Cool Destinations
Top Bermuda activities
Top Bermuda landmarks
Beyond Bermuda
Bermuda trip ideas
  • Tours by category
  • Tours by accessibility
  • Tours by feature
  • Tours by the numbers
  • Top Bermuda landmark tours
  • Tours in nearby places
  • Explore tours
  • Bermuda travel guides
  • Bermuda travel calendar
Language $Currency
Login / Sign up
Bookings
Bookings
Cool Rewards Rewards
$0.00
Cool Rewards Rewards
$0.00
Wishlists
Wishlists
Profile
Help Center
Language
Log out
Top Bermuda landmark tours
Start your search
Change your search
Place or activity
Select Dates

Top Bermuda Sailing Trips

11 Results
Sort by:
Featured
Filter
Languages Clear
Time of Day Clear
6
7
6
Duration Clear
0
11
0
0
0
Price Clear
$0 $500+
Rating Clear
9
10
10
Specials Clear
11
7
0
7
1
Features Clear
1
7
6
0
11
5
Accessibility Clear
0
6
10
Families Clear
3
1
0

Bermuda Tours

Guides

Calendar

Restless Native Catamaran Sail and Snorkel Tour
Likely to Sell Out
Likely to Sell Out
4.9 (1,067)

Restless Native Catamaran Sail and Snorkel Tour

Get the most out of your time in Bermuda with a 3.5-hour sail on a pink catamaran. Your captain makes for a fun guide as...

3 hours 30 minutes • Free Cancellation
4.9 (1,067)
from
$95
Private Catamaran charter Swim sail snorkel cliff jumping SUP
Likely to Sell Out
Likely to Sell Out
5.0 (291)

Private Catamaran charter Swim sail snorkel cliff jumping SUP

This is a 3-hour private catamaran charter, up to 15 guests, with pick up at the cruise ship terminal in dockyard or Hamilton Harbor. Catamaran...

3 hours • Free Cancellation
5.0 (291)
from
$999
Restless Native Catamaran Sunset & Swizzle Cruise
Likely to Sell Out
Likely to Sell Out
4.8 (354)

Restless Native Catamaran Sunset & Swizzle Cruise

Start a night out in Bermuda the right way with a 1.5-hour sunset cocktail cruise aboard a 50-foot catamaran. Sunsets in paradise are always great,...

1 hour 30 minutes • Free Cancellation
4.8 (354)
from
$70
Catamaran Sunset Sail
Likely to Sell Out
Likely to Sell Out
4.8 (52)

Catamaran Sunset Sail

You are on course for a good time with Bermuda's original sunset Sail. Soak up the setting sun and sensual seascapes as we sail in...

1 hour 30 minutes • Free Cancellation
4.8 (52)
from
$94
Good Vibration Catamaran Sail Swim Snorkel
Likely to Sell Out
Likely to Sell Out
4.7 (43)

Good Vibration Catamaran Sail Swim Snorkel

Hop aboard Bermuda's newest catamaran, good vibrations, for a fun-filled excursion of cruising, sailing, swimming, lounging and snorkeling along the shoreline....

3 hours • Free Cancellation
4.7 (43)
from
$111
Private Catamaran Charter on Elusive
Likely to Sell Out
Likely to Sell Out
4.9 (21)

Private Catamaran Charter on Elusive

This is not your average boat charter—Sail Bermuda offers a luxury private sailing experience that’s entirely your own. Whether you want to snorkel offshore reefs...

3 hours • Free Cancellation
4.9 (21)
from
$2,000
Private Catamaran Charter on Wyuna
5.0 (17)

Private Catamaran Charter on Wyuna

This is not your average boat charter—Sail Bermuda offers a luxury private sailing experience that’s entirely your own. Whether you want to snorkel offshore reefs...

3 hours • Free Cancellation
5.0 (17)
from
$2,120
Private Sunset Charter on Elusive Catamaran
Likely to Sell Out
Likely to Sell Out
5.0 (5)

Private Sunset Charter on Elusive Catamaran

At Sail Bermuda, a sunset charter isn’t just a sail—it’s your own private escape, curated with care. You’ll glide across calm waters aboard the luxury...

