Tobago Road Trip: 9 Can’t-Miss Windward Road Stops

Tobago Road Trip Itinerary

Road trips on small islands are great because you get to cover a lot of ground within a short space of time and you’re treated to flawless views along the way! Tobago is no different. As tiny as it looks on a map, the island offers a lot of diversions, from historical sites to panoramic vistas. I indulge in these little escapes to the country as often as I can so by now, I’ve begun to repeat stops. But I don’t mind, because I’m still finding new ways to appreciate each experience. However, for those of you who don’t have the luxury of time to make multiple treks to the east of the island, here are my recommendations for the ideal Windward Road Tobago Road Trip itinerary.

NB: If you begin at 9 am and proceed at a leisurely pace, you should be all wrapped up and back in the west by 5:30 pm.

1. Take in some History at Fort King George Heritage Park

Tobago Road Trip: Fort King George Heritage Park

The first stop on every easterly Tobago road trip along the Windward Road should always be Fort King George Heritage Park. Built in the 18th century and named after King George III, Fort King George is the largest fort on the island. It is also the most well-preserved with several of its original buildings having been carefully restored. A self-guided tour of the grounds will take you to various beautiful stone buildings that once served as the Officer’s Barracks, the Gun Powder Magazine, the Prison Cells and the Bell Tank. This popular heritage site includes a museum full of thoughtfully curated artifacts, an out-of-commission lighthouse, several cannons and multiple vantage points for some of the best views of the capital of Scarborough.

Drive Time: Approximately 20 minutes

Cost: Access to the grounds is Free but admission to the museum is TT$10 | US $2 (adults), TT$5 | US $1 (teens), TT$2 (children)

Estimated Time at Location: 30 minutes

Tobago Road Trip: Fort King George Heritage Park

2. Rum & Chocolate Tasting at Tobago Cocoa Estate

Tobago Road Trip: Tobago Cocoa Estate

The Tobago Cocoa Estate offers a great experience, if you’re lucky enough to secure a tour. The Estate is the source of several award winning chocolates, including the delicious Laura Chocolate Bar, which won GOLD at the 2017 International Chocolate Awards. Tours aren’t offered year round, and require a 10 person group minimum, however if you’re on the island between December and April, I highly recommend it. During the tour you learn about the history of cocoa in Tobago and have the opportunity to participate in the drying and fermenting process. The experience wraps up with a rum and chocolate tasting that you will thoroughly enjoy. Truth be told, Tobago Cocoa chocolates can be purchased in stores around the world, including Europe, however its way more satisfying to sample them right here in Tobago! Note that outside of the regular season, there is still a chance to take the tour, so I strongly recommend contacting them in advance to make arrangements.

Drive Time: Approximately 30 mins

Cost: To be discussed when making arrangements

Estimated Time at Location: 1.5 hours

 3. Drinks & Views at Speyside Overlooking

Tobago Road Trip: Speyside Overlooking Restaurant and Bar

Almost as soon as you enter Speyside, you’ll arrive at a sharp bend that delivers the most spectacular view of the coastline. The only uninterrupted vantage point for this view however, resides within the Speyside Overlooking Restaurant and Bar. The red, yellow, and green wooden facade visible from the street is small and unassuming, but as soon as you enter the establishment you’ll understand why its a mandatory stop on your Tobago road trip. The focal point of the space is the panel of windows that occupy the entire back wall, granting you an unencumbered view of sapphire waters and emerald green vegetation. The owner, Toney, is a friendly guy who won’t pressure you to purchase anything, but its only polite to get at least one beverage if you’re going to soak up his prized view. NB: I also recommend having a light snack as their might be a little bit of a wait at the lunch spot.

Drive Time: Approximately 25 minutes

Cost: Depends on your drink preference

Estimated Time at Location: 30 minutes

Tobago Road Trip: Speyside Overlooking Restaurant and Bar

4. Souvenir Shopping

Tobago Road Trip: Speyside Souvenir Shop

Finding truly unique, handmade souvenirs isn’t the easiest thing, so as long as your Tobago road trip takes you east, you need to capitalize on the opportunity to patronize local craftsman. Seeing that you’re already at Speyside Overlooking, you might as well hop across the street and do some shopping at this roadside stall. On sale you’ll find bamboo bird feeders, wooden carvings, calabash purses and a range of other items crafted by the owner himself. Don’t pass up this opportunity to purchase genuine Tobago items for yourself or friends and family!

