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At Personality Tours and Transfers, we take a different approach. Our tours feel more like reunions with an old friend you're meeting again, for the first time. Driver/guide Don sets the tone with his warm, friendly personality and sharp wit. You may laugh. A lot.
Complimenting Don's affable charm are his deep knowledge and obvious love of the island's history, culture and experiential gems, which he shares enthusiastically as he seamlessly morphs from sightseeing facilitator to life of the party to engaging history professor and back again.
Each tour is a unique experience shaped by mutual exchange as we host couples, families, and friends looking for an enjoyable, relaxed and enriching good time. No hustle, no hassle.
For the discerning traveler.
So come! Let us show you around St. Kitts, from Basseterre to Brimstone Hill and everywhere in between. Book with us today!
Ask for Don.
Not recommended for travelers with spinal injuries
Not recommended for pregnant travelers
Not recommended for travelers with poor cardiovascular health
Suitable for all physical fitness levels
Berkeley Memorial
We will see the Berkeley Memorial, erected in 1883 and dedicated to the memory of Thomas Berkeley Hardtman Berkeley, a legislator and owner of various estates in St. Kitts. The structure contains a clock and drinking fountain. It was designed and produced by George Smith and Co of Glasgow, Scotland.
Independence Square
We will cruise past Independence Square, formerly Pall Mall Square, which was renamed on the 19th September 1983 to commemorate the birth of the new nation of St. Christopher and Nevis. Located on the eastern side of Basseterre bordering the community of Newtown, its' layout was designed to look like a Union Jack. Originally a pasture on the edge of town just east of Fort Street, in its' heyday as Pall Mall Square, the space found life as a market and gathering place for the enslaved Africans, offering some reprieve from the rigors of existence on the plantations.
Pickup included
Cruise port pickup and drop off
Bottled water
WiFi on board
Air-conditioned vehicle
Hotel pickup and drop off
Caribelle Batik at Romney Manor - adult
Brimstone Hill Fortress National Park - adult
Royal St. Kitts Hotel
Zenway Blvd Frigate Bay Caribbean
Timothy Beach Resort
Frigate Bay Caribbean
Koi Resort Saint Kitts, Curio Collection by Hilton
100 Koi Resort Drive Basseterre Caribbean
Marriott's St. Kitts Beach Club
858 Frigate Bay Road, Frigate Bay Caribbean
St. Kitts Marriott Beach Resort, Casino & Spa
858 Frigate Bay Road Frigate Bay Caribbean
For a full refund, cancel at least 24 hours before the scheduled departure time.
32 đánh giá
Tổng số đánh giá và xếp hạng từ Viator & TripAdvisor
anthonybE9167VI,29 thg 6, 2026
- Đánh giá từ Tripadvisor
Upon arriving at St.Kitts for the first time, we found Don’s company. We read the reviews and he did not disappoint! Don’s knowledge about the island’s history and local culture were outstanding. His delivery of the information was personable and easy. We had immense flexibility on the sights we were to see. In addition, he expertly and safely navigated the challenging roads and traffic on the island. I would recommend Don to everyone who visits St. Kitts.

Manatee5,28 thg 6, 2026
- Đánh giá từ Tripadvisor
Absolutely a must-do when in St. Kitts! Don was such a great tour guide, funny, knowledgeable, professional and an all around nice guy! We enjoyed getting to know the island from an insiders perspective and the stops hit the highlights, in addition to additional photo-ops along the way. His hospitality was greatly appreciated and I definitely recommend this for both first-time and repeat visitors to St. Kitts!



Michelle B,28 thg 6, 2026
- Đánh giá từ Viator
Absolutely a must-do when in St. Kitts! Don was such a great tour guide, funny, knowledgeable, professional and an all around nice guy! We enjoyed getting to know the island from an insiders perspective and the stops hit the highlights, in addition to additional photo-ops along the way. His hospitality was greatly appreciated and I definitely recommend this for both first-time and repeat visitors to St. Kitts!



Adventure24863876401,28 thg 6, 2026
- Đánh giá từ Tripadvisor
This tour was the highlight of our family vacation. We learned all about St. Kitts and Nevis from a real Kittian. Don's personality, sense of humor, and wealth of knowledge make the trip very enjoyable. I 100% recommend this tour for all ages. You won't regret it. Worth every penny.

