How to Spend a Weekend in Tobago

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Using two personal days, I took off from my full-time job to spend Memorial Day weekend in Tobago with family. I’ve been to Trinidad a handful of times, but this was my very first time visiting Tobago, and it definitely won’t be my last.

Back in February, my cousin found a flight deal from New York to Trinidad on Caribbean Airlines, and we booked almost immediately. Since we didn’t really want to spend time in Trinidad, we called a few family members and turned it into a quick weekend trip to Tobago instead.

There were good moments, bad moments, and a few very chaotic ones, but overall, Tobago completely surprised me in the best way. If you’re planning a short getaway, here’s exactly how to spend a weekend in Tobago, what to expect, and what I’d do differently next time.

Getting to Tobago: Ferry vs. Flight from Trinidad

Traveling from Trinidad to Tobago by Ferry

Taking the ferry from Trinidad to Tobago is part of the experience, especially if you’re traveling with family. The ferry ride takes about 2–3 hours, depending on the vessel and sea conditions.

After a safety video, they usually play music and a movie. You can bring your own food on board, but snacks and drinks are also available for purchase.

Between the comfortable seating and motion sickness medication, I had some of the best naps of the entire trip.

Helpful tips:

• Vehicles are allowed onboard, which is ideal if you plan to drive in Tobago
• Ferry tickets can sell out around holidays; book early
• Seas can be rough, so come prepared

Flying from Port of Spain to Tobago

If you’re short on time, there are daily domestic flights from Port of Spain (POS) to Crown Point (TAB). The flight is only about 25 minutes and is the fastest way to make the most of a weekend trip. If you’re working with limited time off, flying is the more efficient option.

Where to Stay in Tobago

Villas, Guest Houses, and Hotels: What Works Best for a Weekend

Because this was a large family trip, we skipped hotels and opted for a guest house/villa rental, which turned out to be the perfect choice for us. When you’re traveling with family, or even a group of friends, having shared space makes a huge difference.

We stayed at a 4-bedroom, 4.5-bathroom house called Villa Real. The house was very spacious, and the pool ranged from 3 to 6 feet deep. Even though we arrived late, the kids were so excited they jumped straight into the pool.

Staying in a guest house gave us:

• Plenty of room to spread out
• A kitchen and shared living space
• A more relaxed, “home base” feel for a short stay

If you’re visiting Tobago with family, a guest house or villa is honestly hard to beat.

Hotel Options in Tobago

If you prefer a more traditional hotel experience, Tobago has several solid options depending on your travel style:

• Le Grand Courlan Spa Resort – A resort set on a hillside with ocean views, great for travelers who want everything in one place
• Merci Buccoo – A smaller, centrally located option near Buccoo Beach, great if you want something low-key and walkable
• Mount Irvine Bay Beach Resort – A beachfront resort popular with couples and golfers, located near Mount Irvine Beach

Staying at a hotel in Tobago is a great option if you’re traveling solo, as a couple, or for a quick, no-frills weekend, but for us, staying with family in a guest house made the most sense.

The beach was close to our villa, but not within walking distance, which led to one of our more questionable decisions.

Our Very Failed Beach “Adventure”

Because we could see water from our balcony, my cousin and I decided to find the beach on foot. That plan included:

• Walking through a wooded lot
• Jumping over a ditch
• Running across a road in flip-flops
• Getting blocked by a stream

We turned back and waited until the next day. Tobago lesson learned: having a car makes everything easier.

View the house tour and some highlights in my video below

Getting Around Tobago: Rental Cars

Tobago is small, but getting around without a car can be inconvenient and expensive.

If you’re flying into Tobago, renting a car gives you the flexibility to visit beaches, restaurants, and excursions at your own pace. If you’re arriving by ferry, bringing your personal car from Trinidad is another popular option. Note that some car rental companies do not allow you to take the ferry across.

I recommend comparing prices using DiscoverCars, which allows you to:

• Compare local and international rental companies
• Lock in better rates during busy travel periods
• Add insurance coverage upfront

Just remember that driving is on the left-hand side and roads can be narrow and dimly lit at night.

Tobago Nightlife: Where to Go After Dark

On our second night, we decided to check out the nightlife in Tobago. Since my cousins brought their cars aboard the ferry, we went to an outdoor club called The Shade in Bon Accord.

The Shade is often called the “champion of nightclubs in Tobago.” The DJs played Hip Hop, Dancehall, and a bit of Soca; much less Soca than I expected, but apparently that’s normal outside of Carnival season.

Music preferences aside, it was a fun night and a nice break from family responsibilities. It was also one of the rare times all the women in our age group (minus one) actually went out together.

Other Tobago nightlife options (we didn’t make it this trip, but they’re popular):

• Barcode in Scarborough – known for drinks and late-night vibes
• Jade Monkey Bar in Crown Point – relaxed atmosphere with live music and cocktails

Tobago nightlife is more laid-back than Trinidad’s, but there are still plenty of options if you’re staying near Crown Point or Scarborough.

Things to do in Tobago

Tobago Glass Bottom Boat Tour

One of the most popular excursions is a Tobago Glass Bottom Boat tour. Unfortunately, our trip on Frankie’s Tours’ Island Vibes boat was a nightmare! According to TripAdvisor, they offer the best Tobago glass-bottom boat tour, but everyone had a horrible experience from beginning to end.

To make the experience worse, our boat driver was in a fight while we were at “no man’s land”. The children were scared, and the adults were totally disappointed.

Turtle Watching in Tobago

I didn’t know, but turtle watching in Tobago is a really big tourist attraction. On our last night, we drove to the Turtle Beach Hotel in hopes to see a turtle lay eggs on the beach. After 2-3 failed attempts and almost leaving, one of the men in the area directed us to an area where he spotted a leatherback sea turtle.

It was pretty dark, but we got to see the turtle dig a hole and had a closer look at laying eggs. The turtle was HUGE. Although they weren’t sure of the exact age, that specific turtle had been documented for at least 35 years. Leather-back sea turtles can live well up to their 100s and lay up to 110 eggs on average 2-8 times a season.

Relaxing on The Beach

When we finally found Turtle Beach, it was well worth it. The cool sand and the warm water were all kinds of amazing. Although there were shops selling souvenirs, we weren’t bombarded by people trying to sell to us like on the beach in Puerto Plata.

Staying Connected in Tobago: eSIM Options

If you want to stay connected without buying a local SIM card, using an eSIM is the easiest option. Reliable eSIM providers for Tobago include:

• Airalo – affordable data plans for short trips
• Saily – simple setup and competitive pricing
• Holafly – unlimited data plans, great for remote work

I recommend setting up your eSIM before arrival so you’re connected as soon as you land.

Why Family Time Made This Trip Special

From searching for the doubles man at the airport to promising myself I wouldn’t eat curry for a very long time, being with my family made this Tobago getaway unforgettable.

For a first-timer’s weekend in Tobago, there’s so much more I still want to do, like visiting the house where my father lived as a tween or finally having crab and dumplings. But there’s always next time.

And trust me, I’ll be back.

Read More Caribbean Travel Guides and Tips

The Ultimate Tobago Carnival Guide

Caribbean Festivals and Events to Attend this Year

Things to do in Willemstad Curacao

Have you been to Tobago?