Walking Time: 1 minute

Cost: There are items for any low to mid range budget

Estimated Time at Location: 15 minutes

5. Lunch at The Suckhole

Tobago Road Trip: The Suckhole

After all of that driving, shopping and rum tasting (for everyone but the designated driver) you’re definitely ready for lunch. The only question is, is the lunch spot ready for you? While there are other good dining options in this neck of the woods, I strongly recommend The Suckhole a seaside restaurant in Charlotteville. It’s one of the most popular restaurants in the east and it would be a shame to make it that far and not sample its menu. However, the restaurant doesn’t take reservations, it is always packed, and the average wait time is about an hour. Seriously. But it’s worth it. I promise. When you arrive the small dining area will undoubtedly be crowded, but just let the owner/server know you’re next in line and eventually you’ll be seated. Lunch comes with fries, a rich fresh salad and your choice of meat – whether you do the shrimp, the chicken or the fish, they’re all filling, mouth wateringly delicious!

Drive Time: Approximately 20 minutes

Cost: Estimate TT $200 | US $30 per person for meal and drinks

Estimated Time at Location: 2.5 hours

Tobago Road Trip: The Suckhole

6. Make a Quick Stop at Fort Campbelton

Tobago Road Trip: Fort Campbelton

A brief stop, but a mandatory one all the same. Fort Campbelton is one of those places you visit exclusively for the view, not the experience. With just a couple cannons and not much space to roam, this tiny fort is sometimes forgotten historical landmark. It’s easy to miss as it’s accessed by walking along a narrow lane lined by private residences. In fact, it almost feels like you’re walking through people’s front yards but the residents are accustomed so there’s no need to feel uncomfortable. There’s a small gazebo if you feel inclined to sit, but I generally don’t recommend this spot for an extended stay. Take your time to enjoy the great birds eyes view of the village below but if you linger another group is sure to arise and make the space feel crowded.

Drive Time: Approximately 5 minutes

Cost: Free (although there’s a family with restroom facilities that you can access for a small fee)

Estimated Time at Location: 10 minutes

7. Enjoy The Best view of Charlotteville from Flagstaff Hill

Tobago Road Trip: Flagstaff Hill

The highest point in Charlotteville, Flagstaff Hill also has the best view of the village. There is no better vantage point to soak up the sight of the heart shaped coastline and the sprinkling of boats that dot the surface of the ocean. The panoramic vista includes uninterrupted views of Man O’ War Bay, St. Giles Island, as well as Cambelton Hermitage. The site features a sprawling green lawn, a gazebo, tables and benches, making it a great spot for a picnic if you’re so inclined.

Drive Time: Approximately 8 minutes

Cost: Free

Estimated Time at Location: 20 minutes (however if you prefer to forego lunch at Suckhole and picnic here instead, I highly recommend it)

Tobago Road Trip: Flagstaff Hill

8. Photo Ops at Speyside Estate Ruins

Tobago Road Trip: Speyside Estate Ruins

Road trips are great opportunities for photo ops, and the Speyside Estate Ruins provide the ideal setting. The stone and red brick structure that once housed the sugar factory is fully accessible, as is the waterwheel just behind it. Take the time to explore the space and discover the best spots for your shots. The windows and doorways make great ‘natural’ frames for photos, while the green lawn carpeting offers a beautiful contrast that pops in all your pics. For some strange reason, despite the amount of traffic in the area, this site is always empty, so you’ll most likely have free reign for the time that you’re there.

Drive Time: Approximately 10 minutes

Cost: Free

Estimate Time at Location: 20 minutes

Tobago Road Trip: Speyside Estate Ruins

9. Take in the View from Batteaux Bay

Tobago Road Trip: Batteaux Bay

After your photo op at the base of Blue Waters Inn Road, go to the top of the hill for one last epic view. Batteaux Bay is one of those beaches that seems to always be full-100 when it comes to startlingly blue water. And the lush vegetation that surrounds it emphasizes just how vibrant the water is. From this vantage point you’ll be able to see Goat Island, as well as Little Tobago. It’s a small space at the top of the hill, before you enter the hotel’s property, so its not ideal for a long stay, but I like to linger up there all the same. Can you blame me? It’s so hard to pull myself away from this view! Bonus: The beach below is perfect for swimming and, while its on the hotel’s property, it is open to the public. So, if you have time, and you’re up for a little dip, head on down!

Drive Time: 3 minutes

Cost: Free

Estimated Time at Location: 15 minutes (unless you’re jumping in the water for a swim!)

