Caribbean
Western Mediterranean
Eastern Mediterranean
South Pacific
54
FT — SAILING CATAMARAN
10
GUESTS
5
CABINS
2
CREW
From
$34,000
Per Week
60 reviews60 reviews
The Yacht
PERMABEAR is a 2023 Bali sailing catamaran built for big groups who want bright spaces, easy flow, and nonstop ocean views. Step into the teak-floored cockpit with dining for 10 and a plush lounge bench—made for long meals and lazy afternoons at anchor. Up top, the expansive flybridge delivers panoramic 360° views, up-close sail watching, sundowners, and the best breeze onboard. Inside, the salon is airy and modern with wraparound windows that flood the space with natural light. Sleeps up to 10 in 5 cabins: 3 Queen cabins plus 2 Twin cabins—each with a private ensuite. With multiple social zones to gather or spread out, PERMABEAR keeps everyone comfortable, connected, and smiling. Spacious, sunlit, and seriously fun—PERMABEAR is the kind of charter you’ll talk about all year.
Specifications
Explore PERMABEAR
| Season | 2 Guests | 3 Guests | 4 Guests | 5 Guests | 6 Guests | 7 Guests | 8 Guests | 9 Guests | 10 Guests |
|---|---|---|---|---|---|---|---|---|---|
| Winter 2025 to 2026 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 | $36,500 | $37,000 | $37,500 | $38,000 |
| Summer 2026 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 | $36,500 | $37,000 | $37,500 | $38,000 |
| Winter 2026 to 2027 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 | $36,500 | $37,000 | $37,500 | $38,000 |
| Summer 2027 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 | $36,500 | $37,000 | $37,500 | $38,000 |
Served Daily
Fresh fruit, a variety of homemade breads and muffins, coffee, teas, iced tea, bush tea, fresh juices, mimosas & bloody Mary’s. Eggs are all locally sourced
Bagel Grazing Table
House made fresh bagels served with a variety of cream cheese, pickled red onion, capers, tomato, and smoked salmon
Breakfast Strata
A fluffy baked layered dish of eggs, sourdough bread with bacon, spinach, tomato, mushroom and gruyere cheese, or your choice of ingredients.
Brioche French Toast
Thick, rich brioche French toast with a Lazy Susan of toppings- fruits, nuts, real maple syrup, Nutella, lemon curd, powdered sugar, bacon
Frittata
The classic Italian pan baked omelet with a thinly sliced potato base, caramelized sweet onions, layers of vegetables, pancetta and ricotta cheese
Denver Omelet Breakfast Skillet
Potato, ham, peppers, onions with loads of cheddar cheese served in a cast iron skillet with soft cooked egg
Pancakes
The fluffiest pancakes EVER! Banana, blueberry, or plain stack with real maple syrup with a toppings bar
Shakshuka
The classic North African and Middle Eastern breakfast of eggs poached in tomato sauce with onions and bell peppers topped with feta cheese
Chilaquiles or Migas
Tex-Mex eggs baked with tortilla strips, Chorizo, peppers, onions and topped with avocado and salsa
“Sunday” Breakfast Buffet
A family style breakfast spread of scrambled eggs, spiral ham, bacon, sausage, roasted potato bites, fruit platters, homemade cinnamon buns
Muffin Rama!
Grab & Go Omelets are 2 eggs baked until fluffy in muffin cups stuffed with all the omelet choices. Banana nut muffins, blueberry muffins & buttery corn muffins
Belgian Waffles
Large, fluffy, freshly made traditional Belgian waffles served with real maple syrup and a toppings bar.
Cheese Burgers In Paradise
Organic Grass-Fed Ground Beef Grilled to Juicy Perfection with Brioche Buns and a Self-Serve Lazy Susan with All Your Favorite Toppings, with a Side of Sweet Potato Fries & Crispy French Fries, Served with Jimmy Buffett’s Song!
