One evening our whole group hustled to the airport to catch a flight to Tobago on Caribbean Airlines. They are based in Trinidad and fly 737s to North America but on this 15-minute flight it’s a Dash 8-300 that has a ton of legroom for 12 rows of seats (48 passengers). The flights are busy because locals can buy tickets for about $25 each way so we couldn’t get on an earlier flight. Instead, we all logged on to the airports free Wi-Fi and did some work. The flight going over was scary – we hit a pretty good size air pocket and everyone screamed but for the lone flight attendant. On the way back the flight was as smooth as can be.
FYI: You can’t fly to Tobago from the U.S. Mainland. If you don’t like small planes (the Dash 8 is not that small) you can opt for the two and a half hour ferry.
As I mentioned in my Trinidad post…Tobago is a 120 square miles (300 km) island that’s 25 miles (41 km) long and 7.5 miles (12 km) wide with a population of 54,000. This is by far the nicer island if you are looking to relax and get that Caribbean laid back feel.
Trinidad was a great experience and is worth visiting for the culture (especially Carnival), but Tobago is where you want to chill. There’s no better place then where we stayed which was The Villas at Stonehaven. It’s the swankiest place on the island and is where all the rock stars like Elton John, Celine Dion, Prince, and Shakira stay when they come for the annual Tobago Jazz Festival.
The Villas are part of the Small Luxury Hotels of the World collection and have been featured in all of the travel magazines and called “one of the 10 most romantic Caribbean Retreats” by CNN. There are fourteen, 3,700 square feet villas that all have private infinity pools, 50 foot verandahs, a fully stocked kitchen, and three air conditioned bedrooms with en-suite bathrooms. The most remarkable thing is room rates start at just $303 a night! The only thing I could find wrong with this place is that their internet is slow, but other than that – it’s a great deal.
Just after we arrived I quickly changed and jumped back in the van for a 5-minute ride to Sea Horse Inn for some good continental and Caribbean cuisine. You can sit outside under the stars and hear the ocean a hundred yards away. When a passing rain storm came through, the waiters quickly moved our table under the roof.
Did you know: “According to Wikipedia the earliest English-language source cited in the Oxford English Dictionary, Tobago bore a name that has become the English word tobacco.”
The next morning it was raining which the locals call “liquid sun.” Luckily, the liquid sun didn’t last long as we were off for a coastal boat tour of Tobago. We jumped in a 23 foot, twin engine boat run by Waterholics, and went from one secluded cove to the next. And as my colleague Eric wrote, “each more beautiful than the last.”
The highlight was Paradise Bay which has black sand beaches and can only be accessed by boat – you have to swim a hundred feet to get on shore. After a few hours we had a BBQ lunch on “No Man’s land”. One of Waterholics staffers cooked up quite a spread that included fish, chicken, salad, beans, macaroni salad, and hot dogs. We finished the afternoon by going to this shallow water sand bar they call “Nylon pool” which was named by Princess Margaret. All the tour operators end their tours there for a crazy party around 4 pm so try and get there earlier. To get you in the water they tell women they will shed 10 years of their lives while guys gain five extra inches where it counts. I’m pretty sure the latter didn’t happen but one thing I do know is I became a better traveler from having visited Trinidad and Tobago.
Chase Sapphire Preferred® Card
- Earn 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $750 toward travel when you redeem through Chase Ultimate Rewards®
- 2X points on travel and dining at restaurants worldwide, eligible delivery services, takeout and dining out & 1 point per dollar spent on all other purchases.
- Get 25% more value when you redeem for travel through Chase Ultimate Rewards®. For example, 60,000 points are worth $750 toward travel.
- Get unlimited deliveries with a $0 delivery fee and reduced service fees on orders over $12 for a minimum of one year on qualifying food purchases with DashPass, DoorDash's subscription service. Activate by 12/31/21.
- Earn 2x total points on up to $1,000 in grocery store purchases per month from November 1, 2020 to April 30, 2021. Includes eligible pick-up and delivery services.
The comments on this page are not provided, reviewed, or otherwise approved by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered. Editorial Note: The editorial content on this page is not provided by any bank, credit card issuer, airlines or hotel chain, and has not been reviewed, approved or otherwise endorsed by any of these entities.
Editorial Note: The editorial content on this page is not provided by any bank, credit card issuer, airlines or hotel chain, and has not been reviewed, approved or otherwise endorsed by any of these entities.