then George Town and a beach stop.

Explore-more versionKey West history, Rose Hall or a river excursion in Jamaica, then Stingray City and snorkeling.

What worked for us

We gave Key West and Jamaica a clear theme, and both days felt complete. Grand Cayman stayed too open-ended. For a repeat port, reserve one experience you have never tried instead of assuming the town itself will feel new.

Original trip gallery