Salad Niçoise
Classic French Salad with Butter Lettuce, Seared Tuna, Green Beans, Hard Boiled Eggs, Radishes, Tomato, and Potatoes with Homemade French Dijon Dressing
Mexican Street Tacos
Homemade Corn Tortillas with Grilled Mahi, Pollo, or Carne Asada, Topped with Mango Pico De Gallo, Queso Fresco, and Shaved Purple Cabbage
Greek Lamb Lettuce Wraps
Ground Lamb with Tzatziki Yogurt Sauce, Goat Cheese, Heirloom Cherry Tomato, and Cucumber, Served in Locally Grown Crisp Lettuce
Pasta Primavera
Giant Fusilli with Grilled Green & Yellow Squash, Heirloom Tomatoes, Green, Red & Yellow Peppers, and Onions in a Homemade Creamy Parmesan Sauce
Make Your Own Poke Bowls
Hawaiian Sticky Rice Bowls with Seared Tuna or Sesame Chicken Topped with Your Choice of Grated Carrots, Cucumber, Edamame, Avocado, with Homemade Yum Yum Sauce
Shrimp Polenta
Garlic and Lemon Sautéed Shrimp with Tricolored Peppers Served Over Creamy Cheesy Polenta
Loaded Chopped Salad
Roasted Chicken, Chickpeas, Heirloom Cherry Tomatoes, Cucumbers, Shredded Carrots, Garbanzo Beans, Blue Cheese, Pecans, Dried Cherries, House-Made Raspberry Poppy Seed Dressing with Kale and Spinach, Diced and Served with a Crustini of Homemade Sourdough Bread to Scoop and Eat
Pulled Pork Sliders
Slow-Cooked Pork Shoulder Pulled with Tangy Sauce, Topped with Colorful Vinegar Slaw, Served on Sweet Hawaiian Buns and a Side of Warm German Red Potato Salad
Udon Noodles with Teriyaki Seared Tuna
Topped with Tuxedo Sesame Seeds, Seaweed Salad, and House-Made Yum Yum Sauce
Teriyaki Tuna Udon Noodles
Seared tuna topped with tuxedo sesame seeds, seaweed salad & house made Yum Yum Sauce
Creamy Poblano Pepper & Roast Chicken Enchiladas
Shredded roast chicken wrapped in homemade tortillas and baked in a creamy poblano pepper sauce.
Caribbean Roti
Traditional curried chicken & diced potatoes wrapped in a fresh made roti
Chef’s choice amuse-bouches- small bites packed with flavors and textures served with a fun drink of the day
Baccala Mantecato
Venetian whipped cod spread atop a crustini
Maryland Crab Cakes
Crispy lump crab meat patties with the classic Maryland Old Bay seasoning & house made tartar sauce
Baked Brie with Berry Compote
Served on freshly made baguettes
Flatbread Pizzas
Variety of tasting sized homemade flatbread pizzas
Warm Burrata
House made burrata served warm with grilled heirloom cherry tomatoes, basil, olive oil, aged balsamic vinegar and fresh baguettes for dipping.
Philo Cups
Light, crispy layers stuffed with spinach and artichoke dip
Shrimp Spring Rolls
Served with sweet Thai dipping sauce
Cowboy Salsa
Colorful and packed with flavor salsa of black beans, tomato, sweet corn, red onion, cilantro, avocado soaked in lime juice & olive oil with a dash of hot sauce served with corn chips
Charcuterie Platter
French cheeses, Italian cured meats, fruits, crackers & nuts
Crudités Platter
Loads of fresh vegetables served with hummus
Mediterranean Tapas
French rillettes, Moroccan curried chicken salad, Italian sausages, shrimp in garlic, served with sourdough crustini
These Chef’s pairings are tasting portions that are served to compliment a main course. The pairings, main & dessert create a memorable 4 course dinner each night.