Jennifer W,28 thg 6, 2026
- Đánh giá từ Viator
We were a family of 6, including 2 in their 80s. None of us had ever been to St. Kitts. Don was the best tour guide! He took us all around the island, showing us historical and natural sites. As a native Kittian, he knew EVERYBODY and EVERYTHING about St. Kitts and Nevis. We got the scoop on the Kittian movers and shakers, as well as the common folk. The best part? Don's personality. So funny and nice! Take his tour, I promise you won't regret it. It might even be the highlight of your entire trip, as it was ours.

Thea C,8 thg 6, 2026
- Đánh giá từ Viator
Our family of four (2 adults, 1 teen, and 1 child) had an amazing private tour with Don in St. Kitts! From start to finish, he made the day memorable, fun, and incredibly enjoyable. Brimstone Hill Fortress was an absolute highlight of the tour (wear sneakers), and Timothy Hill provided a fantastic photo opportunity with breathtaking views. We also enjoyed learning about the history of Basseterre, which added great context to the island and its culture. Don is exceptionally knowledgeable, having been a former professor, and his passion for sharing information really shines through. Beyond that, he was kind, timely, personable, and a very safe driver. We spent much of the day belly laughing because he fit so naturally with our family and made us feel completely at ease - uh wheeeeeeeeeeeeee!!! :) We even stopped to enjoy some local beer by the rum distillery, which was a great touch and helped us experience a bit of authentic island life. Don’s pricing was very reasonable, especially considering the personalized experience he provided. If we return to St. Kitts, we will absolutely book another tour with Don again. Highly highly recommended!
Pathfinder627393,28 thg 5, 2026
- Đánh giá từ Tripadvisor
We had THE best day with Don! He was the funniest guy, best guide, let us go at our own pace, dealt with my crazy weird family, and it was so nice to not be stuck with a bus of sweaty strangers! We’d give him 100/10! 11 and 13 year old kids with us and they loved it and joined in on all the banter. We visited places we didn’t expect and they were all super cool and beautiful! Highly recommended!




Mariann S,19 thg 4, 2026
- Đánh giá từ Viator
Don was good ambassador for St. Kitt's. He met us on time as arranged past the cruise terminal. There were 4 of us and we were comfortable in his automobile. Don is engaging, knows the island well and spent plenty of time with us. We enjoyed our day with Don and would recommend him to anyone who likes a private tour with a guide who is from the area.
juliejS9915VN,9 thg 4, 2026
- Đánh giá từ Tripadvisor
After getting his card from our hotel receptionist and reading other reviews of Don's tours, we had to try it ourselves. And safe to say, we were not disappointed! Firstly, we were greeted warmly when contacting Don through Whatsapp, and it was clear we were in very good hands from the start. Don's easy going, fun and welcoming personality made us feel right at home from the beginning, and his knowledge of the island's history and its people were exceptional. All in all it was an amazing day (the best of our trip, our jaws hurt from laughing by the end), and we can only recommend taking a guided tour with "The Don"! Do yourself the favor, you won't regret it! A bonus info: Don is a great driver, and made us feel safe and comfortable during the whole tour. And if you want a fun story, ask him about "small boats and warships" ;-) Thank you for making this day truly memorable! With much love and laughter, Julie & Michael

Steven W,7 thg 4, 2026
- Đánh giá từ Viator
My family had a GREAT time with Don! We cruised out of Miami, and St. Kitts was by far the best stop -- that's 100% thanks to Don. I definitely recommend reaching out to him. Don is a great host, and he's very well connected on St. Kitts. Everywhere we went, people knew him, and he was able to connect us with some other great people on the island during our trip. Don's car was really nice too -- imported Japanese Toyota 8-seater. We had 4 adults and 2 kids, and everyone was really comfortable. Everyone in the car could hear Don when he was explaining the island to us too. I booked with Don in advance to save us time and stress when we got to the port. I also had a few questions before our trip, and he responded to me within a few hours (e.g. customizing the tour, getting cigar recommendations, confirming timing, etc). - Steven

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