3 hours • Free Cancellation
5.0 (5)
from
$2,000
Bermuda By Sunset “Private Catamaran”
5.0 (6)

Bermuda By Sunset “Private Catamaran”

- Private 1.5-hour sunset cruise aboard Kona, a sleek catamaran - Scenic sail along Bermuda’s coastline with golden hour views - Ideal for couples, small...

1 hour 30 minutes • Hotel pickup offered • Free Cancellation
5.0 (6)
from
$580
Private Sunset Charter on Wyuna Catamaran
Likely to Sell Out
Likely to Sell Out
5.0 (1)

Private Sunset Charter on Wyuna Catamaran

At Sail Bermuda, a sunset charter isn’t just a sail—it’s your own private escape, curated with care. You’ll glide across calm waters aboard the luxury...

3 hours • Free Cancellation
5.0 (1)
from
$2,150
Redemption Catamaran Private Day Sail with Captain
Likely to Sell Out
Likely to Sell Out

Redemption Catamaran Private Day Sail with Captain

Departing from either Dockyard or Hamilton, step aboard Redemption, our spacious sailing catamaran, for a fun and relaxing half-day on Bermuda’s crystal-clear waters. Guided by...

3 hours • Free Cancellation
from
$1,133

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Fantastic time!!
New York City
Catamaran Sunset Sail
Maureen_B, Sep 2026
Fantastic time!!
Outstanding!!! Adrian, Taz and Ajohnny were on point!! Very informative and very attentive to all the cruisers!! Taz had gray comments!!
Read more
Unhurried and Beautiful Snorkel Experience
New York City
Restless Native Catamaran Sail and Snorkel Tour
mafarmerga, Sep 2026
Unhurried and Beautiful Snorkel Experience
A wonderful and unhurried introduction to the beautiful undersea world of Bermuda. An easy to reach departure from Dockyard and a pleasant ride to a nearby beach with a truly nice snorkeling site with lots of underwater diversity. The staff, especially Captain Cameron, were friendly and professional. The best part of the experience was that we were completely unhurried. There were other outfits that arrived after us and left before us. If you are only on island for a short time and want an on-the-water experience to remember, we recommend Restless Native,
Read more
Wonderful, Fantastic Experience
New York City
Restless Native Catamaran Sail and Snorkel Tour
amillzy95, Sep 2026
Wonderful, Fantastic Experience
Absolutely lovely experience. They provided snorkeling equipment and swimming supplies. The crowd seemed large while on the boat, but once we reached our destination, there was so much room to explore that it didn't feel overwhelming. The staff was great as well, providing refreshments and answering questions about the local environment. Cannot recommend it enough to anyone visiting Bermuda!
Read more
12th Birthday celebration
New York City
Private Catamaran Charter on Wyuna
jeanesmartinez, Sep 2026
12th Birthday celebration
We had such a fantastic experience! The boat was fully equipped with plenty of fun activities and equipment for both children and adults, so there was something for everyone to enjoy.The crew was excellent—professional, attentive, skilled, and always looking after our guests. You could really tell they knew exactly what they were doing, especially the captain, which made us feel very safe and comfortable throughout the trip.We had a large party, including 25 children, and they handled the group incredibly well. They even provided extra crew for additional support and peace of mind, which we really appreciated.The price was very reasonable considering the level of service, equipment, and attention we received.Highly recommended, especially for families and large groups!
Read more
5-Star - Recommend!
New York City
Restless Native Catamaran Sunset & Swizzle Cruise
JayDjr, Sep 2026
5-Star - Recommend!
Excellent excursion. Met the crew right by the cruise ship with a very short walk to board the ship. Crew was wonderful, very knowledgeable answering questions. Felt safe at all times and what a great view! Will take another excursion with this company the next time we are in Bermuda.
Read more
Catamaran sunset sail
New York City
Good Vibration Catamaran Sail Swim Snorkel
H5803EWbeckyl, Sep 2026
Catamaran sunset sail
John, James, Keanu they were such great tour guides. Keanu keep refilling are drinks and James answered all the questions I asked. Captain John ensured our safety and was very professional.
Read more
Best birthday celebration!
New York City
Private Catamaran Charter on Wyuna
lbattipede, Sep 2026
Best birthday celebration!