Grilled Coconut Shrimp
Served over baby arugula with a sweet & spicy Thai dressing
Seafood Kallaloo Soup
Traditional Caribbean soup in a rich broth with shrimp, crab, snapper, carrots, celery, onions, Caribbean spinach “kallaloo” and okra
Caprese Salad
The classic tomato, mozzarella, and basil drizzled with aged balsamic vinegar
Caesar Salad
Crisp locally grown romaine lettuce with house made Caesar dressing & sourdough croutons
Spring Mix Salad
Fresh baby spring mix with walnuts, slivered purple onion, shaved granny smith apple, dried cherries with a house made olive oil, garlic lemon dressing
Potato Leek Soup
Creamy potato soup richly topped with leaks and garlic
Arugula & Ferro Salad
Baby arugula and al dente ferro served with shaved parmesan and a house made French Dijon dressing
French Provencal Fish Stew
Salmon, cod, shrimp in a tomato base with loads of garlic and tricolored potatoes topped with slivered black olives and a crustini
Ginger Carrot Soup
Sweet & creamy carrot soup with a pop of ginger
Watermelon & Cucumber Salad
Crunchy sweet pairing with aged balsamic and feta
Wedge Salad
Classic iceberg wedge with chunks of blue cheese, bacon, rainbow heirloom cherry tomatoes and house made blue cheese dressing
Butternut Squash Soup
Creamy butternut squash topped with candied pecans and crème fresh
Conch in Mofongo
Puerto Rican smashed plantains served with buttery conch simmered until tender
Goat Water Soup
This scary name for an incredibly rich beefy tasting soup (the National dish of Monserrate!), is slow stewed goat meat with spicy bonnet peppers and island spices
Cucumber Gazpacho
A cool, sweet crisp soup with honeydew, cucumber and topped with feta
French Carrot Salad
Grated carrots, fresh parsley & scallions with house made Lemon Dijon Vinaigrette
Focaccia Bread
House made with a variety of herbs and toppings
Minestrone Soup
House made classic Italian rich broth with sausage, green & yellow squash, green beans, peas, celery, carrots, onions, tomato, cannellini beans and Italian spices
Zucchini Soup
Bright summery, creamy zucchini with lemon and basil
Greek Salad
Classic Greek salad with locally grown lettuce, red onion, tomato, cucumber, bell pepper, Kalamata olives, feta with a house made vinaigrette
Tomato Gazpacho
Cool refreshing tomato/vegetable soup
Spinach Salad
Baby spinach, hard boiled eggs, bacon with warm bacon dressing
Melon wrapped with prosciutto
Cantaloupe balls wrapped with smoky thin prosciutto
Stracciatella Soup
Light creamy broth- known as Italian egg drop soup
Grilled Pork Loin
This smoky, sweet grilled pork loins is served with fresh tropical pineapple mango salsa & mango reduction with roasted red peppers served with steamed zucchini curls
Filet Mignon
Thick, tenderloins cooked medium rare, served with a rich buttery béarnaise sauce & grilled asparagus
Caribbean Stewed Chicken
Slow cooked chicken thighs with carrots, celery, onion, served with Pidgeon peas, rice & roasted plantains
Australian Lamb Chops
Grilled tender lamb medallions, encrusted with garlic & herbs served with jewel roasted vegetables- sweet potato, beet, brussel sprouts & red onion
Braised Short Ribs-
Meaty short ribs, braised in red wine & mirepoix served with brie scalloped potatoes
Snapper Curry
Locally caught snapper, vegetable yellow curry over a bed of basmati rice
Grilled Mahi Mahi
Fresh caught Mahi Mahi (hopefully off our boat!), seared and served with a lemongrass aioli and organic jade pearl rice
Scallops
Pan seared and served over risotto with grilled asparagus
Lobster Tortellini
House made fresh pasta, and formed tortellini with sage, lemon garlic & white wine reduction
Bolognaise
House made fresh tagliatelle with a slow cooked classic beef sauce
Argentinean Braised Beef
Slow cooked beef roast served with house made chimichurri over smashed red potatoes
Paella
Spanish saffron rice dish packed with seafood, chicken and vegetables
Marbella Chicken Roulades
Thinly pounded chicken breasts rolled with prunes, capers, Spanish green olives, cooked until tender and moist in a sous vide with a veloute sauce over a rice pilaf
All homemade desserts are served with freshly made whipped cream or homemade ice creams
Key Lime Pie
Real key limes are used with a graham cracker crust for the perfect tart & sweet treat
Caribbean Rum Cake
Classic Caribbean pound cake soaked in rum
Flourless Chocolate Cake
The most decadent chocolate cake ever, served soft & warm with homemade ice cream
Deconstructed Painkiller
Chef Erin’s ode to the Painkiller! A parfait of coconut cake with homemade pineapple ice cream, topped with homemade Soggy Dollar Rum Carmel & fresh ground nutmeg
Chocolate Mousse
Light fluffy chocolate classic, topped with berries and caramel lace
Fruit Galettes
Flaky French version of pie, served with a variety of fruits and ice cream
Mango & Passion Fruit Torte
Caribbean version of the fruit filled cake served with ice cream
Cheesecake
Dense New York style cheesecake topped with fruit compote varieties for you to choose
Crème Brule
Classic vanilla creaminess with the crispy burned sugar topping-simple perfection!