Not everyone loves packed road trip itineraries (including me) so if you’re planning your own Tobago road trip, feel free to pick and choose from this list. Once you’re on the island though, I strongly recommend renting a car for at least a couple of days. The Windward Road has some great stops that, as you can see, requires an entire day. However, the Northside Road also serves as an ideal route with beaches and bars you won’t want to miss!

Have you ever road tripped in Tobago? What’s your favorite route, and what are some of your favorite stops?

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Tobago Road Trip Itinerary

25 Replies to “Tobago Road Trip: 9 Can’t-Miss Windward Road Stops”

  1. You’re so right, the views are breath taking! That alone can serve as one great reason to take the road trip. The other being chocolate, of course. 😀
    Joking aside, it really sounds interesting to be able to visit the Tobago Cocoa Estate and take the tour. Even though one can buy Tobago Cocoa chocolate in Europe, it would be just amazing to see it all in person. And to taste few samples, of course. 😛
    Thanks for suggesting all these stops, sounds like one great Tobago itinerary!

    1. islandgirlintransit says: Reply

      Yep, the chocolate is definitely a great incentive 🙂

  2. The places you visited are really authentic. I love that tropical fruits, so tasty 🙂 I agree also with you in the possibility to visit all the island in less time.

  3. You had me at Rum and chocolate tasting! I would love to try that. Great article.

    1. islandgirlintransit says: Reply

      Yep it’s a pretty great tour with the perfect ending 🙂

  4. Tobago look perfect to me. History and great views are two things that i really like!

  5. That orange bench is adorable! I love colorful places and Tobago looks right up my alley! And I’d totally check out that cute souvenir stand and gobble up all that yummy food. This is a perfect road trip itinerary!

  6. I love road trip itineraries, plus I’ve never been to Tobago, so I really enjoyed reading this. You completely had me at rum and chocolate tasting tour, um, yes please! I also like the sound of the Suckhole restaurant. I’d happily wait for an hour if the food’s that good.

  7. Every time you read one of your posts I want to book a flight to Tobago. Loving the food and drink recommendations. I would definitely be making a beeline for the overlooking bar. Amazing views

  8. These are beautiful places to visit plus, the pictures are stunning. I would love to see the Stop at Fort Campbelton. It looks so serene and has the perfect balance with nature. Your road trip is really wonderful.

    1. islandgirlintransit says: Reply

      It’s definitely a fun route, I love the views on along this stretch of road 🙂

  9. This place look amazing, I’ve never been to Tobago, but reading your post I felt like being there, Tropical fruits looks yummy, so pleased you enjoyed it!

    1. islandgirlintransit says: Reply

      Yay so glad you felt like you were here, I hope you’re able to experience it in person soon!

  10. Lots of beautiful spots! I especially love the window frames at the estate.

  11. Your pictures are simply breathtaking and these places looks so much fun to explore. I really wanted to visit this country since long. Hopefully I shall be here soon and will refer to your blog 🙂

    1. islandgirlintransit says: Reply

      I hope you’re able to visit some day 🙂

  12. Denny George says: Reply

    Rum and chocolate tasting sound just like my thing. The photographs of the landscapes, especially of Charlotteville look breathtaking. I would love to someday follow in your footsteps on this road trip.

  13. Those views are absolutely stunning! I would take a road-trip on just that alone. I’m always a sucker for turquoise blue waters but I’d enjoy those stops you mentioned along the way. Would love to check out Tobago one day!

  14. The Suckhole! LOL, what a name for a restaurant but that food looked so delicious. And the road trip! Beautiful. There’s nothing like an awesome road trip to make a trip more memorable especially when you’re seeing those gorgeous blue waters and wildlife. Adding Tobago to the bucket list.

  15. Ahh, this makes me miss the Caribbean! I’d love to roadtrip around Tobago, looks like there are tons of spots to hit. I’m always tempted by a great viewpoint, so Flagstaff Hill and Batteaux Bay are must-sees for me. 🙂

  16. What a stunning island with spectacular views, and the combination of rum and chocolate sounds perfect!

    1. islandgirlintransit says: Reply

      Yep, chocolate and rum is a pretty great combo!

  17. This is absolutely amazing! The stops you’ve included on your road trip around Tobago are just spectacular and I’d love to stand atop those spectacular vantage points and admire the pristine waters and beautiful landscapes that the island is blessed with bountifully.

    1. islandgirlintransit says: Reply

      Yes, Tobago definitely is blessed with so many gorgeous views!

  18. That place looks really peaceful! I would love to go on a vacation in Tobago. And who wouldn’t love to be served by those delicious fruits?!

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