We had an amazing time celebrating my 60th birthday with family. Loki and Jackie were great. We stopped at a beautiful spot to paddle board and enjoy the beautiful beach. Kids from 1 yr to 42 all enjoyed it. We had 16 of us on the Wyuna and had plenty of room.
Read more
Beautiful sunset cruise with lots of rum swizzles
New York City
Restless Native Catamaran Sunset & Swizzle Cruise
Stacy_M, Sep 2026
Beautiful sunset cruise with lots of rum swizzles
We had a nice time and the crew was very friendly! Even put out the sail! Beautiful sunset and rum swizzles were plentiful!
Read more
In Making Memories 💚
New York City
Private Catamaran Charter on Elusive
F4521KSgaryp, Aug 2026
In Making Memories 💚
This was my second trip in five years with my niece and her husband, but this year, my son, daughter-in-law, and their four kids aged 11,9,7,&5 were along with us, the Catamaran was all ours.We all had a fabulous time, especially the kids who love the water.Every activity that they offer was available and we sure did use them. Our Captain Tatiana and Mate Kyle were exceptional hosts explaining our different locations. But most of all were great with the kids.The 4hr charter was just enough.
Read more
Perfect experience on the...
New York City
Private Catamaran charter Swim sail snorkel cliff jumping SUP
Clay_G, Aug 2026
Perfect experience on the...
Perfect experience on the water. Relaxing. Georgia and Matt were great. Matt's knowledge and history of Bermuda made the cruise memorable. And the snorkel/caves/cliff diving is a must do.
Read more
Fantastic snorkeling adventure!
New York City
Good Vibration Catamaran Sail Swim Snorkel
mkcoopers, Aug 2026
Fantastic snorkeling adventure!
Smitty, Andrian and Taz were fantastic!  And took us, in Relaxed fashion, to one of the best snorkeling reefs we have been to!  Be still and let the fish come out, and oh they did.  Bring your GoPro.  We are swimmers however, there really isn’t much need for that. Snorkels, masks and fins are provided. Many people had generous rum swizzles in the water floating with a noodle in paradise near the end. The boys were very Islanders and knowledgeable and had just a great Bermuda vibe.  I would have wanted to stay all day but for a wicked burn I got, my fault.  I should have been willing to put a swim shirt on, and so melanine deficit ones, be willing to cover up!  You don’t want heavy sunblock because it just slides off anyway (and damages those amazing reefs-don’t do it!), put sunblock that is reef safe at least 1/2 hour before, and don’t go out til you have to.  But that’s normal.  The craft, crew and trip were wonderful.
Read more
Excellent!
New York City
Catamaran Sunset Sail
Camper21297421075, Aug 2026
Excellent!
My husband and I had a wonderful time!
Read more
Excellent.
New York City
Private Catamaran Charter on Elusive
Crin1972, Aug 2026
Excellent.
Beautiful experience! Jono, the captain, a fantastic, nice, and very, very professional person
Read more
Fantastic Day on the Water
New York City
Private Catamaran charter Swim sail snorkel cliff jumping SUP
Meander510840, Aug 2026
Fantastic Day on the Water
Alex and Mark provided our family a wonderful afternoon on the water. Their experience and knowledge of Bermudan waters made everyone feel safe and comfortable. They took us to a secluded snorkelling spot where we saw rays, squid and tons of fish. Those that didn’t want to get in the water stayed on board and had a wonderful time chatting with Alex and Mark. This experience is not to be missed!
Read more
Highly recommended personal sunset cruise
New York City
Bermuda By Sunset “Private Catamaran”
Jason_A, Jul 2026
Highly recommended personal sunset cruise
Captain Bryan was an excellent tour guide and advocate for his home island of Bermuda. He was generous with his local knowledge and allowed time on the cruise for our us to swim and snorkel in a protected cove before sunset. This was a much better option for us than a party cruise with dozens of others who we don't know. We'd book with him again without hesitation.
Read more
The best thing to do in Bermuda
New York City
Private Sunset Charter on Wyuna Catamaran
440raymondn, Jul 2026
The best thing to do in Bermuda
We had a family group of 12 , from 17-63. Had a renewal of vows onboard. Chose one of the caterers they list and contracted food with them. Communication was great throughout booking to end. Staff was great on board (Loki captains, Kyle as second). Informative, courteous and accommodating to whatever we wanted to make out of our charter. Had 4 that had never been on a real boat before and they all did great. Highly recommend.
Read more
Bermuda Tours
Guides
Calendar
View more