Sticky Toffee Pudding
This British, rich date-based cake is topped with caramel and whipped cream
Banana Foster
Bananas sauteed in Dark Caribbean Rum caramel sauce, served with homemade rum raisin ice cream
Strawberry Rhubarb Shortcakes
Fluffy individual shortcakes with tart & sweet strawberry rhubarb compote topping, with freshly made whipped cream
Mirror Glaze Cake
Special occasion cake with your choice of cake and colors
Variety of Homemade ice creams & sorbets, and warm cookies are options too!
Challenge the chef to make you favorite dessert!!
Vodka: Tito's
Rum: Cruzan (3-4 Flavors, a Dark, and a Light)
Bourbon: Bulleit
Gin: Bombay Sapphire
Tequila: Milagro
Champagne: La Marca Prosecco
Red/White Wine ($12-$15 bottles typically): Josh, 19 Crimes, Apothic, Matua, Dark Horse, Oyster Bay
Cordials: Grand Marnier, Espresso Vodka, Amaretto. Frangelica
Beers: ST. John Brewer's, Leatherback Brewery, Corona
Captain
Ed Irwin
Chef/First Mate
Erin Irwin
3rd Mate- Onboard Friendly Dog
Gus
Capt. Ed Irwin
Born in Newfoundland, Canada, I spent as much time as I could outdoors, fishing the streams for trout and getting lost in the woods. As a small boy, I would drive my mother crazy by wandering off, only to return home with pockets full of fish I caught or birds and small animals I captured, which I wanted to keep as pets.
I have enjoyed backcountry camping, hiking, and canoeing throughout my life. The Boundary Waters lakes and portages are among my favorite places to explore. Riding my motorcycle, lightly packed for discovering remote fly-fishing streams, without a set destination, is my perfect getaway.
I grew up on the small lakes of Northern Illinois, often driving to school in my small motorboat. The first time I was on a sailboat, I instantly fell in love with the simple act of the wind carrying my boat anywhere.
After sailing Lake Michigan for many years, Erin and I devised a plan to set off on our own boat and sail to as many places around the world as we could. We found an abandoned Cape Dory 36, rebuilt it, and outfitted it for long-distance travel. Years of hard work paid off with a beautifully restored and perfectly outfitted classic sailboat that allowed us to live out our sailing dreams.
We have sailed and lived aboard our boat since 2018. In that time, we’ve sailed the Great Lakes, the Chesapeake, and offshore from Norfolk around Bermuda to the Caribbean at least six times. During hurricane season, we sailed north to Maine, enjoying the "down east" summer, before heading back down the eastern seaboard and offshore to the Caribbean once again. At the end of 2023, we flew to the Mediterranean, picked up the Bali 5.4 “Permabear,” and sailed through the Med to Las Palmas before crossing the Atlantic to the Caribbean. After around 30,000 nautical miles of sailing, we still love every moment.
For the past three years, we have been chartering in the Virgin Islands, both the US and BVI, exploring, discovering amazing coves and anchorages, becoming PADI scuba certified, and learning why so many say that once you reach the Caribbean, you don’t want to leave. Our guests often comment on how safe they feel aboard our boat, knowing I am always alert and cautious. We ensure that we create the most comfortable and enjoyable trip on the water for everyone aboard. I look forward to showing guests why the Caribbean truly is a sailing paradise.
My childhood was spent on boats in our summer town of Saugatuck, MI. I loved everything about being on the water and was always the first and last one to jump in, no matter the temperature! I began sailing as a teenager and am seriously addicted to the magic of wind and water.
As the oldest daughter of a big family, and the mother of five kids, I was always at the center of planning family gatherings and parties. I love finding unique themes and creating relaxed, special moments and memories together. Ed and I have found the outdoors, especially sailing, to be the perfect setting for connecting with each other and something bigger. It has always been the best stage for us to find joy, peace, adventure, and excitement, and we want to share that.
I have been baking and cooking since I was a child, and it has always been a joy to create a meal. When cooking for my family, I wanted them to have a healthy diet. Most of our meals were whole foods from our garden, cooked from scratch. My cooking style emphasizes a healthy balance of Mediterranean foods, Asian cuisines, and comfort foods that are adapted to be healthy but still rich in flavor. Having spent a good portion of my life in Chicago, I’ve become an obsessive foodie, constantly searching for the perfect meal at the perfect restaurant. This endless quest has taught me so much about the experience of eating well.
We work hard to make the experience of coming aboard seamless. From the moment guests make their booking, we stay in touch to tailor their vacation to exactly what they imagine. From the food and the itinerary to even having the perfect sunblock, big straw hats, and beautiful beach gear — we want our guests to just bring a small bag and let go.
We especially look forward to helping families find that elusive real time together. There’s just nothing like being on a sailboat to make everything else fade away and allow you to connect with the people you love. We can’t wait to help others find that perfect spot — that perfect moment that becomes a memory that lasts forever.
Very Friendly Onboard Dog
Meet Gus, our adventurous Cairn Terrier and seasoned sailor with over 30,000 nautical miles under his belt! Gus is not just any yacht dog; he's a true seafaring companion with a story that includes befriending a mother dolphin and her baby in Long Bay, as well as making turtle friends who swim up to the boat just to see him. He's also an expert paddleboarding companion.
With a love for kids and hair instead of fur (making him hypoallergenic!), Gus is the perfect family-friendly crew member, known for his quiet and well-behaved nature. Despite his loyalty, Gus loves to snuggle and will always find a way to convince you to give him a moment to prove why dogs are amazing!
07 / Open Weeks
Cruising Grounds
Explore the serene Spanish Virgin Islands: pristine beaches, historic sites, and unspoiled nature await. The ultimate Caribbean sailing escape.
Experience the charm of a US Virgin Islands yacht charter. Discover pristine national parks, stunning beaches, and easy navigation in this Caribbean gem.
Explore a British Virgin Islands yacht charter for an unmatched sailing adventure. Idyllic Caribbean setting, easy navigation, and iconic beach bars await you.
Sample Itineraries
SPANISH VIRGIN ISLANDS · 7 DAYS
Vieques and Culebra by yacht — Bahía de la Chiva, Esperanza, Green Beach, Flamenco, Culebrita. A passport-free, downwind 7-day Spanish Virgin Islands week.
US VIRGIN ISLANDS · 4 DAYS
A 4-day US Virgin Islands itinerary — Maho Bay turtles, Lime Out tacos, Magens Bay, Salt Pond. Crewed charter from St. Thomas with private captain and chef.
BRITISH VIRGIN ISLANDS · 7 DAYS
USVI sailing itinerary that picks up in St. Thomas and crosses into the BVI — Buck Island, North Sound, Jost Van Dyke, Peter Island. Crewed week, day by day.
